Nanny Vanessa, Chapters 1-4

Author’s Note: Commissioned by Rose. Thank you for your pledge, and for all the story ideas!

Chapter One

“Hey, Elliott? Come on downstairs. She’ll be here any minute.”

As in, his babysitter. It was more annoying than embarrassing. Elliott was twenty years old, and way too old to need supervision while his parents were away for the weekend. As they had explained to him, however, this was more about his grades than his ability to stay out of trouble. Though he had coasted through his first year of university, the same couldn’t be said about his time as a sophomore. Elliott had low Bs in half his classes and mid Cs in the others. And, since he was living at home to save on room and board, his parents were well aware that he had a habit of slacking off and choosing video games over studying.

He tried to assure them that he would be fine, just like he had been in December. Admittedly, he had crammed pretty hard in order to pass those exams, yet that also proved he was capable of doing the same this time around. His parents were less confident, especially since failing any of his classes meant that he would lose his scholarship. Which is why they hired Vanessa to make sure he studied properly over the weekend while they were on vacation.

Vanessa was a neighbor, a young adult who had moved in a few months ago and had quickly established herself as a competent nanny. Between her experience and her availability, which couldn’t always be said for younger babysitters, she had great reviews and barely needed to advertise her services any more. Elliott’s parents, for example, met her at a neighborhood event once, and later heard good things about her from a couple a few doors down. There was also the fact that they couldn’t hire a teenager to watch their college aged son, so it made way more sense to ask someone like Vanessa.

Elliott had never met her before, as he didn’t go to those events any more. He was too old to hang out with the neighborhood kids, and too young to have any interest in socializing with the adults. That, and he preferred gaming these days. It’s what he was doing when his mother called him from the main floor. Thankfully, he was playing a single player game with a pause function, or he would have to deal with the age-old explanation of how he couldn’t just drop everything when his teammates were relying on him and he had to finish the round before getting up.

He quietly groaned to himself and stood up, heading out of his room and down the stairs to be polite and greet Vanessa. Maybe she would stay out of his hair if he played nice from the beginning. After all, he was a young adult himself, even if being in university didn’t make him quite as grown up as the nanny who had her own house and was running her own business. Hopefully she would realize that Elliott was self-sufficient enough, and proceed to leave him alone and take the easy money.

The doorbell rang just as he reached the top step. Elliott only hesitated for a moment, before continuing the descent. He wasn’t sure what to expect, though there was really no reason to be nervous. This was all going to be more of an inconvenience than anything else.

He definitely hadn’t prepared himself for Vanessa to be hot. As his mother opened the door, the redhead on the other side came into view, wearing a red dress that was quite the contrast to the t-shirt/jeans combo his babysitters tended to wear back when he was young enough to actually need someone around when his parents went out.

“Good afternoon,” she smiled, “And thank you again for the opportunity. It’s always exciting to work with a new family.”

“I’m just glad you were free this weekend,” his mother said, “Come on in. I can give you a quick tour, and answer any questions you have before heading out. Elliott is upstairs, but should be down in a minute.”

The stairs led right down to the front door, so Vanessa could easily see him in the background. “That must be him,” she said, “Hey, Elliott. Ready for a productive weekend?”

“Something like that,” he muttered. Her attractiveness was a little disarming. Though she was being ever so slightly patronizing with her greeting, he couldn’t help but wonder if he had a chance with her. Maybe not, considering the 5-8 year age gap; it was tough to get an immediate read on how old she was.

Vanessa stepped inside, complete with her duffel bag slung over one shoulder, “A tour would be lovely. Elliott, do you mind gathering your academic materials for me in the meantime? I was given an overview of what you need to get done this weekend, but I’d love to go over the specifics with you.”

Short of being needlessly difficult, he didn’t have a reason to say ‘no.’ The good news was, it was university. His parents only knew what classes he was taking, as well as the broad strokes of his GPA. Unlike high school, they weren’t in communication with his professors or anything like that. Ideally, he could ensure that Vanessa was in a similar boat in terms of not knowing exactly what he had to get done by Monday.

He returned to his room, as there was no reason to tag along for a tour. Unlike babysitters from his childhood, Vanessa would be staying overnight, likely in the guest bedroom. Other than that, he assumed it would be the same. Ordering pizza with whatever money his parents were leaving with her, or perhaps cooking if she was into that; it really depended on the sitter. Of course, he preferred the former option.

As for the materials she requested, there wasn’t much for Elliott to show. The semester was nearly over, which meant he only had a few assignments left to deal with. Other than that, it was simply a matter of studying for his exams the following week, which he hadn’t planned on starting until Tuesday or Wednesday. Not wanting to look bad, he at least took the effort to pull out each syllabus and turn to the last page. Partly to show Vanessa that her services weren’t actually needed, and because looking disorganized would validate his parents’ decision to hire her in the first place.

Other than that, he wasn’t sure what to do while he waited. Deciding to avoid smalltalk and a drawn out departure where his parents were involved, he opted to stay in his room for the time being. It would be easier to figure out whatever his dynamic with Vanessa would be if he didn’t have to do so in front of his family.

It didn’t take long for the tour to bring Vanessa to his bedroom; Elliott hadn’t considered that when returning to his desk and looking up potential builds for one of his mains in the MOBA he and his friends were into. There was no point in resuming what he was playing earlier, as he’d have to deal with Vanessa sooner rather than later anyway.

“Hmm. It’s pretty messy in here,” Vanessa said. Barely one step into the room, and clearly in babysitter mode. “Maybe we should tackle this first? I bet you’ll be more productive in a cleaner space.”

Hopefully she was just putting on a show for his mother, who was standing right there. Elliott did regret not tidying a bit before the tour led them upstairs. In his defense, this had been his bedroom for his whole life, and his habits hadn’t changed much since starting university. And, since he lived with his parents, there weren’t many opportunities for him to have a girl over. Though Vanessa was attractive, it wasn’t as if she was an instant crush or anything like that. At the same time, first impressions were still important.

“Couldn’t hurt,” his mother agreed, “Although, good luck. I’ve mentioned the clutter for years. Anyway, are you all set here, Vanessa?”

“Of course,” she nodded, “I’ve got both your numbers on speed dial for the weekend, as well as Leslie’s next door in case of emergency. Plus Elliott is older than my usual charges, so I’m sure he won’t be a problem. Isn’t that right, Elliott?”

He was definitely old enough to understand a lose/lose question like that. Disagreeing would make him sound immature and needlessly difficult, yet he couldn’t think of a way to answer in the affirmative that wouldn’t sound almost as immature as doing the opposite. “We can still let Vanessa go home,” he pointed out, aiming to make it sound nonchalant. For whatever reason, he didn’t want to potentially hurt her, “Save a little money, and let me worry about school by myself?”

“Vanessa is here because I’m worried about school,” she said, “Besides, she probably turned down another job or two after committing to this; it wouldn’t be fair to fire her at the last minute.”

“You’re too kind,” Vanessa said, “And don’t worry, Elliott. I’m just here to supervise you. As long as you behave and get all your work done, we’ll get along just fine!”

Uh huh. Except it still sounded like she was talking down to him. Probably a habit from being a nanny for said younger charges. “Great. Class information is right here.” He tapped the side of the desk that wasn’t occupied by all of his gaming stuff.

“Thank you for putting that together for me,” she replied, with that same smile, “Why don’t you start by cleaning your room while I get settled? We can get started once your parents are on the road. Sound good?”

Not really. But Vanessa turned and left the room without waiting for an answer.

Elliott wasn’t sure where to start. He still had the teenage mentality that a pristine bedroom was idiotic when it made just as much sense knowing where everything was amidst a bit of organized chaos. His room also wasn’t that bad, especially compared to a number of his friends. Even so, he at least made the effort to pick up a few things off the floor and dealt with some of the more obvious corners that Vanessa might get on his case about. He was assuming she wasn’t expecting perfection, considering the main reason she was hired was for the sake of keeping him on task where his studying was involved.

He only had a few minutes before he was being called down to the main floor again. The goodbye ritual with his parents was fairly quick. After living at home for his whole life, it wasn’t that unusual for them to be gone for a weekend. Normally he would either enjoy the place to himself the entire time, or host a LAN party with his friends that still lived in town. Obviously, either of those options were preferable to studying on someone else’s schedule besides his own.

Once it was just the two of them, Vanessa got right to it. “Okay! Let’s go check on the progress you’ve made with your room, and then we can take a look at your classes.”

“Umm, sure,” he said. Now he could attempt to set up some dynamic with her where she didn’t feel the need to pressure him to study, let alone do something like clean his bedroom. Thanks to the dress she had on, casual as it was, he felt several underdressed by comparison. “I really can deal with the school stuff myself, by the way. My parents are a bit paranoid about me failing, that’s all.”

“Hmm, I guess there’s only one way to find out if I really need to be here or not,” she shrugged. She gestured towards the stairs, “Lead the way. Oh, and is ‘not failing’ really the best goal? I think you could pull a B in every class if you put your mind to it. It might even help to have someone around to keep you on task!”

Elliott didn’t dignify that with a response. It was clear what she was getting at, and he was stuck in an equally impossible position of validating her supervision no matter what he did. Procrastinating would prove her point, while starting immediately would be as if it was happening because she told him to. He simply began walking, weighing other options along the way.

As they stepped into the room together, Vanessa was once again quick to comment. “There’s still so much to do!” Giving the space a more thorough look, she clasped her hands together. “Okay. Why don’t you keep cleaning, and I’ll take a look at all your school stuff. Teamwork, yeah? Then we can make a plan afterwards.”

“Why don’t we just work downstairs? That’s where I usually do my homework, anyway.” A total lie; Elliott was banking on the assumption that his parents wouldn’t have mentioned something like that to Vanessa. He wasn’t necessarily opposed to cleaning his room, though he also didn’t enjoy a nanny telling his young adult self to do so.

“You should still have a tidy room,” she insisted, “Trust me, it will put you in a better headspace for studying. Speaking of your bedroom, it kind of smells like boy in here. Have you showered today?”

He definitely didn’t see that coming. “Umm, yeah,” he said. Most mornings, as he had class every day. Not always on the weekend, as there were some days he would just be lounging in his room without any plans.

“Huh. Well, maybe apply a bit more deodorant, just in case? It also couldn’t hurt to vacuum and do laundry. Don’t worry, I can help with some of that. Your main focus this weekend should be on your studies!”

Well, so much for Vanessa treating him like an adult. She was making it sound like he was a teenager, especially in the way she mentioned his hygiene. “Everything’s on the desk,” he reminded her. The sooner she checked out the syllabi for his classes, the sooner they could move past what was turning into an awkward introduction.

In the meantime, Elliott picked up where he left off in terms of tidying his room. Mostly since he wasn’t sure what else to do. Since Vanessa was at his normal spot, seated in his gaming chair and getting acquainted with what he needed to know for the upcoming exams, that really only left the bed. Plus his phone was still on the edge of the desk, and he was also trying to balance making a good first impression with not letting her treat him too much like a kid.

A few minutes later, she glanced over her shoulder. “Elliott? Deodorant, remember?”

Wait, that wasn’t a suggestion? He honestly didn’t know how to respond to something like that. “I already did,” he said. It had to be a joke. He was way too old to need that kind of oversight. “After my shower.”

“It can’t hurt to apply a little more,” she said, “You don’t mind, do you?”

He frowned slightly in frustration. “I guess not.” It was as if everything she said was a perfectly designed trap, yet always subtle enough that he couldn’t call her out on what she was doing. Such a simple request wasn’t worth arguing over, but being sent to the bathroom as a twenty year old for the sake of hygiene? That, and the fact that an attractive girl was implying that he smelled bad. Or, in her words, ‘like boy.’ Either way, it was tough to avoid feeling self conscious about it, even if he was convinced he had been thorough enough that morning.

One perk of being an only child was that he had his own bathroom upstairs, rather than one he would otherwise have to share with a sibling. It only took a minute to head in and do a quick pass with the stick of deodorant. He was tempted to do nothing and see if she noticed, but decided against it. For all he knew, she could be right, though he was still convinced she was just making a bad assumption. More likely, the problem was his full hamper of dirty laundry, or maybe something else.

When he returned, Vanessa greeted him with a smile. “Thanks, Elliott. Your room is looking better, too. If it’s not too imposing, I’d be happy to take over while you work. I think I have a general sense of your classes, though I’ll definitely look more in depth at all the ones you’re not currently studying in a few minutes. From what I can tell, Sociology looks like one of the more difficult courses. What’s your grade in that one currently, if I may ask?”

Elliott considered lying. That was the thing about his parents hiring someone like Vanessa; she didn’t know anything about his classes or his GPA, nor was she a tutor. It was simply a matter of supervision. “A high C, I think,” he said, only slightly stretching the truth. Last he checked, it was closer to a C- than a C+, which meant it was one of the classes he would be cramming for more than the rest.

“Well, then we have some work to do,” she said, “If you ace your exam, you can for sure bump that to a B. Maybe even a B+, based on the grading percentages I’m seeing here. Want to start with Sociology, then?”

“Sure,” he replied. It didn’t really matter to him. Anything to remind Vanessa that he was a college student, and she was only here to worry about his studies.

“Sounds like a plan,” she nodded, “Okay, get all your things for Sociology and meet me downstairs wherever you like to study. Kitchen? Living room?”

Bedroom. Except he was committed to his recent lie. “Living room,” he said. More comfortable.

“Got it. I can trust you up here alone for a minute or two, right?” she asked, “I’ll be downstairs.”

The moment she turned the corner, Elliott sighed. It was going to be a long weekend.

Chapter Two

Elliott hadn’t ever really studied downstairs. Not recently, anyway. Maybe ten years ago, when his bedroom was more for sleeping and the main floor of the house was for everything else. But as both a teenager and a young adult, he preferred the solitude of his room. Pretty typical for a guy living with his parents, especially once he got into gaming.

As he headed towards the living room, he was already regretting his suggestion for the location change. The whole point of the idea was so Vanessa wouldn’t fixate on his messy bedroom, yet she ended up making him clean up the area anyway. Now he was going to have to work in a more public room, where his babysitter would no doubt be hanging around working on her own stuff. There had to be a better word for Vanessa’s job where Elliot was involved. Nanny, maybe? That was just as bad. He also wasn’t sure of the difference between the two of them. Was one a profession, and the other a thing younger individuals did to make some spending money? It didn’t really matter. Either way, Elliott didn’t need supervision at his age.

While Elliott started looking through his Sociology notes, Vanessa busied herself with the rest of his academic materials. Skimming each syllabus, making notes along the way, and occasionally speaking up to ask what his current grades were, if he had started on his papers, etc. Since he was in college, his parents didn’t have access to all the specifics of his courses, like they did in high school. Since he was living with them, however, they at least insisted that he update them on his GPA every month or two. It put Vanessa in a unique situation of not knowing everything before showing up for the job, though she was quick to fill in those gaps for herself. Never interrupting him, as she would always wait until he paused to take a drink of water, or when he was switching from notebook to textbook.

After nearly an hour, he decided to test the waters. There was no way he was going to spend his entire Friday night studying. And, while he wasn’t the best student, Elliot knew that most people didn’t do schoolwork for hours on end. “I’m going to take a break,” he said, “I’ll be upstairs for a bit.”

“May I please take a break, Vanessa?” she corrected him. Similar to how she had spoken to him so far, Vanessa’s tone was more matter-of-fact, rather than stern or bossy. “I’m in charge this weekend, Elliott. You may think that you’re a big boy, but your parents hired me for a reason.”

He cringed internally at the demeaning phrase. How could she say something like ‘big boy’ so casually? Then again, she was probably used to watching younger charges, making some of her terminology bleed over despite how he was technically an adult. It was enough to throw him off to the point where he wasn’t sure how to reply. Because of his age, Elliott wasn’t sure what Vanessa would do if he refused to be polite about something that he absolutely didn’t need permission for. At the same time, she was pretty, and he really did want her to see him as the mature young man that he actually was.

Taking a breath, and resisting the urge to roll his eyes, he calmly echoed, “May I please take a break, Vanessa?”

She clasped her hands together with a smile. “Much better, Elliott. What kind of break? Bathroom? Stretch?”

What? No. Neither of those required going upstairs. And he absolutely wouldn’t have announced it if he just needed to use the bathroom. “I’m going to play games on my PC,” he said, “I’ll study some more later.” He was still trying to keep some control over his evening, considering this was already way more studying than he had planned to tackle today.

“Oh,” Vanessa said, “A video game break. Well, you’ve only been studying for about 45 minutes now. Why don’t we do another 45, and then you can ask me about that kind of break. Like a polite boy, of course.”

Again, Elliott wanted to push back. The more he let Vanessa dictate such things, the more complicated it would be to decide things for himself moving forward. He just found it difficult to find a good approach, since she kept speaking as if things were already decided. That, and the nonchalant patronizing was a persistent distraction and embarrassment.

Managing to avoid a frustrated sigh, as that would only make her view him in an immature light, he returned to his notebook and continued going through some of the things that would be on the exam. It crossed his mind that Vanessa probably didn’t know much about sociology. He could always half-ass his studying efforts as long as he was looking at the page, though that would also be a waste of time. If he was stuck on the sofa with his materials right in front of him, it made more sense to actually do the work. Either way, he was going to have to cram at some point.

It didn’t help that his phone was right there, with the occasional message from one of his friends telling him to hop online for a game. Either Vanessa didn’t notice the screen occasionally lighting up, or she chose not to say anything about the ‘distraction’ due to how he seemed to be focusing on his notes despite the notifications.

By the time he was pushing an hour and a half of studying, Elliott really did need a break. Even when cramming for tests, he would pause several times along the way to not burn out. The problem was, Vanessa had already brought up shorter breaks, and Elliott didn’t want to risk taking one of those if it meant she might end up resetting the clock. He also didn’t message anyone back, as doing anything with his phone could potentially lead to a similar issue.

The one silver lining of seeing things he couldn’t respond to with the frequency he normally would was the fact that he was able to keep decent tabs on the time. When it had been just shy of fifty minutes since the last time he brought up taking a break, as he didn’t want it to look like he was counting down the minutes–even if that was exactly what he was doing at the end–he reluctantly asked rather than stating what he wanted. “May I please take a video game break?” He half expected her to say ‘no.’ Cordial as Vanessa had been so far, he remembered some of the babysitters he had growing up who would string him along for the sake of making their own lives easier.

Thankfully, Vanessa wasn’t one of them. “You may, Elliott. I’ll be right down here if you need me. Does pesto and a salad sound good for dinner?”

He was ready to get up and head upstairs, and was glad that Vanessa wasn’t going to be so overbearing that she planned on following him and always being in the same room he was. But it was Friday night, plus some part of his subconscious was remembering what evenings with a sitter were like when growing up. “You could just order a pizza,” he pointed out, “Probably easier. My parents left you with some spending money, right?” That’s what they used to do.

“That’s not very healthy,” she replied, “Don’t worry; I love cooking. Why don’t you go play for a little bit? I’ll come get you when it’s time to study again.”

Elliott didn’t need to be told twice. There wasn’t a good argument for why pizza was preferable, when a mature girl like Vanessa was the one making the nutritional decisions instead of one of Elliot’s peers. Plus he really was tired of studying, as well as having his babysitter sitting right there. Both his bedroom and his PC were calling.

The first thing he did when he sat down at his desk upstairs was check all of his messages. As expected, he had already missed a number of games that would have been fun, most of which were no longer possible due to some people taking breaks that poorly aligned with the end of his studying, while others had merely switched genres. He could always jump into his MOBA when those that were already playing finished a match, except he was a little nervous that Vanessa would call into his room and be overheard on his mic. It would be so fucking embarrassing if anyone learned that his parents had hired someone to watch him this weekend.

He ultimately decided on a solo game. By the time he had launched it and settled in after setting his status to ‘offline’ and messaging everyone that he was out for the night, Elliott only ended up playing for 10-15 minutes before Vanessa came upstairs.

“Elliott?” she greeted, lightly knocking on his door, “Break’s over!”

“What?” he asked. That had to be a joke. He at least paused the game to glance her way, but made no move to get up.

Vanessa tapped her watch. “It’s been thirty minutes. Time to get back to studying.”

It was just dawning on him that they never talked about the specifics regarding what she considered a break. Elliott assumed he was going to be able to hang out in his room for a while; apparently Vanessa had a completely different idea of how long he should be playing games compared to working. “I just started, Vanessa,” he said. Trying to compromise, he offered, “I’ll study a bit more after dinner.” That would probably buy him at least another thirty minutes, though even 45 minutes of gaming wasn’t much of a session.

“I gave you a half hour, Elliott,” she said, “Last time I checked, your parents hired me so you wouldn’t waste your whole weekend playing video games. Come on. Be a big boy and show me that you can be responsible with your time.”

“I’m not a BOY.” Finally pushing back on the patronizing way she was speaking to him, Elliott fully turned his desk chair to face her. Under normal circumstances, he wouldn’t mind the term ‘boy.’ Although he was technically an adult, insisting he was a man while still in college didn’t quite fit. It was really the full phrase Vanessa was getting to him.

“Oh,” Vanessa giggled, “Are you a girl? I guess the name Elliott works both ways!”

Her amusement and completely inaccurate interpretation of his response only frustrated him more. “No!” he snapped, “I’m a guy who’s too old to be treated like a child. Look, I’ll study more tonight. Like I said, after dinner.”

“I can see why you need a babysitter,” she said, sounding way more calm in comparison, “Throwing a tantrum when you don’t get your way? You’re acting just like all the other boys I watch, Elliott. Do you want me to treat you like a disrespectful little boy? Or a big boy who can act his age?”

That wasn’t a fair question in the slightest. “Vanessa-”

“Which one, Elliott? Are you a little boy, or a big boy? Or am I going to have to call your parents and tell them you’re already causing problems?”

He flushed, hating that such a simple threat worked nearly as well as it did when he was younger. If Vanessa did call, it would be beyond embarrassing. Considering his age, behaving maturely should be a given. She was just framing it in such a demeaning way.

She crossed her arms. “Well?”

“Fine, I’ll study,” he muttered.

“That’s not what I asked,” she said, “Are you a big boy who is going to act his age? If you are, I want to hear you say it.”

As in, the exact phrase that had started all of this. He was too busy feeling awkward about her insistence to realize that it was a babysitting trick. Undermining his original argument would make it more difficult for him to be ‘disrespectful’ moving forward. Blushing more deeply, he reluctantly said, “I’m . . . a big boy. I’ll act my age.”

“There we go! That’s much better, Elliott,” she smiled, “Do you think it’s more responsible to spend your night studying, or playing video games?”

It wasn’t much of a discussion after that. He ended up following her back downstairs and opening his Statistics binder to begin reviewing his notes from the last few weeks.

Elliott’s next ‘break’ was for dinner, which meant he wouldn’t have any more gaming time before the next round of studying. On top of that, Vanessa continued to be overbearing, clearly unable to separate her usual babysitting habits from what she really needed to be adjusting for someone like him. Telling him to wash his hands before the meal, correcting the way he was holding his fork and knife, and reminding him to thank her for cooking afterwards. He would have done most of that himself, only it ended up looking like he was only doing so because she was going over such etiquette along the way.

His next surprise was at 9:30 PM, when he was just wrapping up another long stretch of studying. Vanessa stood up and took his phone from the coffee table. “Ready for bed?” she asked.

Of course not. He hadn’t gone to bed before 11 PM in years. “It’s way too early for that,” he protested, “And that’s my phone.”

“I know it’s your phone, silly. But we’re working on screen limits this weekend, and it’s not healthy for your eyes to be using anything backlit before bed. Now, it’s lights out at 10 PM sharp. Once you brush your teeth and go potty, you can spend the rest of the time reading or doing a little more studying. It’s completely up to you.”

“I’m not going to bed at ten, Vanessa,” he insisted. In the back of his mind, he knew that arguing with her was pointless when she had all the cards as before, but he still had to try. It was just such an absurd suggestion.

“Let’s make it 9:45,” she said, “Now, be a big boy and get ready for bed. You better be on your way upstairs by the time I count to three, or you’re going to be in trouble. One . . . Two . . . ”

It was embarrassingly effective, just like the prospect of the phone call had been. Grimacing slightly at the fact that he was letting himself be bossed around in such a manner rather than calling her bluff and seeing what would happen on ‘Three,’ Elliott got up and headed towards the stairs, letting Vanessa keep his phone for the time being.

To make matters worse, she followed him to the bathroom up there. She stood there and supervised him the entire time as he flossed and brushed his teeth, reminding him to do the former and timing him for the latter. While she at least gave him some privacy to use the toilet, Vanessa insisted on keeping the door cracked ever so slightly as he did so. She stepped right back in when he was finished, telling him to wash his hands. Finally, she insisted on another round of deodorant, as both he and his room still smelled like boy, and maybe that would help.

When all was said and done, it was basically 9:45 PM, which was Elliott’s new bedtime due to how he had lost fifteen minutes for being difficult. Vanessa went so far as to pull the comforter back before stepping aside and gesturing for him to lie down. “Aren’t you going to thank me for helping you get ready for bed?” she asked.

He still found it hard to believe that she wasn’t amused by the fact that she had been put in charge of someone like him. Every single time she asked a question like that, it was as if she actually viewed him the same as any other boy she would be babysitting. And every time he gave her attitude, it ended poorly for him. Glancing away, he begrudgingly said, “Thank you, Vanessa.”

“You’re very welcome, Elliott,” she said, “Now, get some sleep. Tomorrow is a big day; you need to be well rested for it.”

Elliott felt completely ridiculous as he crawled into bed. Not just because of how early it was, but because Vanessa was standing right there waiting for him to do so. “Lie down,” she casually insisted, “All the way. You’re not going to try and stay up after I leave, right?”

That was the general idea. He replied, “Umm, no.”

“Good,” she nodded. Once he was settled underneath the covers, she walked over to his desk and bent over to reach something behind it. While Elliott was distracted staring at how the dress hugged her ass in such a position, Vanessa found what she was looking for. Pulling out the power cord, unplugged from both his PC and the outlet, she said, “I’m going to hold onto this and your phone until tomorrow.” Before he could argue, she pointed out, “It’s not like you need them before then, right?”

Since he was supposed to be going to bed, there was nothing he could think of to counter that, save for the usual sentiment of how he didn’t appreciate how overbearing she was being.

When met with nothing but his awkward silence, she gave him another warm smile and said, “You were a really good boy tonight, Elliott. I bet you’ll be even more well behaved tomorrow.” She walked to his bedroom door, glancing over her shoulder for a parting, “Good night!”

Then she flicked the switch and turned out the lights.

Chapter Three

Elliott was used to sleeping in. Of course, he also usually stayed up much later unless he had a class that was earlier in the day. In particular, Saturdays were supposed to be for lazy mornings and long gaming sessions. Unless a certain babysitter decided that he needed to start the day the second that the sun appeared on the horizon.

“Rise and shine, Elliott!” Vanessa pulled back the curtains as she greeted the still sleeping boy.

It was just past 6:30 AM. If Elliott had gone to bed when he normally did, this would be an ungodly early wake-up call. Thanks to the embarrassingly early bedtime, however, he got somewhere between seven and eight hours of sleep. Just because Vanessa turned the lights off at 9:45 PM didn’t mean Elliot managed to sleep right away; his usual sleep habits, paired with the lingering frustration of how Vanessa treated him more like a child than an adult, left him tossing and turning for a while before finally drifting off.

Either way, this was the earliest he had been woken up in a long time. Aside from a trip with a morning flight that required setting an alarm before 7 AM, there was never a reason to get up at sunrise; for 8 AM classes, he would typically skip breakfast for a little extra sleep. Groaning to himself, both out of tiredness and annoyance that Vanessa thought this was necessary when Saturday was already long enough to tackle all the studying she was surely going to insist upon spending at least half his precious free time on, Elliott briefly considered telling her to fuck off and to come back in an hour or two.

Of course, that wasn’t actually an option. Vanessa was the ‘perfect’ combination of friendly and overbearing, which left Elliott in a difficult place where he didn’t want to upset her or test how she might react if he started the morning off acting like that. Considering how her babysitting style was already a bit much even when he was behaving, it would probably be better to play it safe until he could convince her that he didn’t need supervision in general.

The sun wasn’t really up yet, though it was still way too bright when he had no time to adjust to the open curtains. Squinting slightly and hoping that his hair wasn’t a total mess when he was still holding onto a shred of hope that he had a shot with the attractive redhead despite how it would be difficult to perceive him as a prospect when she had been hired to watch him for the weekend, Elliott shifted in place slightly and started to sit up.

That was when he felt it.

As soon as he moved out of the position he had been sleeping in, Elliott noticed a wetness below his waist. ‘Fuck,’ he mentally swore to himself. This wasn’t some faint dampness from overnight arousal or anything like that; his crotch was soaked, as were the sheets underneath him. He had wet the bed?! How?? That hadn’t happened since he was super young, and definitely wasn’t something that should happen to a guy his age.

The sheer surprise of it, followed by the reflexive way he adjusted in an attempt to minimize the gross sensations of how his underwear was sticking to his thighs as well as the fact that he was somewhat sitting in his own pee, made him an open book in terms of the look on his face and his awkward body language. “Something wrong, Elliott?” she asked, tilting her head slightly.

It didn’t help that he had been getting out of bed a moment ago, albeit lethargically, and was now in an incredibly awkward situation of wanting to run to the shower while also wanting to keep Vanessa from finding out about this. The end result was him fidgeting underneath the covers, while more or less keeping his body in place compared to before. “I’m fine,” he lied, “Can I just have some privacy? I’ll be downstairs in a minute.”

“Don’t be silly,” Vanessa giggled, “If I leave, you’re just going to roll over and keep sleeping. Besides, I need to supervise your routine to make sure you don’t miss anything. Do you remember everything you need to do before and after bed?”

Elliott was not going to go back to sleep. Even if he had woken up on his own, he would have been disgusted and absolutely mortified that he had wet the bed. It was only worse with Vanessa right there. She already micromanaged his hygiene due to the fact that he wasn’t wearing enough deodorant yesterday; if she caught him like this, Elliott couldn’t begin to imagine what the supervision of his bathroom habits might look like.

Trying his best to keep a straight face, and hoping he would be able to convince Vanessa that he was more than capable of getting ready in the morning without her coaching him through it, he said, “Seriously, I don’t need your help. I’ll floss, brush for the full two minutes, and apply deodorant. Okay?”

She just shook her head. “You also need to use the toilet, and wash your hands afterwards. And, if you’re not going to shower first thing in the morning, you should at least wash your face. See? This is why you need me.”

Obviously, he was going to take a shower. And just because he didn’t list every single thing before entering the bathroom didn’t mean that he wouldn’t do the things she added to his answer. “Look, Vanessa-”

“Look, Elliott,” she cut him off, “We could circle all morning, but you have a lot to do today. Now, come on. It’s time to get up!” She strutted forward and yanked his covers completely off the bed, as a teasingly dramatic way to ensure that he’d be more motivated to get out of bed when not tempted by the comfort and warmth they provided.

“No, don’t!” he exclaimed, but it was too late. Though he had been hiding the accident underneath the covers, he hadn’t expected her to pull them away. And, by the time he realized that was her intention, it was too late to get a grip on them. He probably would have lost a game of Tug-of-War anyway, as Vanessa had more leverage as the only one between them who was standing. Either way, there was no concealing the large yellow spot between his legs, or the fact that the front of his PJs was visibly darker than the natural color.

Vanessa gasped. “Elliott! You wet the bed? And you’ve just been sitting there?” It took her about half a second to connect the dots. “That’s why you wanted me to leave. You’re such a bad boy! Elliott, I’m your babysitter; you’re supposed to tell me about stuff like this, not try and keep it from me.”

His single-mindedness about getting Vanessa out of his room ended up backfiring. Now he had both wet the bed and had been caught trying to hide it. “No, I-” He could feel himself blushing, and realized that no amount of crossing his legs or covering with his hands would hide the embarrassing image. Instead, he scrambled off the mattress, while failing to come up with a reasonable excuse. It made sense in his head, of course, but that was only when there was still a chance that he could convince her to get out.

“I don’t want to hear it. We need to get you cleaned up before you have a rash.” With that, Vanessa closed the distance and gripped his wrist. She then swiveled on her heel and tugged him towards the bathroom.

The way she was talking to him had an unintended side effect of making him feel similarly to how he did when he got in trouble when he was younger. Between his headspace and the fact that he did need to get cleaned up, Elliott didn’t protest as he was led across his room. What he didn’t realize, due to how frequently Vanessa interchanged ‘you’ and ‘we,’ was that the latter was pointing towards what she had in mind rather than just being an expression.

Once they were in the bathroom together, Vanessa let go and said, “Get those dirty clothes off, Elliott. Quickly, now!” She bent over and fiddled with the drain of the tub for a moment, then began running the water.

Of course, he hesitated. As badly as he wanted to remove the pee-stained clothes, stripping in front of Vanessa was rather daunting. “I can-” He was too flustered to come up with a particularly coherent reply. Instead, he just mumbled, “I can do it myself.”

“I know you can do it yourself,” she said, “That’s why I told you to. But, if you need help . . . ”

“I don’t!” he hastily replied, sounding more whiny than anything else. Vanessa already included herself in so many things Elliott had been doing alone since well before middle school; getting undressed wasn’t something he needed her to add.

Still, it was different when a girl was mere feet from him. Today, she was wearing a blouse/skirt combo. Unlike last night, however, Elliott wasn’t in a state where he could appreciate the image of her bending over and adjusting the temperature of the water. He was too busy steeling himself to be bottomless in front of her.

Just as he was gripping the waistband of his pajama shorts, he noticed that Vanessa wasn’t getting a shower ready for him. She had plugged the drain, and was slowly filling up the tub.

In other words, she planned on having him take a bath.

“Wait, I don’t need-” He hesitated, mostly to make sure that he wasn’t jumping to conclusions. But what else would Vanessa be doing with the tub if not that? Finishing his thought, he said, “I need a shower, Vanessa.”

“You just wet the bed, Elliott,” she reminded him. Standing back up and crossing her arms, in the usual balance of stern while not harsh, she said, “I don’t trust you to bathe yourself. You already need me here to put on deodorant properly, and we have to make sure that all that pee is washed off. So, I’ll give you a choice. Let me give you a bath, and behave during it, and you can shower tomorrow with a bit of supervision. Or we can do baths all weekend. What do you think?”

It was a more transparent version of the babysitting tactic of suggesting two things, like peas vs. carrots, and letting the kid choose. Of course, this was hardly a choice, when one option was blatantly better than the other. Elliott also wasn’t in the best state to argue. His underwear and bottoms were still clinging to him, the confined space made Vanessa a bit more intimidating despite how she was rather calm about all of this, and the running water that was filling the bathtub subtly made it feel like it the fact that he would take a bath this morning had already been decided.

Still blushing, and glancing away, he said, “The first one.”

“That’s a good boy,” she smiled, “Now, come on. Get out of those gross clothes and into the tub! The sooner you’re clean, the sooner we can get started with the day.”

In Elliott’s mind, it was more ‘the sooner I can get dressed.’ Vanessa was pretty, sure, though he didn’t want her to see him naked like this. Even so, he returned to the task at hand; it wasn’t as if he could take a bath with clothes on. Turning slightly, as if that would protect his modesty when she was going to see everything anyway in a minute, he carefully stripped his lower half all at once, being careful to minimize how much the wet fabric made contact with his legs on the way down.

Vanessa wasn’t actively watching. She busied herself moving the soap and shampoo to a spot where she could easily reach them, and occasionally tested the water’s temperature to make sure it was still good. Still, she saw enough in her peripherals to know when Elliott was bottomless. “Shirt, too,” she said, “Then you can get in right away. That way, I know how much more water we need!”

She sounded more chipper than before. While it was better than her reaction to finding out that he had wet the bed and tried to keep her from discovering it, Elliott was a little embarrassed that she was acting so normal. Did she really not think this whole thing was unusual, considering his age? She could be pretending for his sake, or maybe she really was in babysitter mode and blurring out the fact that he was older when focused on her job.

After removing the light t-shirt, Elliott reluctantly stepped towards the tub. He was ‘cupping’ his crotch, though it was more of an awkward hover to avoid getting pee on his hand. Still a bit in disbelief that this was actually happening, he lifted one leg and placed it into the water that was admittedly the perfect level of warmth. He vaguely remembered having to wait for the bath to cool down in his early childhood, since starting it too hot was safer than the alternative.

“I’ll be back in a second, okay?” she said, as he dipped his second foot in, “Get comfortable, and turn the water off if it gets too high. Don’t worry, I’ll probably be here before that happens.” With that, she walked out of the bathroom and left the door wide open.

He welcomed the opportunity to lower his body and get settled in the tub without worrying about his nudity with Vanessa right there. Of course, the clear water didn’t do much to cover his bare body. Sure enough, she was only gone long enough for him to get into the bath with fewer hang-ups. That, and to find a large plastic cup that was in one of her hands upon her return.

“Okay,” she smiled, “Let’s start with your hair.” After setting the cup down on the edge of the tub, she took a minute to fold up a towel for her knees before kneeling beside him. “Close your eyes for me, alright?” Vanessa filled the cup full of water and it quickly became evident that she planned on dumping it over his head. Elliott did as he was told, just barely managing to do so before his babysitter started pouring the water.

And they were off.

Vanessa did her best to be efficient without rushing or being too rough with him, which resulted in her being a bit bossy along the way. Once his hair was ready, she lathered up her hands with shampoo and began running her fingers through his locks and massaging his scalp. Admittedly, it felt good, though it was difficult for Elliot to appreciate the sensations when he was way more embarrassed than relaxed.

She rinsed the shampoo out with another few pours of the cup, finally turning the water off halfway through the process now that it was at a good level. Next, she grabbed the bar of soap while Elliott was still squinting his eyes shut to avoid getting shampoo in them. “Keep them closed,” she gently said, “I’m going to wash your face now.”

“I can do that myself,” he mumbled, not realizing that insisting on his independence with the same phrase over and over made him sound more whiny and immature than anything else.

“Mm hmm,” she ‘agreed,’ with the slightest sarcastic lilt, “Right now, I want you to hush and pay attention to my process. Tomorrow, you can try all of this on your own. But it’s going to be a bath, not a shower. Now, are you going to keep talking back, or are you going to behave?”

Just like that, she had come up with a simple yet effective punishment. As for talking back, Elliott didn’t really have that option when her hands started rubbing soap all over his face. He just had to sit in the tub and quietly sulk. In less than half an hour, he had fallen so much further than yesterday in terms of Vanessa’s babysitting approach. He actually was wishing it was as simple as his screen time being limited and dealing with the embarrassment of an early bedtime. Those were both way more tame than literally being given a bath.

After his hair and his face, the next few steps were fairly simple. Vanessa took a washcloth and scrubbed down Elliott’s upper body, starting with his shoulders and his chest. Then she worked down one arm at a time, rounding out each one by having him lift for a very thorough armpit scrub. “This is part of why boys like you smell like, well, boy,” she explained, “You can’t just do a quick pass with some soap and assume the water will get the rest. It’s important to really wash underneath your arms, and around your privates. Don’t forget behind your ears, either, though that’s more for hygiene than smell. It’s just a spot boys miss sometimes!”

He just gave a small nod, still not able to look the pretty redhead in the eyes during this experience that was beyond patronizing.

Finally, it was time for the most daunting part. Vanessa shifted back, rinsing off her hands and the cloth in the water for a moment, then said, “Can you stand up for me?”

Obviously, he could do so physically. The real challenge was willing himself to lose the partial cover his strategically angled thighs and the water had provided him so far.

Before he did so, Vanessa added on, “Oh. Just so you know, it’s my policy that bedwetters wear protection for 24 hours after an accident. You don’t mind wearing diapers, do you?”

Chapter Four

Diapers? Of course Elliott minded. The bedwetting was an isolated incident, as he had never done that before. Even something like wearing protection at night would have been a bit much, but 24 hours? He wasn’t going to have an accident during the day! And, like everything else, he was way too old for that kind of underwear.

“Umm, I don’t need diapers, Vanessa,” he mumbled. It was difficult to be firm when he was naked in front of her, in the middle of a bath.

“I know you don’t need diapers, silly,” Vanessa giggled, “But it’s better to be safe than sorry, don’t you think? You wet the bed. That means diapers. If you can make it to the toilet like a big boy until tomorrow morning, we can forget all about your little accident. I won’t tell your parents about it, either. How does that sound?”

It wasn’t necessarily a threat that she would tell them if he didn’t go along with her policy, though it also wasn’t something he had thought about amidst the nonstop embarrassment of the morning. Elliott had no idea how his parents would react to learning that he had an overnight accident. They already hired a nanny to ensure he stayed on top of his end of the semester studying. Something like this could potentially make him seem immature in a completely different way; he really didn’t want this kind of supervision to become the norm, as his parents traveled at least once a month.

Not pushing for an answer right away, probably because she was in charge and would get her way regardless, Vanessa said, “Think about it, Elliott. We can talk more about your diapers after your bath. Now, stand up for me. The sooner I finish washing you, the sooner we can get on with the day!”

He was still hesitant to lose the cover that he had kept up for the first half of the bath. Couldn’t he just bathe his private areas himself? Apparently not. Vanessa gently yet firmly pushed him to get moving, reminding him that this really wasn’t a big deal for her. It wasn’t the first time she had given a bath to one of her charges, and she added that he was going to be in trouble if he didn’t behave.

While standing up and exposing himself was daunting, he managed to justify it due to the fact that he was already naked. Accepting Vanessa’s ‘logic,’ as they would be done with all of this a lot more quickly if he just did as he was told, he left the cover of his water and the position of his body. As badly as he wanted to cup his crotch with his hands, Elliott managed to keep his arms down. She was going to see him either way, and he was also dirty down there from the overnight accident.

“There you go,” Vanessa smiled, “That wasn’t so difficult, was it? Hold still and pay attention, okay? You’ll have the chance to try this yourself next time.”

Elliott couldn’t help himself. “I already know how to do this myself,” he blurted out.

With a small eye roll, Vanessa replied. “I’m sure you think you know how to do this. But as I’ve been saying, you smell like boy. And like pee, right now.” She leaned in slightly to take a small sniff, then wrinkled her nose. “Gross. As your babysitter, I need to make sure you learn proper hygiene. You don’t want to be a smelly little boy, do you?”

What kind of question was that? As if her words weren’t demeaning enough, he was literally standing there with his bare crotch on display.

“I didn’t think so,” she said, “You want to be a big boy. Right?”

He wanted to insist that he was a big boy, except that would almost sound worse. A guy his age was well beyond such phrases. At the same time, he was kind of trapped between that and the more demeaning description she had just used. So he nodded, unable to bring himself to actually echo her words.

“Good!” Vanessa chirped, “If that’s really what you want, then show me you can be mature about all of this. I’m going to teach you how to bathe yourself thoroughly, and then I’m going to diaper you. How does that sound?”

Humiliating. Unreal. Beyond degrading. All Elliott could muster, however, was, “ . . . Fine.” This wasn’t exactly what he had anticipated when Vanessa said they could talk about the padding. He had just been standing around for so long, and diapers were actually starting to sound appealing if they meant not being naked any more. Elliott was also more of a grower than a show-er, and the cool air of the bathroom wasn’t doing him any favors in that regard.

At this point, he was certain that nothing was going to happen between him and Vanessa, anyway. She was attractive, and he might’ve fantasized about her once or twice since her arrival. However, this was not at all what he pictured in terms of being undressed with her.

Vanessa made a comment about his attitude, though she didn’t dwell on it. The fact that he had accepted her bedwetting policy, albeit begrudgingly, was enough for now. If anything, it only made him seem more like the charges she was used to dealing with. After all, every older kid insisted that they didn’t need a babysitter; this was no exception.

She took the bar of soap and applied a generous amount onto the washcloth and cupped his crotch with the layer between him and her hand. Starting with his dick and balls, she made sure to circle and rub and get every little spot. There was nothing sexual to her touch, and Elliott really didn’t have to worry about getting turned on and further embarrassing himself. Between the temperature and how emasculating this experience was, a pretty girl indirectly touching him down there wasn’t quite enough to excite him.

The friendly yet bossy redhead also explained pretty much everything as she scrubbed. “You should always be thorough when cleaning your private areas, Elliott. And extra thorough when you have an accident. There’s not much hair down here, but you still want to make sure you get this area.” Moving downwards after wiping every inch of his crotch, she continued the explanation with the common phrase she had been using since yesterday. “Make sure you get underneath your balls as well. Remember, you don’t want to smell like boy! That means getting every little nook and cranny when you take a bath.”

. . . Or a shower? He didn’t bother clarifying. By the time Vanessa was done cleaning his most private area, Elliott was deeply blushing. The worst part was, she really wasn’t talking down to him in a teasing or demeaning way. Vanessa spoke in a simple and straightforward manner, nonchalantly lecturing him during the bath as if she actually believed he needed to learn these things.

“Let’s keep the soap there for a minute,” she said, “Your legs will be quick; then you can rinse everything off!” With that, she started scrubbing his thighs, followed by his knees. After having him lift his feet out of the water and talking about how cleaning between the toes is another one of those ‘nooks and crannies’ part of properly taking a bath, she had him turn around so she could repeat the recent process on the backs of his legs. “Alright, rinse off,” she instructed, “I just have to clean your bottom, and then we’re done!”

At least he had already dealt with her seeing his ass once, since she had to do both sides of his legs. Of course, it was different when she was actually washing him back there. Vanessa started with his lower cheeks, then launched into a similar explanation about how it’s important to be thorough. She worked the washcloth in between his cheeks with her fingers, scrubbing up and down while telling him that some boys are nervous to wash this part. But this was part of being a ‘big boy,’ and she was confident that he’d be brave enough to do it himself next time.

After digging a little bit deeper, enough that Elliott eventually blushed again and squirmed a little bit due to how this was the first time a hand that wasn’t his own was down there, Vanessa finally gave him a teasing swat as she announced, “All done! You’re such a good boy, Elliott. Okay, rinse off and wait right here. I’ll be back in a minute.”

He was left alone in the bathroom, wondering whether or not ‘right here’ meant the tub or the room itself. Drying off was the logical next step. The problem was, that could be yet another thing Vanessa planned on doing herself. He was torn between proving that he could do something so simple, or waiting for her permission. There was really no winning when she was treating him like he was one of her younger charges.

Deciding it was better to do something on his own, mostly since it would be awkward just standing in the tub dripping, Elliott grabbed his towel from the rack and started drying himself off. He got most of the job done, when Vanessa returned with an armful of diapering supplies. “Oh! I can help with that, Elliott.” She set her things down on the counter and stepped forward, taking the towel from him and picking up where he left off.

He didn’t bother voicing anything about how he didn’t need her assistance. Better to move things along, as he was still in the mindset that getting to a more normal part of the morning would give him a better chance to remind her that she was really only supposed to be here to keep him on track for his schoolwork. That, and perhaps studying for his COLLEGE CLASSES would give her the hint that he wasn’t some immature boy who didn’t know how to take care of himself.

But for now, Vanessa was fussing over him and making sure he was nice and dry before moving on to the next part. “Okay, Elliott. Now we just have to get you diapered. Well, you also need to brush your teeth and everything, but we can do that in a minute.” She grabbed the diaper from the counter and unfolded it, then knelt down to lay it out on the tile. “Sorry we have to do this on the floor! Your bed would be more comfortable, but your room smells like pee right now.”

Elliott wasn’t sure which was worse–that he was about to be wearing a diaper, or that he wasn’t bothering to argue about it. As motivated as he was to get dressed, since being nude for an extended period of time didn’t do anything to get him used to it, being put in protective padding was a lot. Even if he had wet the bed. And yet, he reluctantly lowered himself to the floor, knowing full well that he had already lost his opportunity to discuss the matter.

As if reading his mind, Vanessa gave him a reassuring smile as she positioned herself next to him. “Diapers are nothing to be embarrassed about, Elliott! Would you rather have an accident in these, or on the sofa?”

Neither. Like pretty much every either/or question she posed to him, there was really only one answer. Though he was old enough to understand the babysitting ‘logic’ that probably worked on the average charge of hers, it still technically worked. Between the two, it was obviously better to not pee on the sofa. Even if he wasn’t going to have a daytime accident.

It was more of a rhetorical question, anyway. Before wrapping Elliott up in the thick padding, Vanessa poured some baby powder all over his crotch. To keep him from getting a diaper rash. In this case, it was more about any lingering moisture from the shower, rather than her implying that he was going to wet himself. Either way, it was just another thing to be embarrassed about on top of the diapering itself.

Vanessa really didn’t drag things out. Unlike the recent bath, there wasn’t much beyond the powder to be thorough about. Ever the experienced babysitter, she was quite adept at putting a diaper on. After making sure it was nice and snug, she taped up the padding and secured the babyish underwear around Elliott. “There,” she said, sitting back, “How does it feel?”

Elliott sat up and then stood up, feeling ridiculous in the thick, white underwear. “Fine,” he mumbled. What else could he say? Just by the way it felt to get to his feet made it clear that it was going to be impossible to ignore the padding between his legs. While putting on a pair of shorts would at least cover the diaper, he was going to be constantly reminded of what he was wearing.

“Good,” she said, “Before you get dressed, can you show me that you remember everything else you’re supposed to do before starting the day?”

Right. He hadn’t brushed his teeth or anything yet. Like last night, Vanessa stayed to supervise him as he flossed, brushed, and applied deodorant. Her presence wasn’t even the worst part; he was busy dealing with the embarrassment of his reflection as he went through the simple routine.

Finally, he was able to leave the bathroom, trying his best to ignore how it felt to walk in a diaper. Like Vanessa said, his room smelled a bit like pee, but it wasn’t so bad that he couldn’t get dressed. He grabbed a pair of loose gym shorts that would hopefully hide the bulge of the underwear, and the first t-shirt he saw in the next drawer down. Vanessa was still supervising him from a distance, and every second she saw him in the childish underwear worked against him in terms of making her see him more as a college student and young adult, rather than a teenage boy.

He pulled the shorts on first, of course, followed by the tee. Just as he was officially ready for the day, Vanessa held out her hand. “Come on, Elliott. Let’s go downstairs. I’ll take care of the mess in here once we have you settled with your studies!”

Did she really expect him to take her hand? Elliott was still too flustered from the last half hour or so to protest. He reluctantly placed his hand in hers, where she gave him a small squeeze. Like so many other gestures, reassuring him that this was all fine. Still being kind and professional, which was both confusing and frustrating at the same time.

Vanessa led him down to the main floor, to the coffee table where he had been studying yesterday. This time, she decided the subject for him. After walking him to the sofa and sitting him down, she pulled out the syllabus for his religion class. Elliott’s college had a variety of General Education requirements, including a handful of religion classes despite it not being a particularly religious school. Of all his classes, this was the one he generally ignored in favor of studying for the ones he had decided were more important in the grand scheme of things.

“You currently have a C+ in this class,” she said, “If you do really well on your final paper, you’ll for sure earn a B minus. Maybe even a B, if you put your mind to it! Do you need my help with anything, or are you ready to get started?”

What Elliott really wanted was some breakfast. Or a few hours of gaming, since it was Saturday morning. Keeping all that to himself, he said, “I’m fine. You can clean, or whatever.” He would have washed his sheets himself, if Vanessa hadn’t caught him before he had a chance to discreetly do so. Since she had already offered a minute, it didn’t feel presumptuous to suggest it. It would just be nice to have a minute to breathe, as she had been more overbearing than yesterday ever since she spotted the wet sheets.

She did head back upstairs to throw his bedding in the washer, and hopefully keep the mattress from getting stained with what could only be from one thing. Meanwhile, Elliott shifted uncomfortably on the sofa, still not at all used to the diapers. Every new movement, every position of his body, seemed to draw his attention back to the padding. He had no idea how he was going to be able to focus on schoolwork when he had such a mortifying distraction to deal with. Vanessa’s policy was 24 hours; that meant he’d be stuck in this all day and all night. That math was simple of course; Elliott just hadn’t fully accepted it yet.

Working on a paper first thing in the morning didn’t come naturally to him either, considering his habits. It took a few minutes of skimming through his notes and the minimal prep work he had done for the essay just to get a sense of where he might start. Before he opened his laptop to get a word on the page, Vanessa stepped back into the room.

“Okay!” she exclaimed, “Right where I left you; that’s a good sign. You have a lot of work to get done today, Elliott. Don’t worry, I’ll be here to keep you on task. And I bet you’ll do a great job. You’ve been such a well behaved boy so far!”

Uh huh. Something like that.

“I’ll get started on breakfast while you work. Just let me know when you have to use the bathroom, so I can take your diaper off. I can supervise you in there, too. Just in case!” With that, she gave his head a pat and went into the kitchen.

Elliott was left sitting there, wondering how things had spun so far out of his control since Vanessa arrived. And what the rest of the weekend with her was going to be like.

(Rose, the commissioner of ‘Nanny Vanessa,’ is unable to continue pledging at the upper tier due to unexpected financial complications. She’s given me permission to offer it up to anyone who might be interested in funding it themselves, complete with their own spin moving forward if so desired. As long as this note is up, anyone may feel free to reach out and inquire about picking up the story!)