The Housekeeper, Chapters 1-20

Author’s Note: Commissioned by EthanDalton96. Thank you for your pledge, and for all the ideas that are making this story possible!

Chapter One

Jess

I couldn’t believe my luck!

University wasn’t cheap, so I had decided at the beginning of my first year there to keep my babysitting business from high school going. My website was already set up and, it may sound braggy, but I was pretty great at my job. Reliable, punctual, great with kids, and almost always asked back. By the time I graduated high school, I honestly could have given up higher education and made a decent living with the rates I had established by the end. Between the referrals and the repeat jobs, the only thing holding me back from babysitting every night was the fact that I still wanted a social life. 

So, since I ended up at a local university, it made sense to keep running my business. I was a lot choosier when it came to the jobs, since I could only give up one or two nights a week while still keeping up with my studies and enjoying the freedom of living alone. Not totally alone, as I had a roommate, but that was still more liberating than sharing a roof with my parents. For the most part, I tried to stick with younger kids with earlier bedtimes, so I could knock out some homework and studying for a few hours at the end of the night. As for the rest, I referred them to friends of mine that were still in high school, as not many other girls my age were still babysitting. For a small, one time fee, of course. It’s not that I was greedy. But textbooks were expensive, and I had put a lot of work into my teenage babysitting career. I wasn’t just going to give more than half of it away for nothing. 

Then, at the end of my sophomore year, I hit the jackpot. Some wealthy family halfway across the state got my name somehow, and offered me the job of my dreams. For starters, it was a lot of money. More money than I currently had in my checking and savings account combined. If that wasn’t tempting enough, the summer job involved watching a teenager. Personally, I’ve never minded babysitting teens. While the attitude can sometimes be an issue, the huge ‘pro’ is that they’re self sufficient. My trick is to just treat them with respect, lay down a few basic rules, and otherwise let them do whatever they want. When I pull it off correctly, they get a whole night of doing their own thing without being bothered, and I get paid for doing nothing but maybe making a meal if the parents didn’t leave money for ordering something. 

Part of the reason I was being offered so much was due to the commitment involved. Six whole weeks staying at their house and watching their kid while they were on vacation. I had only done two overnight jobs before, and both of those were just a Saturday/Sunday thing. This was definitely outside the scope of my usual experience, but that didn’t mean I wasn’t equipped to handle it. It was summer, so I had the time, and it was really good money. On top of that, a quick online search of their address showed me that the family lived at this huge manor, complete with a guest house and a pool. I would probably be staying in the main house, but there was always the possibility of inviting a friend over and having a sleepover across the way after my teenage charge was fast asleep. Oh, and they had a pool. 

In a lot of ways, this could be both a job and a vacation. No parents or other adults around, and a fancy, expensive property for me to relax at whenever Hannah was content entertaining herself. That was the girl’s name–Hannah–though I didn’t get many details about the girl herself. For the most part, the messages were about the job. And it made sense that the girl’s parents were hiring a babysitter. Plenty of teenagers could be trusted to be home alone for a day or two, but six weeks was a long time. Hannah probably didn’t want to be shipped off to some relative’s house for half the summer, so this was the better alternative. 

When the day arrived, I must have spent hours getting ready. Hannah’s parents had an early morning flight, so they wouldn’t even be there to greet me. However, teenagers could be quite judgmental, and I wanted to make a good first impression. Also, I was stuck between being daunted by the fancy manor and wanting to look like my usual summer self. And that was just one outfit. Packing was a whole other thing, though I solved that problem by simply throwing everything I owned into my suitcases and duffel bags. It would be easier to choose future ensembles after seeing how Hannah dressed. Normally I wasn’t afraid to just throw on jeans and a tank top, but that was when I was a middle class girl babysitting for middle class families. This was different. 

Heels were a must. 

I was short for my age; only 4’11”. Breaking five feet would have been wonderful, but I hadn’t grown in years. Now that I was twenty, I was more or less resigned to my embarrassingly short height. Thankfully, I had plenty of other things going for me. My chest was a point of pride. 32C exactly, which made bra shopping simple compared to other girls I knew. I also worked out a minimum of three times a week, leaving me with a well-defined stomach and a hint of tone everywhere else. 

Looking myself over in the mirror after my shower, content with how my naturally tanned skin looked better than usual after a fresh shave, I got to work blow drying my brunette locks so any lingering dampness on my body could air dry at the same time. I’m not vain, but I’m also not blind. I know I’m decently attractive, minus the pathetic height, and today was especially important to highlight and accentuate all my best qualities. After building a good rapport with Hannah, I could probably get away with messy hair and PJs. But on day one, I had to look my best.

Ultimately, I decided on a dark green sundress. It was one of my favorites and, like many dresses of that variety, did a good job of looking nice yet casual. It was comfortable, too. For footwear, I opted for a pair of brown heels that gave me an extra three inches of height. Returning to the bathroom, I made short work of putting in my contact lenses and adding a light curl to my hair. Picking out an outfit was one thing, but I didn’t trust myself with a curling iron without my contacts. Aside from my height, my poor vision was the other thing I wasn’t particularly fond of. That, and my tiny feet. 

My parents were already off at work, so I hauled all my suitcases and duffel bags downstairs and to the car by myself. After triple checking my room for anything I tended to forget when it came to trips–chargers, toiletries, and socks–I jotted a quick note with Hannah’s address and her home phone number in case there was an issue with my cell, and then hopped in the car to make the four hour drive. 

I’d be getting there just after lunch. Her parents had assured me she would be fine for half a day by herself, but I still felt a little bit nervous along the way. Normally, I would arrive and greet the parents before they left, especially for a new job. Halfway through the drive, I considered calling Hannah during my stretch break at a rest stop. I had already added her cell phone number into my Contacts, as well as the landline. After thinking for a minute or two, I decided against it. The average teenager didn’t enjoy talking on the phone, and it would be better if my first interaction with her was face to face. 

Finally, after a healthy combination of podcasts and music, I arrived at Walker Manor. Turns out, the online images didn’t do it justice in the slightest. As I drove through the main gate and looked around with wide eyes, it was difficult to tell where their property ended and nature began. The time it took to get up the road/driveway was enough to get a good look at the perfectly kept grounds, a gorgeous lake off to the left, and the enormous stone house that I would be staying in for the next six weeks. Suddenly, my sundress felt entirely inadequate. I should have shown up in a fucking ballgown. 

Where was I supposed to park? There was plenty of space right in front of the house, but the smooth driveway also looped around the side towards the smaller guest house and perhaps a nineteen car garage. I wouldn’t be surprised. For the moment, I stopped the car near the main door. Hannah would know better than I would, plus this would be easiest in terms of hauling all my things inside. Taking a deep breath, feeling entirely out of my element, I stepped out of the car and approached the front door.

‘Housekeeper.’ That’s what I was supposed to be. At least, that’s what Hannah’s parents had strongly suggested. Since I’d be doing a bit of the cooking and cleaning, like I ended up doing at most of my jobs, they thought it would be a better term than ‘babysitter.’ While I understood where they were coming from, as their idea would be theoretically easier to swallow for a rich teenager who probably thought she didn’t need supervision, I had been in this line of work for a while. Kids aren’t stupid, and that goes doubly so for teens. If I had to guess, Hannah would see right through the white lie. 

But I would try. Jess, the housekeeper. 

As long as Hannah and I could coexist, I’d go with whatever title worked. It was going to be a win/win. I’d get a six week vacation at a place that would cost me thousands if it were a bed and breakfast, and their daughter would get the freedom she wanted. As long as she didn’t destroy the house, I could be flexible about a lot of other things. 

Taking another breath, I took the brass knocker and officially announced my arrival.

Hannah

A babysitter. A fucking babysitter. 

I was going to kill my parents. What, they didn’t trust me because I hosted a party one time when they were out of town? It’s not like I left a huge mess for them to clean up. Hell, I hired an outside maid with my own money to put the whole house together in a matter of hours the next morning. The only reason they even found out is because one of my (former) friends ratted me out. She was too hungover, and bombed a university interview. Her parents managed to interrogate her enough that she cracked and tried to put the blame on me to save her own skin. 

As if. All she succeeded in doing was uninviting herself to every party since then. Were the pity points worth it, Brittany? None of us trusted her with anything any more. Goes to show what happened to girls who crossed me and my friends.

More importantly, I was eighteen years old. A legal ADULT. A high school graduate who absolutely did not need supervision. And yet, my parents decided that it would be a good idea to hire someone to watch me while they went off on some charity cruise. Like they actually cared about whatever their donation was going to. It was just an opportunity to lounge on a boat and see a few exotic countries along the way. Just like their real motivations for their trip was obvious, it was also painfully clear what ‘housekeeper’ really meant. We already had two maids. We had a groundskeeper. So why hire someone new at the exact time they were leaving for vacation? What a crazy mystery. 

My parents were long gone by the time I woke up. It was summer, which meant I didn’t plan on ever waking up before 9 AM. This new hire was supposed to arrive some time after noon, which meant that I had all of three hours to myself. I considered throwing an impromptu day party just to make her deal with dozens of inebriated high school graduates and perhaps some university students as well if I gave my friends the green light to invite their older friends and relatives. 

It was a fun idea, but it wasn’t a smart play. Why risk something that bold before even meeting the woman that was supposed to be supervising me all summer? I’m a people person, after all. I’d rather get a read on her and then plan accordingly. While I hated sucking up to authority figures, it wasn’t beneath me. I’ve done it plenty of times with teachers, especially the male variety, and playing nice with Jess could yield some equally positive results. She would lower her guard, and I could start pushing the envelope. Anything she lets me do once is something I could then do forever. Backpedaling is difficult once you’ve already said ‘yes’ to something. 

Also, what kind of name is ‘Jess?’ Short for Jessica, or maybe Jessamine? Most adults tended to shed such nicknames as they got older. Then again, this woman accepted a babysitter job, which meant she wasn’t well off financially. Maybe lower class types are more keen to stick with nicknames. Or maybe Jess was just an anomaly. Whatever. There could be a million other reasons, but dwelling on something like that was a total waste of time.

Changing into one of my many bikinis, I grabbed a bottled smoothie and some lotion before heading out to the pool. Jess was going to be here in a few hours, which meant this was my last chance to tan while topless. Practically, I just hated having pale orbs on my chest that didn’t match the rest of my skin tone. But also, it was exhilarating to be half naked outside, even if no one was scheduled to work this morning. Low risk, but still alluring to be reminded of my nudity every time a light breeze brushed my bare breasts. 

I stayed by the pool all morning. Texting, scrolling, and occasionally drifting off. I eventually got up to grab myself a pitcher of water, but that’s about it. Once noon hit, I was a little more alert, but opted to keep my top off for as long as possible. I think it was safe to assume that Jess would frown upon such exposure, which meant this would be my last opportunity to tan topless for six weeks. 

Honestly, having a babysitter was going to be worse than my parents being around. They worked so much, I almost always had the place to myself during the day. Now I was going to have to deal with near-24/7 supervision. Fuck me. 

Finally, I heard her. We were the only house in at least a half mile radius, which means the sound of a car was either the mailman or the new ‘housekeeper.’ Odds were on the latter, simply due to the timing. Groaning to myself, I grabbed my bikini top and tied it into place. Goodbye, peace and quiet. Goodbye, freedom. Despite the negativity coursing through me as I walked back inside, I forced a warm smile onto my face. The best way to sell a good attitude was to ease into it. While I was quite adept when it came to all things social, trying to flip the switch from ‘bitch face’ to ‘genuine smile’ was difficult to pull off without showing at least a trace of disdain. 

Just to be sure I had it right, I glanced at my reflection in the kitchen microwave. Perfect. My expression was hospitable, but my bikini-clad body would serve to throw her off guard as I opened the door. A lovely concoction to test how Jess handled herself when facing the unexpected. I waited in the kitchen, as I had no idea where the woman was going to enter. Front door? Side door? Or perhaps she’d just sit in the car and call the house. I had tried to break into my father’s home computer earlier to see if there was an email exchange between him and the babysitter, but couldn’t find the password anywhere in his office. 

Two loud knocks on the front door answered my question and put an end to my impatient waiting. Brushing my hair back and pushing another wave of warmth onto my smile and into my eyes, I sauntered down the hallway towards the front door. Taking my time, but also not making her wait forever. Similar to my appearance, I wanted to strike a decent balance when it came to my response time. 

With no hesitation, as I had always been the kind of girl who just rips off the band-aid, I unlocked the door and opened it wide for her. “Hey,” I said, “You must be Jess.”

Jess

The first thing that caught my attention was the bikini. Matching top and bottoms in a sharp emerald. Coincidentally similar to the color of my sundress, but I was more focused on all the bare skin that greeted me when I had expected Hannah to be clothed. But that isn’t where the surprises stopped. She was tall, easily towering over me despite my heels, and I instantly noticed what else was wrong when I looked up and took in her blonde hair and sharp facial features. 

Wait, what?

How old was this girl?!

When her parents had said ‘teenage daughter,’ I had first assumed that they meant thirteen or so, as that’s about the oldest I’ve ever had to supervise. I find that around that age, parents begin trusting their kids alone for a few hours when they go out for the evening. Since this was six full weeks, I had stretched my assumption to maybe fourteen or fifteen, where the girl could be self-sufficient while still needing someone around to make sure she wasn’t getting into trouble. 

But the girl in front of me had to be older than that. Sixteen, minimum. Or seventeen? Not legally an adult, so therefore needs a ‘guardian’ around in her parents’ absence? The moment she opened the door, I regretted jumping to conclusions and not asking for more details before accepting the job. I was only twenty years old! True, I had a solid eight years of experience babysitting, but still. How could I possibly earn the respect of a girl just a few years younger than me? 

I couldn’t just stare and overanalyze, however. “Hey,” I replied, hoping that she didn’t catch the faint hesitation. The blonde looked friendly enough, rather than a scowling teenager who didn’t appreciate someone disturbing her privacy. “Hannah, right?” I asked. It was a stupid question. Who else would be here in a swimsuit? 

“Mm hmm,” she nodded, “And you’re Jess. Or is it ‘Jessica?’ Aren’t you going to come in?”

“‘Jessica,’ technically,” I said, “But you can call me ‘Jess.’ And in a minute. I should grab my things. Do you-” Catching myself halfway through a request for help, I scrambled to think of something else to say instead. While I’d ask just about any friend for assistance with my luggage, I didn’t want my first encounter with Hannah to include me asking her for manual labor. What if she was the kind of girl that didn’t lift a finger around the house? What if this got us off on the wrong foot? Still determined to make this more of a vacation than a job, both for myself and for her, I pivoted. “Do you know which room I’m staying in? I can get myself settled if you want to go back to the pool. Sorry if I interrupted.”

“It’s fine! You actually got here at just the right time. I really need someone to get my back. You brought a suit, right? You should get changed up and meet me out there. I’d much rather get to know my new housekeeper by the pool, instead of in this stuffy house. Sound good?”

It was a lot to take in. While it would be irresponsible to let the girl burn, I didn’t know how I felt about physical contact like that before establishing my authority. Then she was suggesting that I join her by the pool, and in swimwear instead of my dress? On top of all that, the phrase ‘my new housekeeper’ didn’t sit very well with me. If I wasn’t careful, she’d assume that I was around to be more subservient. That was the opposite of what this dynamic was supposed to be, and suddenly I found myself wishing she did see through her parents' retitling of my babysitter role. 

So much to process, so little time to respond. And she didn’t even answer the question about where my room was! Okay, two could play that game. Remembering that she was a teenager, there was a good chance that she was at least playing a little bit dumb on purpose. “So where’s my room?” I casually asked. Not actually confirming anything, but also knowing that I’d need my own space to change if it came to that. 

To her credit, Hannah didn’t miss a beat. Maybe she wasn’t being difficult on purpose after all. “Upstairs, on your left. The room with the gray sheets.”

“Thanks, Hannah,” I said. Ugh, she was SO tall. The sooner we were both seated, the better. It would be much better laying down a few ground rules when I didn’t have to look up to meet her eyes. “I’ll be out in a few minutes, okay?” In my sundress. While it would be nice to relax by the pool and get some sun, it was way too soon to wear a bikini around her. Now that I was dealing with an older teenager, I’d have to adjust my entire game plan. 

“Oh, I can’t wait to see what you brought for swimwear! Trust me, you’re going to fucking love the pool here. You’re not the boring type who never jumps in, right?”

Boring? Me? Not a chance! I decided to let the swear word go, as that would almost prove her point right then and there. Not that she was making a point. The question had more of a playfully curious tone than anything else. “Of course not. I love to swim,” I replied. It was the truth. 

“Good!” she exclaimed, “Bikini. Pool. Ten minutes. I’ll be waiting, Jessie!” 

Hannah

The moment I opened the door, I had to forcefully shove down a laugh that was threatening to burst through my lips. 

No way. No fucking way!! 

This was Jess?! A short brunette girl who looked almost as young as I was? This had to be a joke. For some reason, I had expected a no-nonsense woman in her late twenties or early thirties. An age that could still work for a ‘Jess;’ an age that was old enough yet young enough to put up with the shit of a rebellious teenager. Or a manipulative one, in my case. Never in my wildest dreams did I imagine that it would be someone so much smaller than me, and so close in age. 

Did my parents know when hiring her? Or did they massively screw up? Only one way to find out. 

I started off friendly, testing the waters. Throwing a bunch of friendly ideas out while acting like she was just another girl like me. I half expected her to flip some domineering switch and lay down the law, but she didn’t. Instead, little Jess just tried to brush past my questions. Nice try, girl. At that point, I was determined to get her into a bikini and down to the pool. I would be her ‘friend,’ and she would have a difficult time fulfilling her babysitting duties when so underdressed. 

Hopefully my parting words would do the trick. Pushing too hard on the subject would put her guard up, so I simply swiveled on my heel and strutted away. Unfortunately, that meant I couldn’t study her reaction to ‘Jessie.’ Oh, well. There would be plenty of opportunities to try out the alternative nickname and see if it made her cringe or object. For the moment, I would once again have to be patient. Either Jess would change and prove that she was a fun girl who wanted to get along with the teenager she was hired to babysit, or she would come outside fully dressed and I would have to shift tactics. 

While I waited, I simply sat by the edge of the pool and dipped my feet in to cool off. Leaning back and killing time on my phone; making it seem like I was content to do so for hours even though I was restless with the countless ideas to put Jess in a situation where she felt more pressured to be a roommate than a babysitter. 

To my partial disbelief, the girl actually came outside in nothing but a bikini!! Not even a towel draped over her shoulders to hide part of her bare skin, which was almost as surprising as the fact that she changed in the first place. I couldn’t help but wonder what the deciding factor was. The excitement about what she brought? The insinuation that she might be boring? The general need to make our first day together as smooth as possible? Probably that, though it was fun to imagine that my directive before walking away was what sealed the deal. 

As Jess got closer, however, my internal smugness quickly evaporated when I caught a glimpse of her breasts. 

FUCK.

I hadn’t noticed it before, as the cut of her dress was more modest at the neckline, but her cleavage was a lot more obvious in the bikini top. How on earth did such a small girl end up with boobs like that?! While I was thoroughly hot, tall, and slender, and could have pretty much anyone I wanted, it would have been nice to have a little more in the upstairs department. And this little college girl had bigger breasts than me? Fuck that.

The plan to shift Jess into more of a friend/roommate was no longer acceptable. Right then and there, I dismissed all the floating ideas that had occupied the majority of my headspace just moments ago. It was one thing for this fucking brunette to show up at my house and think that she could boss me around. I was way too old to need a babysitter, especially one her age and her size. It was something else entirely, however, for her chest to be better than mine. That was bullshit. 

New plan.

I was going to humiliate Jess, and make her regret ever taking this job. She was going to feel small in more ways than one, in front of me and in front of my friends. And, if she was claiming to be my ‘housekeeper,’ then I was going to make sure that she conformed more to that role than anything else for the next six weeks. 

By the end of the day, I was going to make little Jessie bend to my will. 

Chapter Two

Jess

I wasn’t in love with the idea of wearing just a bikini. 

My initial thought had been to wear a sundress over my swimwear, but I ended up changing my mind once I had a moment to myself. Hannah was a lot older than I expected, which meant my game plan needed to change. What if she thought I was a total prude by not doing what she suggested and matching her? She had also suggested I would be ‘boring’ if I didn’t get in the pool. A teenager’s opinion of me really shouldn’t matter, especially not from one I’m supposed to have authority over, but I was still determined to make a good impression.

If I could connect with her, get her to respect me more as a peer than an uptight adult, then maybe the rest of the summer would go more smoothly. After all, I tended to trust advice from friends. If she viewed me as such, then I could gently nudge her away from anything her parents wouldn’t approve of. It would be a delicate line to walk, but I could already tell that my height was going to be a big issue now that I was a lot closer in age to my charge than I expected. I was technically older, but Hannah towered over me!

“Get my back, Jessie?” Hannah asked. She gestured to the sunscreen sitting on the small table next to her chaise lounge chair. Rather than turning away and scooting over so I could sit behind her and apply the lotion, she proceeded to lie down on her stomach and reach back with one hand to untie the strings on her top. 

I flinched at the use of ‘Jessie.’ It was the second time she had said it, and the second time I was reluctant to correct her. The first had been back at the front door, where she had bounded off before I could say anything else. I was left to haul all my things inside and park my car in what I hoped was an acceptable spot. This time around, I was immediately distracted by the blonde’s totally bare back as she pulled her hair over her shoulder so all of her fair skin was on display. It was less about what I could currently see, and more about the fact that one wrong move might give me an inappropriate glimpse of her bare chest. 

Still in that weird headspace where I didn’t want to start things off on the wrong foot, I bit my tongue about everything. Instead, I grabbed the nearest chair and pulled it up so I could sit right next to the girl. “So, I guess we’re stuck together all summer, huh?” I said, trying to make light of this arrangement in an effort to connect with her. Ultimately, my goal was to spin things as ‘I’ll stay out of your way as long as you behave,’ but I needed to work my way there. 

“Guess so,” Hannah replied. Now that she was settled, she lay perfectly still. Waiting for me to get to it, probably. 

If only she gave me something to work with. A chuckle, a more full reply. That was my system for new babysitting jobs–get a read on their attitude, their humor, whatever I could use to figure out whether I needed to be easy-going or stern. “This is going to be a little cold,” I said. Cringing immediately at the patronizing warning, I squeezed a decent amount of lotion onto my hand and hoped she wouldn’t take it the wrong way. 

Once again, nothing. When she didn’t reply at all, I tentatively placed my hand on her back so the majority of the sunscreen was centralized. I should have expected it, but her skin was so warm. The sun would do that, of course, but it gave me enough pause that she mistook my hesitation for something else entirely. “You’re not a lesbian, are you, Jessie?”

What?! “NO.” My response came out a lot more harsh than I expected. It’s not that there’s anything wrong with liking girls–I have several friends that are gay or bi–but Hannah’s question was just so blunt and out of the blue. “No. I’m straight.” I lowered my voice to a more normal level. While it might have been worth explaining that it was more that I felt awkward about this kind of contact with a girl I was supposed to be babysitting, I made a snap decision that ‘less is more.’ Instead, I chose something else to focus on. “And it’s ‘Jess.’” 

“Jeez, no need to freak out about it. I just wanted to check. When I’m home alone, I like to be comfortable. Good to know you won’t be ogling me or anything.”

Comfortable? Like . . . ? I barely registered the subtle idea that she considered herself ‘home alone’ when I was literally going to be there. Instead, I found myself dwelling on what the girl meant. Just because I wasn’t into girls didn’t mean I wanted Hannah walking around in, well, whatever she wanted. “Comfortable, how?” I asked. Little by little, I found myself bailing on the ‘friend’ plan and slipping into the babysitter role I was more comfortable with. It was only after I asked for clarification that I remembered what I was supposed to be doing. Spreading out the sunscreen with my hand, I worked on making it even before rubbing it in. 

Hannah let out a sigh before explaining. “I don’t know; it depends. Long tee and nothing else? Sports bra for a workout? A towel if I haven’t picked out an outfit yet? I mean, it doesn’t really matter. We’re both girls, so it’s not that big of a deal. Right?”

“Umm . . .” Technically, no. I had seen plenty of friends like that. Well, maybe not the t-shirt thing. Still trying to figure out this whole dynamic, I tried to split the difference. “I guess not,” I said, “But maybe get dressed before coming downstairs?”

She simply replied with, “Well see.” 

Noncommittal. Great. I went quiet, focusing on Hannah’s back. Since I wasn’t there when she applied the rest, I made sure to hit her shoulders and sides, just in case. As for her lower back, I only went so far down after the ‘lesbian’ question. She was certainly capable of getting that last area herself, and it was important to keep up boundaries. If I had it my way, this wouldn’t be happening at all, but it’s not like I could deny the girl protection from the sun. 

By the time I was finished, I could already feel my own skin heating up. Unlike Hannah, I hadn’t put on any sunscreen yet. Sitting up and informing the blonde that she was all set, I quickly rubbed the excess lotion on my shoulders. Before I could get much farther, she shifted her head to face me. “So, Jessie. Fuck any guys lately?”

What?! 

Similar to her question about my sexuality, I was completely taken aback. Feeling a blush coming on, I blurted out the first thing that came to mind. “That’s none of your business.” The truth was, I was a virgin. It was a bit embarrassing for my age, especially since it’s not like I was a prude or saving myself. I had gotten to second and third base a handful of times, but those short-lived relationships never felt serious enough to go all the way. 

Plus, even if I had slept with someone or multiple someones, what kind of question was that? Hannah and I just met. It would be one thing if she had asked if I was seeing someone, but that wasn’t at all what she said. 

“Whatever,” she replied, “It’s just sex. I don’t know why people have to be so weird about it. Want to hear about who I fucked last weekend?”

“No!” I exclaimed. Once again, a little louder than I had intended. “You-” I began, before changing course. There was one thing I was dying to know, especially since Hannah was somewhat topless as she lay on her untied bikini top. “How old are you, Hannah?”

To my relief, she said, “I’m eighteen. You?”

The good news was, that made it more acceptable to see her in any number of ways that would otherwise be less appropriate. I had seen my fair share of undressed women in the locker room, after all, though I preferred to change in a stall. The bad news was, I had been hired to babysit an eighteen year old?? How on earth did that not come up when her parents and I discussed the job? It might have been my fault for not asking, or their fault for not looking closely enough at my website. No matter where the blame fell, I was apparently supposed to be in charge of a girl who was practically the same age as me!

I wanted to lie, but decided against it. Since I was going to be there for the next six weeks, there was a good chance I’d accidentally contradict myself at some point. “I’m twenty,” I confessed. Silver lining, Hannah had been told I was a ‘housekeeper.’ If she knew the truth, I could only imagine how insulted she might feel. And how difficult it would be to make her listen to me. Well, that was going to be an issue either way. 

“Oh, cool. Hey, would you mind putting some snacks together? I have some friends coming over in a few minutes.”

Wait, what? “Hannah!” I exclaimed. She had said it so casually, but that’s not at all how I felt about the information sprung on me. “I didn’t-” My voice caught my throat. UGH. Since I wasn’t officially her babysitter, why would she need me to approve an invitation like this? I was quickly finding myself in a difficult position thanks to her parents’ insistence on this charade. “How many friends?” I asked. Thankfully, years of experience had taught me to be quick on my feet, and I pivoted. “Look, you need to ask me about this kind of stuff ahead of time. Otherwise, I can’t do my job as well.”

Hannah sighed. Taking care to grab her bikini top before doing so, she sat herself up. “Jessie. You’re my housekeeper. Isn’t that right?”

‘No. I’m your babysitter.’ If only. “Yes, that’s right,” I nodded. For now. First chance I got, I was going to give her parents a call and try to work this out. Either I needed to be able to tell Hannah why I was really here, or they needed to tell her that she had to listen to me. “And it’s Jess.”

“Then please do your job,” she said, “Snacks and drinks. You should also bring out some towels for us, and maybe some more sunscreen? There might not be enough in this tube for everyone.”

Oh, God. She was talking to me like a servant. Swallowing my pride, I nodded again. “Of course, Hannah. I’ll be right back.”

Not wasting another second with the presumptuous blonde, I went back inside. I had no intention of actually following the girl’s orders. My phone was just up in my room, and I also no longer felt comfortable wearing a bikini. It was one thing when I was trying to get Hannah to warm up to me, but she clearly didn’t see me as much of a friend. That, and apparently her friends were going to be there soon. I’d have better luck compelling respect if I dressed like the young adult that I was, rather than trying to hang out at the pool like ‘one of the girls.’ 

Closing the bedroom door behind me, I grabbed my phone from the top of the dresser and called the number on the mobile note I had made about the summer job’s details. Straight to voicemail. “Fuck,” I huffed. They could be on a plane, or simply enjoying their vacation if they were already there. I hated leaving voicemails, so I just sent off a text politely asking them to call. 

I made short work of stripping off my bikini and tossing on a skirt/blouse combo that was one of my favorites. Just for good measure, I added a pair of heels. Normally I wouldn’t wear shoes inside, but I was feeling extra self conscious about my shortness compared to Hannah. 

The entitled eighteen year old had said ‘soon,’ but I didn’t realize just how soon she meant. By the time I made it downstairs, I practically ran into an unfamiliar redhead as I turned the corner. She was wearing short shorts and a bikini top, and I honestly wouldn’t have been surprised if that’s how she drove. Before I could get out a word, she said, “Oh! You must be the new housekeeper. Is that your car out front? You should probably move it before it messes up everyone’s parking.”

Shit. I had hauled all my stuff up to the guest bedroom, but hadn’t found a chance to park my little sedan properly. It’s not even that I had forgotten about it; I just wanted to ask Hannah if I could have one of the garage spots. With no idea how many people were coming over, and with at least one already here, there wasn’t any more time for that. I ran up to grab my keys, then hopped in my car as soon as possible. Two other empty vehicles were already out there, and I maneuvered mine to line up with the others on the opposite side of the driveway.

Hurrying back inside, not wanting to leave the girls unattended for too long, I made a beeline for the pool. My initial plan of calling Hannah’s parents had failed, and preparing refreshments for everyone would solidify a subservient image of me in her eyes. Instead, I strutted outside in the hopes that I could pull her away from her friends for a quick one-on-one. I wasn’t totally sure what I wanted to say yet, but I’d figure something out. I was a professional babysitter, after all. 

Right away, I was faced with the exact kind of situation I had been hired to prevent. Hannah, the redhead, and one other girl were all sitting together and drinking. Like, drinking. All three of them were holding hard seltzers, which was absolutely unacceptable. Day one on the job, and I was already failing miserably. The ‘housekeeper’ role was working against me, and my charge was illegally drinking under my watch.

“HANNAH.” Raising my voice, I began storming over. “Absolutely not. Your parents were very clear about the house rules when they hired me.”

“Relax, Jessie,” Hannah said. Her bikini was tied up again, thank God, which made it easy for her to stand up and meet me halfway. Despite my heels, she still had a good bit of height on me. “They don’t have to know, do they? I won’t tell them. You won’t tell them. So, what’s the problem?”

“It’s Jess. Get it right,” I insisted. Narrowing my eyes and not letting the fact that I had to look up to match her gaze deter me, I continued. “And no, I’m not going to cover for you. But if you hand it over, this can just be a warning. Okay? Otherwise, I’m going to have to call your parents.”

“Ooh, call my parents? So scary!” she giggled for a second, before going totally deadpan. “Fuck off. This is my house, and you can’t tell me what to do.”

“Yes. I can.” Screw this. I tried the ‘housekeeper’ cover story. It clearly wasn’t working. Maybe coming clean and embarrassing her in front of her friends would do the trick. As a former teenager, I could only imagine how it might sound to hear that you still need a babysitter. Eight or eighteen, some attitudes need a firm adjustment. “Hannah, I-”

But that’s as far as I made it. Out of nowhere, she dropped her can and shoved me with both hands. Hard. Unable to react quickly enough, I stumbled backwards only to find no ground waiting for me. Gasping at the way too late realization, I fruitlessly flailed my arms to no avail before plunging into the pool behind me.

My body submerged completely and I scrambled to upright myself and resurface. The section of the pool was too deep to find any footing, so I had to awkwardly tread in my clothes once my head was above water. The other two girls were sitting there with dropped jaws, before finally giggling as they came back to reality. Meanwhile, Hannah was just smirking down at me as she picked up her partially spilled drink for a victory sip. 

I was furious. FURIOUS. But I couldn’t yell at her from the pool. Plus the chlorine was going to ruin my clothes and my contacts. Ugh, and my hair. It clung to part of my face in what I had to assume was an unattractive way, and I quickly pushed it to the side as I paddled to the nearest ladder. My heels caught on one of the metal steps, and I was pissed off enough that I cared a lot less about my height than before. Quickly undoing the straps and pulling them off, I climbed out of the pool barefoot with shoes in hand. 

“Hey!” I yelled. My clothes clung to my body, and I was dripping all over. I didn’t need a mirror to know that I must look ridiculous, but I tried my very hardest to be intimidating anyway. “Laugh while you can. I’m going to take a shower, and then you’re going to be in deep shit.” It felt lame threatening an eighteen year old like that, but what other ammo did I have? Trying not to lose steam, I added on, “Your friends better be gone by the time I’m back, or else.”

“Whatever you say, Jessie,” Hannah said, “Now, go get naked.”

Not dignifying that with a response, even though it’s technically what I was about to do in order to rinse off, I marched back to the house. Normally, I would care a lot more about dripping inside, but I was over it at this point. What was I thinking? Of course I wouldn’t be able to control an eighteen year old rich girl. At this point, I was strongly considering quitting. I had never bailed on a job before, and I had dealt with some pretty awful kids over the years. But a whole summer of this? It was good money, but Hannah wasn’t some tween! For the life of me, I couldn’t think of a way to course correct without involving her parents. It would make me look so weak, relying on someone else in order to achieve authority. Groaning to myself after the glass door was fully closed behind me, I made my way upstairs, being careful not to let my bare feet slip out from underneath me on the way up the stairs. 

The warm water helped. Not with the Hannah situation; it was just nice to have a moment to myself. To breathe, to calm down. Thank goodness I had taken a minute earlier to set the hallway bathroom up for myself. While I didn’t mind getting the rest of the house a little wet, I would hate to do that to my own room and give the smirking blonde the satisfaction. 

I couldn’t believe Hannah’s audacity! What if my phone had been in my pocket? Plus, any kind of water was terrible for contact lenses. Thankfully, I had some spares lying around, so I could go grab a fresh pair while the current ones sat in solution. My wet clothes monopolized the towel racks for a moment, though I’d be running them through the wash the moment I was done showering. Initially, I had planned to be quick about it, but eventually settled into the idea that the longer I stayed behind the fogged glass doors, the longer I could pretend the outside world didn’t exist. 

Eventually, however, I had to face the music. The voices through the bathroom window were a pretty good indicator that Hannah hadn’t listened to me in terms of sending her friends home. I could only hope that my long shower had given her parents enough time to check their messages so I could reach them momentarily. Turning off the water and finding myself twice as blind as usual thanks to the blurry vision and the heavy steam around me, I pushed open the door.

No.

No, no, no.

How could I have been so stupid?! Even with my poor eyesight, I could see what was wrong: The entire bathroom was empty. No clothes on the racks, no stack of towels on the sink where I left them; nothing. Even the towel that had previously been laid on the floor to prevent dripping had been taken. This had to be Hannah, or one of her friends. And I couldn’t help but blame myself a little bit–leaving the door unlocked? Horrible move. 

I hated being seen naked. It’s why I changed privately no matter the setting. I mean, I’m confident enough about my body, but it’s MY body. And I could already imagine a gaggle of girls waiting on the other side of the bathroom door, cameras aimed to capture every second of my exposure. Hell, I was lucky they hadn’t quietly been waiting in here. With that in mind, I was extra careful as I peeked my head farther out of the shower. 

Wait, there was something in here! On the back of the door. A towel, or a robe, or something. I couldn’t see very well, but I immediately let out a sigh of relief when I realized Hannah missed something. Taking a second to brush as much water off my bare form as possible, I wrapped my arms around my private areas and padded across the bathroom, bracing myself for someone to barge in at any second. The tile on the outside of the shower was a lot cooler than on the inside, and I grimaced as the bottoms of my feet dealt with the cold, hard surface. Without the warm steam, my nipples almost instantly stiffened as I delicately moved forward. 

Once I made it a few feet away from the warmth and safety of the fogged glass, the blurry thing on the door came into view enough for me to make out what it was. My heart sank and my cheeks flushed at what I saw.

Hannah had left me a fucking french maid dress.

For a second, I froze. The dots weren’t difficult to connect. I was supposed to be her housekeeper, so she wanted me to dress up like a subservient little maid. But what else could I do?! I was tempted to scream out her name, but the last thing I wanted to do while buck naked was draw attention to myself. And hiding in the bathroom wouldn’t do anything for me. Wrapping the outfit around myself as a towel crossed my mind, but it looked small and that felt too risky if I ended up outnumbered even two to one. Ugh, why did it have to be frosted glass for the shower? If there was a curtain, I could use that as my makeshift towel/bathrobe. 

Groaning more loudly than before in pure frustration, I snatched the hideous thing from the door. What other choice did I have?

I was going to put it on.

Chapter Three

Jess

I couldn’t believe I was dressed like a fucking MAID.

It was so embarrassing. Even without my glasses, I could see and feel all the things that were wrong. The whole dress was too small; my breasts were uncomfortably smushed behind the fabric up top, and the skirt sat so high on my thighs that I was worried that something as simple as walking would risk exposing me while I didn’t have underwear for protection. The outfit also awkwardly clung to me a little bit, since I was still damp from not being able to dry off after my shower. My hair was a whole different story, but I was just going to have to deal with that until I got my hair dryer and brush back. 

The worst part? This was probably exactly what Hannah wanted. 

Well, I’m sure she would have been satisfied with me being naked as well. Either way, I now had to brace myself for Hannah and company poised to take countless photos the moment I opened the bathroom door. Wait, speaking of smartphones, where was mine?? With my blurry vision, I had only been focused on the lack of clothes and towels in the bathroom. Toiletries, too. Now that I was thinking about potential ways out of this mess, I realized that I didn’t even have the option of calling Hannah’s parents. The girl had taken my fucking cell phone. 

Now that I was stalling, I took the time to examine my surroundings a little more carefully. Right away, I noticed there was something I missed. In my half blindness, I had mistaken it as something to do with the soap dispenser by the sink, but upon closer inspection I found that my glasses were waiting for me. 

It was anything but a relief. True, I would be able to actually see, but at what cost? There was a reason I always wore contacts. The prescription required for my horrible eyesight didn’t have a lot of cheap options for glasses. And, since I couldn’t afford the prettier ones, my ‘last resort’ was an incredibly ugly pair. I hated, hated, HATED how they looked on me, and pretty much only wore them for studying when I was secluded in my dorm back at university. Even then I was on edge, as I had a roommate. 

On top of that, this meant that Hannah had pilfered through my things while I was in the shower! My glasses had been stashed away in my backpack. While there wasn’t anything particularly private that I had brought with me for the summer, I still felt violated thinking about the blonde teenager strutting into my room and checking out all my stuff. God, I could just imagine her turning my suitcase upside down and ruining the way I had everything perfectly folded. And then there was my precious laptop; it was password protected, but it would still be frustrating if she ‘confiscated’ it along with my phone. 

‘One thing at a time, Jess.’ Projecting like that wasn’t going to help with my current predicament. Taking a deep breath, not particularly ready to face the reality of how I looked, I put the glasses on anyway. 

It was even worse than I imagined. From the waist down, I looked like a total slut. My thighs were fully on display, and a quick turn to check out my backside confirmed that the skirt barely, barely covered my ass. The top half was the total opposite. While some tight bras and tops would make my boobs ‘pop,’ the neckline of this maid outfit was high enough that my chest was just squished and nothing more. The perky Cs I was normally so proud of looked at least half their normal size without a bra for support and when trapped behind the awful dress.

My hair actually looked better than expected after a good cleaning, but I knew from experience that it would get a little messy if left to air dry without proper care. And, without make-up, my face looked a lot more youthful. Then there were the glasses themselves, which were as horrible as always. Overall, my appearance was the weirdest combination of immature, slutty, and awkward. And there wasn’t a damn thing I could do about it.

Nervously padding over to the bathroom door again, cringing at the continued wave of coldness against my bare feet, I cracked the door ever so slightly. “Hannah?” I quietly asked. In my mind, I had been aiming for something a little more assertive. After all, I was supposed to be the one in authority here. But in my current state, I felt slightly at the blonde’s mercy, at least until I was dressed in my own clothes again.

To my surprise, no one was waiting for me. Similar to when I found my glasses, I felt more worried than relieved. If not right outside the door, then where was she? Around the corner, waiting to get a more full picture of me when I stepped out into the hall? After all, I currently had a door to hide behind. “Hannah.” Finding a little more backbone as the frustration of the situation began creeping in and outweighing the embarrassment, I curtly addressed the girl. “Hey. Bring me back my things. Right now.”

Silence. She and her girlfriends were so giggly earlier; either they had a lot of self control at the moment, or they weren’t here. But all it would take was one photo for this whole thing to get more complicated.  “Hannah!” I yelled. So much for not drawing attention to myself. 

Nothing. 

Fuck it. Exhaling in annoyance, I crept out into the hallway, bracing myself to skitter back to the bathroom at the tiniest sound. Actually, wait. Running to my room was a better idea. Being conscious of the fact that my feet were still slightly damp, I made a beeline for the door as quickly as I could manage while being safe about it. Of course, there was always the daunting thought that Hannah could just as easily be waiting in the guest bedroom. If she would shamelessly dig through my bags, then what was stopping her from waiting in there for me?

Instead, I found a totally different issue waiting for me: The door was locked.

Groaning at the unexpected obstacle, I aggressively jiggled the doorknob for a few seconds in the hopes that maybe it was just stuck or that Hannah’s latest trick wouldn’t hold. No luck. The door held fast, and none of my efforts to make it budge seemed to matter. I had felt so close to a fix, and it was such a psychological blow for that hope to be snatched right away from me. Still in that odd limbo of embarrassed and pissed off, I stormed down the hall towards Hannah’s room. She was bigger than me in every way, but I’d still prefer slightly baggy clothes to the maid dress. 

Just like the guest room door, hers was locked. “Come on!” I whined. What about her parents’ closet? It felt a little wrong borrowing clothes from my employers, but that was still a better alternative than my current getup. All the upstairs doors were closed, so it was no surprise when the master bedroom was locked as well. For fuck’s sake. 

I could always try the downstairs bathroom for a towel, or the laundry room to see if there were any clean clothes to change into. Hell, I would strongly consider putting on one of Hannah’s used outfits if it meant keeping her from the victorious smirk I could already visualize if I walked outside wearing this. From what I could tell from the faint female voices in the distance, she and her friends were still outside. And it was definitely more than three girls at this point. If she had gone through the trouble of making sure all these doors were covered, it was safe to assume she had been just as thorough downstairs. Fucking brat.

It didn’t matter. I was the babysitter here, and she was the entitled eighteen year old. The girl in the bathroom mirror didn’t look particularly intimidating, but that was before I had gotten worked up by the audacity of the teenage blonde who clearly didn’t respect me in the slightest. But she would.

Not wasting another second circling the house in the hopes for something different to wear, I just swallowed my pride and made my way downstairs. Taking a deep breath in the kitchen, followed by several more with closed eyes in an attempt to calm my nerves, I finally stepped back outside.

My eyes instantly went wide at the sight before me. How many friends had Hannah invited?! From what I could tell, there were at least ten girls clad only in skimpy bikinis. A handful were hanging out in the pool, but most of them were sitting or lying under the sun and gossiping about who knows what. The self conscious girl within said I could easily be the subject of the giggling. Even worse, there was alcohol everywhere. Empty cans of beers and seltzers littered the ground, each and every girl had a drink in their hand, and it was easy to spot a handle of vodka sitting near the bitchy blonde who had started all of the trouble.

“HANNAH.” A bit more shrill than I had wanted, thanks to the unexpected crowd and illegal mess that I had literally been hired to prevent, I tried not to let my first impression ruin everything. Striding forward with a purpose, I ignored the other girls and set my sights on Hannah. She was lying in the same lounge chair as before, and hadn’t done much in response to my arrival; she just slightly shifted her head to glance my way. “Inside. Right now.” I didn’t care about privacy in terms of her reputation with her friends. Admittedly, it was mostly because it would be easier for me to handle this without an audience. 

Considering how I was dressed, I had braced myself for laughter. That’s definitely how my university friends would react to seeing me in something so ridiculous. These girls, however, didn’t know me. If anything, they looked more annoyed than anything else. And I was about to see why. 

“What’s up with your maid, Hannah?” one of the brunettes in the pool asked, “Is she allowed to talk to you like that?”

I could feel myself starting to fume even more. It was so rude to talk to someone right in front of their face, and doubly so when that girl was your elder. The only reason I didn’t bite her head off is because I wanted to walk the line between collected and authoritative. That, and this was between me and Hannah.

“I-” I opened my mouth to assert my demand for Hannah to meet me inside, but that’s as far as I made it. 

“No, she’s not,” Hannah said, “But little Jessie is a recent hire. She hasn’t learned how things work around here. Although she’s not a ‘maid.’” For a moment, I thought she was actually defending me. A stupid notion, considering what I was stuck wearing thanks to her thievery. “She’s my housekeeper for the summer.”

“What’s the difference?” the girl next to her asked.

“It’s simple. Maids are only responsible for all the inside chores. Jessie will be handling everything outside, too. Which is good, because we really need someone to clean up this mess.”

It took a conscious effort to keep my jaw from dropping. Was Hannah serious?! Stealing all my personal possessions was already over the line, and now she was still pretending like this was all normal? “Hey. Hannah-”

“Jessie.” Hannah set her glass down hard enough that I could actually hear her attitude from the gesture. “You’re serving as my housekeeper this summer, right?”

NO.

That’s what I wanted to scream. Before I had been pushed into the pool, I was prepared to drop the whole ‘housekeeper’ act and lay things out for the spoiled, presumptuous brat. To hell with her parents’ idea that I present myself as something more posh. But now that I was standing in front of all her friends, I was quickly hit by a number of potential complications. 

It probably didn’t take twelve girls to pull off the prank that led to me being out here dressed like this. Unless all of them were acting their young hearts out, which I wouldn’t necessarily put past a bunch of pretty rich girls, there was a good chance some of them actually thought I was a housekeeper and nothing more. If I asserted why I was actually here, how much respect was I going to get if they all saw what Hannah did to me within the first hour of my arrival? And unless I could get my phone back, which could be hidden anywhere at this point, I had no means of reaching her parents. Well, my laptop had their numbers in an email somewhere, but Hannah had definitely gone through my things. What if she took that, too? Even if I was supposed to be babysitting the girl, how was I supposed to get a whole party of irresponsible eighteen year olds to take me seriously?

Then there was the other thought. What if part of this was about their family’s social standing, and less about putting Hannah at ease? Any of these girls could gossip to their own parents about anything they witnessed here, and maybe it would reflect poorly on Hannah’s parents if their recently graduated daughter needed supervision? It’s not that I owed them anything at my own expense, especially if something like that was never communicated to me, but all of this would be for nothing if they decided not to pay me for ‘breach of contract’ or whatever. 

Regardless, my inner fire was dwindling against the peer pressure before me and the embarrassment of how I looked. Screw it. “Not your housekeeper,” I replied. Waiting until I could get a one-on-one with Hannah sounded more appealing, but that didn’t mean I had to fully roll over. “Your parents hired me, Hannah, and they gave me specific instructions to follow.” Read between the lines, girl. As for everyone else, I was hoping it would make it sound like I wasn’t a total pushover.

My hopes for some semblance of authority and respect were quickly dashed when the same girl in the pool spoke up. “I can totally see her vagina.”

It was said so casually, but the mortifying observation was enough to make me gasp and throw my hands over my crotch while trying to pull the skirt down a little bit as well. The motion caused the back to ride up and expose part of my ass; my immediate instinct was to cover my backside somehow as well, but I fought that urge when I realized no one was behind me. It felt wrong to allow it to stay like that, but what else could I do?

“She’s kind of a slut,” Hannah said, “A shameless little lesbian, too. She probably couldn’t resist showing herself off when she saw all these hot girls in bikinis. Seriously, Jessie. You did bring something more modest, right? Or underwear, for that matter?”

“I’m not- I didn’t-” Still recovering from the fact that all the girls in the pool probably got a good look at my womanhood before one finally pointed it out, I wasn’t prepared at all for the subsequent accusations. Now that I had allowed the ‘housekeeper’ thing to continue, of course Hannah could fucking say that this was MY dress. “I’m not a lesbian!” I finally exclaimed after the flustered sputtering. For some reason, that felt like the most important thing to clarify. Not only was I very much a straight girl, but the suggestion that I dressed myself like that to get attention was outright false. There were just too many fronts to fight on. I wasn’t really a housekeeper. I wasn’t a slut. My name was JESS, despite the constant use of ‘Jessie’ recently. And all my real clothes and underwear were in the locked guest room. 

Trying to say all that out loud, however, would be a total mess. 

“Jessie.” Hannah snapped her fingers twice. Vaguely gesturing to the poolside around her and the other girls, she said, “No more talking. Be a good little girl and clean all this up.”

That same fire from earlier started pushing up. Narrowing my eyes and looking right at Hannah, I started saying, “You-”

“Yes, Hannah!” The two girls beside her said it in perfect unison. Like twins, totally in sync, despite how they looked nothing alike. It wasn’t intentional, apparently, as they both looked at each other in surprise before bursting into a fit of giggles. 

“That’s right,” Hannah said, “That’s how you’re supposed to respond, Jessie. Thanks, girls. See, they have maids, too. I know you’re new to this whole serving thing, so we’ll give you a pass or two. Now, let’s try again.”

“But-”

“Jessie. Clean up this mess. Now.”

Blushing deeply and still clinging to my skirt in the name of keeping myself covered, I reluctantly responded the way I was just instructed. “Yes, Hannah.” What else was I supposed to do? I had already resolved to play along until I could find a private moment with the girl, so any pushback would make me look worse and worse. No longer prepared to face off with the bitchy blonde, I just wanted to go back inside and kill time until her friends left. No, not kill time. I was going to find a way to pry my bedroom door open.

“One more time, Jessie,” Hannah said, “So you can get used to it. You’re welcome. Now, be a good little maid and clean up this mess.”

Sighing in defeat, I muttered, “Yes, Hannah . . .”

Chapter Four

Jess

Right away, I realized that my plan might not be as simple as I expected.

The whole point of begrudgingly going along with the bullshit role I was trapped in, thanks to Hannah’s parents and my own inability to sort things out with their daughter when an audience was around, was so that I could ‘do my job’ and avoid the girls while trying to find myself something less humiliating to wear. 

Surely not all the doors locked, right? I’m sure there had to be something around. I hadn’t tried the downstairs rooms yet, and I’d honestly prefer to wear one of Hannah’s dirty outfits in the laundry room than the way too small french maid dress. However, I couldn’t exactly retreat inside when the blonde eighteen year old just demanded that I clean things up around the pool. As her ‘housekeeper,’ it’s not like I could pick and choose which messes I wanted to clean up. The title had sounded fine when I thought it was just some posh term that implied I had some degree of authority, but I probably would have thought twice about it if I knew how old Hannah was before arriving on her doorstep. 

Hannah and her friends all looked like bikini models, with perfect hair and perfect bodies as they lounged by the pool. I would have expected rich girls to have some class to go along with such pristine appearances, but perhaps they were used to being waited on hand and foot. Rather than simply placing their empty drink cans down on the numerous side tables, most of their trash was strewn about the side of the pool on the ground. That came with two separate problems. One, there wasn’t a recycling bin out here, and there were only so many cans I could hold at the same time. Two, the skirt I was wearing already threatened to expose me with every step I took while standing. How was I supposed to bend or squat to pick things up without showing off everything?

“Well, Jessie?” Hannah said. She vaguely gestured to the area surrounding her, “Hop to it. And what do you say?”

Swallowing my pride, and a good bit of anger and frustration as well, I repeated the demeaning phrase. “Yes, Hannah.”

Normally, squatting was the safer play. But not this time, when I was pretty sure the whole dress would ride up on both sides and leave literally nothing to the imagination. Choosing the lesser of two evils, I approached the first few cans I saw and bent over to retrieve them, purposely keeping my backside away from the nearby girls. I could feel the outdoor air on my lower cheeks, and immediately blushed at the thought of how I must look from behind. My proximity to the nearest girls also made me feel self conscious, in that my hair was wet from my shower and no towel, while pretty much all of Hannah’s friends were perfectly put together. 

I managed to secure an armful of cans without mooning anybody, and suddenly had the hopeful thought that perhaps a lack of receptacle would work to my advantage. Taking a second to adjust the back of my skirt and praying it would cover me, I turned back towards the house. Drop off the empty cans, and then take advantage of the solitude and the empty house to hunt for my things instead of coming back out. 

“Where are you going, Jessie?” Hannah asked, after I had barely taken a single step. 

Feeling self conscious all over again as her voice cut through any other little side conversations and brought the attention back to me, I tried to glance over my shoulder without fully stopping. “To toss these,” I said, “I’ll be right back.”

“Taylor will go with you! She can get the door. Then come back right out, okay?”

Was I that transparent? My intentions weren’t supposed to be so obvious, especially since I had feigned obedience. Or maybe Hannah was just micromanaging me and it happened to screw with my idea. “Yes, Hannah,” I muttered. So much for getting a moment to myself. 

With a different bikini clad escort every time, as the bossy blonde clearly enjoyed sending one babysitter after another to open the sliding glass door for me and linger so I couldn’t stray beyond the kitchen, I gradually cleaned up all the cans from the poolside. No one made another comment about my exposure, but there were plenty of whispers and giggles going on throughout the experience. With only one hand to cover most of the time, I could only imagine how often the girls caught a glimpse of me despite how carefully I tried to position my body and keep the too-short skirt down. There were just too many of them around, which made it impossible to find a modest angle for my body most of the time. Next, I was made to scoop all the leaves out of the pool, and then clean up a few more empty seltzers that the girls had finished by the time I finished that task.

“Come here, Jessie!” Hannah called out to me after my latest trip to the kitchen. I was already headed back her way anyway, though of course now it seemed like I was doing so because she summoned me. Once I was close to her chair, and trying not to blush as the group of girls all watched the interaction with interest and curiosity, she held out an unopened can. “Here. You look thirsty.” 

“No, thanks,” I said. My hands were devoted to keeping my outfit in place now that I wasn’t stuck doing chores, though I had to resist wiping a bead of sweat from my forehead. Every other girl here got to lounge in a bikini, but I was the one moving about in a dress. The summer heat wasn’t my friend after nearly a half hour of work, though the constant stops inside kept me from fretting about burning like before. Regardless, I wasn’t about to drink on the job. I had enough working against me already.

“Come on, Jessica,” she smiled, “Live a little. Tell you what? Shotgun the whole thing, and you can go inside.”

It really was that easy. “Fine,” I said. Taking the can from her, I cracked it open without a second thought. Anything to let me go inside so Hannah could stop bossing me around. Besides, it was just one drink. I may have been small, but I wasn’t that much of a lightweight. Although the smile and the lilting way she said my full name didn’t exactly put me at ease. Was it really that difficult to stick with ‘Jess?’

“Good girl,” Hannah said, “Okay, you have thirty seconds. Starting . . . NOW.”

Wait, what? Even though the word ‘shotgun’ was involved, I didn’t expect her to put a timer on my chugging. With such a full audience, however, I immediately fell for the peer pressure. Lifting the can to my lips, I tilted it back and began drinking. I wasn’t the best at downing things quickly, and the coldness and the carbonation of the hard seltzer served to be a more daunting challenge than expected. Taking as big of gulps as I could manage, my eyes widened when one of the girls called out ‘Fifteen seconds!’ There was definitely more than half a can left, so I redoubled my efforts in order to avoid Hannah going back on her word or something if I failed the task I didn’t realize I had signed up for until it was too late. 

Near the end, most of the girls joined in chanting, “FIVE . . . FOUR . . . THREE . . . TWO . . . “

Finishing off the last of it, I sharply exhaled as I removed the cool metal from my lips. Done. I felt a little bloated from both the bubbles and the speed at which I downed the drink, and there was also a hint of internal warmth from the alcohol making its way into my system. Unless I was imagining the latter. 

My victory was short lived, however, as Hannah sat up and brought the attention back to herself. “Good job, Jessie. Okay, girls! Let’s go inside.”

Wait, what?

It didn’t take me long to sort out that Hannah technically never said I would be going inside alone, although her phrasing had hinted pretty strongly at it. As she and her friends started to get up and collect whatever drinks they had yet to finish, I spent a few seconds debating how to proceed. My whole plan had hinged on getting back into the house alone, but it’s not like I could complain. I was outnumbered, and any number of the girls around me could come to Hannah’s defense about what was said. Besides, it was the blonde’s house, and I wasn’t exactly in a position to tell her she couldn’t go inside. 

So, I simply followed the group of girls, making a point to slightly lag behind. Anything to keep my backside from being revealed again as I held down the front to obscure my womanhood that was also on the precipice of exposure at pretty much all times. The price to pay for being the last one inside was that I was once again the center of attention as all the girls had congregated around the spacious kitchen island. 

“This isn’t your first housekeeping job, is it, Jessie?” Hannah asked, only after I slid the door closed behind me. 

I had been a babysitter for quite some time, and a pretty professional one at that; doing a few chores came with the territory, often after the kids went to bed. And, since Hannah had put me on the spot, I couldn’t overthink my answer. “Of course not,” I said. One, this was supposed to be a similar job to what I was used to anyway. Two, any confessions about being inexperienced with wealthy clients and unprepared for an unexpectedly older teenager would give her more room to define the job for me. More than she was already doing, that is. 

Hannah set her glass down with an idle smile on her face. “Good. We’re going to put some clothes on and hang out in the other room. You should get started on snacks.”

Right. I had completely forgotten about that task given to me earlier after everything that had transpired since then. The prideful babysitter within was tempted to berate this girl for talking to me in such a way, but we were well past that. I was supposed to be in charge, sure, but that’s not exactly where things stood at the moment. “Yes, Hannah,” I said. Still playing along, in the hopes that the girls before me would scatter and I would finally have a second to breathe. 

That was somewhat the case, though Hannah insisted I stay in the kitchen to work. Once she and her friends were settled, I’d be told what to do next. 

What did rich girls even snack on? Hopefully something easy, as their taste in alcohol clearly wasn’t as snobbish as I might have expected from someone who grew up in a house like this. After a minute of searching, I found a pantry full of junk food that would hopefully suffice. I found a few appetizer bowls and took the effort to prepare the snacks beyond the boxes and bags they were packaged in, then made a small pile of fruit on the counter as well. Ever the responsible girl, I at least had to try to offer some healthy options. 

It didn’t take long for the girls to filter into the spacious living room. Bringing them snacks was only the first part of this new ordeal. I figured out quickly that my new role would be something of a waitress, or perhaps female butler. Despite my insistence to Hannah that I knew what I was doing, this was all new to me, and I couldn’t think of a way to avoid being taken advantage of. 

Calls of ‘Jessie!’ were nonstop. A different voice almost every time, requesting a new drink or a snack refill. Every time I delivered something, I was to clear the various surfaces of used bottles and glasses as well. My other task was to clean the kitchen from top to bottom; according to Hannah, it had to sparkle by the time I was done. However, I’d barely get three minutes into one of the many areas required before I had to drop everything to tend to the girls. 

A number of them had decided to swap to liquor, and I also became their bartender. Rum and coke, vodka cranberry, gin and tonic; their requests were simple, but ensured that the counter was constantly full of liquor and mixers. At first, I attempted to barely put a splash of liquor in each drink, as a way to subtly control the situation. After a number of complaints that I was making everything too weak, however, I gave up and actually prepared alcoholic drinks for the group of eighteen year olds I was supposed to be watching. 

All the while, I cleaned whenever possible, but hardly seemed to be making a dent due to all the interruptions. I kept trying to think of ways to get out of my predicament, but found it difficult to think most of the time. I needed to get upstairs and break into the guest room somehow, but I was summoned so frequently that there was never a minute to slip away. And with all the gossiping and giggling and other piercing girly noises from one room over, it was impossible to focus.

I also hadn’t gone to the bathroom since before my drive. First I had been reeling from the surprise of Hannah’s age, and my next trip to the restroom had me too concerned with getting all the chlorine off. Add a chugged can of hard seltzer to the mix, and I found myself with a possibly broken seal and an urge that was no doubt heightened from something that would have naturally come up around this time anyway. 

Stepping away to get into my room and get out of the degrading maid uniform was one thing, but I was well within my rights to take a bathroom break. Hannah and company would just have to deal with a minor delay if one of them needed something. Even so, I found myself tip-toeing out of the kitchen to avoid having to deal with a conversation about it. The cool hallway was almost worse on my bare feet than the kitchen tile due to vent placement, and I ended up faced with a series of closed doors. Which one was the bathroom, again? It didn’t matter, because every single door I tried was locked. Just like upstairs after my shower.

Inwardly groaning to myself when I heard one of the girls call out for me, I ducked back into the kitchen to approach from that direction. Taking the empty glass, as well as two half empty ones that a couple of the other girls decided they wanted topped off, I retreated back to the kitchen. Instead of getting to that right away, I made a quick trip upstairs, only to find that the bathroom I recently showered in was also closed and locked. Seriously?

After an aggressive jiggle on both the bathroom door and my guest bedroom on the off chance that one of them would yield, I dejectedly went back downstairs. Taking care of the drinks, I returned to the living room and was half tempted to ask Hannah why she was keeping everything locked up. Surely her friends would need bathroom breaks as well, especially since they were drinking so much. But asking in front of an audience would be so embarrassing. Hannah’s babysitter–or rather, housekeeper–essentially asking permission to use the restroom? No, thanks.

Instead, I threw myself back into my work. Making the kitchen shine in an effort to avoid Hannah finding another excuse to make the afternoon difficult, and constantly waiting on the girls whenever they called me. After another hour, however, the urge became too pressing to ignore. In fact, it was much worse this time around due to the fact that I had put it off for so long. Hannah and her friends seemed content to drink and snack and hang out to their hearts’ content in the other room, and I couldn’t wait any longer. 

The next time I returned to the living room with a new bowl of chips and a refill for Hannah herself, I paused next to her and hoped that the fact that I was standing and she was sitting would at least give me a modicum of authority despite my getup and the fact that I had been serving them for half the afternoon. “Hannah, I need to use the restroom,” I said. Direct, and to the point. Even if it was embarrassing to say it in front of a whole room of eighteen year old girls. “And all the rooms are locked.”

“That’s not a very polite way to ask,” Hannah said. Brushing back her hair with a smug smile, she glanced up and met my eyes. Clearly not daunted at all, despite the height disadvantage she had against my standing self. “Try again, Jessie.”

Swallowing my pride, I began saying, “May I please-”

“Ah, ah,” Hannah held up her hand, “What do you say when I tell you to do something? Try again, Jessie.”

I was tempted to slap her. But with all her friends here, something told me that wouldn’t end well. “Yes, Hannah,” I said. Starting with the housekeeping phrase she was pushing on me, I then went on to ask the full question. “May I please use the restroom, Hannah?”

“Hmm,” she mused. Deciding rather quickly, Hannah said, “Maybe in a minute. First, I have some questions for you. We all do.”

Chapter Five

Hannah

This was going better than I thought it would. Way better.

Especially since it’s not like I had a plan. My friends had already been set to come over, as it’s not like having a ‘housekeeper’ meant that I was grounded or anything. But once I had decided to put little Jess in her place, having power in numbers certainly wouldn’t be a bad thing. The brunette was young, and small, and poor; why else would she take a summer job? And with the lovely title my parents had given her, as well as her inexperience when it came to my lifestyle, it would be simple enough to push her into the role she had technically signed up for. 

Drinking with my friends set her off just like I hoped it would, and it was SO satisfying to watch her flail backwards into the pool. The way her wet top hugged her chest, however, was a reminder of how obnoxiously well endowed she was. Something would need to be done about that ASAP. And, sure enough, she gave me an opportunity to really screw with her. Taking a shower. 

I took half of my friends upstairs once I heard the water running, and put them to work stealing everything in the guest room Jess had chosen for herself. While they handled that, I took the job that was both more fun and more risky. I soundlessly slipped into the bathroom and scooped up Jess’s pile of wet clothes on the floor, followed by the clean ones she had left neatly folded on the counter. All the while, I stayed low, making sure my blondeness and my movements wouldn’t be easily noticed through the fogged glass. Last but not least, I swiped all the towels; even the hand towels, so the naked girl wouldn’t have a single thing to dry off with.

When I returned to the guest room to check on my friends’ progress, I was happy to see an empty room waiting for me. Jess had just arrived, after all, so it’s not like she had unpacked much. To finish things off, I locked the door. That would keep her out for a while. And, if she somehow picked the lock or climbed in from the outside, then she would learn that her efforts were totally wasted. 

Just when I was relishing in the fact that I had stranded my babysitter buck naked in the bathroom, as I went so far as to lock ALL the doors in case she decided to pilfer through my stuff or my parents’ closets out of desperation, I thought of something much better for the girl. I had no idea how long Jess would be in the shower for, so I was suddenly running down the hall in my bikini to find the french maid outfit. It was more of a costume than a uniform, designed to be slutty for girls who liked to wear such things on Halloween. Or, in my case, to use for roleplay every now and then. I had a number of costumes for both girls and guys, because I appreciated both genders equally. 

Only for Jess, this wasn’t about sex in the slightest. I just wanted to visually seal her in the role of ‘housekeeper.’ And, if she happened to look a little slutty at the same time, all the better. 

I snuck into the bathroom again. The french maid number was left on the back of the door, and I also swapped her contacts out for a pair of ugly glasses that Taylor found deep in one of the pockets in Jessica’s backpack.

Shame there wasn’t a way to install a few cameras in the room to watch the girl’s reactions to what I had stolen and left behind. At least, not at the time. Maybe I could order some cameras for a few rooms of the house. Correction; maybe Jessica could order them. I had her wallet now. Her credit cards were mine to play with, and I assumed her driver’s license would have the zip code required for online purchases. But that was fun I’d have to have later. For now, I was happy drinking with my friends and waiting to see if little Jessie opted for nudity, the slutty maid costume, or something ridiculous like finding curtains or a rug to cover herself up. 

To my delight, she went with the costume. And it was amazing! The top half squished and flattened her breasts to the point that she no longer looked bigger than me, and the skirt showed everything. I don’t think even Jessica was aware just how often she was exposing herself. Because my friends and I were all seated by the pool, some in chairs and some with their legs dangling in the cool water, we all had great angles to check her out. 

The subservient girl was totally bare down there. Her pale little ass was nothing to write home about. And, most importantly, her tiny slit was easily visible again and again from both the front and the back. With her modesty being stripped away, as well as her dignity while cleaning up after us like a proper maid, I could tell that none of my friends would take little Jessie seriously moving forward. On top of everything else, I took a lot of pleasure in how hot I looked with my perfect hair and perfect body in comparison to Jessica’s damp hair, nerdy glasses, and pathetically petite frame wrapped up in a slutty french maid costume. 

For a while, I just bossed her around with the help of my friends. Not only for the fun of it, but also to get Jess used to her role moving forward. If my parents were dumb enough to label her a ‘housekeeper,’ and if Jessica was enough of a pushover to allow all of this to happen with very little protest, then I wasn’t going to relent any time soon. Instead of a babysitter, I was going to have an obedient little maid for the next six weeks.

It was a great afternoon. My girlfriends and I got to hang out and drink to our hearts’ content, and for once we didn’t have to take turns dealing with snacks and clean-up. Instead, we simply had ‘Jessie’ do everything for us. I could tell that Jess wasn’t a huge fan of her full name, but her little reactions to the alternative nickname made it clear that I had found something she liked even less. And, after making her serve us for a few hours, she voiced that she needed to use the bathroom. Better yet, she politely asked for permission after just the tiniest bit of prodding. 

She was at her most vulnerable yet. Dressed up like an obedient slut, worn down from all of our orders, and needing to pee. The perfect time to strike. 

“So, Jessie,” I began, enjoying the subtle twitch of distaste that always seemed to follow my new name for her. Give it time, Jess. You’ll get used to it. “You said you’re not a lesbian?”

“No!” she immediately snapped. 

“You didn’t say that?” I clarified, “So you are a lesbian, then?”

“Ugh, no! I’m straight.”

Boring. But also predictable. 

Just to my left, Lillian was the first to pick up on this new game I was starting. Granted, it wasn’t that new. Jess wasn’t the first girl we had grilled. There were plenty of parties where my friends and I were able to overwhelm a girl we wanted to destroy with difficult questions. And, when said questions came from all sides, it seemed more like intense group curiosity than a targeted attack. “How many times do you masturbate a day, Jessie?” Lillian asked. 

Jess’s cheeks turned SO red. “W-what? That’s- that is none of your business!”

“Jessica.” Opting for the full name this time to get her attention in a different way, I flatly said, “Answer the question. If you want a break, then act like one of the girls.” Gesturing to all the bikini-clad high school graduates around me, I explained, “We do truths like this all the time.”

“But-”

“Yes, Hannah,” I said. 

“Yes, Hannah . . . ” she echoed. 

“Good girl. Now, how many times do you masturbate a day?”

The look on her face told me everything. There was absolutely no way to safely answer a question like that. Because she was right; it was super personal. Any number would basically be telling the whole room that she pleasures herself. Girls that were confident in themselves and their sex lives would be able to say anything and not give a shit what others thought. But it was clear that Jess wasn’t like that. 

Amusingly enough, her answer was exactly what I thought it would be. Nervously glancing away, the little brunette mumbled, “Once . . . ”

Easily the tamest answer without seeming like a total prude. I actually had no idea whether or not it was the truth. Just because Jessica was a doormat didn’t necessarily mean that she didn’t take time to play with herself multiple times a day. Girls could be unpredictable like that. I didn’t have time to press about it, however, as Lillian followed up right away. “Just once? Cute. How do you do it, Jessie? Fingers, or toys?”

“Umm . . . ” One look towards me and my stern gaze was all the girl needed to comply. “Fingers.”

It was difficult to tell whether it was the questions that were causing the girl to fidget, or the need for the restroom. While it wasn’t quite the cliché bathroom dance, it was close. Since Lillian was the one interrogating Jessica at the moment, I was free to look the slutty maid up and down. The most noticeable movement was the way her hips were slowly gyrating as she adjusted her thighs and posture again and again. Then there were little things, like the way her bare toes would twitch, and how her hands couldn’t stay still. 

True, it could have been the cold floor under her feet, or the fact that she was the center of attention during the uncomfortable line of questioning. But I knew better. If it was just those things, then the college girl would have pushed back harder against the barrage of inappropriate questions. No, little Jessie was trying to keep from bursting, and playing along only because it felt like the only way to get the bathroom key. If only she had managed to think outside the box–our property was pretty secluded, and sneaking outside to pee behind a bush would have probably been more comfortable than subjecting herself to all of this. 

Taylor spoke up when Lillian was done asking about fingering technique, and porn preferences, and a number of other questions that made Jess stammer out the most vanilla and minimalistic answers in an attempt to save face. “What’s your favorite sex position?”

Jessica’s face went white. 

In contrast, my eyes lit up. I knew it. I KNEW IT. She was a fucking virgin! If she had a real answer to the question, even something as boring as missionary, her reaction would just be awkward and hesitant like it was when it came to her masturbatory habits. Instead, there was a distinct panic in her expression and body language. The kind where she’s about to be caught in a humiliating truth in front of the worst audience possible. Worse than peers; we were girls she was supposed to be in charge of. And there was no getting away from this. Not if I had anything to say about it. “Jess.” My tone was gentle, as I gazed at her with a fun combination of pity and curiosity. I wondered if she caught that it was the first time I had used her preferred name in quite some time. “Have you never fucked a guy?” Less scary than the V word, but still with a swear in there to make the question blunt and a tad intimidating. 

Jess

This was my worst nightmare.

So far, I had managed to avoid anyone finding out about my virginity. At university, I would simply lie by omission. It was easy enough to imply that I had experience in the bedroom, and it’s not like it was a total lie. I had done pretty much everything except penetration. But now Hannah was calling me out, and I was totally on the spot. I was a lot better at half-truths than flat out lying, and it sounded like she already knew the answer. But could all of her friends tell, too?

“That’s none of your business,” I meekly replied. Same attempt as before, and I could tell right away that it wasn’t going to stop the blonde from pushing the matter.

“Jessie, tell us the truth,” she said, “Or would you rather continue your chores naked? And without those pretty glasses?”

She wouldn’t! The sarcasm in regards to my glasses hardly registered, as I was too busy worrying about being stripped. While Hannah had claimed to her friends that this mortifying outfit was mine, technically it belonged to her. Which meant she could take it back if she wanted to. Plus, the urgent need to pee was still there. “Hannah, please . . . ”

My plea fell on deaf ears. “Answer the question, Jessie. Have you ever fucked a guy?”

Wincing at the crass way to describe the first I had yet to have, I blurted out the simple answer before I could stop myself. “No . . . ” I didn’t even bother explaining myself. My answers to the deeply personal questions so far had been bad enough; they didn’t need to hear about my second and third base experiences. 

A few hushed whispers and giggles filled the room, but Hannah didn’t partake. Instead, she kept her gaze trained on me. “And what does that make you, Jessie?”

I knew what she wanted to hear. With a lump in my throat, I practically whispered, “A virgin.”

“What was that? Say the whole thing, girl.”

“I’m a virgin.” My lip quivered the slightest bit as I said it for the whole room to hear. Deep down, I knew it wasn’t that big of a deal that I hadn’t had sex yet. But that internal logic was impossible to listen to when this was the very first time I confessed my virginity to anyone, ever. And, of all people, it was to Hannah. And friends.

With a smirk, the blonde picked up one of the water bottles I had recently delivered the girls. Apparently they knew how to hydrate amidst day drinking. Rather than tease me about my lack of sexual experience like I expected, Hannah simply held out the water from the fridge. “You look exhausted, Jessie. Sweaty, too. Why don’t you show us those chugging skills again?”

But- but- 

No way. I couldn’t drink a whole bottle! My bladder was already feeling a bit bloated and pained from waiting so long to speak up about my need to go. The last thing I needed was a drink. “Hannah-”

“Go on, Jessie. Then we’ll talk about your break, okay?”

Okay. I guess that was fine. If I was able to use the restroom immediately after downing all the water, then it wouldn’t be a problem. And, as I had already learned, arguing with Hannah was impossible. It would just drag things out and result in her getting what she wanted anyway. So, resisting the urge to sigh, I simply said, “Yes, Hannah.” Unscrewing the cap and steeling myself with a huffed exhale, I pressed the bottle to my lips and tilted it back.

The first half of the process was fine as I opened my throat and allowed the cool liquid to flow through as quickly as possible. The rest, however, made me regret the decision to do as I was told. As I drank, I felt an intense pressure on my bladder. Oh God, I had to go SO badly. Chugging more water was beyond counterintuitive, but I forced myself to keep going. Just a little more . . .

Gasping as I finished the last drop, and pressing my thighs together as tightly as possible, I was suddenly worried about my ability to walk to the bathroom without disrupting the delicate balance I had created with my posture. “There. Now, can I please have the key?”

“Hmm, what do you think, girls? Does Jessie deserve a break? Show of hands.”

Not a single hand went up in the air.

“And who thinks she should get back to work?” Hannah raised her own hand, and literally every girl followed suit. Putting on a mock pout, she said, “Sorry, Jessie. Majority rules. You’ll have to hold it. Now, how about a fresh round of drinks?”

“NO.” My voice came out a little more shrill than I had expected, but I tried not to let it discourage me. Volume was more important than tone. “Hannah, I need to use the bathroom. Like, now!” Like, desperately. “Look, just-”

“JESSIE. God, what the fuck? You’re supposed to be my housekeeper this summer. That means serving me like a mature, proper girl. Not acting like a pathetic little baby and whining about the toilet. You should have gone when you got here, or before your shower.” She stood up. Towering over me with each step forward, she demanded, “Now, are you my housekeeper? Or an immature brat? And for fuck’s sake, Jessie, stop fidgeting.” 

Hannah placed her hands on my shoulders and jostled my body into a more proper stance, which was enough to cause the inevitable to happen. I had no choice but to slightly pivot one of my feet to keep from falling over completely in response to her movements, which slightly separated my thighs. It wasn’t much, yet it completely destroyed the dam I had been working so hard to maintain. 

I was completely powerless to stop it. Tensing up, and gasping in horror, the floodgates opened and I began wetting myself right there in the middle of the living room.

Chapter Six

Jess

“Jessie, what the fuck are you doing?!” Hannah exclaimed. 

What could I say to that? I was literally peeing in front of the rich blonde and all of her friends. Without any underwear on, as I was stuck going commando underneath the demeaning maid outfit, there was nowhere for the urine to go but the floor. A faint trickle quickly gave way to a nonstop stream, which was when Hannah realized what was going on and began yelling at me. “No- umm- I . . . ” I stammered. Every fiber of my being wanted to run away, but I couldn’t do that while peeing and I also couldn’t make myself stop. 

Hannah seemed to have a similar idea in terms of what I should be doing. “Jessie, stop! Right now.”

“I- I can’t!” I exclaimed. It wasn’t until this mortifying release that I realized just how badly I had to go. Obviously I knew it was an emergency, but I had mostly been concerned with a squirt or two escaping when I wasn’t wearing anything to catch it. This was BAD. And, despite how much I didn’t want to be humiliating myself in such a way, I actually found myself slightly bending at the knees. It was a natural instinct, as going to the bathroom standing up didn’t work as well, and it clearly wasn’t helping me hold back. 

“God, you’re pathetic,” she scoffed, “For fuck’s sake, Jessie. How old are you?? I told you to hold it.”

Cheeks turning crimson, I muttered. “You- you-” I was trying to get out ‘You didn’t listen!’ How many times had I told her that I needed to go?! But not only was there no excuse for a girl my age to be wetting myself, I also felt awkward about talking while I was going to the bathroom. Instead, I closed my eyes to shut the other girls out and prayed that this was all some horrible nightmare. 

No such luck. It was at least a full minute of continuous peeing before I finally felt the flow begin to slow down. I should have gone to the bathroom when I arrived at the mansion, or before my shower. There had been too many surprises and distractions, and now I was paying the price. As I opened my eyes, seeing the predictable judgment and amusement on the faces of all the girls lounging in Hannah’s spacious living room, the one thing I hadn’t accounted for was the fact that all the teenage girls had phones. “No!” I exclaimed, gasping both at how many cameras were trained on me as well as how the puddle below expanded to nudge the sides of my feet at the same time. Jumping both away from the mess and from my blonde charge, I ignored the need to wipe both my feet and my crotch for a moment as I begged, “Don’t. Please delete those!” 

Hannah just laughed. “You think you get to make demands? Please. Jessie, you just fucking pissed yourself in front of my friends. Putting aside the fact that you should really be potty trained by now, aren’t you a professional housekeeper? How do you think this makes me look?” 

How it made her look? I was humiliated. Humiliated. And she was talking about her rich girl reputation? “Hannah-”

“No! Bad girl!” she snapped, “Until I say otherwise, your only vocabulary is ‘Yes, Hannah’ and ‘No, Hannah.’ Fuck it up, and the internet sees a fun new video about a slutty maid having an ‘accident.’ Do you understand?”

I was supposed to be her babysitter, and she literally just told me off like I was a dog. And yet, I just felt my blush deepen as I mumbled, “Yes, Hannah . . . ”

She and the other girls giggled at the immediate obedience, and perhaps also from what I had so recently done right in front of them. All I could do was tighten my lips and avert my gaze from the gaggle of girls staring at me. Being locked out of my room was one thing, but this fresh round of potential blackmail was something else entirely. A group of eighteen year old girls would be more than capable of finding me online. While my social media presence was limited and set to private, they could probably find enough friends and family if they put their mind to it. The maid outfit was awful enough, but I would absolutely die if anyone I knew saw what I just did. At least these girls were strangers, albeit strangers I’d have to see all summer. 

“Stand still. Don’t move an inch.”

“Yes, Hannah.”

She whispered something to one of the girls, and that girl smiled and left the room. Then Hannah proceeded to have everyone else send their videos to her. She was conducting the whole process in front of me, but knew there wasn’t a damn thing I could do while she collected various angles of my mortifying experience. The blonde even made a point to loudly say, “Oh, good! You took pictures. We obviously have enough videos. Ooh, these turned out so well. You can see everything!” With that, she glanced up at me with a small smirk. 

It wasn’t long before the girl that went off came back with an armful of things. The first things that caught my attention were the small bucket and the cleaning supplies. I was surprised she even knew where to find them, if these were all the types of girls who had maids and such. But then I noticed what was folded over her arm. It was one of my blouses! The pretty green one that I packed in case I needed to dress up slightly more than the casual tops I was planning on wearing most days as Hannah’s babysitter. Forgetting my directive, I blurted out, “Hey! That’s my-”

“JESSIE. BAD GIRL.” Hannah immediately cut me off, loudly admonishing me as she stood up and stormed over. Raising her hand like she was about to slap me across the face, she instead held her hand to the girl after being satisfied that she made me flinch. Taking my nice green outfit piece, Hannah offered it to me. “Wipe up your mess, Jessie. Right now.”

With- with my own blouse?! It wasn’t a rag; it was one of my more expensive outfit pieces. Obviously Hannah knew that her order was beyond insulting and insensitive, and I kept waiting for her to play it off like she wasn’t actually being serious. Except she never did. Her stern gaze and the silence that followed her words both lingered long enough for me to choose one of the only two phrases I was allowed. “No, Hannah?” It came out more as a question. I really didn’t want to ruin my pretty top, but I also wasn’t exactly in the best position to push back. 

She knew so as well. Rather than yelling at me again, or threatening to do something with all the pictures and videos she collected, Hannah went in a direction I didn’t expect at all. Stepping forward with her lips pursed in a small smile, she reached under my too-short skirt with no warning whatsoever. Using my blouse, she gave a quick wipe between my thighs. 

My eyes widened at the invasion, but Hannah was already pulling away and speaking before I could say something about her audacity. “There,” she said, holding up my nice green top so I could see the bit of wetness from how it had more or less been used as toilet paper. “It’s already dirty. Now hurry up and clean my floor before it gets stained with your piss.” 

It was the second time she had used the more crass term, and I slightly flinched at both the word and the fresh reminder of my recent mortifying experience. That, and I was more on back foot than ever now that Hannah had gotten further than any guy had in terms of touching me. There was nothing remotely sexual to the way Hannah had wiped me, and her hand didn’t actually make contact with anything, but she had still gone under my skirt for a second. Not technically a ‘first,’ but enough that my virgin self was a little offended at the violation. 

And, of course, she had waited until I wasn’t allowed to speak. I so badly wanted to tell her off, but I couldn’t. Not after wetting myself, and wearing what I was wearing, and being stuck as more ‘maid’ than ‘housekeeper’ until I could contact Hannah’s parents and sort out this mix-up. 

I was supposed to be her babysitter. Instead, my authority was absolutely nonexistent at this point. 

“Well?” Hannah said. She extended her arm, pushing the slightly dirtied top into one of my hands. “If I have to ask again, you’re going to be doing it on your hands and knees.”

At that, I got moving. Blushing more deeply, if that were possible, I took my blouse and murmured, “Yes, Hannah . . . ”

I squatted down to get started, praying that the skirt wasn’t riding up too much on either side, belatedly realizing that the angle and balance was too awkward to efficiently clean. Shifting to place one knee on the hard floor, I reluctantly bunched up the nice top and used it to soak up as much of the puddle as I could while keeping my hands clean. It’s not like the blouse would be ruined, as long as I could get it into the washer as soon as possible, but that didn’t change the humiliation that came with using my nice outfit piece as a rag. 

The girl who had returned with the cleaning supplies stepped forward and opened a trash bag at Hannah’s request. I carefully placed the soaked top into the bag, suddenly nervous that the bag would simply be thrown away. “I can take that to the laundry room,” I quietly offered. In a way, I was actually leaning into the maid image in the name of protecting my blouse. 

“You’re not done yet, Jessie,” Hannah said. 

Just like that, one of my skirts was dropped in front of me, followed by a few tank tops. All I had wanted was my own clothes. Changing out of the slutty maid uniform had been such a high priority, and it wasn’t lost on me that I could have combined the skirt, blouse, and one of the tank tops for a decent outfit. Instead, I proceeded to wipe up the rest of the gross wetness with my skirt and then took the cleaning supplies and used the tank tops as rags to scrub and then dry the floor. Each article of clothing made its way into the trash bag, but I knew better than to speak up again. 

It didn’t help that all the attention was still on me. The room was mostly quiet, save for those hushed teenage comments and bits of muffled laughter here and there. I kept my gaze on the floor the whole time, unable to bear the thought of literally everyone staring at me as I not only served as a maid, but worked to clean up a mortifying mess I had just made in front of all of them. 

The moment I was done, standing while holding my skirt in an attempt to keep it as far down my thighs as possible, Hannah spoke up. “Well, virgin, I’ve personally had quite enough of you for one afternoon. Bring us a fresh round of drinks, and then go water everything in the garden. When you’re done, clean up this room and finish what you started in the kitchen. We’ll probably be in the basement. The second you’ve finished all that, you are to come down and inform me. Got all that?”

I was stunned and embarrassed right away as the blonde so casually addressed me as ‘virgin,’ but she moved on too quickly for me to respond or even for me to dwell on it. Drinks, garden, living room, kitchen. Fully a maid, not even remotely a babysitter. And there was even less to do about it than before. Publicly wetting myself just added to the impossible dynamic I found myself stuck in without being able to call Hannah’s parents or talk to the girl without her friends around. 

“Yes, Hannah.” It was all I could think to say. As much as I loathed being so subservient, there was the small silver lining that this would finally give me some space away from her and the girls. After what I just did in front of them, I needed that space way more than I needed it before. 

At this point, I had resigned myself to the fact that the girls were going to be drinking whether I liked it or not. I had already refilled their glasses plenty of times, and supplied new cans to those that were drinking beer or seltzer. One more trip was nothing if it meant that I wouldn’t have to deal with any of them for a while. Still, that didn’t change the fact that it was wrong on multiple levels; allowing it in the first place, and then giving drinks with my own hand. But I did it. And, after topping everyone off, I retreated outside before Hannah could change her mind. 

It wasn’t until I reached the edge of the pool area that I realized that being barefoot wasn’t ideal for the impending job. While the extensive garden had a main path, watering everything would require walking through a ton of grass and other uneven surfaces. I would have to be thorough, as Hannah’s parents would kill me if their beautiful landscape was ruined. Although was I even responsible for outside? My list of housekeeping responsibilities was as unreachable as everything else was thanks to how I was locked out of my own room. Plus it wasn’t even about her parents at the moment. For all intents and purposes, I was Hannah’s maid/housekeeper rather than her parents’ housekeeper/babysitter. 

Watering everything took forever. My steps were awkward and hesitant wherever I went. The cement paths were hot on my feet from the afternoon sun, the grass was itchy, and the other paths required careful advances to avoid stepping on any sharp or awkward rocks. Also, I didn’t want to get burned. Taking shade breaks prolonged my exposure, but didn’t help with how hot it was. While the maid outfit was plenty skimpy, it was still a bit much to be wearing in the summer sun. I almost wished for my bikini from earlier. I had showered so recently, but the effects were quickly being undone as I felt myself sweating along the way. Watering wasn’t even that active of a job, but the heat still took its toll. And, finally, the garden was huge. While the hose was probably the best money could buy, with great water pressure coming from the faucet, I still had to thoroughly hit every single plant. 

The job soured my solitude a bit, but it was still nice to be alone for so long. I had hoped that the separation from Hannah would give me time to think, but I couldn’t come up with a single way out of the mess I was in. Provided her friends left, and it was just the two of us, I’d still be dressed like I was without access to any of my belongings. Would coming clean about the babysitter thing at that point make a difference? I was in no position to be taken seriously, and had no way of contacting her parents. How was I going to wrestle back control when she was holding all the cards? And it was going to be nearly impossible to come back from having an accident in the middle of the living room. 

Ugh, I was so fucked! For the second time that day, I considered the idea of simply quitting and driving away. Of course, the first time the idea crossed my mind was when I was under the impression that I would be able to return to my room and collect my things. Now? I didn’t think Hannah would necessarily force me to stay against my will, but she would certainly have her fun before letting me go. How much would I have to beg before being granted my things? I could already see her smirk as she made me dance for what was already supposed to be mine. 

Also, I really did need this job. Nothing else I had looked at for the summer came remotely close to what Hannah’s parents were paying me. Somehow, I needed to figure this out. There was no way I could stomach being an obedient little maid for six weeks. It was humiliating, especially when she was the one who was supposed to be listening to me. For now, however, I just needed to make it through the day. 

After finishing up with the garden, and praying that this wouldn’t be an everyday task her parents had assigned to me, I headed back inside after using the pool to rinse off my feet. While the air conditioning was instantly refreshing, as well as the quiet of the main floor in contrast to the laughter of drunk girls from before, the disaster of the kitchen and living room had me sighing in frustration nonetheless.

I had barely survived half a day of Hannah, and I had well over a month with her to go. For now, it was very much a ‘one step at a time’ mentality. So, despite my distaste of serving as her maid, I took a deep breath and got started with the next round of chores.

Chapter Seven

Jess

It was much easier to clean the kitchen without the constant interruption of Hannah and her friends. Before getting started, I collected all the cans, bottles, and glasses from the living room and gave a good wipe to all the surfaces. Being in there was enough for the mortifying memory of wetting myself in front of everyone to resurface, and it took a good ten minutes of washing dishes before I could feel the burning on my cheeks fade.

While I had dealt with an embarrassing moment or two replaying while trying to get to bed every now and then, like many people deal with at some point, this was a lot more persistent and way more difficult to push out of my mind. I was twenty years old, for fuck’s sake. And apparently that little phrase of Hannah’s as it rang in my head along with the rest. 

Though I had showered twice already–once that morning and once after being shoved into the pool–I already felt the need to do so again. The slutty maid dress was more horrible to wear now that I had been stuck in it for so long. Between the sweating under the outside sun and the constant chores in the tight uniform, the thing was slightly itchy everywhere and my breasts were noticeably sore after being crushed for so long. I also hadn’t really eaten since getting in the car, and the girls had taken their snacks down to the basement with them. Obviously I was in the kitchen, but I figured it was better to have the room spotless before looking for a little something to snack on before whenever dinner was. 

It wasn’t until all the dishes were done that I realized that I was alone. As in, everyone else was downstairs. While I had known that ever since stepping back inside, it didn’t truly hit me in terms of the possibilities offered. If there was ever a time to get into my room, it was now. While I was still very much outnumbered and on my back foot after the public accident, the least I could do was change back into my regular clothes and try to call Hannah’s parents again. Try to steer things back to the way they should be. I was the babysitter, and the bossy blonde was the teenager. 

Padding up the stairs as quietly as I could, to avoid any creaks that might notify the girls what I was up to, I found the upstairs hallway just like it was before. Every single door was closed, and presumably locked like before. I wasn’t sure what the plan was. With no experience picking locks, all I really could do was aggressively shake the door handle. Plenty of kids I had babysat had attempted to lock themselves in their rooms, however, and I had learned that most inside doors didn’t lock as intricately as the locks designed to keep people out of the house. Of course, Hannah’s borderline mansion and the doors within could be made better than the average suburban house I was used to. But I had to try. 

Bailing on my efforts to be as quiet as possible, I did everything in my power to loosen the door handle. The girls were drinking in the basement and being loud in their gossip and giggling and whatever else they were up to. While I still didn’t condone them consuming alcohol when I was supposed to be in charge and keeping them from such partying under Hannah’s parents’ roof, it was a welcome distraction for the time being. Perhaps it would even work to my advantage, as I could report it on the phone call and give them something to actually yell at her for. Pushing me in the pool seemed like too much of a childish thing to complain about as a babysitter, and the rest of it would be too difficult to explain. 

To my great relief, the lock actually gave in. After nearly a minute of trying different motions to get the handle to do anything but be stuck in place, I smiled to myself as I was able to push the door open. Unfortunately, that relief didn’t last for very long.

“Jessie!! What the fuck are you doing?!”

Just as I was going to step into the room, my head whipped to the side to see Hannah standing at the top of the stairs with a hand on her hip. I hadn’t heard her in the slightest, though she would naturally know how to quietly take the stairs from actually living in the house. Still, I had expected her to actually call me if she needed me; I had been keeping an ear out for just that, so I could sneak back downstairs before she or any of the other girls realized what I was up to. 

While her harsh tone instantly made me nervous despite how I was supposed to be regaining my authority, I knew that this was the time to make a stand. “I’m going to my room for a minute. To change.” Drawing whatever strength I could find, I made the effort to keep my voice from wavering as we faced off. “I finished all the chores, Hannah. And I need to check in with your parents.” The last time I had threatened that, she had laughed in my face. Hopefully alluding to it would yield better results than straight up saying it. 

She just rolled her eyes. “Clearly you need some more training. I leave you unsupervised for one minute, and you go somewhere you aren’t allowed. Your bedroom is for sleeping, Jessie. Nothing else.”

I was tempted to argue back against pretty much everything she said, but I knew it wouldn’t be worth it. Hannah had already proved that she was capable of twisting pretty much every word I said while this ‘housekeeper’ thing was still happening. And until I had the means to let the game go and make it more babysitting than cleaning, I wouldn’t be able to spin things back to my favor. Instead, I just repeated myself. “I’m changing.” Then I walked into the room without waiting for her to reply. And gasped.

Nothing was in there! Well, almost nothing. Both of my suitcases and my duffel bag were sitting on the bed, but all three pieces of luggage were open and it was clear that they were empty. As for my backpack, it was nowhere to be seen. No laptop, then, or any of my other personal things. And, in retrospect, it was stupid to assume that my phone would be sitting there waiting for me. Hannah had taken it from the bathroom, after all, which means she could have put it anywhere. 

“Changing into what, virgin?” Hannah asked. She followed me into the room with a smirk on her face. “I told you, this room is for sleeping. If you want to change, you will need my permission.”

“Hannah!” I exclaimed. How could she- what could I- this wasn’t fair! Part of me wanted to scream at her, but another part felt completely deflated as I realized that all of my recent efforts had been for nothing. Hannah had moved all my possessions somewhere else, and not even breaking down every door in the house would bring them back to me. The property was just too big, and she knew all the nooks and crannies better than I did. Hannah could have hidden them anywhere, and I knew right away that she would be the only one who could return them to me. 

Still very much smirking, she asked, “Yes?”

I couldn’t yell at her. Not now. I would have to play nice, somehow, and hope that this would be over at the end of the day. Surely the eighteen year old bitch wouldn’t keep this going. Most of all, I needed my cell phone. Failing that, my laptop so I could send an email. Without anything, however, I would need to be patient. “May I please have my things, Hannah?” I asked.

“Hmm. I don’t know, Jessie. You could have gotten everything back if you had kept being a good girl, but this is not appropriate behavior. Did you ask permission to come up here?”

Blushing as I knew the ‘proper’ way to reply, I said, “No, Hannah.”

“And what if you broke that lock? Is that going to come out of your paycheck?”

“Yes, Hannah.”

“You’ve been a bad girl, haven’t you, Jessie? I think you should apologize.”

Swallowing my pride, and feeling smaller than ever as Hannah towered over me and made me regret the idea of coming up here and breaking into my room, I muttered, “I’m sorry, Hannah.”

“Sorry for what?”

“For being a bad girl.”

“Say the whole thing.”

“I’m sorry for being a bad girl, Hannah.” 

“Better. Try to be that proper from now on, okay? I’m the lady of this house, after all. You’re just my obedient little maid. Isn’t that right?”

“Yes, Hannah . . . ”

The blonde teen sighed. “We just went over this, Jessie. Say the whole thing.”

Blushing darker at just the thought of the words, I somehow managed to force them out. Barely above a whisper, I said, “Yes, Hannah. I’m your obedient little maid.” 

“Good girl.” 

With that, she ordered me to make a fresh round of drinks for herself and her friends. I followed her down two separate flights of stairs to the basement and once again had to feel self conscious as all of them stared at me with various expressions of amusement. All of them had changed out of their bikinis and into casual summer clothes, still making me the one that was very much out of place in comparison. At Hannah’s direction, I asked the whole room for their drink orders and then left to fulfill the request. It took all my focus to remember the list of drinks. Before, I only needed to do one or two at a time, and just from the kitchen to the living room. Now I had to walk back up from the furnished basement and repeat the list over and over in my head before making each drink and grabbing the required bottles and cans. Thankfully, not all of them had wanted mixed drinks, though it seemed that the majority were leaning that way now that it was getting later in the day. Or perhaps they just wanted to make it more work for me. 

When I returned to the basement, looking more subservient as ever as I carried a tray full of drinks for everyone, I was made to take away the empty glasses and top off their refreshments before they were satisfied and I could stop running up and down the stairs. Once I was done with my last trip, Hannah pointed to a spot in front of all the sofas. “Stand right there, Jessie.”

I really didn’t want to be the center of attention again, especially after what happened last time I was in a similar situation on the floor above. But I had learned better than to argue while Hannah held all the cards. “Yes, Hannah.” Then I stood where she ordered while all the girls got to sit comfortably and wait for what their ringleader had in store for me next. 

“So, how pathetic is it that little Jessie here is still a virgin?” Hannah asked, “Everyone else here has had plenty of sex, right?” When everyone confirmed what she probably already knew about their own promiscuous antics with nods and a number of confident affirmations, she went on. “You’d think after 25 years, she would have found a girl to fuck by now.”

My jaw practically dropped at that as I looked at Hannah in disbelief. I was only twenty years old! She was just exaggerating how embarrassing it was that I was still a virgin. And, even though 25 would still be perfectly fine for someone to have waited, this room of sexually active eighteen year olds was spinning it negatively. And it was absolutely working. But, on top of that, Hannah was once again pushing the lesbian thing. This time, a lot more effectively. By saying it so casually, it seemed more real. To the others, at least. 

All of them reacted with their own gasps and giggles and whispers as they both turned to each other and glanced towards me plenty as well. One of the girls–I think her name was Lillian–cut through the noise with a particularly scathing remark. “How is she possibly that old? She looks younger than us. Like, way younger!”

“She also acts way younger,” Hannah said right away, jumping onto the comment, “Seriously, what kind of adult woman isn’t able to make it to the bathroom?”

I began to defend myself, but didn’t make it very far. “You-”

“Did I give you permission to speak, lesbian virgin?” Hannah snapped, “Remind me what you are, again. Speak, Jessie.”

For a moment, my voice caught in my throat. I couldn’t say that, could I? Not in front of all these girls. But I knew that I had to. Consistently blushing at this point, especially after the constant judgment and laughter from the last few minutes, I quietly answered, “I’m your obedient maid.”

Hannah immediately corrected me. “My obedient little maid.”

“Yes, Hannah. Your obedient little maid.”

“Good girl.”

Hannah

Little Jess literally WET herself. 

I couldn’t believe that stalling her for so long actually worked. Honestly, I expected her to figure something out. Doing her business outside like a dog, perhaps, or at least fleeing from the room to have the amusing accident in a part of the house that didn’t involve so many witnesses. However, she clearly waited too long. And getting her to clean the floor with her own clothes was just icing on the cake. 

From there, I decided to leave her be. A little catch and release, in a way. If I kept babysitting her and attaching myself and my friends to whatever she was doing, it would be almost too easy to run with the momentum of her humiliating display. I had six full weeks to play with the girl, and she had already fallen so far into submission on just the first day. No fun. Sending her outside while simultaneously taking my girls down to the bachelorette pad was the perfect way to offer her some space. Both to give her a moment to catch her breath before whatever came next, and also because I was curious what she would do with said space. None of this was planned. With the lovely warmth of liquor flowing through my body, I was in true impulsive/improv mode with a minimal amount of thinking. And honestly, being a little tipsy just made the whole situation that much more entertaining. 

My family had a few inside security cameras lying around, as we sometimes used them after hiring new staff to make sure they weren’t poking around where they shouldn’t be. They hadn’t been set up for Jess, but I was happy to take one and stick it up in the corner while she was outside. Using my phone, I kept tabs on the feed that showed the stairs on the main floor. I had expected her to circle back inside a lot more quickly than she did, but apparently my ‘housekeeper’ decided to do all her outside chores before coming back in. 

Finally, she made her move. The moment I saw the petite brunette tiptoeing up the stairs, I began doing the same. Sneaking back to the main floor and then following her up, I was more than happy to chew her out for being where she wasn’t supposed to. What’s more, the look on her face as she took in the empty guest room was priceless. From there, it was simple enough to bully her back into submission. Even after a lengthy breather from myself and the others, it seemed little Jess was nice and submissive in the face of all the short term and long term surprises I had set up for her to walk into. 

Once she had served us like the obedient pet she would be 24/7 by the end of her stay, I was delighted to see how quickly my friends jumped on the judgment train. And, now that she was back to feeling helpless and outnumbered by a bunch of pretty and popular girls, it was more than easy to get her to stand there quietly and just take it. To be a young woman who was a virgin and a ‘lesbian.’ A short little twig that hardly looked to be the age that I claimed she was. A pathetic girl who wet herself in the middle of the day. 

But it wasn’t enough. 

Maybe it was the alcohol going to my head. I wasn’t at all a lightweight, but my girlfriends and I had been drinking pretty much since they had arrived. And, despite my plans to take things slowly and gradually humiliate the girl who clearly had been hired to babysit me, I couldn’t help myself. She was standing there and affirming her obedience, and the temptation to test that obedience while simultaneously breaking her was just too great. 

Before I knew it, I was sitting up and pushing my usual smirk onto my face. Normally the expression was reserved for peers who were about to incur my verbal wrath, but it served just as well to show my college aged babysitter who was boss. Scowls were boring. I much preferred showing that I was in control and enjoyed being in control. 

“Jessie,” I said, meeting her eyes. Let’s see just how obedient you are, girl. “Strip for us. Right now. We need to see why no girl has fucked you yet. You have sixty seconds, little virgin.”

And this was just day one.

Chapter Eight

Hannah

Of course, I didn’t expect Jessica to simply roll over and willingly expose herself without putting up a fight. As delightful as that would be, I was well aware that this would be the first time that she was truly naked in front of all of us. She had flashed me and my friends plenty of times when she was cleaning up the poolside area in that short skirt, and I had personally seen her in a bikini, but this would be completely nude. Much more daunting for a girl who clearly was a little more reserved when it came to others seeing her body, which made it all the better for me. 

Fidgeting in her slutty maid outfit and looking nothing like the self assured girl who had tried to assert her authority earlier, she voiced a weak protest to my demand. The look in her eyes told me all I needed to know–it wouldn’t take long for her to break down and obey. “Now you have fifty seconds, virgin.” A little more cold than my smug tone before. Any little servant of mine needed to know her place. “You just said you were my obedient little maid? Were you fucking lying, Jessie?”

She nervously stammered out, “N-no, I just-”

“You just want to strip for me,” I completed her sentence, “because I told you to. Come on, Jessica. We’re all girls here. And if you can’t do as you’re told when you’re told, we’re going to have a big problem.”

Her eyes widened a bit at that. “But . . . ”

“But nothing,” I smirked, “Thirty seconds. Strip, NOW.”

That seemed to do it. The short brunette scrambled to get her outfit off, which I knew wouldn’t take so long unless she hesitated. It was a slutty costume designed more for the bedroom than anywhere else, after all, and it’s not like she was wearing underwear underneath. Sure enough, it didn’t take much for her to get the thing loose. Letting it fall from her body, however, was clearly a more difficult task.

Thankfully, I had a group of girls who I had been scheming with while dear Jess was toiling away at her chores upstairs. They were more than happy to let me be the ringleader here, considering that it’s my house and my ‘maid.’ I’m the usual default leader, of course, but I’m socially adept enough to spotlight my friends enough to keep them feeling like they’re not just followers. Just enough leash, of course, and often while subtly pitting them against each other. That’s how you stay on top.

But for this? There weren’t many nuances required. My friends appreciated how devious I could be, and right now we all had a common target that united us. So I didn’t think twice about snapping my fingers and nodding towards the brunette. One of them would understand the gesture. 

Or two of them, apparently. A duo of my girls sauntered up together and proceeded to yank the dress down Jessica’s body. She gasped and tried to cover, but the girls were too quick. Each of them grabbed one of the now naked maid’s arms, both holding her in place and standing in a way so her entire body was bared to the room. The squirming was expected, but I was most excited by how deep she was blushing. Maybe it was the liquor coursing through me, but I felt more eager than ever to really take the girl down a few pegs. 

As if she hadn’t fallen enough already. 

“So, what does everyone think? Why is little Jessie a virgin? Feel her up if you want. I bet she’ll enjoy it, being a lesbian at all.” Hmm, actually. Forcing it wasn’t as fun. Seeing her obey would be more interesting than holding her in place. “Wait,” Taking a step closer, I stared my new toy down. “We need her permission, don’t we?” Shifting my smirk more into a scowl, I said, “How about, virgin? Can we touch you everywhere?”

The panic in her eyes was intoxicating. It was pretty obvious she wanted to say ‘no,’ but it wasn’t exactly that simple. Because keeping me happy was important, and I could only imagine what was going through her mind. She was already naked. Was it really worth it to get on my bad side now that she was already in this deep? Maybe being a good girl was the best way for her to earn my approval and perhaps get her things back. If she wanted out of this mess, she would first have to choose to make a bigger one for herself first. 

Jessie’s mouth opened and closed a couple times. The poor girl was at a complete loss for words, and I wasn’t about to help her. Instead, I decided to wait and see what she came up with herself. To my amusement, she actually agreed without any further pressure from me. “Okay . . . ” she murmured.

I couldn’t help myself. “Okay, what, Jessica?” The patronizing use of her full name was perfect. At this point, it was forever going to be ‘Jessie’ or ‘Jessica.’ Or ‘virgin,’ of course. Pretty much everything but the nickname she introduced herself as. 

Her blush deepened, somehow. Or maybe I was just assuming that was the case, as it probably wasn’t actually possible for her to be any more crimson. Perhaps the embarrassed way she averted her gaze and stared at the floor just exaggerated her mortified look. Her words were barely audible as she mumbled, “You can touch me.”

“We can touch you everywhere?” Now I was back to the smirk.

She meekly nodded. “Y-yes. Everywhere . . . ”

I was tempted to make her say the whole thing, but there was no need to drag things out. She had given us permission, and my friends were ready to pounce. And, while I had my shit together while drinking–mostly–I knew that at least a couple of them were bound to be impatient with all this build-up. It was delicious to me, as I was the girl Jess was supposed to be babysitting, but they were just seeing a girl I was effectively destroying for the fun of it. 

Unlike them, I was patient. So, with a casual wave of my hand, I said, “You heard her, girls.” They were welcome to go first. I would strike after she was even more vulnerable from being violated in such a way. Permission or no, I doubted she was prepared for what was coming. 

Content to watch, I found the nearest seat and comfortably leaned back. Drink in hand, I pursed my lips in a smile as my friends descended upon the helpless girl. They made a decent effort to ensure that I could watch, but the aforementioned inebriation only allowed for so much visibility as they got carried away with their fun. Starting with Jessica’s hair and face, they fiddle with her brunette locks and brushed their fingers over her cheeks and lips, commenting the entire time. “She really doesn’t know how to style her hair.” “Her lips don’t feel that kissable.” “She’s more cute than hot. Guys don’t like that.”

Eventually, they got to the better parts. Groping her ass, and giving her a few pinches and slaps from behind. I watched with pleasure as she squeaked and squirmed from the sensations, but she seemed to be trying her best to hold still and not give more satisfaction than she was already giving. Judging her as always, they continued with the scathing remarks. “She doesn’t even have an ass.” “So bony!” “There’s barely anything to pinch.” “My little sister has more curves than this.”

Finally, they moved onto her boobs. Unlike before, the words weren’t the insulting kind I would have preferred. “But damn, the little virgin has a rack!” “How do you even fit boobs like this on such a small body?” “Come on, Jessie. Stick your chest out for us.” The girls began squeezing and prodding at the girl’s impressive breasts, marveling at how they reacted to various touches and motions. “That’s a good handful. Almost makes you bangable. Too bad the rest of your body is so, well, you know.” Lillian gave a few pokes to one Jessica’s boobs, before sharply pinching her nipple to contrast the playful contact from before. 

Little Jess yelped and squirmed, and was clearly embarrassed about how she was being mercilessly judged, all while being publicly groped in a way that I’m sure she had never experienced before. I should have enjoyed the whole situation more, but the sight of her chest and the backhanded compliments were more than enough to remind me why I left the dress in the bathroom in the first place. It wasn’t just so she would constantly end up flashing her lower parts to us; I also wanted her annoyingly attractive breasts to be flattened by the top half of the slutty outfit. On my body, such curves would make sense. But I was still super annoyed that a petite little thing like Jess ended up with boobs like that.

Once again, patience was required. I couldn’t lash out too hard when my friends were still here. While they were clearly into this kind of torment, I had already tested each of their limits on a number of things. While the cruelty I had in mind for Jess would definitely fly with a couple of them, I’d have to wait for the others to leave before proceeding. Of course, that didn’t mean there weren’t other things I could put the naked girl through in the meantime. “Alright, girls. Let’s give her a break,” I said, “Oh, someone take her dress. She’s fine how she is for now.” After Taylor made the pathetic virgin step out of the maid uniform pooled around her ankles, I turned my attention fully on the subservient girl. “Jessie, you will not move an inch unless given permission. Do you understand?”

Looking as awkward and embarrassed as always, she merely nodded.

“That means no speaking, and no covering. Your feet are glued to the floor, okay?”

She nodded again. Not much to do when someone takes your voice, is there? 

“Good girl,” I said, “If you break one of those rules, you will be punished. We still haven’t explored that last frontier, have we? Maybe that will help explain how you’re still a virgin, somehow.” At that, she tensed. That’s what I thought. “Don’t want that? Then you better fucking behave. No moving. No speaking. Until further notice, you’re a statue.” I’d allow a bit of natural squirming and shivering, but that’s about it. This next part would be more fun if she simply stood there and let it happen. And if she protested or broke her rules? I’m sure one of the girls would be happy to touch Jess down there. As far as I was concerned, this was another win/win.

After waiting a few seconds to make sure Jessica would do as she was told, I gathered my group of girls around the sofa. Pulling out my laptop and opening it on the table in front of us, I waited a few long seconds before procuring the next item–one of Jess’s credit cards. “Who wants to do a little shopping?” I asked. Doubting the naked girl would be able to tell her card from all the ones my friends and I owned, I made sure to specify, “It’s Jessie’s treat. A little ‘thank you’ from her for letting her stay here all summer. And all of you have been such good hosts today.”

To her credit, Jess didn’t spring across the room to snatch the card from my hand. Instead, she just squeaked and met my eyes. It was hard to tell whether the look was an incredulous one, or a fearful one. It could easily be a hint of both, but I was assuming it was the latter. While I hadn’t yet found a way to break into her checking account, I could only imagine how little money a girl like her had compared to myself and the girls around me. Even if it was a decent amount from her perspective, there was no way she’d ever buy the kind of stuff that the 1% would buy for themselves without blinking. 

“One item per girl, okay?” I suggested, “Lillian, I know you’ve been eyeing a few of those designer dresses. Do you want to go first?”

“Absolutely!” she exclaimed. Her parents had capped her allowance after a particularly spendy trip she had taken over spring break, so I knew she would be more than happy to get the ball rolling on this. “Just one?” she pouted.

“Hmm, for you? Maybe a few.” Whatever. It’s not like it was my money, and it was wickedly amusing to think about how Jessica would end up more or less doing this job for ‘free’ if I siphoned off all the earnings she was supposed to be making. Six weeks of this? I didn’t know the exact figure, but I could guess a ballpark based on how well my parents paid other employees. Once I convinced Jess to give me her passwords, I would be able to track down the messages between her and them to know for sure what the agreed upon amount was. 

Of course, it was one thing to actually babysit for free. But this? She was my ‘housekeeper,’ and going through all of this for no capital gains was a lovely thought. 

I made sure to ‘ooh’ and ‘ah’ with the other girls over the potential dresses Lillian showed us. She had plenty of ideas saved to her phone, and it was easy enough for me to pull up each and every one of them on my laptop for an audience. Once she narrowed it down to five unique styles/colors she really wanted, I shrugged and said, “I’d hate for you to choose. They’re all so gorgeous!” Further breaking my original limit in terms of how much each girl could buy, I decided to spoil Lillian and set a precedent for the rest of the girls. “Go on, buy them all. And remember to thank your favorite virgin when you do.”

While Lillian got to work inputting Jessica’s information, complete with the zip code I pulled from her driver’s license, I got up and sauntered over to the girl who had so far managed to be the statue I had ordered her to be. “Just one question, Jessie,” I calmly said. Looking down into her eyes and taking pleasure in the height difference, I asked her, “May I have your phone’s password? You have my permission to shake or nod.”

She remained silent and still for a moment. Then, no doubt after weighing the consequences of both options, she slowly shook her head. No, then. Fun. That’s what I was hoping for, as working a ‘yes’ out of her was far more enticing. “Hmm. Okay.” I sharply pinched her nipple, which resulted in the most comical whine forming in the back of her throat due to how determined she was to follow my directive about staying quiet. Apparently she thought doing so was important in terms of maybe not being naked in my furnished basement any more. Unfortunately for her, being obedient was only succeeding in avoiding further humiliation. The nudity was going to be a thing for the rest of the night. Of course, she didn’t need to know that. 

By the time I made it back, the last of Lillian’s dresses were being purchased. Making sure to voice the total that was well over $2K, I let the next girl take a seat to look at some jewelry she had been meaning to treat herself to. I looked on throughout the process and encouraged her to get a bracelet that matched the rest, once again showing that I was no longer limiting any of the girls. At least, not as long as they stayed kind of in the lane in which they started. 

Calling out that total as well, I stood up and walked back over to the naked brunette still awkwardly standing in the middle of the room and exposing herself while the rest of us were comfortably seated and enjoying some online shopping. “How about now?” I asked. “Phone password?” Just a bit of healthy extortion. Don’t want your credit card maxed out, girl? The solution is simple. Just be a little more forthcoming with your personal information. 

Once I had access to her phone and, by extension, her social media accounts, I’d start working her for e-mail access, bank account info, etc. While I had plenty of connections in terms of tech savvy people who would probably be able to crack her passwords with access to her phone alone, it would be much more fun for her to willingly offer them up. Well, mostly willingly. Then she would only have herself to blame, rather than being able to fully pin everything on me. ’’If you didn’t want me messing with your accounts, Jessie, you shouldn’t have given me access.’ Oh, this was going to be so much fun. 

Again, she resisted with a tiny shake of her head. I just shrugged. One way or the other, I knew she would cave eventually. The nervousness in her eyes was telling enough, and it was cute how she thought being strong would make a difference. Every inch of her was exposed, and she was literally being obedient to me despite being the older girl. She served me and my friends drinks, and then pissed all over the floor. And here Jessie was, defending a simple four digit passcode. The time to show a little backbone was a LONG time ago, dear. 

Shooting the brunette a playful wink, I swiveled on my heel and turned back to the rest of the girls. “Alright, who’s next?” I asked.

Chapter Nine

Jess

I didn’t know what to do. 

This was supposed to be a babysitting job. I was supposed to be in charge!! Yet somehow, I was standing there naked in front of Hannah and all of her friends. No covering. No speaking. And I was obeying her, fully exposing myself as I stood like a statue in the middle of the room. But what choice did I have? The horrid blonde had stolen every possession I brought with me for the summer. She and her friends had taken countless pictures and videos of me. It had gotten to the point where I had accepted the fact that I didn’t have the necessary experience or skills to resolve this myself. Until I could call Hannah’s parents and/or collect enough of my things to drive away and never look back, I had to swallow my pride and continue doing everything these girls demanded of me. 

Despite how I had just allowed my body to be groped in ways not even guys had explored me before, I was still determined to cling to whatever would keep this from getting worse. My phone password, for example. If Hannah had access to my contacts and mostly unlocked social media accounts, I couldn’t begin to imagine how much damage she could do. The wicked girl had proved time and time how insensitive she was where I was involved. What if she combed through my texts and replied as me? What if she compiled all the media taken of me and shared it with the world in a way that would ensure everyone that actually knew me would see it first? I absolutely could not risk it. 

An unfairly tall and slender redhead slid into the seat in front of Hannah’s laptop next. “I’ve been waiting for airline prices to go down for my Europe trip,” she said, “I could have bought a ticket weeks ago, but my father is making me be all responsible and shit with my cards. ‘Just because we have the money doesn’t mean you get to waste it.’ Lame. The whole point of being rich is to buy whatever you want whenever you want.”

“Good thing you waited,” Hannah said, “Little Jessie can treat you, and maybe you can get away with spending that flight money on something fun. Like doubling your shopping spree budget once you’re there?”

“It’s easy to be ‘responsible’ when you have more money than expected,” the redhead giggled, “I wish my parents were as whatever about money as yours.”

“Mm hmm. They left me alone for the summer and paid for a live-in housekeeper for me. Too bad she’s not very well trained. Hell, she’s not even house trained.”

“Look on the bright side, Hannah. It’s not a bug; it’s a feature. I mean, things are more entertaining with a maid like her.”

For a couple minutes, the two of them went back and forth about the kinds of things only two rich girls could talk about. My friends and I would never in a million years complain about the kinds of limits we couldn’t even reach if we tried with our collective savings. If I didn’t keep up a part-time job each semester, textbooks and meals alone would start eating into my account. That’s why I took the lucrative summer job in the first place, as it was a better financial decision than lounging about or finding something that would ultimately be more work for less pay. Perhaps that’s what I should have done after all. That, or at least get more details. I assumed I was getting paid a lot because Hannah’s parents were rich; never once did I consider that her age or cruel nature might be a factor.

The red haired girl finished up with her browsing, speaking the total out loud. “See, that’s not even that expensive. $9500 for round-trip first class? Whatever. It’s not like waiting another week would have made much of a difference.”

Hannah smirked. “Jessica can cover that for you. But since she’s my maid, I expect you to bring me back something nice out of that extra $10K you’re getting to shop with! Sound fair, virgin?”

I couldn’t help but let out another one of those embarrassing squeaks from the back of my throat. Hannah was addressing me, but I wasn’t supposed to be talking. So I kept my lips clamped shut, not wanting to give her an excuse to make an already mortifying situation worse for me. This whole credit card thing had already given me butterflies since the very first purchase. I wasn’t 100% sure whether or not they were actually using my card or not, or simply using it as a scare tactic. The laptop was facing away from me, and Hannah easily could have her own card info programmed into her browser. If they were spending thousands of dollars of my credit, however, I’d have to go through the hassle of reversing the charges. More importantly, if I got maxed out, which was already dangerously close to happening if this international flight purchase went through, I wouldn’t be able to use my cards for anything until I sorted things out with the company. 

Also, why hadn’t anything been flagged yet?! Considering how modest my own uses of the credit card were, surely expensive clothes and jewelry should seem out of place. But again, I didn’t know if they were bluffing or not. Regardless, the thought of being on the hook for ten thousand dollars was daunting. 

“And, done!” the girl grinned, “God, it’s so much easier with another girl’s money.”

Hannah stood up without a word and sauntered back over to me. “All I need is your password, Jessie,” she quietly said, “Unlike you, I’m allowed to move. If I could get into your phone, I could undo some of those charges. Wouldn’t you like that? You may nod.”

Nervously looking up into her eyes, I gave the smallest shake of my head. No. It wasn’t worth the risk. 

She just sighed. “Suit yourself.” Before I noticed what she was doing with one of her hands, Hannah’s fingers were tracing up my bare slit. No doubt noticing my gasp and reflexive attempt to shift backwards and away from her hand, she glared and reminded me, “Do NOT move. Not a fucking inch, Jessie.”

I froze, with wide eyes. What was she doing??

“Here’s the deal, little virgin,” she quietly said. Fingertips tracing up and down my outer lips, she paused in the center to give the smallest of taps, “Either the first person to ever penetrate you outside yourself will be a girl . . . ” To emphasize her point, she lightly pressed into me. Just enough so I could feel how easily she could push inside, but she backed off at the last moment. “ . . . Or you tell me what I want to know.” With another teasing stroke up and down, grazing her nails against me this time as she moved against my womanhood, Hannah settled in the same precarious spot as before. “What’s it going to be, Jessica?”

I wasn’t stupid. I knew exactly what Hannah was doing. Objectively, it didn’t count. Since I was actually straight, it’s not like another girl touching me like that counted. But it would still undeniably be a first, and letting Hannah of all people take that from me? I would forever have to live with the knowledge that I had been willingly violated in such a way. Because, while I could push the blonde away and retreat away from her, it was like my feet were rooted to the spot. Partially from the repetition of Hannah’s orders, and also because moving in the slightest risked the eighteen year old’s fingers pushing inside me before I succeeded in getting away. 

Frozen in indecision, I closed my eyes to temporarily escape the cocky smirk and the piercing eyes gazing down at me. I didn’t even consider the fact that doing so might make it look like Hannah’s touch was affecting me in some way. 

Hannah wasn’t okay with that, however, and quickly snapped, “Fucking look at me, virgin. I asked you a question.”

Cursing myself for giving her an excuse to chastise me, when I had just lectured myself about not providing such opportunities, I opened my eyes right away and forced myself to look up at her smug yet stern face. Right away, I was tempted to avert my gaze. I was already pretty bad at lingering eye contact, but it was so much worse when I felt beyond vulnerable in my fully undressed state. 

“Do you want me to, you know . . . ?” Hannah gave my slit another tap with her fingertips, followed by a threatening/teasing push. 

Cheeks turning crimson, I gave a small shake of my head. 

“Then . . . ” she trailed off again. Not needing to say what she wanted again, Hannah merely maintained the pressure on my outer lips. It would take so little for her to actually slip inside. I could already feel myself naturally parting for her. Not that I was excited by this in the slightest, but it was still someone touching me down there. My body was reacting the same way it did when I pleasured myself. I mean, my fingers were feminine. Since that’s what I knew, and Hannah was also a girl . . . it’s like my body didn’t know the difference, even if my mind did. 

It was painfully impulsive, but I quietly blurted out, “1163.”

And that was that. “Good girl,” Hannah said. Fulfilling her either/or setup, she dropped her hand from my most private area right away. Before stepping back, however, she continued facing me while addressing her friend. “Lillian? Check.” Lowering her voice again, she turned her words back towards me. “You didn’t lie, did you? Because pathetic little virgins who misbehave get punished.”

My voice abandoned me again. All I could manage was another shake of my head. The small left/right motion made my unkempt hair shift enough to remind me that I hadn’t been able to dry it properly or style it after my shower. Insult to injury, really. The maid uniform obviously stripped away my authority, as did being naked, but I also wasn’t put together in the slightest like the rest of the girls here were. 

Lillian replied, “I’m in.”

“Good girl,” Hannah echoed, “And the plane ticket?”

“Completed!” the redhead exclaimed.

“Great.” Calm as ever compared to her tipsy friends, the blonde before me swiveled on her heel to face the rest of the room. “Move the party back to the pool. Bring the snacks and drinks, too. Jessie and I will join you shortly. After a private chat.”

No one complained or objected. Chattering away like this was just any other sleepover, the girls made short work of grabbing whatever drinks and snacks they were still working on. They left the empty glasses and containers, of course, no doubt for me to clean at some point like the maid they all believed me to be. I couldn’t believe that I agreed to the ‘housekeeper’ role. More importantly, how could Hannah’s parents think it was a good idea? It was one thing to trick a tween in such a way, but Hannah was technically an adult. I could see how she and her friends needed supervising, however. They certainly acted like teenagers, and spoiled ones at that. But clearly I wasn’t the girl for the job. 

Hannah patiently waited until the furnished basement cleared out completely. Whichever girl was last out of the room closed the door at the top of the stairs behind her. Even then, Hannah remained quiet. She was back to facing me, and was uncomfortably close compared to the distance I’d normally take when conversing with someone. I still wasn’t allowed to move or talk, so I simply continued blushing and twitching my fingertips against my bare thighs in nervousness as I kept my arms down. 

What was she waiting on? 

After another minute or two, the house was quieter than before, no doubt as the girls upstairs trickled outside to continue drinking. And to gossip about me, probably, as a lot more had happened in the basement to supplement what they had already witnessed.

Then, out of nowhere, Hannah slapped me between the legs. HARD. 

I gasped in both shock and pain, and was unable to stop myself from instinctively covering myself with a hand. Self preservation overcame the fear that Hannah had instilled in me, but that wouldn’t last for very long. 

As I was still reeling from the jolt of pain that had raced up my spine from the way Hannah struck me, she reached forward and sharply pinched my nipples. “What the fuck, Jessie?!” she snapped. Digging her nails into my flesh and twisting my nipples in opposite directions, she glared daggers at me. “You’re a little girl. You’re a pathetic virgin. How dare you have boobs like this?” She stamped down on both of my bare feet with her own, and roughly shoved me backwards by my breasts. 

My arms flailed as desperately as they had tried to keep my balance when I had been pushed into the pool, but to no avail. With my feet pinned, it was literally impossible to do anything against the force of her hands. I fell to the ground with absolutely zero grace, wincing as I landed on my bare ass. As her friends had so kindly pointed out, I was pretty scrawny back there. My tailbone collided directly with the floor, and the firm carpet did very little to protect me from what I assumed was concrete below. Gasping again, although with very little breath due to how the fall knocked the wind out from me, I looked up in horror at the blonde girl now towering over me. 

“I asked you a fucking question, Jessie!” she spat out. Taking a step forward, she narrowed her eyes and repeated herself, “What the fuck is a miserable servant girl like you doing with boobs that big?”

Abandoning her former directive to stay still, I couldn’t help but scramble backwards in an attempt to get away from the intimidating girl. She didn’t seem drunk, but I also knew this would be a lot more difficult to handle if the alcohol had gone to her head in a way that wasn’t outwardly noticeable outside of this. Or maybe she was stone cold sober and just upping her game. Either way, I didn’t love the position I was in. Outside of being low key terrified of the girl who had made my life a living hell for the last few hours, I was also utterly bewildered. I mean, it’s not like I chose my breasts!! While I certainly appreciated them, considering the rest of me was less womanly in comparison, that’s just the way I developed. How could she be mad about something completely out of my control?!

Continuing to unleash her fury on me, Hannah kept her voice raised like it had been when she yelled at me for the accident I had earlier. And even that wasn’t my fault! “Oh, and I’m getting real sick of you resisting and complaining. You are my fucking maid, Jessica. That means obedience. Like, all the time. You do anything I say, no matter what. I swear to God, if you put one more bare toe out of line, I will strand you just how you are in the middle of town. Or maybe you’d like that. What do you think? Naked in public, or naked and obedient here?”

My mouth hung open in disbelief. She wouldn’t do that, would she. She couldn’t! This was already the most mortifying thing to ever happen to me. But a bunch of girls moderately close to my age seeing me fully nude, compared to this latest threat? It was a completely unfair either/or, but I immediately knew which one I would prefer. “I-I, umm-”

Glaring at me, Hannah harshly demanded, “ANSWER.”

With watery eyes and a suddenly very dry throat, I meekly uttered, “H-here.”

“Stop. Stop fucking moving right now, virgin. Tell me that you will be fully obedient, like a good little maid.”

I did as I was told. Instead of scooting backwards on the rough carpet, I awkwardly let my ass and then legs settle down while making the effort to keep my thighs clamped together to protect what little modesty I had left. Now that I was no longer moving, Hannah continued walking forward until her legs made a V over me. Her calves brushed against my bare midriff, and I felt more vulnerable than ever. Naked, as physically beneath her as possible, and somewhat pinned as well. Temporarily distracted by the development, it took me a moment to come to my senses and repeat her words. “I’ll be obedient,” I said, “A good maid.”

“A good little maid,” she clarified, “And fully obedient. Say the whole thing, Jessie.”

“I’ll be a good little maid. I’ll be fully obedient,” I quietly echoed.

“You’re a lesbian virgin?”

Deeply blushing, I nodded. The sexuality part of it wasn’t true, but now was not the time to deny pretty much anything. After a threatening look, I actually said it out loud. “I’m a lesbian virgin.”

“That’s what I thought.” Hannah began bending over. She brought her face closer and closer to mine, and eventually ran her fingers through my hair until she was cupping the back of my head. For a moment, I thought she was going to kiss me. I had absolutely no idea what I would do if that ended up being the case. Instead, she pursed her lips into the same casual smirk she had before yelling abuses at me. Lowering her voice to a borderline sensual whisper, she said, “Because the next time you misbehave . . . ” 

She paused, staring me down. After a few seconds of intense silence, her fingers grasped and twisted at my hair before she abruptly yanked me upwards by my long, brunette locks.

Chapter Ten

Jess

I gasped in both pain and horror as my hair was abused in such a way.

Hannah wasn’t just pulling on my hair; she was dragging me by it. Before I could get my feet under me from the harsh, upwards yank, the tipsy blonde was storming forward without relenting in the slightest in terms of her grip. My scalp was on fire as my locks were used in such a way, and I scrambled to do anything that would lighten things up there. Hannah forced me to the base of the stairs, giving a sharp twist to my hair before starting to slap at my bare boobs.

Out of reflex, I tried to squirm away and cover up, but the tipsy blonde wasn’t having it. “HEY. You said you would behave! Hold still, right the fuck now. That’s an order.”

Belatedly recalling all the things I had agreed to recently, albeit under duress, I had to go against every instinct my body was telling me in order to keep my hands down as she continued her assault.

After another few hard slaps to both sides, Hannah pinched down on one of my nipples and twisted it to what felt more than 180 degrees. “Apologize for your boobs!” she hissed in my ear, “Or I swear to God, I’ll rip your nipple off.”

I was already terrified of the girl, especially when it was pretty clear the drinks she had consumed had put her in a state that was nothing at all like the cold and collected way she had presented herself as earlier even before her friends had arrived. Or maybe this fury was always there, and it was only just now boiling over. And for what?? Again, it’s not like I chose my body! If I did, I would have given myself some more height and an actual ass to pair with my larger breasts. It made no sense for Hannah to be this mad about my figure, but she was also a drunk teenager. “I’m sorry!!” I rushed the words out, trying to contort myself in the desperate effort to alleviate some of the awful sensations on my chest. “I’m sorry for my boobs!”

Not letting up quite yet, Hannah twisted a little bit harder and dug in her nails, “You will do everything I say, and you will not hesitate or complain. At ALL, Jessie.”

“I will, I will!” I hurriedly exclaimed, “Anything! Please, Hannah.”

At that, she let go, but not without delivering one last SLAP to the same breast she had been pinching. “Run upstairs. Sit on the sofa and spread your legs. Smile for the camera when I walk in.”

I didn’t need to be told twice. It was honestly less about her directive about how I needed to be immediately obedient, and more about how I was jumping at the chance she was giving me to get away from her. Very much running like she suggested, I yelped in surprise as she slapped my ass when I turned around, I didn’t let it slow me down. Hurrying up the stairs and bursting through the door at the top, I only paused after turning the corner to process the rest of her words. My legs . . . and a camera?

But Hannah could be following me up any second. If she caught me standing around instead of being obedient, I could only imagine what she might do. Clearly she had set that up so her friends wouldn’t see her being so aggressive, but she had also proven there was plenty she had in her arsenal to use against me when they were there as well.

Against my better judgment, like so many other things I had gone along with since I was always stuck choosing between the lesser of two evils, I returned to the now empty living room and gingerly sat myself down. Even though I was the only one there, I still somewhat cringed as I lifted my legs and splayed them for the crowd of zero. Hannah would no doubt be up shortly, and I was beyond tempted to slam them shut before she arrived to protect my modesty. This was more than I had been showing off downstairs, and I had been directly told that there would be a camera involved.

Sure enough, Hannah appeared around the corner not much later. Unlike my quick, worried pace, she was clearly content to take her time. Sauntering in with more of the smug expression from earlier in the day, rather than the harsh ‘I’m going to destroy you’ demeanor she had been displaying downstairs, she wasted no time in holding up her phone and training the camera on me. “Smile, virgin,” she bluntly said.

Considering the low key torture my most private areas had gone through, combined with my full nudity and current slutty exposure, it was a pretty tall order. Still, I had to obey. For all I knew, she had already taken a picture in case I ended up chickening out. Forcing a meek smile onto my face, I looked at the lens and clung to the hope that somehow doing exactly what Hannah said would eventually lead to me getting my things back. That’s all I really needed; phone, wallet, keys. Then I would peel out of her property and never look back. I would just have to pray that I could manage the damage control all on my own, considering her parents were still out of the country. Credit card company, and potentially pictures online. It wasn’t fun to think about, but staying would probably land me in deeper trouble than I was already in.

Moving on, she stepped a few feet closer and instructed, “Now say, ‘I’m a lesbian slut.’”

Nervously swallowing and keeping the faintest trace of a smile on my face in case that was something she still wanted, I echoed, “I’m a lesbian slut.”

Staying quiet for a few seconds, no doubt so the clip of the phrase would work before she insisted on the next one, Hannah said, “My name is Jessica, and I’m a pathetic little virgin.”

Once again, I said it word for word, blushing a bit at the fact that I was using my full first name. God, my reputation would be obliterated if anyone on campus saw this. Or family, or . . . Wait, she had my phone password!!

Before I could mentally project much further in terms of the daunting possibilities that were now racing through my mind, Hannah was taking things further. “Almost done, Jessie. Just one last thing. Touch yourself down there, grab a boob, tilt your head back, and start moaning.”

The reluctance on my face must have been easily apparent.

“Do as I say!” she snapped, “You’re my obedient fucking maid. Or would you rather be punished again?”

That got me moving. Keeping my legs as wide as they would go without the assistance of my hands, I touched myself both above and below where I had been told to. Absolutely mortified, yet pushing through nonetheless, I tilted my head back and closed my eyes. She hadn’t demanded the last bit, but it would have been a little weird to keep them open. That, and it helped in terms of shutting the world out to some degree. Hannah hadn’t told me to actually get off, and I’m not sure I would have even been able to on command. I had only done that in the solitude of my bedroom, which meant I was suddenly in the first situation ever where I would need to fake it. For a video, of all things, rather than to boost the confidence of a future partner. Despite Hannah’s games, I was very much a straight girl, and had been told that guys weren’t always the most successful when it came to that kind of satisfaction.

I wasn’t the most vocal girl in terms of pleasure, especially since I had mostly touched myself in my dorm room and in my bedroom at home when I was on break from university. Both of those places required biting my lip and keeping things as breathy as possible, but now I found myself at the total opposite extreme in terms of making noises. How was I supposed to ‘perform’ for the camera when I barely knew what I sounded like?

Since I couldn’t hesitate or complain without risking Hannah’s wrath, however, I went right for it. Moving my lower fingers just enough to try to spark some of those memories and lean into them just enough to satisfy Hannah’s desire to humiliate me, I parted my lips and let out a quiet moan. Guessing that it wouldn’t be enough, I forced a shaky inhale before using the exhale to fake a louder feminine sound that sounded way more slutty than I intended due to the breathy quality of it.

Hannah’s voice sounded in the darkness a couple seconds later.

“More, Jessie.”

Trying not to cringe at what I was doing, I started moaning out in a more pornographic way. I didn’t even watch stuff like that, but I also wasn’t naive; plenty of people talked about the cliché over the top sounds that were often found in those videos, and I was experiencing firsthand how it wasn’t natural in the slightest compared to how I would actually react to any kind of touch.

After a couple of exaggerated moans, complete with rubbing and squeezing myself mostly so my hands weren’t just awkwardly frozen on my body, I was told to stop and open my eyes. Back to her outwardly cold and indifferent self, Hannah didn’t even comment on anything I had just done by her command. Instead, she simply said, “Kitchen. Now.” Then she swiveled on her heel and led the way out of the room.

Quickly getting to my feet, still nervous about what she might do if I failed to obey in a timely manner, I barely had any time to think about what I had just done. At least everything else had been contained to the cruel blonde’s house, mostly, but this latest act would singularly be enough to completely ruin me. While she hadn’t actually threatened anything, the existence of the video was enough for me to sweat at the potential implications and mortifying possibilities.

Now that I had just been holding myself in those areas, I was keenly aware of the fact that I was truly naked. Shivering a little bit as I rushed to catch up to Hannah, I wrapped one arm over my chest along the way, and used my other hand to cup my crotch. Despite everything, I still felt the need to maintain a bit of modesty. I hated being naked around other people; locker rooms were bad enough, and this was not at all a normal situation to be completely undressed.

Glaring at me as I stepped through the threshold into the kitchen, Hannah snapped, “What the fuck are you doing, Jessica? Arms down.”

I dropped my arms. “Sorry,” I mumbled. As the apology escaped my lips, it dawned on me just how far I had fallen. I was supposed to be babysitting this girl, under the guise of being around to also take care of the house. In less than half a day, I had somehow allowed myself to be fully stripped and was now bending to her will in more ways than an actual maid would. True obedience, down to continuous nudity brought on by her demands, and there was absolutely nothing I could do about it.

Once I had complied, she gestured to two large bottles of water that were waiting for me on the counter. “You need to stay hydrated, virgin,” she said, “Drink.”

Stepping forward right away and picking one of them up, I saw that each bottle was a full liter. A single one would normally be what I would drink over the course of maybe an hour, unless I was particularly thirsty, and she was pressing me to consume double that amount.

Under normal circumstances, I would have said something. That I had plenty of water already throughout my drive today, or how I was pretty sure she was doing this in response to the fact that I had somehow wet myself in front of all of her friends thanks to how I had waited and waited and waited to use the bathroom only to find myself delayed by all of their invasive questions and denied the privilege until I couldn’t hold it any more. Did she want that to happen again? Or was this just yet another way to make me uncomfortable, as well as a test to see if I would choose to jump when she said jump vs. opening the door for more punishments? Still very much scared of the latter, particularly now that I was averse to my hair or my body being yanked around in ways that I never wanted to go through again, I didn’t waste any time. Undoing the cap, I pressed the bottle to my lips and started drinking.

Mere seconds after my first swallow, Hannah yelled at me anyway. “Why are you taking so long? Hurry the fuck up, Jessie! I want to get back to my friends. Do you really think I want to hang out with some naked virgin with stupid big boobs?”

Blushing deeply at the crass comments about me, I did the best as I could to suck the water down. This was the third time I had been compelled to chug something since Hannah twisted the ‘housekeeper’ thing to work completely in her own favor, and this instance wasn’t any better than the others. First it was bubbly alcohol that was difficult to down quickly, paired with the knowledge that I really shouldn’t have been drinking something like that on the job. The second time was far less water than I was currently faced with, but it had also added pressure to what was already a borderline emergency. Now, I was buck naked and feeling more self conscious than ever, all while trying to reach a pace that was completely unattainable as Hannah kept pushing for me to do better.

Panting out an exhale as I finished the last few drops, I barely had time to recover from how bloated and breathless I was feeling from the non-stop drinking. Hannah shoved the second large bottle into my hands. Towering over me in just her bikini and short shorts, she sternly demanded for me to stop wasting time.

Earlier, I had felt a little weird about wearing a bikini at her place, especially once I heard that she had guests coming over. Now, I would have given anything to be wearing skimpy swimwear or lingerie if it meant I could have something to cover with. Bracing myself with a shaky breath, I repeated the process of bringing the second bottle to my lips, knowing full well that the coming round would go more slowly. I was already feeling a little bloated, and a liter was a lot for me. Two back-to-back felt impossible, but I was in no place to protest.

Little by little, I chipped away at the task, going as quickly as I could without stopping for a break. Hannah berated me and insulted me pretty much the whole time, which did succeed in getting me to try my very hardest to avoid her judgment and potentially worse. After what felt like forever, the last of the water was in my cheeks, although I took an extra few seconds to get from the chipmunk-like moment to actually swallowing the last of the water.

Not praising me or looking particularly impressed like most girls would after a successful dare, not that that’s what this was, Hannah flicked both the bottles off the counter. “Get back to work, Jessie. This kitchen needs to fucking sparkle.” She pulled open a couple drawers and lower doors. “Oh, wash these, too. All the pots and pans look a little dusty, and these utensils probably need a good scrub.”

My heart dropped at what she was suggesting. If I hadn’t felt so vulnerable, and so full from my latest ordeal, I might have been more stunned at the audacity. Everything Hannah was telling me to wash was already clean. They were put away properly, and I had to guess whoever the wealthy family had last hired to cook and tidy was good at their job. This was just work designed to make my night more miserable, and the blonde teenager knew it. Her little smirk made that crystal clear.

Hannah walked right up to me and slapped one of my boobs. “Behave, virgin. Leave the sliding door cracked, too. This is the same job as before; you’re my maid and you’re our little drink bitch for the night. When we call for you, you will drop everything. Say it.”

“I’ll drop everything . . . ” I mumbled, averting my gaze for half a second before looking back up at her in case a lack of eye contact was bad.

“Good girl,” she said, “As long as we have snacks and fresh drinks at all times, we’ll be happy. You do want us to be happy, right?”

Still very much blushing, and partially in denial that all of this was really happening to me, I nodded, “Yes, Hannah.” Just like I had been taught earlier. It was so demeaning, but I knew it was the best way forward.

“Of course that’s what you want,” Hannah rolled her eyes, “You’re a horny little lesbian virgin; you probably have a crush on all of us. Especially me. Do you have a lesbian crush on me, Jessica?”

Such a trap. I instantly regretted showing off my retention skills, as now it felt like I only had one response to choose from. Anything else, and I might piss her off. Not a great idea when she was so inebriated and entirely unpredictable.

So, I quietly murmured, “Yes, Hannah.”

Chapter Eleven

Hannah

With Jessica naked and more submissive by the second, I knew it wouldn’t take much longer to break the girl. Maybe I could even pull it off by the end of the night.

Some of my friends probably assumed that I had already succeeded at that endeavor, but I knew better. Sure, the brunette had been thoroughly humiliated, but people were more complicated than simply drawing a line from X to Y. I could tell by both Jess’s body language and the look in her eyes that she was a lovely concoction of embarrassed by her nudity, frustrated yet unable to do anything about those frustrations, and desperate to somehow get this ‘housekeeper’ job back on track. The latter two were always the interesting ones. It’s what made the game fun, but it also required a delicate balance. If I pushed too far, little Jessie would snap. But not if I cleverly kept holding so many things over her head while simultaneously offering the slightest shred of hope along the way.

If she could just get through this evening, then maybe things would get less awful for her. Maybe. Even when tipsy, I was more than capable of reading the look in people’s eyes. All it took was mentioning the logistics of carpooling home. On the surface, it seemed like I was simply having Jess stand there for nothing while I talked to my friends; in actuality, I wanted her to hear that there was a little light at the end of the tunnel–this wouldn’t be a sleepover. Not tonight, at least. Although since everyone present had been drinking, they’d be using app-based services to get home. And, since all the girls were leaving their cars, there would be a perfectly good reason for me to host the following day as well. As for the current evening, I wanted Jess to look forward to it being just the two of us. Surely she’d want to have a serious conversation. I doubted that she’d pull such a thing off while buck naked, but it would be amusing to see her try.

For the time being, however, I would work on conditioning the girl, and setting herself up for more embarrassment.

The first thing I had her do as ‘drink bitch’ was bring us all a fresh round of cocktails, all with unnecessarily specific instructions. We were running a little low on cans anyway, plus I enjoyed the thought of Jess toiling over each individual drink now that she was no longer in a place where she could get on our case about drinking. I also had her bring out two liters of water. Of course, I didn’t tell her that the water wasn’t so my girlfriends and I could hydrate alongside our alcohol consumption. Instead, I demanded Jess to chug them.

I wasn’t totally sure that I could make the little brunette have two public accidents in one night, but it worked for me either way. Even if she managed to somehow find somewhere to go this time around, I’d still get the pleasure of watching her squirm with desperation leading up to it. Her awkwardness was hilarious to me, as was her total lack of control when she was supposed to be the one in charge this summer. The best part? She didn’t protest in the slightest. Jess just started drinking, as she was clearly getting the memo that she had to do anything that I said or face the consequences.

While I enjoyed seeing that she was also being obedient when it came to my directive about not covering up, that also meant that I had to see her obnoxiously good boobs. Letting my annoyance drive me a little bit, I started sending her off to do chores that didn’t even need doing. While it was partially in line with my devious thoughts about ensuring that she had absolutely no down time, I also wanted to remind Jess that she had to do everything I said. Aside from her outstanding assignment of making the kitchen spotless, as well as providing us refills whenever we called her back, I told our nude servant girl to dust all the blinds, give the trim in every room on the main floor a good wipe, and polish every knob and handle she could find.

Thirty minutes later or so, I got a notification on my phone that the cameras I ordered arrived. God, it’s great to be me. There are so many companies that go out of their way to impress families like mine, as they know that quality and efficiency will result in repeat business and possibly referrals. Sure, plenty of places strive to do that for as many customers as possible, but it’s a special case when they know someone like me will spend hundreds (sometimes thousands) of dollars without blinking an eye. After calling Jess outside and telling the girls to keep her busy for a few minutes, I went in to set a few pieces of the tech up. I definitely didn’t have time to do everything, nor was I sober enough to install all the necessary components that would ultimately sync up for my viewing pleasure on whatever device I wanted, but I could at least get a couple videos going. The one in my bedroom was easy to mask with all the other things on my desk. As for the one I stuck in Jess’s room, I’d just have to hope she was too blind to notice the camera that I stuck just above the window. The curtains would mask the cord well enough, but I wasn’t able to mask the rest of it very well. I still wasn’t 100% sure what the rest of the evening would look like, as I was still playing a lot of this by ear, but presumably Jess would either end up sleeping on my floor or on her mattress that was currently stripped of even the fitted sheet.

On my first pass of her room, I had simply taken everything out of her bags so she would be faced with the dramatic reveal that all of them were empty. Once I decided it would be best to keep the girl naked for the foreseeable future, however, I circled back to remove anything that she could possibly grab to cover up. Shame that I couldn’t pull down the curtains, although I doubted little Jess would go so far as to yank the rod off the wall. Besides, now they worked in my favor, at least until she was defeated to the point where she knew the cameras were there and was too scared of the repercussions to unplug them or take them down.

As for the security cameras that had previously been used for the tail end of what could be considered ‘phase one,’ I’d have to get my tech-savvy friend to pull all the footage of Jess before deleting the rest. I normally didn’t give a shit about that kind of surveillance, as it was really only there as a ‘just in case’ measure. But with my parents on vacation for so long, I couldn’t say for certain whether or not they would check in on me every now and then. The kitchen and the pool were already a blind spot for them, as I had a video looping system that I used all the time in order to get away with stuff like drinking and skinny dipping. As for a naked brunette waltzing around the rest of the house, however, I’d have to be a little more diligent about making sure I was the only one who had access to those feeds.

Whatever. Now that I had sent my parents a message from Jess’s phone, telling them things were going smoothly, I doubted they would log into the house’s security system until they were unpacked and had reliable Wi-Fi. By that time, I would be using my personal cameras–bought courtesy of Jessica’s credit card–and the usual equipment would be manipulated to show my parents only what I wanted them to see. Hmm, although I’d need some stock footage of my babysitter . . . Oh! That would hardly be a challenge. I’d just get one of my brown haired friends to put on Jess’s glasses and walk around doing chores and checking in on me in a variety of her outfits. Simple enough. My parents wouldn’t be in detective mode; as long as I changed tops whenever my friend did for each shot, they’d be none the wiser. We could film all that tomorrow, preferably in the morning, as I was confident that I could keep Jess outside for a couple hours the same way I did today.

Now, back to business.

This was the first time Jess was at my friends’ mercy without me serving as their ringleader. I was quite curious what they had gotten up to in my absence. It was honestly the opposite of FOMO; the mystery was actually kind of fun, as I hadn’t really left them any instructions beyond ‘keep Jessie outside until I’m back.’ Luckily, I wasn’t the only wicked one around.

They didn’t disappoint. As I stepped back into the warm night air, the first thing I saw was Jess being coached through various yoga poses. One of my bendier friends was showing her what to do, which made it doubly comical as the bare brunette fell short each time. Not only was she not as flexible as Taylor, but it was pretty clear that being so exposed made Jess hesitant to commit all the way to each move. Smirking to myself at little Jessie’s less than impressive backside, I hung out just a few steps outside the kitchen for a minute, wondering when the naked girl would notice me. All my friends glanced over right away, but their drunk giggling and not so hushed whispers apparently weren’t enough to clue Jess in while she was degrading herself in such a way.

I padded a little bit closer, wondering how far I could sneak up on her, but paused halfway as I noticed something exciting. Last time my petite ‘housekeeper’ had to pee, she had been dressed in the slutty maid outfit. Now that she was fully nude, however, I could tell even from my angle that she was a little bit bloated. After all, I had seen Jess in a bikini earlier. Her stomach was normally flat, but forcing down so much water at once made it visibly clear how full she was. Once I recognized what was usually just a sign that someone had too much to eat, often at holidays, it was easy to perceive some of the other signs. I had assumed that Jess’ occasional fidget since my arrival had merely been nerves and self consciousness from being continuously naked and bossed around by so many younger girls, but maybe it was more than that.

Bailing on my plan to surprise her from behind, which may or may not have involved pushing her into the pool, I instead made my existence known with a blunt question. “Hey, virgin? Do you have to pee?”

I was satisfied when my voice had the intended effect. My friends were one thing, but my little stunt in the basement no doubt left Jess most intimidated by me. She jumped a little bit, and promptly forgot that she was supposed to be mirroring Taylor in the latest bent over yoga pose. Jess’s arms twitched, as her reflexes to cover temporarily kicked in, but she managed to keep them down. Good girl. Less than 12 hours, and she was already wonderfully obedient.

When Jess’ startled silence dragged on for a few seconds too long, Lillian piped up instead. “She does look like she needs to go, doesn’t she?” I wasn’t sure Lillian could see the same signs as I could, but I didn’t mind that she was going for it. Talking about another girl as if she wasn’t there was always a solid social tactic when you wanted to bring her down a peg or two. Or ten. “Although clearly your pet isn’t house trained yet. Wait! Pets don’t use toilets, do they?”

Willow, my red haired friend that was clearly a little more intoxicated than the rest, gasped and then grinned. “No! They go outside!”

Not a terrible idea, although perhaps not tonight. I gave her a small smile of approval, mentally pinning the idea for potential later use, but I was still more interested in watching Jess have another accident. I hadn’t expected all that water to go right through her; now that they had, however, the gears were quickly turning. Was there a way to spin this where it would be even more embarrassing than last time? Obviously it happening twice, the second of which involved nudity, was pretty good. But surely there was a way to make it even worse for the girl, as I was still determined to make this night as miserable as possible for her. Not just for the fun of it, either; the further she fell tonight, the better the next morning would go.

“I asked you a question, Jessie,” I said, turning my attention back to the exposed girl, “Do. You. Have. To. Pee?”

The look on her face was priceless. And I understood. It was so direct and a little crass, not to mention that she was being asked in front of all my friends. Still, she eventually found her voice. Averting her gaze, Jess said, “Yes, Hannah.”

Two for two, girl. Not bad. No covering, and proper terminology. Almost good enough, but she could stand to do a little better. “Yes, Hannah, what?” I pressed, “Tell me what you need, pet.” Honestly, it was jumping the gun a little bit to call her ‘pet,’ as I had planned on easing her into that concept with the ‘obedient maid’ thing, but it was different now that I was bouncing off Lillian’s use of the word. I could always roll things back based on Jessica’s reactions. If anything, it was more like this opened the door to pivot between titles for the girl. I was still most fond of ‘Jessie’ and ‘Virgin,’ with the occasional ‘Jessica’ when I wanted to snap her to attention. Still, it wouldn’t hurt to add the maid/pet combo to the rotation.

She was a little more hesitant this time around. Since I was watching carefully, I even noticed the tiny breath of courage she tried to take without tipping anyone off to what she was doing. Nice try, Jess. She blushed and said, “I need to go to the bathroom.”

Not good enough. And unlike her, I had all the time in the world. “That’s not what I asked, Virgin.” Pausing mostly to make her more nervous, but also to build suspense for anyone who didn’t quite catch what I was going for in their inebriated states, I clarified, “Do you have to pee?”

And there it was. I saw a flash of realization in her eyes, followed by a darker blush on her face. Clearly Jess was desperate, as she didn’t whine or argue when it came to what I was pushing for. A bit more quietly than before, she muttered, “Yes, Hannah. I have to pee.”

A few of my friends snickered at the admission, but I managed to keep a straight face. I was the collected, dominant girl. She was the flustered, submissive maid. Though I wasn’t totally sober myself, I was quite committed to keeping my shit together at the moment. Setting up a dynamic like this was just too perfect, especially now that dear Jess was once again in a position where she needed my permission to relieve herself. And that was on top of the fact that she was naked, and still far from earning a single stitch of clothing.

“See? Was that so difficult?” I asked. She was probably too overwhelmed to fully process that I was verbally reversing the roles for the fun of it, and making myself sound like the authority figure that she was supposed to be. “Go on, then. But use the one on the first floor. I don’t want you straying too far.”

Once again, I could read her like a book. Considering how closed off most of the house was earlier, since I had been pretty diligent about locking as much as possible when she was in the shower, of course Jess was nervous that she would run into a similar problem. “Is it unlocked?” she hesitantly asked.

Good. Seeing how she was a little nervous about basically everything was both validating, and was useful in knowing how easy she would be to pressure and manipulate moving forward. “Yes,” I lied, “You do realize the rest of us have needs as well, right?” Theoretically, the locked door didn’t matter. If the little virgin was as obedient as I was hoping she would be, then she wouldn’t make it that far. And if she did, then I would get to punish her for disobeying.

It was a win/win for me, and the idea I had in mind would also allow the other girls to get involved without me needing to actually explain it like I had done ahead of time in regards to Jess’s credit card.

She gave me one last look, clearly waiting for the other shoe to drop, but I was completely unreadable compared to her own transparent expressions. The perks of being a pretty, popular girl. I was quite adept at showing only what I wanted to, and that was around people that were on my level. Jess definitely didn’t fit that bill, nor was she at all in the headspace to study me like that anyway. Not that I had ever gone this far with a target of mine, and yet the ideas kept coming.

I waited until Jess was just a few steps from the house, and then called out to her. “Come back, Jessie! Lillian needs a refill.”

Chapter Twelve

Hannah

It really was too easy.

Now that little Jessie had been conditioned over the course of the afternoon to be obedient to me and my friends, especially now that I had thoroughly intimidated her and shown her that there were consequences for not listening, she clearly didn’t have the backbone to ignore our calls.

For a couple minutes, we continued to summon her back, always waiting until she was just within reach of the kitchen or the hallway beyond. A fresh drink, a new bowl of chips, a towel from where one of my friends had left hers on the porch. We were pretty much done with swimming at this point, despite the fact that we were still hanging out in bikinis, but Jess didn’t need to know that. The naked brunette had said out loud that she would drop everything for us when called, and we were all more than happy to put that to the test.

I was actually a little impressed at how well the girl was hanging on.

It had been nearly an hour since she chugged all that water, and I had expected her to look more desperate at this point. She was so little, so I assumed holding that much would have been more difficult. Jess wasn’t squirming like before, although I could tell by her expressions that each return trip was taking its toll. Since she had already admitted that she needed to pee, I had to imagine it wouldn’t be that much longer, but I also wasn’t sure if that meant five minutes or another thirty. Patience wasn’t even my issue; it would just be kind of boring to make her refresh drinks over and over again. Not only would that game get stale, but my friends and I were already pretty drunk. We couldn’t continuously knock back each glass and can Jess brought us; pouring them would be an option, but again, that would get old sooner rather than later. It honestly wasn’t worth the effort.

Instead, I outsourced creativity to the other girls. I had already done plenty, and would be fully in charge of Jess when they left for the night. Might as well let them get in on the action while they had the opportunity.

Besides, I deserved a small break, unlike Jessica.

Jess

I knew they were doing it on purpose.

Before, Hannah and her friends had ordered a new round of drinks all at once. That had been a different kind of torment, as I had to keep track of each girl’s specific cocktail while my mind was already overwhelmed with embarrassment and disorganized thoughts about how I might get this job back on track. This time around was objectively more simple, as the majority of the requests were much less involved than before, and only one or two at once, but that wasn’t the point. The issue was that I was trying to make it to the bathroom to relieve myself, not to mention how a small breather from the clique of girls would be nice.

But they wouldn’t let me make it past the kitchen. There was no way in hell I was going to humiliate myself in a similar manner to what had happened in the living room earlier. And yet, they were obviously trying to orchestrate something like that. Or maybe they just wanted to make me uncomfortable and subservient all at the same time, flexing how far they could take Hannah’s latest insistence about how I needed to come running basically whenever she snapped her fingers.

I tried my very best to feign indifference. Without a word, I continued to bring them anything they asked, while also keeping myself fully exposed. It went against every instinct I had, considering that I never walked around naked due to how I had only ever lived with my parents and currently a roommate at university. I just held onto the weak logic that they had already seen every inch of me. Covering wouldn’t really do anything, even if that would be my preference.

When I returned with the first cocktail after four separate trips for four cans, one of Hannah’s friends hopped up from her spot and walked over to me. “Look how flat she is!” the girl exclaimed. There was definitely a small slur to her words, reminding me how badly I was failing at my job. Instead of keeping them from drinking, I was serving them alcohol. “I mean, not like, her boobs. Those are fucking huge. I mean, here!” She gave my stomach a sharp slap. “So FLAT.”

I gasped from the unexpected hit. It’s not that it really hurt or anything, but the surprise was enough. Also, I certainly didn’t feel flat down there. I was so bloated from all the water I had chugged, and the slap awkwardly confirmed that my stomach wasn’t exactly as flat as she was commenting due to the current water weight. Also, it was only just now dawning on me that I hadn’t eaten since lunch on the road. No wonder I was feeling a little weak beyond the general submissiveness.

While I so badly wanted to slap the girl’s hand away, both from how she was violating my personal space as well as the rude way she was commenting on my body, Hannah’s stare alone was enough to keep my arms down. I couldn’t berate her or any of her friends when I was completely at their mercy. Until I figured out a way to contact her parents and get back to the role I was supposed to have here, I had to play nice. More than nice, really. I had to let the drunken girls treat me like I was their servant.

Hannah smirked, giving me one of those judgmental once-overs that only a rich, popular girl could pull off. Only instead of checking out my outfit, she was giving a cursory look to my bare body. “You’re right,” the young blonde said, “I guess little Jessie lives up to her cute name.”

“Mm hmm!” the girl next to me nodded. She reached out and gave my stomach a harsh pinch that instantly made me wish she had just given me another slap down there. “And yet the boys don’t want her? Why not?”

“We’ve been over this,” Taylor rolled her eyes, “Boys like hot girls, remember? She’s a virgin because she’s short and cute. No ass, either, speaking of ‘flat.’”

“And she’s a lesbian,” Hannah added, “Although she obviously can’t get any girls for the same reasons.”

“Ooh, I have an idea!” The redhead, Willow, hopped up from her spot and tagged in. Sending the other girl back to her seat, Willow placed a hand on my shoulder and made sure we were both fully facing the rest of the girls before going on. “Out of all of us, who do you want to make out with the most?”

I definitely wasn’t prepared for that. There was always a way for all this to get worse. No matter how many times Hannah and her friends proved as much, I kept falling for it. As mortifying as serving them drinks while completely exposed was, at least I could disassociate and try to blend into the background while they carried on with their immature conversations. Not that there weren’t eyes on me, of course, but I had been able to somewhat ignore them by focusing on the task at hand. That wasn’t possible when literally all of them were staring at me.

Interpreting my silence as something else, Willow gave my shoulder a playful nudge, “Don’t worry, you can choose me if you want.”

That was not my concern. I was still working through the surprise of the question, as well as where my answer might lead. If I answered, would they try and make me kiss that girl? While I had allowed a lot to happen, including the fact that I gave them all permission to touch my body everywhere in the name of figuring out why I was a virgin, making out with a girl was different. Mostly in that it would require active participation on my end, in contrast to how I merely had to stand still and swallow my pride when I had allowed all of Hannah’s friends to degrade me with their hands and their words earlier. Also, I had only ever kissed boys, and not that many of them. The idea of doing it with the opposite gender was quite daunting, considering that I wasn’t actually the lesbian Hannah was portraying me as. And to do something so intimate in front of others? Even if I knew I wouldn’t enjoy it, it was still a pretty big first, and one that would forever stand out in my mind due to how it came to pass.

The buzz from knocking back the seltzer earlier had long faded, especially after what Hannah had put me through when it was just the two of us in the basement. Liquid courage would be nice at the moment. Kiss or no kiss, there was no good answer to the redhead’s question. And everyone was staring.

“Well, Virgin?” Hannah pointedly asked, “Are you going to make us all wait forever, or are you going to answer the fucking question?”

A quick scan of the bikini clad eighteen year olds confirmed that I didn’t find any of them attractive. Partly because I wasn’t actually into girls, and partly because none of them were the company I would enjoy even under normal circumstances. Shallow, popular girls were bad enough, and adding ‘entitled’ to the mix just made it worse. Still, Hannah’s tone was enough to spark a little fear and remind me that I had to play along with whatever evil games she and her friends came up with.

“L-Lillian,” I nervously stammered. There was very little thought given to the name. I only knew a handful of the girls’ names in general, and I was worried that Willow would kiss me right then and there if I said her name due to the proximity. Hannah was obviously out. Despite how far I had fallen, I was still clinging to whatever scraps of dignity and defiance I could find. There was no way I would give Hannah the satisfaction of choosing her when she was the spoiled brat I was supposed to be babysitting.

She was quick to crush those weak embers, however. “Excuse me?” Hannah rose from her lounge chair and took a couple steps towards me. Not fully in my personal space, but enough to remind me just how tall she was in comparison. Intimidating, too. “Are you saying I’m NOT the hottest girl here?”

I half expected Lillian to look offended that Hannah was questioning my choice, or perhaps one of the other girls when Hannah implied that she was basically hotter than all of them, but they all seemed fine with it. Probably because she was still the one ultimately running the show here. If it made things more interesting when it came to their target, then naturally they wouldn’t bother bickering amongst themselves over who was the most attractive.

My focus was more on Hannah, anyway. After seeing what she was capable of earlier, it felt as if her very gaze was causing me to shrink. I instantly regretted my choice of Lillian, as I clearly hadn’t thought things through where Hannah was involved. Avoiding her amusement and satisfaction had seemed appealing in the moment, until I saw the flash of anger in her eyes. My resolve crumbled right away, and I tried to backtrack, “No, you are,” I awkwardly replied, “The hottest, I mean. I just- Lillian looks like a good kisser . . . ” The silence was deafening. After a few seconds, I couldn’t take it any more, and said, “I’d rather make out with you, Hannah.”

“Sounds to me like you’re a slut,” Hannah said. She took one more step before placing a hand on her hip. “It’s always the virgins that end up being the thirstiest, right? You want multiple girls, Jessica? Didn’t you just meet all of us today? And you already want to make out with a couple of us. Wow.”

Every time I managed to push away a blush, a new one seemed to come back in full force whenever Hannah or her friends talked about me in a new, demeaning way. And she was totally twisting my words! I didn’t want to make out with any of them. This was supposed to be a ‘if I had to choose’ thing. That’s it. “No, I-”

“Did I give you permission to speak, Virgin?” Hannah snapped. “And don’t try to deny that you want me.” She turned to her friends, taking the opposite side of me than the one Willow was on. “Jessie tried to kiss me in the kitchen earlier, but I denied her. Obviously. I’d never go for someone so small and pathetic. So if anyone is ever alone with Jessica the lesbian slut, watch your back. Especially you, Lillian!”

I looked at Hannah in horror, mouth slightly agape as I processed her blatant lie. That never happened!! It was one thing to be coerced into ‘admitting’ that I was a lesbian, but now it seemed like I was as desperate as she was claiming. That I tried to kiss the girl I was hired to babysit. Or, as her friends saw it, the girl I was supposed to be serving. “That-”

“JESSICA.” For a second, it looked like Hannah was going to slap me. Instead, her aggressive body language shifted into a more casual stance as she turned her scowl back into a smirk. Still training her gaze on me, she said, “First of all, we’ve been over this. No speaking unless you’re given permission. Nod if you understand.”

This part wasn’t new to me, although it was a lot more difficult to comply with when she was spouting humiliating fiction about me. I reluctantly nodded, immediately feeling conflicted. For starters, I knew I wouldn’t be able to defend myself in regards to any other lies Hannah decided to say about me. I had also already said out loud that I needed a bathroom break, and still hadn’t been given an opportunity to do so. While I didn’t want to be in the same situation as last time, asking when it was far too late, I was also nervous about potentially being punished for speaking up or taking a break when they were trying to call on me for something.

“Good girl,” Hannah said, “Honestly, you’re going to have to improve your game if you don’t want to be a virgin for life. You’re already so weak in the physical department. Do you really think some girl is going to kiss you just because you go for it?”

“Her lips aren’t even kissable!” Taylor exclaimed, “Trust me, we felt them.”

Hannah just shrugged. “Whatever. She’s our little servant girl. It’s not like she has a chance with any of us anyway.”

What did that even mean?? I had kissed people before, and I knew that the way they were all talking about me right in front of me was designed to make me feel self conscious, but it somewhat worked anyway. Although I was older than all of them, I wasn’t particularly experienced. It was difficult to ignore their insulting and judgmental comments when they all sounded so sure about what they were saying.

“Jessie. Go get a can of seltzer. Any flavor.”

Something as simple as a new command left me unsure of what to do or say. I had been pushed to say ‘Yes, Hannah’ to the blonde’s demands leading up to this point, but I had just been told that I wasn’t allowed to speak. Trying to communicate how I was torn, I glanced towards Hannah and gave her a small nod. I slightly pivoted my body, preparing to head back inside, but also lingering just enough for her to correct me if she wanted to. Once again, in a situation where I felt the need to wait for Hannah’s approval.

Observant and socially adept enough to pick up my confusion, she quietly scoffed. “Those two words are allowed, Jessica. I told you to do something, didn’t I?”

“Yes, Hannah,” I quietly muttered. There was my answer, then.

Making yet another trip to the kitchen, I grabbed the first can of alcoholic seltzer I saw in the fridge’s drawer. Shivering a bit from the latest wave of cool air, and noticing just how much the girls had gone through the collection of drinks they had brought over, I headed back out to the pool. They were drunk; I was naked. No matter how many times I thought about it, it was difficult to convince myself that this wasn’t somehow my fault. I was failing spectacularly at this job, and I really should have put my foot down hours ago.

It was way too late for that, however. So for the umpteenth time, I approached the girls without covering, with drink in hand for whomever needed a fresh can this time around.

After a few seconds of silence, as I was committed to not speaking, Hannah smiled from the seat she had returned to. “That one is for you, Jessie. And you have to chug it for us. What do you think, girls? Thirty seconds, like last time?”

“How about 25, to see if she can beat her record?” Lillian suggested.

“Good idea!” Hannah replied. She pulled out her phone and tapped it a couple times, “Okay, Virgin. You have 25 seconds, or you’re going to be in serious trouble with all of us.” She glanced up from her screen with her lips pursed in a smile, “And after that, you’re going to play a little game with us.”

Chapter Thirteen

Jess

Another can of alcoholic seltzer wouldn’t do anything from an inebriation standpoint, as it had been ages since the last can I had been pressured to chug. And even if I was drinking more regularly, I’d probably end up staying sober anyway due to how exhausting and humiliating my time with Hannah and her friends was. However, a full twelve ounces of liquid was its own problem. I already needed the restroom, and had expressed as such; drinking more was the opposite of what I should be doing.

And yet, it’s not like I had a choice. I was naked and couldn’t muster up the courage to put my foot down about how I should at least be allowed to cover. Hannah was impossible to argue with, and this was more of the same. Besides, I really didn’t want to get in trouble again. Hannah had been so harsh earlier, and I was also outnumbered with all of her friends here. For all I knew, knocking back a can of seltzer was incredibly tame compared to the unknown alternative.

The time limit didn’t help. Hannah started the clock before I opened the drink, leaving me scrambling to pop the tab. I must have wasted five seconds just getting started, and then there were the same difficulties from the first time around–something cold and bubbly was not easy to drink quickly, and downing fluids when there was already noticeable pressure on my bladder made me incredibly nervous. There was no, no, NO way I was going to wet myself again. Now that it had happened once, they were obviously trying to recreate the circumstances, but I refused to let myself lose any more dignity.

“Ten seconds!” Hannah announced.

I was barely halfway done. Steeling myself as best as I could without having time to take a breath, I started sucking down the drink even more than before. Although I miraculously managed to finish just before the one second mark, as the girls started counting together once Hannah prompted it with ‘five,’ it wasn’t much of a victory. My throat stung from such an aggressive intake of cold, and I felt a bit bloated as well.

Seemingly unimpressed, Hannah said, “Looks like Jessie doesn’t suck at everything. So, Willow. What was that game you were talking about?”

“What? Oh! Musical Statues,” the redhead replied, “Like, instead of chairs, you use your bodies. We all dance, and the last one to freeze when the music stops is out.”

“Fun!” Taylor exclaimed, “Let’s do it. Maybe our little college girl has some moves we don’t know.”

I practically froze in fear. Even under normal circumstances, I was self conscious about my dancing abilities (or lack thereof). But dancing while I was fully nude, and while the majority of those present would be making a point to watch me? I’d rather die. Honestly, I would rather be doing naked chores. I couldn’t believe I was thinking about such a ‘preference’ when I hated being exposed to anyone in general, but anything would be better than this.

Too nervous to directly protest, I tried to get around the issue by suggesting something else, “Shouldn’t I-”

WHACK.

Hannah swiveled my way and her hand cracked across my face. “JESSICA,” She snapped my full name while glaring down at me, “You do not speak unless you are given permission. Seriously. It’s not that fucking difficult.”

That’s all it took. The longer I was under Hannah’s control, the more submissive I was to her. With watery eyes and a stinging cheek, I merely gave a meek nod of affirmation. I was supposed to be in charge of this girl, and yet her parents’ bullshit title for me ended up landing me in this enormous mess. Without my personal possessions, I was totally helpless and unable to assert my own authority. That, and I had no idea how to handle such aggressive confrontation, especially when undressed.

Hannah’s personality shifted, as if her awful chastising of me never happened. “I can DJ,” she said, turning back towards her friends, “I’m synced to the speakers, anyway. Not to mention my amazing music tastes.”

“And your dancing would probably excite the lesbian virgin too much,” Taylor pointed out.

“True,” Hannah smirked, “Maybe Lillian should sit this one out, too?”

“No way!” Lillian whined, “I want to dance. It’s not my problem if little Jessie can’t keep it in her pants.”

“What pants?” Willow giggled.

All I could do was blush and avert my gaze as the girls talked about me as if I wasn’t right in front of them. I was still trying to figure out how I was supposed to dance outside without wearing any clothes, when I was awkward enough at school dances that I got roped into attending with friends.

Of course, Hannah was thinking ahead and took away a possible escape route before I found it myself, “No lame or lazy dancing,” she said, “And no getting out on purpose. If I catch any of you breaking the rules, then there will be hell to pay.” While she didn’t directly call me out, it was obvious that her words were meant for me. “Everyone ready? Find some personal space.”

That was maybe the only break I would be getting. Not having to dance with one of Hannah’s friends. Then again, dancing alone came with its own set of challenges. Without anyone near me to steal the spotlight and partially hide my nonexistent moves, I would have to somehow dance in a way that wasn’t ‘lame’ or ‘lazy,’ whatever that meant to Hannah. Losing intentionally would have been a good idea, too. Unfortunately, Hannah thought of it first.

The other girls got up from their spots and spread out. One or two of them dramatically whined about how they had been comfortable, but it was pretty clear that no one was actually complaining. From what I had seen, they were all confident. Generally, the hot, popular girls were the first ones on the dance floor, and Hannah’s circle of friends all seemed to be that type.

No amount of time in the world would prepare me, although an extra few seconds would have been nice. Hannah started the music, and I was half tempted to simply resign myself to whatever punishment she had in mind. Maybe if this had happened earlier, I would have followed through on that thought. But now? I was way more intimidated by the blonde, and testing her felt like a horrible idea.

I started swaying and idly bouncing, which was no doubt what she considered ‘lazy dancing,’ except there was a reason I was doing it. Instead of trying to magically become a girl who was moderately good at dancing, I took a few seconds to watch her friends and see if I could copy one of them. What I didn’t count on, even though I really should have, was the fact that my braless boobs were going to be a problem. I wasn’t even doing that much, and they were already shifting about and bouncing along with my movements. Embarrassing, yes, but mostly uncomfortable!

“Come on, Jessie. Dance!” Willow exclaimed. She skipped over to me and took both of my hands, then used them to guide my arms backwards and forwards in opposite directions. The sharp movements caused my breasts to bounce around much more erratically, and I also felt a much stronger urge to pee when my legs couldn’t fully stay still in response to how I was being led to dance with the smiling redhead. My cheeks must have been burning as bright as her hair. I had never wanted a bra so badly; it took a conscious effort not to wince at the sensations on my chest, and it certainly didn’t help when Willow stared right down at my bare boobs. “I’m jealous,” she said, “They’re so much bigger than mine!”

It took a lot not to look down. Although she was wearing a bikini, there was plenty of movement on her own chest as well from the way she was dancing with me, and that was before she verbally drew attention to them. Since I wasn’t allowed to speak, I merely kept my eyes up and awkwardly let her tug me this way and that to the music.

That wasn’t enough for her. “You can look, virgin,” Willow said, “How about this? If you ogle me and tell me that you love my boobs, I’ll think about returning those plane tickets I bought earlier. It’s okay, I’m giving you permission to say it.”

That was a tough offer to reject. International flights weren’t cheap, and I still wasn’t sure how simple it would be to get those charges on my credit card reversed. The card had technically been stolen, although I had also been right there while it was used. I also had no idea how that process worked, as I had never had anything falsely charged before. Maybe it would be simpler to have Willow undo the damage herself? Of course, there were all the other purchases, too. Still, it was a start.

The only reason I considered going for it was because Hannah’s music was so loud. No one would hear me saying the mortifying words. As for looking . . . I was already somewhat tuning out any stares by focusing on Willow, anyway. Maybe they wouldn’t notice anything if she and I were dancing face to face. Feeling my face heat up more than before, I forced myself to look down at her cleavage and mutter, “I love your boobs.”

“What was that, Jessie?” she asked, “Speak up.”

As if it wasn’t awkward enough to be led in a shimmy-like dance with the girl, I had to keep staring at her chest now that I had started. “I love your boobs,” I said a little more audibly, after clearing my throat for good measure.

“Louder, babe. Or I’m going to get you in trouble with Hannah.”

“I love your boobs!”

“Louder!!”

The music stopped just as I yelled, “I LOVE YOUR BOOBS.”

Everyone around us froze per the rules of the game, but only from the neck down. They couldn’t hold back their gasps and giggles in response to my piercing proclamation. I wanted the ground to swallow me up. Also, Hannah and Willow definitely planned that, but I had no idea how. At the end of the day, it didn’t really matter. Once again, I had embarrassed myself in front of everyone, and made the whole ‘lesbian’ thing more believable as well.

“God, she’s such a slut!” Willow scoffed, “Hannah, can you please control your pet? Believe it or not, virgin, most girls don’t enjoy being ogled. My eyes are up here.”

I gave Willow an incredulous look. Seriously?! Not only was she calling me out for something she compelled me to do in the first place, but I was still baffled about how all of them kept calling me both a virgin and a slut in the same breath. Especially when the latter was paired with the implication that I was a lesbian, which was 100% not the case.

“Sorry, Willow. That’s what you get for playing with a maid who isn’t fully trained yet,” Hannah smirked, “Oh, and you’re out. Jessie stopped moving before you did!”

Willow just shrugged, then slapped my left breast out of nowhere. “Slut. You’re literally getting paid to behave, aren’t you?” With that, she strutted back to her lounge chair.

“Maybe we can start docking her pay each time she fucks up,” Hannah suggested, “Hmm, she’d probably end up in the negatives pretty quickly. How about it, Virgin? Want to start paying me for your services?”

She couldn’t do that, could she? Regardless, I just gave a small shake of my head. Now wasn’t the time to debate, and I wasn’t sure if a question for me counted as being given permission to speak. I was assuming the reason I hadn’t been yelled at for talking about Willow’s boobs was because the whole thing had been orchestrated.

“Then behave,” Hannah said, “Now, who’s ready for Round Two?”

The second time around was similar to the first, where one of Hannah’s friends was quick to invade my personal space and get me to dance with her. She didn’t jostle me as much, although the turns I was being led through made me a little dizzy. I also lost the ability to keep my thighs closer together, and I could already feel the seltzer catching up to me and piling onto the urgent need that had already been present before I came out to the pool area.

While I didn’t need to embarrass myself like before, I still ended up being kept in the game for the same reason. Hannah claimed that the girl dancing with me was the last to freeze, so she was out. I could easily see the trend, but couldn’t call Hannah out without incurring her wrath. She would just call me a liar, or get on my case about speaking out of turn, or any number of things. I was still the naked maid, and she was still the girl in charge of me despite what my role at her house was actually supposed to be.

Between Round Three and Round Four is when I tried to give Hannah a desperate look. I really, really needed to go. It didn’t help that I had made several attempts to go back inside, which I’m sure subconsciously signaled my body a few times that it was time to go. Circling back numerous times to deliver drinks had been tough enough, but it felt like I was near my breaking point now that I couldn’t stay still for very long.

Hannah didn’t appear to register my look, or maybe she was just ignoring it. She simply skipped to the next song on her phone.

Taylor stepped up to take a turn with me, although we didn’t get too far. The second my legs were separated from one of her gestures that shifted me sideways, I couldn’t hold it back any more. Gasping as I felt the floodgates open for the second time in a single day, I started peeing and was completely unable to hold it back.

My ‘dance partner’ noticed immediately. “Jessie!” she exclaimed. Shoving my backwards while stepping away herself, Taylor shouted, “Oh my God, she’s peeing!”

At that, Hannah stopped the music, which made things a thousand times worse. Suddenly everyone was staring at me now that Taylor drew attention to my ongoing accident, and the sound of my urine splashing on the concrete below me. No one said a single word, although a couple of them took out their phones. My hands reflexively twitched, as I knew deep down that I should be trying to cover myself up. The thing was, I had been trained. After just half a day, I felt the need to keep my arms down despite the fact that I was being filmed. Even though I was naked. Even though I was wetting myself.

Although I was being obedient about that particular directive, Hannah snapped at me anyway. “What the fuck, Jessica?” She stormed over until she was a few feet in front of me, no doubt because she didn’t want her bare feet to be in the splash zone. “I gave you permission to use the bathroom, and you chose to wet yourself instead?! You’re not doing this on purpose, are you?”

“N-no!” I protested. It felt so weird to talk while I was still mid-stream, but I couldn’t stop the ongoing accident now that it had started. I had waited too long to use the bathroom, and now I was paying the price. Again. While I knew that it was mostly Hannah’s fault, it was impossible to not blame myself. I was a young adult, and more than capable of making it to the toilet. Maybe I should have been more vocal about my needs, even if Hannah had stripped away my ability to speak as easily as she had taken my clothes? I was too flustered to think straight, especially when Hannah was yelling at me.

“So you’re having another accident?” she suggested, now that I had denied the alternative, “You know what, Jessie? I’m done. If you’re not going to use the bathroom when you’re told, you don’t get the privilege. From now on, those doors are staying locked.

Her words didn’t process right away, probably because I was too distracted by the fact that I was literally peeing myself in front of her and all of her friends. When the embarrassingly long stream faded to a trickle, however, it finally hit me. But- but that didn’t make any sense. How was I supposed to . . . “Hannah, please-”

“Hannah, nothing,” she calmly replied, “And you better not wet yourself again, either. You’re going to be in major trouble if you do. Now, what do you say?”

It took me even longer to put together the additional command. This was just like when she was shouting at me about the size of my breasts. It didn’t make any sense! I didn’t choose my body or anything, so how could she be mad at something like that? Now I wasn’t allowed to use the bathroom, but also wasn’t allowed to wet myself? What did Hannah expect me to do? Just hold my bladder for six weeks?!

Lillian spoke up. “Yes, Hannah! Remember, Virgin? That’s what you say whenever your owner tells you what to do.”

My what?

“That’s right, pet,” Hannah nodded, “From here on out, your bathroom privileges have been revoked. Yes?”

“But-”

WHACK.

“Your bathroom privileges have been revoked. Do you understand?”

“Y-yes, Hannah.” I had never felt so defeated in my life. Stripped and humiliated in front of so many girls, and completely powerless to fight back. And if Hannah meant it, what was I supposed to do when I needed to use the restroom? I’d have to find out later, as I obviously didn’t need to go any more.

“Good girl. Now, go get your cleaning supplies and take care of this mess. Are you listening, Jessie? I said now.”

Hannah

It made a lot more sense for my friends to stay.

We had sleepovers all the time, especially when we were drinking. Although we were rich enough to afford it, it was kind of dumb to order a ride home only to turn around and do the same thing the following morning to get our cars when we were sober. Besides, power in numbers didn’t hurt at the moment. Until little Jess was truly trained and broken, it would be a lot more difficult for her to fight back when I wasn’t the only girl she had to deal with.

And yet, I still wanted to send my friends home. For now. While all of them seemed to be amused by Jessica’s first accident, no doubt because of the shock value, I could tell that a couple of them felt a little awkward the second time around. Only a few of us really enjoyed being cruel to the girls that deserved it, which meant I would need to be selective moving forward. Willow and Lillian? Definitely keepers. Taylor? Possibly. She was good at embarrassing girls sexually, but I wasn’t sure how she would fare when it came to utterly destroying my babysitter.

I’d have to sleep on it. Plus I couldn’t send most of my friends home while telling a few of them to stay. Being leader was a tricky game. They would all do my bidding because I had proved time and time again that listening to me yielded positive results, and crossing me was a huge mistake. Playing favorites, however, was a surefire way to sew mistrust.

Most importantly, I could truly be myself if none of them were present. No holds barred, which sounded all kinds of fun now that Jess was being more obedient. I saw the fear in her eyes earlier, and I had already seen through some trial and error that it didn’t take much to stoke that emotion now that I had shown her what I was capable of.

Once Jessica had cleaned up outside, giving everyone one last little show as she both squatted and bent over as I dictated the ‘correct’ way to clean, I sent her inside to continue her job from forever ago. She still had plenty of work to do in the kitchen, considering how many times we dragged her away to wait on us. And while she was distracted, I would send my friends home. That way, they could still serve as a background threat despite not actually being present.

It wasn’t difficult. I just lied and said that one of my parents’ colleagues was swinging by the house tomorrow morning to ‘collect some files.’ Or, in other words, to check on me and my new ‘housekeeper.’ It was a plausible enough story, and my friends had seen with their own eyes how well trained Jessica already was. With all of her possessions confiscated, as well as the collection of blackmail my girlfriends would send me, they fully believed that I could pressure my short babysitter to temporarily get dressed and play the role without giving anything away. But if a bunch of cars were in the driveway, and someone saw that I had a friend over the first night I was left on my own? Way more suspicious.

None of the girls questioned it, not even the few that knew me better. It made perfect logical sense, and it didn’t take long for all of them to clear out. We only had to order two rides, as they could share, and the waiting time was just enough for those still in bikinis to get dressed and slip out the side door. I made sure that each and every one of them took a couple empty drinks in. Not to help Jess, but to keep adding to her job while making sure she didn’t leave the kitchen at the same time.

Finally, when it was just the two of us, I stepped into the kitchen. Crazy enough, she was almost done making the room sparkle. Almost as if committing to a chore made her more efficient. But I wasn’t going to let her off the hook that easily. “What’s left? You may answer, Virgin,” I said. Anyone else might have taken pity on her. She looked so beaten down, and almost numb to the fact that she was washing the last few dishes while naked. But Jess deserved it. Thinking she had the right to tell me what to do in my own house, and walking around with curves like that? Bullshit.

“Just the counters,” she replied. If the brunette noticed how quiet it was without my friends here, she didn’t mention it. Good. Docile and obedient was a much better look on her.

I was about to say something when I heard her stomach rumble. Interesting. I hadn’t even thought about the fact that my friends and I had been snacking all evening, but Jess hadn’t had a single bite since arriving on my doorstep. And she probably hadn’t eaten for a while before then, either. Maybe since lunch? Fluids certainly weren’t enough to stave off hunger, and the audible growl was enough to inform me that the long day was catching up to her in that regard. And yet, I was willing to bet that she was too scared of me to ask permission for something like that when she still had work to do.

“Good. Now hush. If you talk back, I’m going to slap you again,” I said, getting right to the point. Nurturing that fear, while also getting ahead of a potential response to my next fun idea, “When you’re done with the dishes, put the sponge down. You’re going to scrub the counters with your boobs.”

The look on her face was priceless. It definitely took a few seconds for her to register the full implication of my demand. Not surprising, considering how outlandish the task must have sounded to someone who wasn’t prepared for it. Thanks to my reminder, she managed not to speak, although her lips temporarily parted like she wanted to.

I wonder if she even realized how conditioned she was at this point. That was the funny thing about blackmail. That kind of compliance only came in short bursts, and eventually faded to the background. The rest? I was no psychologist, but I had witnessed countless girls falling into the habit of obeying me simply because it became the norm. With fewer and fewer reminders of why they were doing as they were told. Apparently it worked on college girls, too, when they were given the proper motivation.

Not relenting, but at least clarifying in case she was too confused and taken aback by what I was telling her to do, I said, “You heard me. Put the soap on your boobs and rub it around, Jessie. I want to see bubbles. Do I really have to spell this out for you?”

It must have finally computed, at least to the point where she reluctantly reached for the bottle of dish soap. I kept a straight face, but I knew why she was so hesitant. The majority of her evening had been ‘naked chores.’ While the total lack of clothes was obviously embarrassing for her, the tasks themselves were mundane, and she had probably done most of them before. This, however, was brand new and would be amusingly uncomfortable for her. Not only did it draw attention to her bareness, especially her sizable rack, but it also tested her obedience. If she would do this for me with no outward argument, how else would she bend to my will?

I had so many plans for the girl, most of which were coming to me out of nowhere and bouncing around my mind with the ones that already existed up there. This was all brand new territory for me, as I normally had limited time with the average target. On top of that, most of those targets didn’t irritate me as much as Jess did.

First, I would relish every second of her bending over and scrubbing down every inch of every counter with her breasts. And oh, I would make sure she was thorough.

As for the rest of the evening, all I knew was that she wouldn’t be going to bed until I was sure she was well and truly broken.

Chapter Fourteen

Jess

It was one of the most awkward things I had ever done.

Being naked in front of just Hannah was definitely more tolerable than not being allowed to cover in front of all of her friends, until she found a way to degrade me in yet another way where my nudity was involved.

Cleaning the counters with my boobs was beyond humiliating, and not just because of the obvious reason. I was also too short to merely bend at the waist and position my chest for the impending task. All the surfaces in the kitchen were a little too tall, meaning I had to stand on my toes and somewhat contort my body to get the necessary leverage to actually scrub. Hannah was insistent about the fact that she expected the counters to sparkle when I was done. Therefore, I couldn’t just make a few light passes for the sake of the ‘show.’

In the meantime, Hannah switched to wine. She had briefly left the room to change out of her bikini and into casual shorts and a tank top. Thankfully, she hadn’t stripped in the middle of the kitchen, which I wouldn’t have put past her, although I did have to deal with the fact that she wasn’t wearing a bra. Crossing one leg over the other, she was more than happy to point out countless spots I missed between sips. “Make sure you get every nook and cranny, virgin,” she said.

And I did. The worst spots were the corners and edges farthest away from me, as the only way to get those areas was to hold one of my breasts and press it into place before scrubbing back and forth. More often than not, I would end up rubbing one of my nipples against the marble. I wasn’t sensitive enough that it caused a reaction below my waist, but the sensations still made me quietly gasp and wince every now and then when I wasn’t expecting that part of my chest to be shifted in such a manner. I also fairly regularly had to reapply soap, as my bare body didn’t create suds quite as efficiently as an actual sponge did.

It took nearly half an hour to scrub all the surfaces in the kitchen. I spent way longer than should have been necessary on each counter; not only because cleaning them with my boobs took way more time and effort than it would have taken with my hands, but also because I was scared of Hannah’s judgment. Determined to make them shine to her rich girl standards, I ended up going over each area multiple times. Just in case. She also added the kitchen table to the list when I was nearly done with everything else, yet didn’t move an inch while I worked. With the cruel blonde in the way, I was forced to bend over a couple times near her, and also ended up putting my boobs right in her face when I had to get her side of the table. Blushing profusely from the constant exposure as I worked, while also being careful to keep from accidentally touching her as I cleaned the areas closest to her–Hannah had informed me she wanted to drink her wine with no disruptions–I eventually stood back and resisted covering up my bare, slippery chest. I wasn’t sure if the ‘no talking’ rule was still in place, so I merely waited until she noticed that I was no longer cleaning.

Hannah was busy with her phone for what felt like forever. When she finally looked up, she casually asked, “What is it, Jessie?”

“Umm, I’m done,” I said, “I did all-” Before I got much further, my stomach let out a LOUD growl. All the bending and shifting must have moved my core enough to remind my body that I hadn’t eaten all afternoon and evening. “Sorry,” I mumbled. Not that I was in control of the noises my stomach made.

“Aww, are you hungry?” Hannah made an exaggerated pout with her face, “Poor little virgin. Unfortunately, pathetic naked maids only get to eat when their work is done.”

But- but I was done! Every surface in the kitchen was now clean, and I had done the mortifying task without a word of complaint. I knew better than to outright argue with Hannah, however, so I merely said, “I’m done with the counters. And table.”

She gave the recently cleaned wood in front of her a cursory look. “I don’t think you are, Jessica. Look at all this soap.”

Well, yes. I still had to wipe everything down. “That’s next,” I nodded.

“You still have to use your boobs,” she said.

Wait, what? “Hannah, I can’t!” I exclaimed, mostly out of desperation. Scrubbing with my chest had been one thing. But getting rid of the suds? I needed a rag or handful of paper towels to take care of that.

“What the fuck did you just say?” she snapped, “Get to work, Virgin. One more word out of you, and you can clean the floor with your boobs. Might as well get some use of them, right? They’re so big. Since you’re not having sex with anyone, you can use them as sponges instead.”

My lips parted to say something in response, but then I processed Hannah’s threat. The counters had been bad enough; the floors, however, would probably make me die of humiliation and/or exhaustion. How would I even do something like that? Inchworm around the kitchen and rub my chest against the dirty planks? The image alone was awful enough. Shaking my head to nonverbally reject her idea, I scurried back to the other side of the kitchen.

Similar to the way I used my hands to put soap on my boobs, I went about doing the same with water from the tap. Then I placed my chest back down on the counter and started nudging all the visible soap towards the sink. It was even more arduous than the cleaning process. To ensure I wasn’t merely moving the suds around without making any progress, I had to wet my boobs every few passes, all while seeing Hannah out of the corner of my eye. As if witnessing me degrade myself in such a way wasn’t bad enough, I had to assume she was further documenting my continued nudity and mortifying obedience. I was supposed to be babysitting her, and instead I was going along with her every horrible whim.

Nearly an hour later, the counters and table were truly finished. As if clearing off the soap wasn’t enough, Hannah also made me dry every surface with my boobs as well. The nonstop degradation was bad enough, but my hunger made everything worse. The initial growl had reminded me that I very much would have eaten dinner quite some time ago on an average day, and my stomach also felt the need to inform me of what it needed every five minutes or so. At some point, Hannah snapped at me to keep quiet, which I was completely incapable of doing. Her comments only got worse, as she suggested that I clearly had no control over my own body. A tough criticism to ignore, considering I had wet myself twice in front of Hannah and her friends.

When I was finally done with using my boobs as sponges, rags, and towels, Hannah hardly seemed to care despite the effort that had been required. She just gestured to a closed door near the fridge. “Go get more ice,” she said, “Refill what the girls used tonight.”

More ice from where . . . ? I wasn’t sure what she meant, although I didn’t hesitate too much before responding with, “Yes, Hannah.” The sooner I took care of yet another task, the better. It was nearing midnight, and I doubted the blonde would stay up forever. At the same time, she was eighteen, which was the kind of age where her sleep habits could be pretty much anything.

My initial assumption was that her house had a chest freezer just off the kitchen. That was a fairly common thing for people to keep around, even on the less wealthy side. I was dead wrong. As I entered the unfamiliar hallway, it wasn’t long before I came across a large metal door. If that wasn’t enough of a clue, there was an exterior thermostat that showed a temperature that was way colder than what her house would be set at. Sure enough, I found myself faced with a walk-in freezer after giving a pull on the door.

I was not looking forward to this. The thought of carrying a bag of ice while naked had already given me pause. My body shivered from the draft alone, and the only thing keeping me from slamming the metal door closed again was the fear that Hannah would punish me if I ended up taking too long. Taking a huge breath to steel myself, I stepped forward into the icy cold room.

My bare feet were instantly affected by the dramatic shift in temperature. I let out a stifled squeak from how the freezing tile felt on my soles, and was this close to jumping back out into the hallway. Closing my eyes and taking another much needed breath, I exhaled and took my hand off the door. The only way to get through this was to rip off the bandaid. Shivering as the rest of my body was hit with the cool air that surrounded me and every inch of the freezer, I glanced around to take stock of the room.

This wasn’t my first time in such a space, as I had done retail work before that required fetching frozen items, but that had been different. For starters, I had been wearing clothes. There had also been a degree of training involved, rather than how Hannah merely sent me here with very little instruction.

Dancing in place as I surveyed the shelves, I ended up needing to circle around the middle section before spotting a few bags of ice stacked up on the other side. Hurrying over, grimacing with just about every step I took, I heaved up one of the twenty pound bags before I could talk myself out of it. As if I wasn’t cold enough, I now had to deal with the ice pressed up against my chest. The thin layer of plastic did very little to protect me, and my nipples perked up even more than they had when I first closed myself into the freezer. For a girl my size, there really wasn’t a better way to carry the large bag.

Hurrying forward to complete the loop I had started, I gave a good shove to the metal door with my shoulder . . . It didn’t budge. Swearing under my breath, I stepped back to see if there was a handle or something I should be using. In my experience, opening such doors from the inside should be simple, considering that most people will have their hands full on the way back out.

Just like I thought I remembered from my approach, the back of the door was completely flat. With nothing noticeable on the door itself, I looked just to the side to see if there was a button or lever or something I was supposed to use. Literally nothing. Frowning at the total lack of visible options, I stepped back and gave the door a much harder shove with my shoulder. Maybe it was just one of those things that stuck, especially right after being closed.

When the metal didn’t budge in the slightest, my eyes widened as I was hit by a full shiver from the combination of the cold door, ice, floor, and air. “No . . .” I whispered, “No, no, no.” This was not happening. I was not stuck in the freezer while buck naked. Would Hannah even hear me through this door and down the hall? I had to try. “HANNAH!!!” I screamed.

Dropping the ice to minimize the number of things making me cold, I yelled for her again.

Hannah

It really was getting too easy. Not that I was complaining.

A perfect concoction of blackmail, humiliation, and the slightest droplet of hope had Jessica right where I wanted her. And, of course, fear. While she no doubt wanted all of her personal possessions that were stashed away, I had made it quite clear that I was not a girl to be messed with. Obedience was better than all the ways I could potentially make things worse for her, as evidenced by the fact that she fucking used her BOOBS to clean the kitchen.

I hadn’t actually expected her to fold on that one. An intelligent college girl like herself? Despite everything I had put her through, I had assumed she would push back when it came to such an amusingly demeaning and inefficient task. Apparently not. She barely whined at all before lathering herself up and getting to work. It took a serious amount of willpower to keep the stern, bitchy act up. The wine was a helpful prop, as I could always take a sip whenever my expression threatened to slip.

As always, I twisted the knife as well. Pretty much any time the brunette demonstrated that she was willing to do something, it was simple enough to pile on. If she would clean the counters with her boobs, then it wouldn’t be that big of a deal to clean the table. If she would wash, then surely she could rinse. And, like before, all it took was a harsh alternative for her to crumble back into obedience.

Her obvious hunger was just the cherry on top. I certainly wasn’t planning on feeding her for the rest of the evening, and it would also be a lovely motivator for the following day. Instead, I sent her off to the freezer to see how well her totally bare body would do with a bit of cold.

Following Jess was simple. The moment the door to the side hall closed behind her, I was on my feet. Though dressed, I was still barefoot, and I doubted she would hear me padding across the kitchen when she was too busy dealing with her nudity and likely sore nipples after rubbing them around for over an hour. Sure enough, she had already gone in, and I smirked to myself as I locked the door behind her.

She would be fine. I wasn’t going to leave her there forever, and I’d let her out before she caught a cold. In the meantime, I stood on the other side of the thick metal and replied to a few texts as she called for me. “I’m right here, Jessie,” I replied under my breath. Of course, she didn’t know that. After desperately calling my name a few more times, it sounded like she was trying to knock the door down, or maybe feel around for an escape latch that wasn’t readily apparent at first glance. Then she was back to yelling. I was too busy checking my nails to help her right away, unfortunately.

After I deemed that she had been suffering for long enough, I unlocked the door and swung it open from my side. Scowling at her and managing to hold the harsh gaze despite the look of surprise and relief on her face, I snapped, “What the hell, Jessica?! You were taking ages. Is it really that difficult to find a bag of ice?”

She looked ready to race out of the room, yet seemed to realize she couldn’t do so quite yet. I was standing in her way, for starters, and I had also oh so kindly reminded her what she had gone in there for in the first place. “I- I was l-locked inside . . . “ she meekly replied. It was honestly tough to tell if she was stuttering more because of the cold or merely because of her overall nervousness around me. The best part? Her arms had been wrapped around herself to keep warm when I had opened the door, but she lowered them after registering that my presence meant that she wasn’t allowed to cover.

“How could you be so careless? Aren’t you supposed to be a professional housekeeper, Jessie? And yet you locked yourself inside my freezer?” Flipping the narrative so it seemed like it was her own damn fault she was stuck in there for so long until I let her back out, I gestured to the bag of ice on the floor. “Well, what are you waiting for? Not everything has to last as long as your virginity.”

She didn’t defend herself in the slightest. Not when getting back to the warmth of the rest of the house was a higher priority. She awkwardly bent over and heaved up the bag, earning herself enough room to slip between me and the open door. The bare brunette was noticeably shivering, which I immediately told her off for. Slamming the door closed behind her, to which she slightly jumped and I slightly smirked, I donned my annoyed frown again by the time she whipped around. “Grow up, Jessica. It’s not that cold.”

Her reaction was amazing. My insensitive judgment sparked something in her eyes, only for the flame to be snuffed out in an instant. And not even because I made the effort to knock her back down. The girl was just too exhausted to fight back. She wanted to, if just for a fleeting moment. Except I had defeated her too thoroughly, especially now that she was tired and hungry as well. So instead of standing her ground or saying a word, she turned back towards the kitchen and hauled the ice to the nearest counter.

There were at least fifty tasks I could think of to make her do next, but I decided while she was filling the fridge with ice that it was about time to call it a night. Less because Jess deserved a break, and more that it was late and I had had a fair bit to drink. Sleeping would refresh me for tomorrow, which would be my first full day with my babysitter. If I managed to put her in her place in a single afternoon, I could only imagine how she might look at the end of twelve hours or more of torment. It’s not like I’d be pressing the ‘reset’ button, either. She would start the day naked, and we’d proceed from there.

“Okay, Virgin. It’s time for bed.” The second she was done discarding the empty bag, I got her attention for what I was hoping would sound nice initially before I subverted expectations. “Do you want to sleep in my bed? I’ll strip all the way down so we match, and you can warm yourself up with my body.”

Bullseye. Her face paled at the suggestion, and I could see the gears turning as she parted her lips without actually saying anything. Because she knew better than to simply reject me. Also, I was eighteen, and the girl she was supposed to be babysitting. Even if we technically didn’t do anything sexual together, crawling into bed with me in such a way would still be crossing a lot of lines I assumed she wouldn’t want to cross. That, and she wasn’t really into girls. Although who can deny a hot blonde like myself?

Giving a small shake to her head, and no doubt choosing her words carefully, Jess said, “Umm, no, thank you. I should probably sleep in my own bed . . . ”

“But your room is locked, isn’t it?” I sweetly reminded her, “You might as well share with me tonight. Then we can sort all that out tomorrow.”

“Please, Hannah? I’m supposed to be in the guest room, and-”

“And nothing, Virgin. You know what? Fine. If you don’t want to sleep with me, then I’ll have to put you somewhere else.”

She was probably thinking that I had let her off easy. Considering how firmly I had pushed her to rinse the counters with her boobs, I could imagine that deep down she knew that it wouldn’t take much for me to command her into my bed if I truly wanted to. Rather than explaining my vague alternative whatsoever, I swiveled on my heel and strutted out of the room. In case she was too dumb or too tired to understand, I called out without breaking my stride. “Let’s go, Jessie.”

Heading up the stairs and into my own bedroom, one that was far more spacious than the locked guest bedroom, I walked halfway into the room before turning around and waiting for her to catch up. Once her naked self turned the corner, I sternly told her to stay right where she was while I got ready for bed.

Taking my sweet time, I proceeded to brush my teeth in my private bathroom, wash my face, and strip down to just my underwear. Something told me that Jess seeing me naked would fluster her almost as much as being exposed herself. Plus it would remind her that not going along with my latest plan for her would result in having to spoon me while we were both fully nude. Finally, I pulled out a single queen bed sheet from the small linen closet in the corner of my bathroom.

Walking back into the bedroom, plenty confident about my own body and not ashamed in the slightest to flaunt myself, I instantly smirked at the way her eyes went wide and how she immediately blushed and averted her gaze after momentarily being drawn to look at my chest. Less because she actually wanted to look, and more because it’s difficult not to stare at bare boobs when they’re unexpectedly sprung on you. It was a trick I had used before on other girls, so I assumed it would work on a repressed girl like Jess.

Acting as if nothing was out of the ordinary, I sauntered over to the visible AC vent near the corner of my room. “Here,” I said, dropping the white sheet next to it, “Your bed.” She would have to somehow make do. Surely the hardwood floor would be more bearable now that she had a tiny bit of bedding, and I was curious to see how much of it she would use to cover her body vs. keep underneath her. Of course, it wouldn’t do for her to toss and turn all night. I needed my little servant well rested for the long day on her horizon. Finally paying her a little more attention, and guessing that my topless self approaching her would make her all kinds of nervous, I opened my hand and offered her three identical tablets. “To help you sleep,” I explained. I wasn’t lying. Knocking her out with a strong dose of sleeping pills was the best way to ensure she stay asleep until it was time to get up.

She looked a little suspicious; I didn’t blame her. Displaying my annoyance with a heavy sigh, I went through her options again–she could take the pills and sleep on the floor, or I could take off my underwear and she could sleep with me. With the no-win scenario presented to her, she reluctantly took the medicine from my hand that had been perfectly positioned so she would have to check out my breasts while I was standing right in front of her.

Without a drop of water to help her, she swallowed one at a time until they were all gone. I was quite curious to see how well quickly the dosage would take. Not only was it slightly more than recommended for a girl Jessica’s size, but she also hadn’t had a bite to eat in quite some time. I planned on sleeping in, after all, which meant that I couldn’t have my babysitter stirring before I was ready to get out of bed.

When she was done, I quickly reached up and removed her glasses. Stripping the last bit of ‘clothing’ she had, and also covering my bases. Now even if she happened to wake up ahead of schedule, she wouldn’t be able to do much. “There,” I said, “Now go to bed, Virgin.”

What choice did she have?

Jess seemed to find her way over to the other end of the room without the help of her nerdy accessory. Not that there was anything really in the way. I was curious to see how she’d fare in a more cluttered and/or crowded room. Easy enough to add to the ongoing mental list. She awkwardly got as settled as she was able to with the limited options available to her. Considering how quickly she dropped to the floor and wrapped herself up, something told me she was far more interested in finally protecting her no longer existent modesty than she was in simply going to bed.

Meanwhile, I was reveling in the fact that I had well and truly broken the girl.

Sending her to bed without a stitch of clothing, making her sleep on the floor, and not hearing a single complaint about it? Not bad, Hannah.

The sound of her rumbling stomach was music to my ears, and I couldn’t help but wonder about how long I could make her go without any food. 24 hours? 36? At some point, she would need something to keep her going, although then I could split the difference with a liquid diet. Enough calories to sustain her while still maintaining the feeling of being hungry and weak, with the added benefit of expediting her need to use the toilet again. Because if little Jess wet herself twice, it wouldn’t be tough to manipulate it to happen again.

When she finally drifted off in the darkness I helpfully provided, proving that the pills paired with her exhaustion were enough to overcome her uncomfortable sleeping arrangements, I turned on my bedside lamp and gave her one last parting gift to round out the evening. Quietly padding over to her, I carefully placed my bluetooth headphones over her ears and adjusted them so they would stay put all night long. Then I shuffled a short playlist I had made just for her–the sounds of rain, crashing waves, a mountain stream, etc.

I really doubted she would wet herself overnight, mostly since she hadn’t had much to drink since her last accident, although it would be a great way to prime her body for the following day. And considering how busy her morning would be, not to mention how she was banned from using the bathroom anyway, it probably wouldn’t take much for her to be dancing and squirming all over again.

Satisfied with my latest handiwork, and how everything had gone in general since her arrival, I returned to my bed and gradually drifted off myself.

Chapter Fifteen

Jess

A wave of cold snapped me out of my slumber.

It was actually a wave of freezing water, which I realized moments later as the thin bed sheet clung to me following the way Hannah had so rudely decided to wake me up. I was half sitting/half lying on the hardwood floor from the way the contents of the now empty bowl in her hands were all over me. As I looked up at the scowling young blonde above me, it all came back to me.

Apparently yesterday hadn’t been an extended nightmare. I was still very much naked save for the soaked sheet I quickly made sure to clutch over my chest, my body was all kinds of sore from how I had slept on her bedroom floor all night, and the mere sight of Hannah was enough to cause countless humiliating memories to come flooding back.

“Did I tell you that you could sleep in, Virgin?” she coldly asked, “You’re my housekeeper. Don’t tell me that my parents hired some lazy girl. Come on, you’ve had more than enough sleep. Get up. Now.”

Maybe a good night’s sleep would have prepared me for a fresh day with Hannah, but I didn’t feel rested in the slightest. I was cold, sore, and hungry. Also, as I shifted in order to get my feet under me, I realized that I really had to pee as well. While that’s usually what I did first thing in the morning, it was more part of my ritual than a necessity. This kind of urge also didn’t make sense, the more I thought about it. I hadn’t had a drop to drink since my last accident.

It wasn’t just the wet fabric clinging to my body as I stood up. Hannah’s bedroom was also so cold. Had she been blasting the AC all night? Not uncommon for people to do in summer, although she had a warm bed to counter the indoor temperature; I had been sleeping with a lot less. I probably would have been tossing and turning in discomfort all night with so little protection from the cool air, except for the fact that she had made me take a couple sleeping pills before bed. Well, it was technically my choice, although the alternative would have been both of us sleeping together while buck naked. That would have been more comfortable, objectively, but I could only imagine how that would make the ‘lesbian’ thing worse.

And no wonder I slept in! I couldn’t help it. Maybe she gave me the wrong dosage or something. That, and I really had been both mentally and physically drained by the time Hannah put me to bed.

I had to say something, right? Starting the day by letting her walk over me didn’t set a great precedent for things moving forward. “Look, Hannah-”

“No.” She held up her hand and sternly met my eyes. “Not before my coffee. Go to the kitchen and get that started for us. You are not to touch anything besides the espresso machine, Jessica. Nod if you understand.”

My lips parted to speak, but no sound came out. Instead, I merely gave a meek nod. I was in no state to push back right now, especially not when Hannah was as bossy and demanding as always. Maybe in a few minutes, when I had managed to shake off some of the grogginess.

Hannah wasn’t done quite yet. Turning her hand palm up, she plainly said, “That needs to be dried.” Noticing my reservations about giving away the only covering I currently had, she added, “I’ve already seen you naked, remember? You’ll have a chance to earn something to wear soon, Jessie. But only if you follow my rules.”

I assumed she was implying the ‘no covering’ directive. It felt so counter-intuitive, exposing myself in the name of getting clothes to cover up with. Especially since that was normally such a basic right. As much as I hated the prospect of not only being naked again, but making a conscious effort to keep my arms down, Hannah kind of had a point. Not a very good point, considering how she was completely disregarding my own feelings and the fact that being fully nude before didn’t necessarily mean I was comfortable doing it all over again, yet she was right. I didn’t have anything to hide from her at this point.

There was still the matter of my dignity, but right now I was focusing on the delayed gratification that would come with being obedient. So I reluctantly pulled the sheet off my body, shivering as the cold air hit my damp body.

Naked. Again.

Hannah had no shame about checking me out, either. Once she took the only covering I had away from me, she looked me up and down before saying, “Now apologize for your boobs.”

I had never made it past ‘tipsy’ the previous night, as no alcohol in the world would have been enough to overcome how sobering the mortifying events of the evening had been. Still, her harsh attitude towards my chest had been a lot to handle when I had been slightly buzzed. Now it was happening again, albeit with a less aggressive approach than before. I was confused as ever, as how was my body’s dimensions my fault?! “What- what about them?” I hesitantly asked. Simply apologizing like the last time would have been easier, but I was trying to understand. She was a girl, too. Surely she knew that I had no say in my size. My arms reflexively lifted to cover myself up now that she had drawn attention to my bareness, but I managed to stop them halfway and lower them back down to my sides. Though I couldn’t do anything with my upper limbs, I did my best to clamp my thighs together and keep my womanhood from being on display.

“Do you remember what you said, Jessie?” Hannah placed a hand on her hip, “Because I do. You swore you would be a good maid, and you would be fucking obedient. So do as I say, right now. Apologize for your boobs.”

I did remember. Less about what I said, and more about how she had treated me throughout the process. Maybe it was the drinking paired with the power tripping that had led to that, although I wouldn’t put it past her sober self to be just as harsh. Especially not when she was tired and moody and sounding rather impatient. “I’m sorry,” I muttered, blushing from both my perpetual exposure and how unfair being pressured to apologize for something completely out of my control.

“Sorry for what?” she pressed.

“I’m sorry for my boobs.”

“You’re my obedient maid?”

Housekeeper. Or, more accurately, babysitter. Was there no way to get things on the right track this morning? I doubted it, considering how quickly I had just caved in regards to such an absurd apology. Reluctantly nodding, I echoed, “Your obedient maid.”

“Good girl,” she casually replied, “Now go do as you were told. When you’re done, sit at the kitchen table and don’t get up until I say so. What do you say when I tell you to do something?”

That one had definitely been drilled into me. “Yes, Hannah,” I said.

It wasn’t until I was in the upstairs hallway that I considered rectifying my blurry vision. I was used to dealing with it each morning and evening, before putting in or removing my contacts. With those stashed away wherever the rest of my stuff was, I only had my unattractive glasses, and I couldn’t remember where I had put those before bed. Or had Hannah placed them somewhere? The end of the evening was just as blurry as my sight currently was, and I was really tempted to head back into Hannah’s room to ask.

I decided not to risk it. She was such a wild card at all times, and I had just affirmed that I was more her servant than her babysitter. I would just have to deal for a little while.

About halfway down the stairs, my stomach let out a loud growl. Now that I was on my feet and a little more awake, I was more aware of just how painfully empty my stomach was. When was the last time I had fasted this long? According to Hannah, I had slept in. I had no idea what time it was, but I obviously hadn’t had dinner yesterday. A later breakfast was clearly compiling to my growing hunger.

By the time I had made it to the kitchen and found the coffee grounds, I could feel a migraine coming on. Mostly due to the blurry vision, I imagined, though I’m sure the empty stomach didn’t help. If all that wasn’t enough, I also felt a stronger urge to use the toilet. As badly as I wanted to find the closest bathroom in the still rather unfamiliar house, I was worried that half the doors nearby would still be locked. Hannah coming down to find that the coffee hadn’t been started on due to my detour wouldn’t bode well for me.

I was feeling a bit weak as well, due to the hunger that was difficult to get out of my mind now that I was aware of it. Trying to think clearly was more of a challenge. I needed to figure out how to overcome all the leverage Hannah had on me, and make myself more of an authority figure despite my height disadvantage and how naturally submissive I was when up against a girl like her. Why hadn’t her parents told me that she was eighteen? Could they have really overlooked a detail like that when giving me the job, or had they not known how old I was when offering the job? I would never known until I had a chance to look back through those messages, which I wouldn’t have the ability to do until I had my phone or laptop back.

For now, I needed to figure out the espresso machine. I was used to making a pot of coffee, or occasionally treating myself to one at a coffee shop or chain. As long as Hannah just wanted a basic cup, I could manage that. The buttons were straightforward enough, and the only real difference was using beans instead of grounds. After a few minutes of trial and error, I succeeded in getting the machine to make coffee in the mug I had picked out for her.

Sighing in relief as it started whirring and dripping, I went over to the table and sat down. Not even because that’s what Hannah told me to, but because standing for a prolonged amount of time was tough with a growling stomach and a migraine that was only getting worse. As I waited for Hannah to come down, I wrapped one arm around my stomach and crossed my legs. Technically not covering, as my boobs were still on display, but doing what I could to alleviate my desire to use the restroom as well as trying to stop the embarrassing sounds from my core. It was also almost as cold as it was downstairs as it was in Hannah’s room, causing my bare toes to curl and uncurl in discomfort. Or maybe it was in desperation, as I was finding it nearly impossible to sit still.

Looking around the room for the first time since arriving, as I had been too distracted before, I saw on the microwave that it was nearly 9:30 AM. I guess I had slept in, as I was usually awake closer to eight. How long had Hannah been up? Long enough to fetch a bowl of cold water, obviously, though I didn’t want to think about how I would have looked if she woke up well before that. The eighteen year old girl, brushing off a hangover and getting up early on a summer day where she had no commitments, while her university-aged ‘housekeeper’ continued to sleep on the floor.

It took nearly thirty minutes for Hannah to appear. All the while, I twitched and fidgeted in the wooden chair, practically staring at the clock while wondering if I should get up and resolve any of my current problems. I was literally in the kitchen. Surely there was something I could eat to tide myself over, even if it was some of the unhealthy snack foods the girls were grazing on throughout the evening prior. Mostly refraining due to how I kept thinking that Hannah would arrive any minute, I kept delaying and delaying until my temptation to get up was countered by the fact that all my obedient waiting would have been for nothing if I ended up getting caught and reprimanded.

Apparently Hannah had decided to shower. She looked perfectly put together in a simple sundress, and clearly didn’t think about how her morning routine might affect me. In fact, she didn’t address me or look my way in the slightest at first. She merely strutted over to the espresso machine, picked up the mug, and took a sip.

With a small grimace, she finally turned my way. “It’s cold,” she flatly said, “And there’s no sugar or cream.”

Well, yeah. She took forever to come downstairs, and I had no idea how she liked her coffee. In my experience, making it at home meant making it exactly the way you prefer. I started to express as much, but didn’t make it very far. “I-”

“Whatever.” Cutting me off and striding towards me, I was momentarily scared that she was going to throw the coffee on me in a similar manner to how she had woken me up. Instead, she pointedly set it down on the table. “Drink, Jessie. This one is yours, now. When you’re done, you can make me a fresh cup. Two creams, one sugar. Memorize it. Be a good maid. Your job is to anticipate what I want so I don’t have to waste my breath on you, yes?”

It was the most demeaning thing I had ever heard, and she said it so bluntly. “Yes, Hannah,” I reluctantly answered. She and her friends had trained me well. Until I found a good time to broach the subject about how this summer was supposed to be with me as her ‘housekeeper,’ probably when I was at least dressed, I was stuck being as obedient as I told her that I would be.

“Good.” She stepped back and crossed her arms. “Drink up, Virgin. I need my coffee, and you can’t make it for me until my mug is empty.”

Or she could dump the coffee into the sink. Or get a new mug. Or make an iced drink, considering the season; that would be less wasteful.

Like Hannah, I didn’t really like plain, black coffee. And drinking it at room temperature would only make that worse. Instead of protesting about the task itself, I tried to explain the more pressing worry. “Umm, may I use the bathroom first?”

“No,” Hannah curtly replied, “We’re running late, Jessie. / slept in when she should have been doing her job at sunrise. You have about two seconds to finish your drink, or you can stay naked all day for all I care. Well . . . ?”

It was so easy to push my buttons and she knew it. I hated being exposed in general, and it was much worse when I wasn’t allowed to cover myself up in the slightest. Between giving Hannah the satisfaction of chugging another glass of something vs. humiliating myself with more naked household chores–I certainly hadn’t forgotten how she made me use my boobs as a sponge–it was hardly a choice. Quickly lifting the mug to my lips, I sucked the liquid down as swiftly as I was able.

The coffee was so bitter. I couldn’t remember the last time I drank coffee without anything added to it, and the morning drink the espresso machine made also tasted a lot stronger than what I was used to. Wincing at the influx of fluid as well as the increased pressure on my bladder from chugging the entire mug, I glanced up to see if my speed met Hannah’s approval.

She merely gestured towards the machine. “What are you waiting for? Make mine.”

Right. That was why I provided her an empty mug in the least convenient way possible. Standing up and trying not to think about how my bare body was shifting right in front of the blonde eighteen year old, I walked over to the counter and got to work on her coffee. Fully aware that my backside was on display the entire time, rounding out my visible nudity for the second day in a row, I went to retrieve what Hannah wanted. The cream was simple enough to find in the fridge, although it took me a minute to find where her family (or personal chef, more likely) stored the sugar.

By the time I was done with the drink, Hannah was checking her phone at the table. She barely looked up when I set the mug down. “Pour it in a thermos for me,” she said.

Of course. I wanted to scream at her that such a task completely contradicted her insistence on wanting the exact mug I had picked out for her at random in the first place, but she could easily be trying to bait me into a reaction that would give her an opportunity to punish me. Instead, I picked up the mug without a word and went to look through the water bottles and other to-go containers I had seen during one of my kitchen explorations. After securing the coffee in the thermos, I set the container down in a similar manner to how I did before.

“Good girl,” she casually said. Locking her phone and sliding it into her pocket, she rose to her feet and strutted out of the room with thermos in hand. “Jessie, come. You do want something to wear, don’t you?”

Of course I did. I was quick to follow, and Hannah led me to the front door. My brief nervousness and skepticism faded when I saw a stack of clothes sitting on a nearby side table. Speaking of traps, I was a little hesitant to go right for them. As badly as I wanted to get dressed, I didn’t trust Hannah to make things so simple and straightforward.

Sensing my trepidation, she sighed. “Come on, Virgin. I told you, we’re behind schedule. Get fucking dressed, or you can leave the house naked.” To punctuate that concept, she put her hand on the doorknob.

“Wait!” I squeaked. Rushing over to the clothes, I quickly picked them up and started putting them on. It didn’t take very long for me to notice that nothing she had given me was mine. Not even the underwear. That didn’t particularly slow me down, although I would have much preferred wearing an outfit of my own rather than the t-shirt/shorts combo she had given me. I assumed they were her clothes, as the top was somewhat tight on my chest while the bottoms didn’t sit quite perfectly on my hips. Rounding out the simple ensemble by slipping on a pair of flip-flops waiting for me on the floor, I gave myself a once-over.

“I’m taking you out, Jessica,” Hannah explained without being asked, “You don’t think I want to be seen in public with some girl who wears clothes like yours, do I?”

Taking me out . . . where? Those words could sometimes have a date-like connotation, though that’s not at all what it sounded like as Hannah said them. More like we were just leaving the house, and I was along for the ride while totally in the dark in regards to our destination. As for the insult to my wardrobe, I didn’t comment or dwell on that. I was wearing something; that’s all that mattered. A bra would have been nice, and it’s not like anyone would see something like that under Hannah’s tee if I was allowed to wear one of mine, but anything was an improvement compared to nearly sixteen straight hours of nudity.

We were taking Hannah’s car, apparently. She made me sit in the back seat; according to her, ‘incompetent maids aren’t allowed to sit in the front.’ I blushed a bit at how she was talking to me as I got in the car, but I was pretty distracted by what my body was telling me. Still needing to pee, as that urge was only more persistent now that I knocked back a full cup of coffee, I was also starving. Hopefully part of this trip would involve breakfast. I was wise enough by now to not say anything or complain, at least until I had a chance to speak with the girl’s parents and ideally get them to tell Hannah that I was in charge. For the time being, I just shivered in silence when she turned the AC up to max in the car. Even with clothes on, I wasn’t as acclimated to Hannah’s cooler preferences.

It didn’t take long for Hannah to turn on the latest pop hits. She completely ignored me as we pulled out of her long driveway, which I was actually fine with. While I didn’t truly have privacy, being in the back seat and not having to serve Hannah in any capacity was a much needed reprieve. At the same time, I wasn’t fully relaxed. I had no idea where we were going, and I was worried we’d just end up at one of her friends’ houses for me to strip and be a naked maid for multiple rich girls all over again.

I definitely didn’t expect her to take me to the mall.

As we pulled into the parking lot and she drove right up to the curb next to one of the more high end department stores, I was stunned as someone came out to provide her valet services. I had never heard of something like that for anything shopping-related, though it didn’t totally surprise me now after seeing Hannah’s house and surrounding property. If this place knew she was here to spend a bunch of money, of course they would go the extra mile for her and probably a number of other wealthy clients.

Before we stepped into the store itself, Hannah squared off with me and placed her hands on my shoulders. “Do you remember what you’re supposed to say when I tell you to do something, Jessica?”

My full name always hit me so much harder when used in such a pointed and casually demanding way. Willing myself to look up and meet her eyes, I reluctantly said, “Yes, Hannah.”

“Good,” she nodded, “I’ve decided to use your credit card for my shopping today. If you carry my bags and behave all day, I’ll think about paying you back and you’ll get a bunch of free points. Okay?”

Not okay. It wasn’t lost on me that thinking about something wasn’t the same as actually doing it, and that was on top of how I would be relying on Hannah’s unfair and unrealistic definitions of behaving. Like, how was I supposed to know her coffee preferences if she never told them to me? I was already thinking about how such logic might apply to this shopping trip and what she might expect me to magically know before being told. “I don’t think-”

“It’ll be fine, Virgin. Maybe we can have a chat about all those sexy pictures and videos lately. Or about all those things my friends and I had to confiscate from you. What do you say, Jessie? But choose quickly. There are a lot of stores I want to hit, and we’re already behind thanks to you.”

Just like that, I was considering her offer. Not that I necessarily trusted her. Hannah had already proven that she could use my card one way or another, so I doubted I could convince her otherwise if her heart was set on putting my less than impressive finances in jeopardy. And I could still contact the credit card company and try to explain things, though I had never had my card ‘stolen’ before. Not only was the whole process unfamiliar to me, but I also would obviously need my phone or laptop to get the ball rolling on that.

“I want my things,” I awkwardly replied. One way or another, that was still the highest priority. My phone was the key to both contacting Hannah’s parents and undoing all the damage she and her friends had done and was about to continue doing with my credit card. Honestly, I was surprised it hadn’t been flagged yet. I never spent as much as they did last night at one time.

“Then you have to give me permission,” Hannah calmly said, “Tell me I can use your card for all of my shopping.”

But- but I also needed some assurances from her first. Right now, nearly everything was not so subtly phrased in a noncommittal way. ‘Maybe,’ and ‘I’ll think about it.’ Wanting a little more than that, I tried to press, “And then you’ll give my stuff back? Everything in my room?” Literally negotiating for my own possessions that she had no right to take in the first place. How far I had fallen.

Patting her purse, Hannah replied, “I have the key to your room right here. It’s yours if you’re a good servant today. That means treating me to a shopping spree and carrying all my things. Yes?”

I really wanted to push for a swear or a promise. Instead, I reluctantly said, “Yes, Hannah.” This was the first time she had offered to undo anything from the previous day. I was worried that if I wasn’t careful, she would change her mind. Of course, I was also concerned she would pull the rug out from under me anyway, yet it was a risk I had to take. Better than not trying at all. Right . . . ?

“The whole thing, Virgin,” she insisted, “I can shop with your card, and you’re my servant all day.”

Blushing at both the demeaning words, as well as how this scene might look to anyone looking our way from the parking lot and/or from inside the store, I quietly echoed, “Yes, Hannah. You can use my card, and I’ll be your servant all day.”

Chapter Sixteen

Jess

It wasn’t until we had actually been walking around the mall for a minute or two that I started appreciating just how nice it was to be wearing underwear again, as well as something on my feet. Similar to being able to breathe out of both nostrils after a few days with a stuffy nose, the simple feeling of wearing clothes after being naked for so long was a relief. Though I was sure that I was only allowed such things because Hannah had no choice in the matter. She might have had enough wealth and influence to be treated like a princess at the mall, but it’s not like she could leave me exposed in a more public setting.

It didn’t matter that I was wearing Hannah’s clothes. Just one look at us would inform anyone of the fact that we weren’t two friends out for a day of shopping. She was the rich socialite everyone waited on hand and foot for the sake of a fat commission while I was the plainly dressed girl awkwardly tagging along and waiting in the corner as she tried on outfit after outfit. Nearly every store we went to had employees either greeting her by name or coming to her merely because she looked like the type that deserved such special attention. And if her image didn’t do the trick, surely someone would notice the armful of bags I was carrying for her and hint that she was potentially going to buy just as much there.

Each and every time she checked out, I had to watch in silent horror as she swiped my credit card. The first store alone rang her up for a total that was higher than how much my checking account currently held. That wasn’t even counting everything Hannah’s friends had bought for themselves online yesterday. I just kept reminding myself of the same thing as before–it was credit, and the charges could be reversed. Or, better yet, Hannah would just pay me back, as that would greatly simplify things.

Whenever she wasn’t trying on clothes, I was constantly lagging behind despite my best efforts. Hannah walked with a purpose, for starters. Not only was I shorter, but I was also walking around in footwear that wasn’t designed for such a brisk pace, and I didn’t have nearly the shopping stamina that she did. Oh, and she was strutting around with nothing but a phone in her hands, while I was weighed down by all of her bags. I was pretty sure she enjoyed being in front, having her servant girl tail behind her, though she also made a point to regularly snap at me to not fall behind at the same time.

At some point, I ended up abandoning my flip flops and stuffing them into one of the bags that would fit them without risking any part of the summer footwear touching Hannah’s new purchases. It wasn’t an easy decision. While the mall floor was probably cleaned somewhat regularly, it was still a very public space with lots of traffic, and I didn’t want to think about how gross it was to walk around without anything between my bare feet and the floor. There was also the whole ‘no shirt, no shoes’ policy that I kept waiting for someone to call me out on. However, I just couldn’t risk tripping and totally wiping out when holding all of Hannah’s expensive new things. Keeping up with her felt like more and more of a falling risk, and I knew that I would be way more balanced without the borrowed flip flops that weren’t the greatest fit.

Around the time my arms were threatening to give out from being Hannah’s pack mule, not to mention how my mid-section was rumbling from all the walking on an empty stomach, Hannah decided that she wanted to stop at a café for a break. Spoiled as ever, she picked a booth that was way too big for just two girls, so we’d have ample room for all of her shopping bags. Then she instructed me to sit quietly while she took care of everything.

Similar to the special treatment she had gotten ever since we pulled up to the mall, this spot was no exception. Most people in the café were lined up to order at the counter. Hannah didn’t bother with that; she merely raised a finger and a barista came over to our table when she saw that we were ready. Unlike the high end stores, there was no commission to be had at a place like this. And yet, Hannah still somehow had VIP status. I was guessing she was a regular and tipped exceedingly well, unless there was something I was missing.

“Should I start you with a latte this morning?” the young woman asked.

“Yes,” Hannah nodded, “And a large iced coffee. I’ll also have some breakfast this morning . . . ” She proceeded to order without a menu in sight. Based on how she requested each item, I doubted it was because she was intimately familiar with their options. She just assumed they could make what she wanted until she was told otherwise. “What about you, Jessie? Care for a bite?”

Yes. Absolutely I did. Until I caught the subtle look on Hannah’s face as she glanced at me. Though I barely knew the girl, she had bossed me around and intimidated me enough yesterday for me to know how to read a number of expressions in the name of self preservation. If I wasn’t stuck being her servant for the day, maybe I would have been impressed at how she managed to give me such a look while also not making it obvious to our server how much power Hannah had over me.

“Umm, no thank you,” I said. More manners in those three little words than in anything Hannah had said since we first stepped foot into the mall. She always knew what she wanted, and expected to get it. When those expectations were always met, she really had no need to bother with ‘please’ or ‘thank you.’

Once it was just the two of us again, Hannah didn’t bother giving me any of her attention. Whipping her phone out and proceeding to text her friends and check her socials, if I had to guess, she busied herself with the smart device while I had to just sit there and twiddle my thumbs. I had no idea where my phone was. Likely back at the house, for starters.

When our drinks arrived, Hannah told me that my iced coffee needed to be empty by the end of the meal. I looked at the large plastic cup with trepidation. The nonstop shopping had managed to distract me for a while; now that we were sitting and there wasn’t anything else to distract me, I was back to paying attention to the faint pressure on my bladder that had persisted ever since I had downed the room temperature coffee earlier. Yet there was no denying Hannah. At least I wasn’t being forced to chug the whole thing; as long as I took decently sized sips as she ate her breakfast, I would be able to complete the task given to me.

The various aromas wafting about the café were bad enough when paired with my hunger, but it was so much worse when the collection of sweet and savory plates were placed down in front of Hannah. And of course she could eat such a full spread while still maintaining her hourglass figure. Though between her age and her wealth, she could obviously stay fit with a combination of metabolism and possibly a personal trainer. I vaguely remembered her friends talking about such sessions the other night, though I was too distracted at the time to really be listening to their conversations.

She ate in silence for the most part, save for the occasional quiet chuckle at whatever she was looking at. I just sat there and drank my iced coffee; though the temperature was better than the drink from earlier, it was still black coffee. Not my favorite, yet I had already mentally committed to a faster pace than what I’d normally take with something that made me slightly grimace from the taste.

A few minutes in, my stomach growled loudly enough for Hannah to give me an annoyed look. “Unbelievable,” she muttered. She set half a slice of toast on one of her already empty plates, followed by a small piece of bacon. Not nearly enough food to satisfy me after the multiple skipped meals, but technically better than nothing. Hannah slid the plate across the table, “There. Eat, Virgin. And what do you say?”

There were a lot of things I wanted to say. But I just swallowed my pride and muttered, “Thank you, Hannah.” As badly as I wanted to just grab the toast and scarf it down, I didn’t want to give her the satisfaction. Trying not to look desperate, I did my best to pick up the pathetic excuse for a snack and eat it more like a lady. The silver lining to doing it that way meant that it forced me to savor each bite and parse out what little food I had been given.

Hannah went right back to ignoring me, up until she was done with her meal. Of course, my few bites were long gone at that point. No pacing in the world could make me finish my plate as slowly as she worked through her assortment of breakfast selections. As for my coffee, I hadn’t made nearly the progress I had aimed for. And Hannah was quick to point that out. “You’re not done yet?” she asked, after the barista from before collected our dishes and went to settle the bill, “It’s really not that difficult, Jessie. Here, I’ll show you.” She picked up the roughly one third full glass and brought it to my lips, tilting it back with very little warning.

It was fine for a swallow or two, but then I couldn’t keep up. I also couldn’t tell Hannah to stop with a mouthful of cold coffee. Stuck in an impossible situation, as both pulling back trying to communicate pretty much anything would result in a spill, my hesitation ended up making that happen anyway and then some. When I was at chipmunk capacity, the iced drink started trickling down my chin and neck. I couldn’t hold any more, and a small shake of my head only caused the lid of the cup to shift from my lips. Hannah seemed oblivious to my plight until it was too late. Or, more likely, this was her plan from the beginning despite how she was feigning ignorance.

Since the tall cup was tilted so much due to how much was left, separating myself from the plastic caused the entirety of the remaining coffee to spill onto my chest. My reflex would normally be to gasp, except my cheeks were still full of coffee. Instead, I just tensed up from first the cold, followed by the sensation of the borrowed shirt clinging to my chest. Belatedly remembering that I wasn’t wearing a bra, I flushed and threw my arms over my breasts. I wasn’t looking down yet, as I was focused on swallowing the coffee as quickly as I could without choking on it, but I had to assume that my form would easily be seen when the already tight shirt was wet.

“Jessie!” Hannah exclaimed. Pointedly putting the now empty cup down, she shifted back and immediately started berating me, “Be more careful! You could have spilled on me. And look what you did to the shirt I loaned you. Ugh! Now we’re going to have to buy you a replacement.”

Finally managing to get the rest of the coffee down, I belatedly tried to protest, “But, you-”

“But nothing!” Hannah snapped. Rolling her eyes, she gave an impatient glance towards the barista at the counter, “That’s what we’re doing next. I can’t have my servant girl looking like that,” she said, vaguely gesturing to my soaked and stained top.

Being Hannah’s pack mule had only gotten more and more exhausting as the bags piled up leading up to brunch at the café, as had the mental turmoil every time she swiped my card and berated me along the way. That collective list was now longer; having a wet shirt was physically uncomfortable and made me worry about any number of strangers staring at my bra-less chest as the thin top clung to it.

I had also gotten used to the routine of standing around while Hannah tried on countless outfits at each store. Tedious as it was, at least I had plenty of moments to myself. That wasn’t the case any more. The very next store was going to require more active participation on my part, as Hannah was quite insistent on getting me something to replace what I currently had on.

Objectively, it wasn’t a bad idea. Spilling coffee on myself was a lot different than if it had happened with water, so changing into something clean and dry would be preferable. Except if I had it my way, I’d end up grabbing something cheap and simple. Instead, Hannah and I circled the department store as she grabbed shirt after shirt for me to try on. All the while, I had to continue hauling her bags around. And due to how full my arms are, it wasn’t really possible to cover my chest and hold all her purchases at the same time.

After what felt like forever, she walked me to the dressing rooms and pointed to a spot where I was to leave everything. It was the first time I hadn’t been able to stick around and guard them after putting them down, though Hannah didn’t seem particularly concerned about that. Not when she could just hand the nearest assistant a bit of cash and tell them she didn’t want anyone touching her stuff while we were busy in the changing rooms.

I didn’t realize until we were given a stall that Hannah had no intention of letting me change alone. Though we were in too public of a setting for her to say anything about the previous night, all it really took was another one of those looks. ‘I’ve already seen every inch of you.’ Something like that. I had literally nothing to hide when it came to Hannah and her friends, plus the bossy blonde had so many incriminating pictures and videos of me. Baring my boobs between trying on new shirts was hardly anything compared to everything I had already been through.

This particular store seemed to be below Hannah’s standards, as she hadn’t picked out anything for herself. I was the only one that was going to be changing, and she made short work of hanging up all the potential options I had. When looking at them altogether, it appeared as if she had taken them off the hangers at random. An assortment of tees, blouses, and a couple tank tops were displayed before me, and Hannah gestured towards my current top with an expectant look. “Well?” she asked.

“Yes, Hannah,” I replied. It was a submissive phrase I was getting accustomed to, considering I was now saying it to an implied demand.

I peeled off the borrowed shirt, flushing right away as my boobs popped out of the tight outfit piece. Out of instinct, my arms lifted halfway in an attempt to cover myself up before I remembered that I wasn’t allowed to cover. Also, I was about to try on nearly a dozen new tops, and it was unlikely I’d be able to keep from exposing myself in the somewhat confined space even if I tried.

She held out her hand, and I reluctantly handed over the still damp shirt. In exchange, I was given a tank top to try. Desperate to cover myself again, I was quick to pull it over my head and down over my chest. With a bra, it might have been a decent option. I was far more interested in the various blouses, as those had a far better chance of hiding the fact that I wasn’t wearing anything else on my upper half.

Hannah seemed to agree that the tank top wasn’t great, though her way of putting it was far more crass than anything I would have said. “Your boobs are way too big,” she commented. After giving my chest a once-over that wasn’t remotely subtle, she added, “Almost like a girl like you shouldn’t have a rack like that. Next, Jessie.”

One by one, we went through each of the shirts she picked out for me. Though I did like a couple of them, Hannah ultimately decided that none of them suited me. She collected all of them in her arms to hand back in. It surprised me that she would actually do anything herself instead of snapping her fingers and making me do it instead, until I realized that my original tee was amidst the crumpled pile she was now holding. By the time I processed that, however, she was slipping out of the changing room and leaving me in there alone and topless.

“Hannah, wait!” I exclaimed. I had no choice but to talk with her through the door, unless I wanted to risk flashing my breasts to anyone in the area. The store had been fairly busy when we were walking through it, and I had no idea how many other women might be waiting on a stall at the moment.

“Relax, Jessica. I’m going to find you something better. I’ll be back soon, ‘kay?”

And that was that. I tried calling after her one more time, but didn’t get a response. Anything else would just draw attention to me, and attention was the last thing I wanted in my current state of undress.

Considering I was too hesitant to even poke my head out, there was no way in hell I was about to venture out into the shop to look for Hannah. All I could do was sit down on the changing room bench and wait for her to return.

I hadn’t noticed the air conditioning before, no doubt due to how hauling around all of Hannah’s bags while practically speed walking had actually caused me to sweat a little bit throughout the day. Now that I was standing still and fully topless, however, it didn’t take long for the changing room to get noticeably cold. It was summer, so of course the mall was blasting the AC. I wrapped my arms around my chest both to stay warm and to cover my bare breasts; mostly the former, as I hadn’t forgotten Hannah’s rule.

The girl in the mirror was hardly the confident university girl who arrived for a lucrative babysitting job yesterday. I turned away from my reflection after only a few seconds, hating the image of myself so exposed.

Without a watch or a phone, I had no idea how much time was passing. Every minute felt so long as I impatiently waited for Hannah to return, though I knew how easy it could be to misjudge time. Especially in a situation like this. As I shivered in the cool stall, I was hit with yet another urge to use the toilet. Summoning whatever willpower I could muster, I repressed that need as best as I could. I would be absolutely humiliated if I wet myself right here.

What would Hannah say? Would she whisk me out of there, or make me suffer through the reaction of bringing the closest retail worker over to see what I had done? The mental image of the latest thought was difficult to shake once it had invaded my mind.

Just about the time I started worrying about what the chances were of Hannah leaving me here to get out of this mess myself, as she could probably easily find someone else to carry her bags to the car in exchange for a sizable tip, my heart skipped a beat when someone gave a firm knock to the door. “Jessie.” It was Hannah. For once, I was actually glad to hear her voice, as the alternative would be a saleswoman trying to free up one of the stalls and me trying to explain why I was still in here.

I doubted she would be okay with me covering my boobs even for the sake of modesty in public, so I undid the latch and stepped as far as I could to the side in order to avoid anyone else catching a glimpse of me.

Hannah strutted in, giving my topless form an annoyed look before considering the idea that maybe closing the door behind her would be a good idea. Taking her sweet time, she gave the two of us a little privacy again before tossing me a new shirt. “Already bought it for you,” she informed me, “Well, you bought it for you. Go ahead; try it on.”

What? Why- She didn’t think to let me do that before making the purchase? Considering how many options I changed in and out of before, I was skeptical about whether she would approve of this one. But it was already done, and I knew better than to complain.

It took all of one second of examination for me to realize that the top was too small across the board. For my height, for my size, and almost certainly for my chest. Yet Hannah had already told me what to do, and I had agreed to be her servant for the day. Reluctantly pulling the shirt on, I tried my best to take solace in the fact that I’d at least be able to cover with the outfit piece, as clothes were essentially the only way I could do so in Hannah’s presence. Technically, the shirt wasn’t a crop top, but it might as well have been. It was WAY too small, definitely smaller than I thought. The plain tee exposed a substantial portion of my stomach, while flattening my chest in a similar manner to what the maid uniform did yesterday. This was worse, actually. Because while the slutty outfit at least hid my upper form, this shirt squished my boobs back while also blatantly displaying my nipples at the same time.

In short, I would have preferred to put the damp top back on instead.

“Well, what do you think?” Hannah asked, “I figured that one reason you might still be a virgin is because of the way you dress. This should help.”

“But . . . it’s too small,” I weakly protested. It was easily the sluttiest thing I had ever seen on my own body, and she expected me to leave the changing room like this?

She just rolled her eyes. “You’re fine. It’s either that, or go topless. Up to you.” With that, she turned right around and left the stall. This time, with the door wide open.

By this point, I was too desperate to do anything but accept what she had given me. I obviously couldn’t walk around topless, both because it wasn’t allowed as well as the fact that I would die of humiliation and discomfort, and I also couldn’t stay in the changing room. Hannah certainly wasn’t going to wait on me for very long, and I had no means of communicating with her if she decided to abandon me here with nothing but the skimpy outfit I was wearing.

So, ignoring the knot in my stomach and the flush on my cheeks, I hesitantly followed Hannah back out to the main area.

I could only pray this mall trip was almost over. And that Hannah didn’t have any other casually wicked plans for me while we were out . . .

Chapter Seventeen

Jess

At some level, I knew that what I was wearing wasn’t the end of the world. Plenty of girls wore skimpy outfits in public these days, from crop tops to short shorts and everything in between. The difference is, those girls left the house after dressing themselves, no doubt aiming to look both attractive and put together. I didn’t feel like either of those things in the top Hannah had picked out for me, and was worried with every step that people would be staring at my nipples. Since I was stuck hauling all of Hannah’s purchases, there wasn’t much I could do to cover, either.

She led me through the mall at her usual brisk pace. I did the best I could to keep up, barely able to do so with the weight of the shopping bags. We ended up in a tanning salon, which I barely even recognized until I followed her into the place. Hannah told me to sit and wait, and she went up to speak with the girl at the front desk. A minute later, she was swiping my card and then coming back over to me. “Okay, Jessie. Time to fix that super pale skin of yours.”

Wait, what? This appointment was for me, and not for her? “Umm . . . ” I nervously muttered, glancing between her and the salon around us, “I don’t think . . . ”

“What, you think I need this place?” Hannah scoffed, “I’m plenty tan already, and I have a fucking pool to lounge by all summer while you clean my house and bring me my drinks. Plus you said you’d be my obedient servant all day. I’d hate for you to fail now after being such a good girl so far. Mostly.”

“Yeah, but-”

“But nothing. You’re so fucking pale. Come on, this is our last stop. The sooner you get in there, the sooner we can leave.”

I tried to voice my concerns one or two more times, only to end up being cut off. Even though this was something a lot more permanent than everything else Hannah had put me through so far, she was technically right. Though I had never imagined something like this when I reluctantly agreed to be obedient so far, that didn’t change the fact that I had said it. And I was admittedly tempted by her point about this being the end of our mall trip. Thanks to what I was wearing, I very much wanted to get out of the public eye, which both a sunbed salon and Hannah’s car achieved. And, of course, I was still quite easily intimidated by the girl, which made it difficult as always to stand up for myself.

Before I knew it, we were being escorted to one of the private rooms. The second Hannah and I were alone again, she demanded that I strip off my remaining clothes and climb inside. As much as I disliked being naked in front of other people, Hannah had already seen everything there was to see. At this point, any protests of mine would just be wasting time and making things more difficult for myself, so I took off Hannah’s shorts and the skimpy top I had bought for myself via the card in the blonde’s hand a few minutes ago, all under the watchful gaze of Hannah.

I had only ever done this once for a spring break trip, and it really hadn’t been worth the money. Because Hannah was right–I was pretty pale, and I had been nervous back then that everyone I knew would judge me for being noticeably tan the next time they saw me. So I had done the lightest setting for a pretty short length of time.

With Hannah, I wasn’t in control in the slightest. Rather than managing the settings myself, or letting me watch, she waited until I was lying down before making her selections. The soft beeps of the machine did nothing to inform me of what she was choosing. Apparently, there was a music option. When she was done with everything else, Hannah played the sound of a babbling brook, and proceeded to increase the volume by a few clicks.

“Don’t move a muscle, Virgin,” she said, “The bed will open when your session is done.”

Then she was gone. Or maybe she was just being quiet, and standing around texting to make sure I didn’t immediately get out. As if I was confident enough to do that; I had no idea how to operate the machine, and maybe it wasn’t as simple as pushing up on the metal. Either way, I was more or less alone with my thoughts in the solitude of the tanning bed.

The very first thing that crossed my mind was that I had applied lotion for the other appointment. ‘Should I have . . . ?‘ There was nothing I could do about it now. I just had to hope the lack of protection would be fine. And then there was the sound of running water, which did nothing to alleviate the pressure in my bladder. I somehow managed to hold it in until the cycle finished, though it was getting impossible to ignore now that I had been suppressing the need again and again whenever I felt it.

I stepped out of the sunbed and hurried over to the closest mirror. Gasping in horror, I could see right away that my worries were justified. My entire body was slightly burnt from the high intensity, prolonged exposure, lack of lotion, etc. It would take days for this to tan out, and that was a best case scenario. Based on former burning experiences, I could just end up with peeling skin and ultimately no tan to show for it when all was said and done. Either way, Hannah had found a way to make being naked even more embarrassing; my boobs were particularly rosy, which would certainly not go unnoticed.

Amazingly, Hannah had left my clothes sitting nearby. I quickly got dressed and reunited with her in the lobby, blushing right away when she gave me a onceover followed by a knowing smirk. She had done this on purpose! It wasn’t that much of a surprise, but still. Was there no limit to her actions where I was involved? Obviously she did need someone to keep an eye on her and somehow reform her casually cruel behavior.

I definitely wasn’t the girl for the job.

True to her word, this ended up being the last stop. One final humiliation for me, as I was now walking around with an unattractive burn on top of how pretty much anyone glancing our way would see the exact shape of my chest in the crop top. I carried all of Hannah’s shopping like usual, all the way back to the initial store where we had to wait another minute or two for the valet to return with her car.

“Clothes in the trunk, Virgin.” Not bothering to confirm that I was obeying, as she could easily assume at this point, Hannah got in the driver’s seat and settled in.

I knew better than to keep her waiting. Quickly yet neatly arranging all the bags in the trunk, I climbed in the back seat like before. On the way to the mall, I hadn’t loved being relegated to the back when it made way more sense for two girls our age to sit up front together. Now? I was just happy that I could cross my arms over my chest for the first time since buying the new top. My hands were finally free, and I also had the car door to cover if Hannah insisted that I leave them down.

She didn’t seem to notice or care. As we pulled out of the parking lot, she asked without so much as looking at me in the rearview mirror, “Want to stop for food, Jessie?”

In the back of my mind, I was skeptical. After everything I had been put through thus far, there was a good chance that this offer was not as simple as it sounded. Yet I found myself eagerly agreeing anyway. “Yes, Hannah,” I said. For starters, I was starving. The only thing I had eaten all day was the ‘snack’ I was given in the café that morning, which was barely more than a few bites of toast. And stopping somewhere would give me a better chance to use the toilet. Now that I wasn’t hauling Hannah’s bags around, it would hopefully be easier to excuse myself.

What I didn’t account for was that Hannah being part of a wealthy family did exclude her from cheap and easy meals. Rather than taking us to a restaurant, she pulled into a fast food drive-thru. So much for one of my two needs.

Rather than asking me what I wanted, she merely ordered a burger and fries for me, as well as an extra large soft drink. When she was handed the meal, as well as a small bag of fries she got for herself, she placed all the food in the passenger seat. “Here you go, Virgin,” she said, passing me back the enormous drink after removing the lid, “Finish this, and you can eat.”

I hesitantly took the heavy paper cup. The last thing I needed right now was more fluids in my system, but I was well aware that any little movement of the car would threaten a spill since she had taken off the one thing that was supposed to prevent that from happening on the road. I wasn’t sure I had what it took to down the whole drink in my current state, but I quickly took a few big sips to lower the contents to a safer level.

As we got back onto the main road, I was hit more fully by the scents up front. I wasn’t even that into fast food, yet a single whiff in my current state made my stomach growl. Tentatively taking a few more swallows of the carbonated drink in the hopes of working my way through it to earn some much needed food, I had to stop pretty quickly when I felt a renewed pressure below the waist. I had to be at my limit. There was no way I could finish the last two thirds without having an accident in the car.

Just when I was coming to that realization, Hannah slammed on the brakes.

I wasn’t prepared in the slightest. My body jolted forward, only to be abruptly caught by the seat belt. The whiplash caused the mostly full drink to spill down myself, all over my clothes. Gasping and wincing from the cold, as there had been a decent amount of ice in the cup, as well as from how my top was clinging to my chest and the rest of the soda was seeping into my shorts and underwear, I glanced up to find Hannah glaring at me in the mirror.

“Jessie! Are you serious?!” she snapped, “For fuck’s sake. If you’re not going to look after your clothes, you aren’t going to get any. Strip. Right now. And use what’s still dry to wipe up the mess you made.”

“But-”

“NOW. I’m not asking, Virgin. You have about two seconds, or I’m going to pull over and do it myself.”

But- but we were in the car! Being naked at her place was already a lot to handle, even if it was all girls. However, we were on a pretty public road, and Hannah’s car wasn’t particularly tall. Just about anyone at our height or above who happened to glance our way would see, especially if I was drawing attention to myself with the act of stripping. Which is why I knew I had to act as quickly as possible, as I had learned again and again that I was incapable of standing up to the girl I was supposed to be babysitting.

Starting with my shorts and underwear, mostly to keep from flashing my more visible half to anyone on the other side of the car window, I shifted and shimmied as I worked them down. Though Hannah’s shorts were more awkwardly fitting than they were tight, it didn’t change the fact that I was seated and the borrowed clothes were soaked. Thrusting my hips too far forward was a concern as well, so I did my best to keep my ass barely elevated over the leather until I managed to get the wet garments past my thighs. Before settling back down, I used the dry parts of the fabric to wipe at the seat beneath me like Hannah had told me to do.

Unfortunately, a soft drink wasn’t that easy to clean. No matter how thorough I tried to be, the leather was still sticky on my bare ass when I sat down. And after nervously looking left and right towards all the other cars and pedestrians, I tentatively peeled the crop top off my upper half, wincing at how it was clinging to my skin as well as how the exposure made me shiver from the AC that Hannah was blasting just like she had done on the way to the mall.

Fully naked. In the car.

Maybe not a new low, considering how I literally had to use my boobs as a sponge the other night, but certainly a new round of humiliation. I sank down in my seat and curled into a ball as we drove through the busy street, hoping that Hannah wouldn’t yell at me for covering up. There was just no way I could handle sitting properly in the car. Not only was I scared of being seen, but what if someone took a picture or video?! Hannah had a reason to hold onto the leverage she had on me, but a random stranger would have no problem sharing it with friends and the internet alike.

Rather than getting on my case about it, Hannah took pity on me. “Do you want to take the scenic route home, Jessie?” she casually asked.

I nodded right away. “Yes, Hannah.”

I should have known that her intentions were anything but pure. In my desperation to get somewhere more secluded, however, I failed to think about the lessons I had learned about Hannah over the last 24 hours.

We left civilization behind rather quickly. Her house was rather secluded, now that I was thinking about it, so it made sense that she didn’t have to take the main road if she wanted to. Letting out a quiet sigh of relief at the practically nonexistent amount of cars around us, I continued hugging my arms around my knees. I still hated my chest being bared, even if it was just Hannah now, and I was also cold.

Though I hadn’t consumed much of the large drink before spilling it all over myself, I still had to pee quite badly. I had briefly forgotten about the pressing need amidst everything else, but it was my singular focus as Hannah drove us down a number of winding roads. Letting out a tiny squeak as we hit a patch of rough terrain, I barely managed to hold it in. What could I do?! Hannah had been pretty insistent about not allowing me to use her bathrooms earlier. Surely she wasn’t serious, right? As I had wanted to point out at the time, it was impossible to both not use the restroom and not have any more accidents. Honestly, I would be willing to jump out of the car and relieve myself on the side of the road at this point. Yes, the thought of being naked outside was daunting, but there wasn’t a single car within sight at the moment. Plus I could use her car for cover.

Meekly piping up, feeling beyond self conscious from both my state of undress and how the pressure in my bladder was getting unbearable, I said, “ . . . Hannah?”

“No, Virgin. I’m not going to fuck you. Find another lesbian to take your V-card.”

“That’s not-”

“Jessie, shut up. I’m trying to enjoy the scenery.”

I fell silent again, not sure what to do. Thirty seconds later, the decision was out of my hands. The vibrations of another bumpy road proved too much for my body, and I couldn’t hold back a large squirt of pee. “Hannah, please,” I started, but it was too late. No amount of willpower or physical tensing would save me from what I had put off for way, way too long. The faint trickle started up despite my best efforts, quickly shifting into a steady stream as I rapidly emptied my bladder all over the seat.

Since I had unintentionally preempted the accident by getting Hannah’s attention, she noticed what was happening almost right away. Her response? Turning off the music. In the now quiet of the car, there was absolutely no hiding what was happening. If the faint hissing from between my thighs wasn’t enough, it wasn’t long before there was a warm puddle underneath me that created the same audible tinkling noise a toilet made when the water was disrupted.

I was absolutely mortified. Again.

Disgusted, too. At least my last few accidents had been onto the living room floor, and later the cement by the pool. This time, I was literally sitting in my own mess. And apparently, that’s how it was going to be for the rest of the journey.

“I’m not even surprised,” Hannah rolled her eyes, “This is exactly why you don’t deserve boobs like that. You can’t even make it to the bathroom like a mature girl. You haven’t had sex, either.”

I was already blushing from the prolonged accident, but my cheeks turned crimson from her remarks. “I tried-”

“Whatever. Sit still and try not to make an even bigger mess. When we get back to the house, you and I are going to have a talk.”

Chapter Eighteen

Jess

There wasn’t anything else I could do.

Hannah was driving on rural roads at this point, so it wasn’t as if she could pull over and let me clean up somewhere. Also, I was naked, so that wouldn’t be an option anyway unless she allowed me to put back on the borrowed clothes first. The one thing that I would do, if given the option, was scoot over to the opposite side of the car. At least then, I wouldn’t be sitting in my own pee. But I was way too intimidated by Hannah to do something perfectly reasonable like that, especially when she was already judging me.

So I sat there for the rest of the journey, still shivering from the nonstop AC and resisting the urge to cover my bare chest like I so desperately wanted to.

The sight of Hannah’s house was quite the relief. Though I had been through all kinds of mortifying experiences there, at least it had been secluded. While I didn’t love being exposed to the blonde and her friends, that was slightly preferable to wearing skimpy clothes at the mall and being naked for any nearby drivers to see. I was still clinging to the hope that I could somehow get this summer back on track. At the moment, I was definitely in no position to make such an attempt.

Rather than pulling all the way to the end of the driveway, Hannah merely parked the car adjacent to the front door. “Bring all my shopping bags inside,” she told me upon turning off the engine, “And try not to make a mess. If you spill on the floor, you’ll be cleaning it up with your toothbrush. Oh, and wash my car. Starting with your piss, obviously, but you might as well scrub the whole thing while you’re at it.” She popped the trunk, then opened the garage door in the distance. “Meet me around back when you’re done.” With that, she strutted into the house without another word.

I scrambled out of the car, very much wanting to get out of the dirty puddle I had been stuck in for at least fifteen minutes. Hoping that Hannah wasn’t planning on looking back or watching me from inside, I started awkwardly shaking my hips to remove as much moisture as I could. Using my hands was out of the question, as that would be disgusting and unsanitary, so I had to suffer through the awkwardness of my boobs shifting and bouncing in response to the movements. Without a bra to keep them in place, or my hands to cup them, there was really no avoiding it.

It made the most sense to start on the car so I could air dry, not that I’d ever feel clean down there until I could actually take a bath or shower. Honestly, I’d take a wet wipe at this point. However, Hannah started by telling me to bring in her bags. She could have just been rambling off demands without caring about how I executed them, or she could have meant for me to go in order. I didn’t want to risk it, so I started with the first thing I heard.

After so much nudity yesterday, you’d think that I would be a little desensitized to it. That definitely wasn’t the case. Then, it was later in the day, and everything I was subjected to had transpired behind the house. Now, it was a sunny, summer day. I was standing on the driveway in front of Hannah’s borderline mansion and more conscious than ever about my nudity. Though her friends weren’t here, and I’d easily see a vehicle in the distance, it didn’t change the fact that being naked in broad daylight was beyond uncomfortable for me.

I grabbed a few shopping bags, deciding that multiple trips was the way to go. Though it meant prolonging my time outside, I didn’t want to risk dripping in the house. A few trips later, I had successfully carried all of Hannah’s purchases into the house. I briefly considered that she might have meant that she wanted them up in her room, even if she hadn’t specified anything beyond ‘inside.’ Because I could still feel the dampness of my thighs and lower cheeks, however, I figured it would be best to tackle the car wash first. I could always bring the bags upstairs afterwards.

As for the coming task, I was going in completely blind. I had already learned where plenty of the cleaning supplies were as Hannah’s ‘housekeeper,’ yet her garage was brand new territory. Thankfully, Hannah hadn’t made me remove the flip-flops when making me strip in the car. I could only imagine how hot the driveway was after half a day of baking in the sun.

I made my way into the spacious garage, letting out an exhale of relief simply due to being partially inside. Objectively, it didn’t make a difference where I was when no one else was around, but it still felt more acceptable to be naked indoors. Of course, I would have preferred clothes. It was only a temporary comfort, as I still had a car to wash. After poking around the outskirts of the garage, I eventually found what I needed. The supplies were well organized and logically placed right next to the hose that was no doubt set up for this very job. I had been bracing myself to drag the backyard one around the house. This wasn’t a huge convenience in the grand scheme of things, though it helped a little bit.

This time, I was determined to make it in a single trip. I poured a little soap into the bucket and grabbed a large sponge, then took the hose with my other hand. Ideally, the car would have been a lot closer, though it wasn’t too much trouble to carry everything halfway down the driveway. I did have to double back to turn the water on, still feeling constantly nervous and self conscious whenever the outside air brushed my exposed body.

It had been a while since I washed a car by hand. The good news was, it wasn’t particularly complicated. Similar to how I’d give myself a shower, I sprayed down Hannah’s sedan with the water, then proceeded to scrub with the soapy water I had made for myself in the bucket. I couldn’t help but think back to how I had been made to use my boobs as a sponge the previous night, and prayed that Hannah wouldn’t come back out here to demand the same thing for her car.

I was also worried about burning. My skin was already a bit red from my too long/too high setting in the tanning bed, and now I was under the sun without a trace of lotion protecting me. With that in mind, I worked as efficiently as possible, occasionally ducking back into the garage to avoid non-stop exposure to what was surely a high UV index. I was tempted to give the dirty areas of my body a quick pass with the sponge, except Hannah could still be keeping an eye on me from one of the windows. Anything I did that wasn’t a direct order from her would potentially lead to a punishment.

It wasn’t until I finished rinsing all the soap off her car that I remembered that cleaning the inside was supposed to be the priority. “Shit,” I muttered to myself. My focus had been all over the place, and I had been thinking too much about the mess on my body rather than where I had been seated. Scurrying back to the garage, I grabbed a handful of rags while praying the leather would be fine. It was difficult to be quick and careful, as I really didn’t want my hands to touch the pee as I did an initial few passes to wipe up the accident. Then I got to work actually cleaning the back of the car, realizing that I wouldn’t be able to roll the windows down without Hannah’s keys. Letting out a frustrated groan, I dried everything off to the best of my ability, then left the door wide open while I started putting everything away. Hopefully the very same sun I was worried about burning from would be enough to air dry the back of the car; I needed to close the door soon, as she would kill me if any bugs or whatever ended up inside.

Taking the initiative to close the garage door with the same clicker Hannah had used, I reluctantly closed her car back up and had to assume that the sun would still be enough to do the rest on a summer day. Now what? Hannah had told me to meet her around back . . . Did that mean I should cross through the house like she did, or circle around from the outside? The visual of the latter was already in my mind, as I had pictured myself doing it to get the hose. And because the young blonde was needlessly cruel, she would probably prefer me to stay out as long as possible while I didn’t have a stitch of clothing on.

Opting for the more humiliating route, if only to avoid more trouble, I reluctantly made my way towards the very pool that had started all of this. I should have never hopped in the shower without locking the door first.

Hannah was outside.

Wearing the same bikini as yesterday, lounging by the pool without a care in the world. Easy enough to do, considering she didn’t have a single chore or responsibility to worry about as the entitled eighteen year old that she was. She was much more than rich and spoiled, of course. I would have been able to handle a girl like that. When she noticed me approaching, she said, “Took you long enough. I need a drink, but not before you get cleaned up.”

Speaking of showers. Although this time around, I was much more inclined to head upstairs and do just that, even if she planned on sticking me with a slutty maid uniform afterwards. In fact, that was highly preferable to my current nudity. In retrospect, I couldn’t believe I hadn’t thought to give myself a scrub along the way when washing Hannah’s car. A few passes of the sponge would have been better than nothing, and the sun would have dried me off afterwards.

“Yes, Hannah,” I said. At least I was dry at this point, if not clean. Heading towards the house in a similar manner to my countless trips last night to refresh drinks again and again, I only made it a few steps before Hannah spoke up.

“Where the fuck are you going, Virgin?” she asked. Sitting up slightly, she pointed towards the edge of the poolside area, “Shower out here, where I can keep an eye on you. Actually, I don’t even trust you that far away from me. Here.” With that, she stood up and walked over to what I realized was an outdoor shower. The other day, I just figured it was some kind of storage area. When Hannah opened the wooden door, however, the showerhead within made it clear what it actually was.

I knew some houses by lakes and beaches had such things. Why did Hannah’s family have one? Then again, I hadn’t loved being unexpectedly covered in chlorine from my ‘fall’ into the pool. Maybe Hannah and her friends liked to rinse off out here after a swim. Either way, I had a much different reason for needing a shower at the moment.

“Keep the door open,” Hannah said, “And there’s no need to waste hot water on you.” She grabbed what I assumed was the cold knob and started the water. “Well?”

So much for privacy. And comfort. While I was a bit hot from being out in the sun for so long, a cold shower was hardly the cure. A dip in the pool would be one thing. This is what Hannah wanted, however, which meant that it would be what I did. With a nervous swallow, I stepped forward and tried not to think about the impending wave of cold water. Maybe it wouldn’t be that bad?

Demonstrating her impatience right away, Hannah groaned and snapped, “Now, Jessie!” Placing both of her hands on my back, she gave me a good shove.

Stumbling forward, and just barely able to keep myself from tripping over the raised stone that divided the shower from the area leading up to it, I gasped as my entire body was doused in the freezing water. It was not at all refreshing like I had expected; if anything, the fact that my skin had been warmed by the sun made the abrupt shift in temperature that much worse. I was also temporarily blinded by the water in my eyes, as I had more or less been sent in face first, rather than the way I’d normally step into such a thing.

Out of pure instinct, I mostly removed myself from the cascade. It’s what I would do in a normal shower when waiting for the water to heat up, or to adapt to the temperature one way or another when first stepping in. Of course, this wasn’t a normal shower in the slightest.

“Jessica!” Hannah exclaimed, “Do I seriously have to babysit you through this whole thing? Get back under the water. Rinse your whole virgin body off. Hair, too. Come on, I don’t have all day.”

Blinking the water away until I could mostly see again, though my vision was still terrible without my glasses or contacts, I preemptively winced as I moved back into place under the showerhead.

Taking shallow breaths as I forced myself to stay in the freezing shower this time around, I tried to go through the motions of my usual routine despite having an audience and having to deal with the awful water. I raised my arms and ran my hands through my hair until my brunette locks were thoroughly rinsed, doing my best to not think about how my breasts were blatantly on display as I did so. Then I turned in a slow circle to make sure that every inch of me was hit with the water for at least a few seconds.

After being overly thorough for the sake of avoiding even more judgment and chastising from Hannah, I finally moved away from the center of the outdoor stall. I still needed to wash myself, and the only way to do that was to be slightly removed from the falling water. Briefly looking towards the blonde to verify that what I was doing was okay, I reached down and picked up the shampoo. My vision was blurry, but I wasn’t blind. Besides, this was how I was used to showering, as contact lenses weren’t meant to be worn in the tub.

When Hannah didn’t yell at me or get on my case about anything, I got to work. My hair was definitely going to be the worst part. Rinsing out my long, brunette hair was normally relaxing in a steamy shower, but it would take forever when holding my head underneath the cold water. But I was in too deep, and Hannah was standing there watching my every move. I was caught between wanting to get this over with as quickly as possible, while also tempted to stall ever so slightly for the sake of letting the sun warm me up a little bit while I worked the shampoo through my dark locks.

I couldn’t delay the next part forever. Plunging my whole body back into the frigid water and flashing back to my prolonged time in the freezer last night, I hurried to rinse all the suds out so I could get back out and get started on my body. There wasn’t a washcloth or loofah within sight, and I definitely wasn’t about to ask Hannah for something like that. This was literally an outdoor shower, and she would almost certainly scoff at such a ‘need.’

Instead, I simply lathered up my hands and hesitantly started on my shoulders. It wasn’t going to be too long before I had to move on from my arms to more or less fondling my bare breasts in front of Hannah. That’s not actually what I would be doing, but that’s basically what it would look like when washing my chest with my bare hands. Of course, she already had blackmail of me touching myself in a much more damning manner. I just had to get through this, just like I needed to get through so many other recent ordeals.

Feeling the heat rush to my face, I lowered my hands to my chest and began spreading the soap around. As badly as I didn’t want to put on a show for the blonde, I had to assume that she wouldn’t be content with me doing the bare minimum. So I gave myself a few squeezes, blushing all the while. I couldn’t even bring myself to look up, as it was easier to remain ignorant of whether or not Hannah was training a camera on me.

My stomach offered a brief reprieve, though it wasn’t long before I had to touch myself in another inappropriate manner while both outside and while being observed the entire time. Rubbing myself between the thighs for a few seconds, I cringed upon realizing that I couldn’t shift my focus nearly as quickly as this time. I had been sitting in my own mess for so long in the car, which meant I really had to scrub all the areas below my waist.

“Hey, Virgin,” Hannah said, speaking up for the first time in a while, “When you’re done, turn off the water and put your hands on your head.”

Leaving me in suspense beyond that, she told me to get back to it.

Chapter Nineteen

Jess

I didn’t have much left to clean by the time Hannah told me what to do after the shower.

Stalling was out of the question. It didn’t matter that I wasn’t looking forward to what she had planned for me; it was going to happen no matter what, and every minute I spent bathing myself was another minute I had to be naked while Hannah’s eyes were directly on me. Despite the ‘lesbian’ comments about me over the last 24 hours, I had no idea whether she was straight or not. Either way, it didn’t matter; there was no way she was into me like that. This was all purely to heighten my embarrassment.

Finishing up with my legs and feet, grateful that my backside was facing away from her while I did so, I took another minute or so in the outdoor space to make sure that I was fully rinsed off. Knowing Hannah, she would absolutely punish me for something as little as not showering to her absurd standards. Plus I’d rather not have any soap on my body afterwards.

Then, after reminding myself that the blonde had already seen every inch of me, not to mention all the lewd pictures she and her friends had taken, I turned off the water and reluctantly obeyed Hannah’s latest command. Placing my hands on my head and pivoting my body towards her, as I assumed that’s what she wanted, I blushed right away as I realized that the position slightly caused my chest to jut out. There was really no avoiding it; the only way I could protect my modesty was by keeping my thighs together as tightly as possible as I awkwardly displayed myself.

I could only imagine how unattractive I looked, too. Shivering with cold, brown hair plastered to my head, dripping in the outdoor shower as I continued dealing with the nudity that I doubted I would ever get comfortable with. I was confident about my body, though a bit of extra height would have been nice, but that didn’t mean I wanted to be seen naked. Not like this, anyway.

Also, I found myself wishing for the summer heat that had been such a problem when washing Hannah’s car. Not only was I in the shade of the house, but the sun was also behind a cloud at the moment. There wasn’t a towel within sight, either. I wanted to ask Hannah for one, of course. After a freezing shower, the last thing I wanted to do was air dry. However, I first had to get through whatever she had planned.

As unpredictable as she could be, I actually ended up being correct about her initial motivation for making me stand in such a way. With an idle smile, she picked up her phone from a nearby table and trained it on me. “Don’t move an inch,” she told me, getting ahead of my instinct to turn away at the thought of being photographed while buck naked, “Stick your chest out, and smile.”

I wasn’t sure which of the two directives was worse. My chest already was slightly out from my arms being up and, because of that, my shoulders being pulled back. And as for the latter demand? Smiling when told to was bad enough already, and then there was the absolutely humiliating day I had gone through.

Doing my best to obey, knowing that I would only be standing there for even longer if I didn’t, I arched my back and pushed my breasts forward to the best of my ability. Blushing more deeply, I hesitantly parted my lips and gave whatever smile I could muster under the circumstances.

Naturally, it wasn’t enough. Hannah scoffed. “A real smile, Jessie. Or would you rather go back to the mall?”

‘No!’ The first trap had been more than enough. My arms were still sore from carrying all of her bags, my body was burnt from the tanning bed, and I didn’t even want to think about how many people had seen the shape of my breasts and nipples in the tight top I had been stuck wearing at the end. Then there was the fact that my credit card had been charged for every single purchase throughout the day, and Hannah had really expensive taste. I didn’t even want to think about how many thousands of dollars she had spent between today and the way her friends had treated themselves the night before.

With that in mind, I pushed the biggest smile possible onto my face, going so far as to give a quiet exhale of laughter to myself like I might do when trying to make my face look natural for a more normal photo. All that, while still arching my back in what was easily the most unnatural position for my chest.

“That’s better, Jessica,” she said, “Now how about a shy pout? Should be easier for you.”

She wasn’t wrong. Although pouting on purpose felt so awkward and immature, especially since I was supposed to be the housekeeper/babysitter here. Still, I did as I was told. Feeling a bit like a slutty influencer who baited guys into donating money, I gave some form of a pout for the camera. It wasn’t an expression I ever normally made, and I wished I had a second to check with a mirror before letting Hannah capture whatever my blind attempt looked like.

Hannah snapped another few pics, each one with the volume on to add insult to injury, then set her phone down after telling me to stay in place. “Actually, no,” she said, somewhat changing her mind, “Come here. But keep your arms up.”

I wasn’t sure what to expect, though I knew that I had to do as I was told. Slowly stepping out of the shower, making sure not to trip over the stone between the tile and the main pool area, I walked up to Hannah. By the time I was right in front of her, I had to slightly crane my neck to meet her eyes, and re-arch my back when she reminded me that my chest was supposed to be pushed out.

Once I was how she wanted me, baring myself while glistening all over and still trying not to shiver, it didn’t take long for Hannah to slip back into ‘completely unpredictable’ mode.

Out of nowhere, her hand slapped one of my bare breasts.

I gasped. Between how hard she had hit me, as well as the surprise of being struck in such a sensitive spot, it took everything in me not to drop my arms and wrap them around my chest. It wasn’t the first time Hannah had slapped me in such a way, but it had been a while. Staring at her with wide eyes, I remained frozen in absolute indecision. Hitting her back was a bad idea, as was snapping at her. It dawned on me all over again just how much control Hannah had over me after less than 24 hours. Rather than defending myself or fighting back, I was still standing there with my entire front side on display for her to see and to potentially hit again.

Apparently Hannah recognized this, too.

“You’re pathetic,” she bluntly said, “Apologize for your boobs. Right now.”

It also wasn’t the first time she had demanded an apology for something that I had no say over. Briefly hesitating with my mouth agape, I echoed the phrase from the other night, “I’m sorry for my boobs . . . ”

Hannah stared me down. “You should be. Wetting yourself in the fucking car? A childlike girl with no self control doesn’t deserve boobs like that. You’re a naughty virgin who deserves to be punished.”

“I’m sorry,” I muttered. What else was I supposed to say? It wasn’t fair how she was treating me, though it was a lot more difficult to deny the merit of her scathing remarks. I had wet myself in the car, and had barely said anything regarding my needs. In my defense, Hannah had revoked my bathroom privileges, provided she had been serious about that. But being a virgin? Though that was ‘my fault’ in a way, it’s not like it was something worth punishing!

“Chores. Now.” Hannah pointed towards the sliding doors that led into the kitchen. “Make me a snack and a rum cocktail for starters. Then get started on the windows. Every window, Jessie. Both the inside and the outside. Why the fuck are you still standing there? Hop to it, girl. Wait. Glasses.”

She stepped forward and produced my glasses out of thin air. Or maybe I was so blind without the unattractive accessory that I just couldn’t tell that she had them ever since I stepped out of the shower. Placing them on me and subsequently coming into focus, the unfairly hot blonde stepped back again. Still not sure what to say, I awkwardly fumbled for some form of gratitude. For giving me something that was mine in the first place. “Umm, th-”

“What did I say, Virgin?” she glared, “Hop to it. Right now.”

I didn’t need to be told twice. Assuming that she didn’t want me awkwardly crossing the patio with my arms over my head, I dropped them back down and hastily made my way towards the house. Anything to separate myself from the needlessly cruel girl, even if the cost was allowing her to see my bare backside as I scurried away. It wasn’t until I actually reached the doors that I hesitated. I was still soaking wet, and of course Hannah hadn’t considered giving me a towel. Making the call to be obedient, as water was just water at the end of the day, I hesitantly stepped inside.

Stiffening at the wave of AC that crashed into me, instinctively wrapping my arms around my chest as I shivered from head to toe, I cringed at the thought of what Hannah might do if she perceived me as covering up. For all I knew, she was following me in. Even though it was more a reaction to the temperature, I doubted she would see it like that. So I lowered my hands to my sides, trying to remember if the house had been this cold yesterday. Maybe it was just due to the fact that I was covered in water.

I wasn’t much of a cook, nor did I know what Hannah wanted. Last night it had mostly been fruit, along with various chips and crackers. Taking a similar approach this time around, I decided to do some iteration of a charcuterie board, mostly because I figured it was the safest way to make sure there was at least something she liked. Between cheese, meat, crackers, and fruit, hopefully she would be content grazing after already having a bite at the mall.

Speaking of keeping Hannah happy, I opted to start on her drink first. She could work on that while I prepared the more involved part of her request. As I pulled out the handle of rum, I tried not to think about how I was once again not only allowing the girl I was supposed to be supervising to drink, but actively making a drink for her. I dried my hands off on the nearby hand towel, it belatedly registered that something like that would be better than nothing for the rest of my body. With a single pass of the towel, I wiped myself down enough so I wasn’t dripping. That would have to do. If Hannah needed to dry her hands later, she might get annoyed that the hand towel was soaked.

Honestly, I was more concerned about the floor than I was about anything else. Normally a room where people regularly came in from the pool was bound to have wet floors along the way. Except this house really nice, and Hannah also had completely unrealistic expectations for what one girl could do. I wasn’t even supposed to be here as her maid! Yet here I was, wondering if there was something I could use to wipe up the floors to avoid Hannah’s judgment.

For the time being, I just had to take one step at a time. Starting with making a simple Rum & Coke like I did last night for . . . for her? For one of the girls? It was all a blur.

I definitely didn’t want to go outside again in my fully exposed state. If anything, the glasses made everything worse. While I very much appreciated being able to see properly again, which would hopefully mitigate the headache from so many hours of everything being so blurry, it also meant that I was more aware of my own nudity. Not that I really had to see that I wasn’t wearing clothes; it was just one more sense I now had to deal with.

As usual, I tried to cling to any silver linings I could find. Like how the sun on my body, self conscious as I felt walking around like this in broad daylight, at least warmed me up a little bit.

The last thing I expected was for Hannah to be nude as well. Well, not quite as nude as I was. She still had her bikini bottoms on, but was lying on her poolside chair completely topless.

I froze for a moment. The blonde was probably still expecting me, but like this? It wasn’t fair. I hated being so exposed around others, and Hannah was lying there and baring her chest without a care in the world. I doubted she was even doing it for the sake of making me uncomfortable. This was just her house, her pool. And as I had seen on two separate drives now, her property was quite secluded. Hannah was just confident and shameless as ever, and I assumed she was just avoiding tan lines.

“Umm, Hannah?” It took all my willpower not to look at her boobs. Unlike she and her friends had suggested countless times, I wasn’t a lesbian. I wasn’t bisexual, either. But I also wasn’t used to being around girls that lounged about without a stitch of clothing above the waist. That made my eyes naturally want to drift to the unfamiliar/out of place. Making a conscious effort to keep my eyes on her face, I held out the drink.

She lazily opened her eyes. Glancing up at me, then towards the glass in my hand, she simply let her eyelids fall again. “Leave it on the thing,” she said, dismissively waving her hand towards the little table beside her.

I couldn’t believe how much of a servant I had turned into. Even when she wasn’t watching my every move and threatening me with XYZ, I was still waiting on her hand and foot. But what else could I do? I had already tried and failed to get my stuff back, and I didn’t even know where my clothes were at this point. If I couldn’t succeed in that endeavor while dressed in the maid uniform, I certainly didn’t have a chance of searching her place in my current state, even if she was outside and not bothering to keep tabs on me.

And what would I even do if I did manage to get dressed? She had pictures and videos. She had my phone. Until I found a way to contact her parents and to somehow destroy that evidence–which was no doubt saved in multiple places by this point–I was stuck being 100% her housekeeper and 0% her babysitter.

Heading back inside, I got to work on the next task. Still not loving the AC, and feeling super weird preparing food while buck naked, I spent a couple minutes looking for a wooden board before pulling out whatever I could find from the fridge and pantry. One step at a time. I knew it was naive to think that Hannah would let up if I behaved exactly how she wanted me to, but that was the only ‘strategy’ I had for the time being.

Just when I was putting the finishing touches on the charcuterie board, a bit jealous of the spread that was at least five times more expensive than what my friends and I could afford in terms of cheeses and such, I looked up when I heard the sliding doors opening. Apparently I hadn’t been quite efficient enough.

“Jessie! What the actual fuck?!” Hannah exclaimed. Gesturing to the kitchen floor all around her, she said, “There’s water fucking everywhere. You’re my housekeeper! You’re supposed to be doing the opposite of making messes.”

“But, I- You said-” Floundering immediately, as I was getting worse at handling Hannah with every passing hour, I blushed deeply as I mumbled, “I’m sorry.”

“Stop talking. Stay right there.” With an annoyed huff, she swiveled on her heel and strutted out of the kitchen and towards the stairs.

Once I was alone, and thoroughly daunted by whatever was in store for me, I cringed as my stomach let out a long, loud growl. Right. I had only had a literal bite to eat all day, and had mostly been on my feet as well. The charcuterie board before me was so, so tempting. The meat, especially. Some protein would do me good, and would last a lot longer than the bits of carb scattered around the edges. But Hannah hadn’t given me permission. If she smelled it on my breath, or caught me by turning the corner a lot sooner than expected . . .

Though she had made it rather clear that she would tell me off for just about anything, I wasn’t quite hungry enough to intentionally risk incurring her wrath. So I merely waited, hoping that she would realize it wasn’t fair to blame me for something that only happened because she sent me to the kitchen right after my shower. At this point, my body was mostly dry, yet the floor was still soaked due to the indoor temperature preventing much evaporation.

Hannah returned, holding up one of my nicer sundresses. Unfortunately, I quickly learned that she had no intention of letting me wear it. “Here,” she said, bunching it up in her hands and throwing it at me, “You can use this to wipe the floor.”

Chapter Twenty

Hannah

All in all, it was a solid day.

Seeing Jess get more and more tangled up in her obedience was delightful. There’s definitely a degree of natural submission where she’s involved, but it’s not nearly as obvious or overwhelming as some of the other girls I’ve put in their place throughout my teenage years. Most of what the brunette had been doing was less about any submissive tendencies, and a lot more about the way I set things up for her to fail. Personal possessions confiscated, bathroom privileges revoked, and a non-stop barrage of lose/lose scenarios that kept her under my thumb all the while.

My most recent achievement? Jess didn’t even eat anything when left alone in the kitchen, nor did she ask for any food when she was clearly starving. It took most of the day for her to clean the inside and the outside of all the windows in my house, complete with making her get onto the roof naked to scrub the outside of the ones on the upper floors. We didn’t have any neighbors that would see her, nor a busy street anywhere close to our secluded property, but still. Just the fear of being seen would probably be enough for the girl, as well as the prospect of her sunburn getting worse if she wasn’t quick enough.

I didn’t feel the need to hover or overly supervise along the way. While all kinds of amusing, breaking the girl who had been hired to babysit me wasn’t my only summer interest. Of course, I would still check in. To tell her off for the noises her stomach was making, for fidgeting and shivering, and to top her off with more black coffee. Ever the thoughtful girl, I wanted to make sure Jess had the appropriate energy to tackle her chores on so little sleep. It wasn’t my fault if her bladder could only handle so much.

Deciding to order takeaway for dinner, as there was only so much cooking I trusted my maid with before she got better at her job, I made sure to call Jessie down to prepare my plate and make me a good cocktail to go with it. The seasoning on the still steaming meal made the starving girl visibly salivate, and her stomach rumbling was noticeably loud in the resonant kitchen. Naturally, I told her off all over again, and informed her that she could eat once she finished her chores. Just for good measure, I made a big show of openly eating in front of the girl while she cleaned up the kitchen. Her expression was so amusingly desperate, yet she was obedient enough to not ask for anything herself. That, or too scared to do so. Her little fidgets and twitches only got more noticeable throughout the afternoon and evening as well, yet she didn’t say a word about her jittery state or need to use the bathroom again. And, of course, I didn’t bother commenting or asking her about it. That was her problem, not mine.

By the time Jessica was finished with everything I told her to work on, it was time for bed. Shame. That meant she didn’t have time to eat.

Similar to the previous night, I offered her a handful of tablets to take. “To help you sleep,” I said, just like before. Except this time, the three identical pills would do the complete opposite. Last night, I wanted her to manage to crash on the hardwood floor, and wake up feeling all kinds of uncomfortable after doing so. After a full day with me, however, I thought it would be more fun to counter her exhaustion with caffeine tablets.

After she took her medicine, I swiped her glasses and told her she could have them back in the morning if she behaved. Then, when her vision was less clear, I closed and locked the bedroom door. Doing the same with my en suite bathroom after going through my evening routine, I crawled under the covers of my comfortable bed, knowing full well that I would be asleep within minutes.

“‘Night ‘night, Jessie!” I smirked, with a lilt to my voice as I clicked the button on my bedside remote to kill the lights.

Jess

I was wide awake.

WIDE awake.

Honestly, I was a little bit worried what the sleeping pills would do to my body when Hannah offered them to me. In theory, it sounded like a good idea, considering the caffeine coursing through my veins. Except what would it feel like when I started feeling both tired and jittery at the same time?

The floor was just as uncomfortable as before, and the small blanket I had did very little to counteract the AC that felt as if it was blasting through the house. It probably wasn’t that dramatic; I had just been naked literally all afternoon and evening, and was positioned rather close to the vent. Meanwhile, Hannah was wearing PJs in the form of a tank top and loose athletic shorts, curled up underneath her comforter on the other side of the room.

I could not sleep for the life of me. There wasn’t a clock within sight, either. Hannah probably just used her phone to keep track of the time, not that I could blame her; that’s what I did as well, when my phone wasn’t being kept from me by a younger girl. Between the humiliating memories, the knowledge that I was no closer to getting back into housekeeper/babysitter mode than I had been yesterday, and the fact that I was freezing cold and painfully hungry, how on earth was I supposed to drift off on the hard floor? I felt as jittery as ever, too, and really, really had to pee. The last time I had gone was in Hannah’s car. Between the quantity of liquid she had pushed me to drink since then, as well as the diuretic effect of the caffeine, it was no wonder that it felt like I had to burst.

Maybe I should have asked? I had considered it when Hannah was getting ready for bed, but she had made it clear earlier that I wasn’t allowed to use the bathroom and that I would get in trouble for wetting myself. Impossible, obviously.

After however long I had been tossing and turning and keeping my thighs tightly pressed together all the while, I couldn’t take it. Getting in trouble for using the toilet was better than getting in trouble for pissing on Hannah’s bedroom floor, right? I actually didn’t know. The blonde was so unpredictable, and needlessly harsh to boot. Quietly getting up and padding across the room, freezing every time my bare feet made the tiniest creak of the planks below, I finally made it to the bathroom door . . . only to find out it was locked.

‘FUCK.’ Did she seriously do that?! It was just like when her friends were over. Did that mean the rest of the bathrooms in the house were locked as well? Well, I had to try. Worst case scenario, I could slip out and relieve myself in the grass. I couldn’t believe that I was considering peeing outside like a dog, but it was better than squatting down and doing it on the floor.

Apparently I wasn’t going to be able to explore the rest of the house. Hannah’s bedroom door was locked! Did she do that last night, too?! That was- I was baffled. Not just at the audacity, but about how unsafe it was. What if there was a fire, or some other emergency? All to keep me trapped in her bedroom? Unbelievable.

I had half a mind to shake her awake and demand the key. Except it was Hannah, and I didn’t even want to imagine the kind of rage she would have if I disrupted her slumber.

At the same time, I knew I wouldn’t last the night. I had needed the bathroom since around the time her dinner arrived. Looking around the dim room in desperation, it didn’t seem like there was a cup or mug or whatever I could pee into. And without anything to use to clean up after myself, I couldn’t just piss on her floor.

Going with a version of my earlier last ditch option, as I couldn’t think of anything else when I had to go so badly, I scurried over to the window. At least that wasn’t locked. And I was a little more comfortable on the roof of Hannah’s place now that I had been wiping windows out there for a good portion of the afternoon. Climbing down to use the yard as my bathroom had briefly crossed my mind, but I really didn’t trust my upper body strength.

Instead, I awkwardly squatted on the slant of the roof, holding onto the window for support. Relieving myself in the cool evening air, letting the embarrassingly extended stream flow down into the gutter, I prayed along the way that it would rain soon to wash away whatever didn’t drain or evaporate naturally. If anyone had told me just a few days ago that I would be peeing on the roof, I would have called them insane. Yet there I was, doing whatever it took to avoid waking up my tormentor or getting in trouble the following morning.

When I was done, I wasted no time in awkwardly climbing back inside and returning to my not-bed on the floor after closing the window behind me. The last thing I needed was for Hannah to roll over and catch me in the act. Though I no longer had to pee, I was still jealous that the blonde teenager was fast asleep in a warm bed after enjoying takeout, while I was freezing cold, painfully hungry, and wide awake. With yet another mortifying memory to add to the ever growing reel, I did my best to drift off . . .

Sleep never really came to me.

The caffeine was probably the worst culprit, and the tablets Hannah gave me didn’t seem to be doing anything. I had lost track of just how many cups of coffee I had been given over the course of the afternoon and evening, though I knew it was way more than I’d normally consume in my everyday life. It was basically an unintended all-nighter. I faded out a couple times, but that felt similar to trying to take a nap in a well lit room with people talking just around the corner. There was really no quality the entire time, and I ended up twitching awake pretty much every time I got close to actually finding sleep.

By the time the sun was starting to rise, I knew it was a lost cause. Hannah didn’t keep her blinds closed, or down for that matter. If I couldn’t drift off in the darkness of her room, I certainly wouldn’t be able to do so when sunlight was streaming in.

Naturally, Hannah didn’t set an alarm. It was summer, and she was an eighteen year old with no responsibilities. She began stirring just before mid-morning, not that I knew the exact time. Propping herself up on her elbow and pushing back her hair, she retrieved her phone from the nightstand and only seemed to remember my existence after checking a few notifications. “Oh, good. You’re awake,” she said, “Can’t have my maid oversleeping every morning. Nice to see you up early for once.”

It wasn’t lost on me that this was literally my second morning here. She was making it sound like sleeping in was a regular occurrence of mine, which was both unfair and hypocritical. However, I needed to be really selective about my battles, and this definitely wasn’t one worth getting into. “Morning,” I mumbled.

“Sleep well?” she smirked. Fully sitting up and swinging her legs over the side of the bed, she walked over to the bathroom door and unlocked it for herself.

Did she- Did she know I had been up all night? Or was that a jab about how she assumed I tried one or both of the locked doors at some point? Also, I hadn’t been watching carefully enough. The key obviously ended up in her hand by the time she reached that side of the room. Had it been in bed with her, or stashed away in the nightstand? I should have been paying more attention, in case she decided to pull a similar stunt tonight. Of course, it was difficult to think clearly when I was so out of it.

While she brushed her teeth and combed her hair, most of which I could vaguely see from where I was sitting up myself on the floor, I tried to sort out what to do or say myself. It was still freezing by the vent, and I honestly was more interested in using the thin blanket to stay warm than to keep my body covered. Not that I was numb to being naked, despite going through a full afternoon of chores without a stitch of clothing on. I still hated being casually and perpetually exposed. There was just very little I could do about it while Hannah held all the cards.

Hannah stepped out of the bathroom a minute later, looking annoyed. “What the fuck are you doing, Jessie? Get up. Make my bed. Do your fucking job.”

Right. Chores. Did I make her bed yesterday morning? I actually couldn’t remember. Everything was a blur. Not just figuratively, either. As I stood up, reluctantly leaving the blanket behind, I realized that I had no idea where Hannah had put my glasses after taking them last night. It wasn’t exactly a battle, though it felt worthy of bringing up after the migraine I got yesterday from being deprived of the ugly glasses for so long. Ideally, I would be wearing my contacts. But anything was better than my terrible vision. “Umm, my glasses?” I hesitantly asked. Hannah really had done a number on me. Asking for something as simple as one of my basic needs felt like a reach.

“Bed.” Rather than sounding amused at my predicament, she came across as cold and no-nonsense. “Then I’m going to dress you, as I don’t trust you to do anything yourself. If you want your glasses, then behave. We have places to be, and I will punish you if you make us late.”

Places to be? Was it just an expression, or did she mean more than one? I had gone through so many humiliating experiences at the mall with her, and was definitely not looking forward to another outing. Either way, it was clear she was taking me along. Similar to yesterday, that was apparently the trade-off of getting clothes. Hannah couldn’t exactly drag my naked self into public. At the same time, she had already proven that leaving the house with her could be just as bad as being deprived of clothes in the privacy of her home.

Still, I didn’t want to get punished. I proceeded to make Hannah’s bed. Doing so affirmed that it was the first time I had done so as my memory caught up; before, she had sent me straight down to the kitchen to get started on her coffee. Something told me she wasn’t actually the type to care about a tidy bedroom. This was just a new demand she must have thought of to ensure my day started with me doing a task that an actual maid would take care of.

By the time I was done, she had thrown on a sundress. “Come here, Jessie,” she said. Still standing by the dresser, with what looked like a small stack of clothes set out on top. My vision was embarrassingly bad when I didn’t have the exterior help that I needed.

Doing as I was told, complete with a blush and a ‘Yes, Hannah,’ I crossed the room to join her. All the while, I had to make a conscious effort to keep my hands by my sides; being nude was particularly uncomfortable when she was fully dressed by contrast.

“Let’s get you dressed, Virgin,” she said.

Further demeaning me, I wasn’t allowed to do anything myself. She had me step into a pair of neon pink panties that were a strange hybrid of lace and regular cotton. The front wasn’t as soft as I was used to, but I wasn’t about to complain. Next was a pair of black short shorts and a white tank top. Both outfit pieces were definitely hers, rather than mine. The shorts mostly fit my body; like yesterday, however, the top was way too tight. I was immediately worried about my bra-less form being as on display as it was at the mall, as well as the white fabric potentially being a little see-through.

The one time I did want coffee, I wasn’t offered any. I was so fucking tired, yet Hannah didn’t seem interested in making a trip to the kitchen. Maybe she planned on stopping somewhere on the way? She seemed like the stereotypical teenager who liked her coffee in the morning, though again, I had only experienced a single morning with the girl. Literally anything she said or did could just as easily be her playing games with me.

She gave me the same pair of flip flops as yesterday before dragging me out the door. I could only pray that there wouldn’t be as much walking involved, as they were terrible as long-term footwear. The sight of her car reminded me of the accident I had in the back seat, as well as the thorough washing I had given it afterwards. Like before, she made me sit in the back.

After turning the key in the ignition and finding a suitable pop music station, she began driving. “By the way,” she said, as we neared the end of the long driveway, “We’re using your credit card again today. You don’t mind, do you? Also, Willow and Lillian will be there.”