Impressing The Boss (Patreon)

A story for Daymare

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Jenna had so much on this month. First, she had the work party to organize. Then, she had to prove to Mrs Perkins that-

Wait. Oh no. She’d slept in!

This was not going to impress Mrs Perkins. Not one bit. Her boss had already been doubtful about Jenna’s ability to manage the role, given that, well, Jenna could easily fit in diapers and strollers sized for Mrs Perkins’ amazonian background. And, heck, Jenna had seen a fair few Littles like herself in diapers and strollers around town as it were. The line was very blurry for some about what constituted a child unable to handle adult responsibilities.

Fortunately there was that law.

It had helped Jenna feel confident enough to take the job, after her previous role some years earlier had almost ended with her in diapers in her former boss’s mansion. Several of the other Littles who had worked there had not been so lucky. They were all been groomed for a return to nurseries, it had turned out. She should have seen the warning signs then, the daycare being added to the business, with a direct line to her boss’s office… She just thought the CEO might have been intending a real baby, or perhaps had adopted a hapless Little outside of the company. As long as it didn’t involve Jenna, she’d not given it much thought. She’d had a career to build.

But Mrs Perkins couldn’t groom her. No siree. There was that law. Even if she sometimes spoke like she was...

Jenna groaned, and didn’t want to open her eyes. Perhaps she should just roll over and go back to sleep. It wasn’t fun to start the day imagining how her former co-workers now found themselves. They’d be waking up in thick diapers, as they had for, goodness, all that time now, and hoping for a change.

Jenna scrunched up her nose. She could almost imagine the diaper today. Thickly between her legs, pushing at her in every which way. Vaguely teasing her with its pressure on her privates… Well, she’d thankfully avoided ever wearing diapers since she could be aware of doing so, and could only imagine it would be like that. Though it felt all too real even just based on her imagination. To experience the real thing… urgh.

Thankfully that law was quite serious, even if Mrs Perkins sometimes didn’t act like it. Her boss had been giving her gifts. Technically there was nothing wrong with that. Some of the gifts were even kind of nice. They were both women, so it couldn’t as easily be claimed to be a sexual harassment thing. And while there had been a certain glean in Mrs Perkins’ eye, it hadn’t exactly been sexual, not entirely…

The free healthcare cover had been nice, though Jenna had needed to go to a doctor provided by the company. And she’d needed to have frequent checkups to keep the account open, even if she had no real need. They’d mostly just given her vitamins and vaccinations. The nurses only gave her a lollipop once, which she had to guiltily admit that she’d sucked at home, after stomping around in a fury over it.

But then there were other gifts...

There was the offer for a pool membership, yet when Jenna had shown up, she’d discovered that there were swimming lessons for mothers and children scheduled that day, and she’d spotted Mrs Perkins in the pool, wearing an enormous, one-piece swimsuit.

God, Mrs Perkins’ bust was enormous.

A few Littles had been wearing identical pink swimsuits, with little tutus which barely covered diapers, which seemed to be the required uniform for anybody that size. There had been sing-song encouragements, along with warnings about spankings on thighs.

Jenna had thankfully hightailed it without being seen. She told herself that it was perhaps just a mistake, and Mrs Perkins hadn’t intended for Jenna to join them in that pool.

Besides, there was that law… It was ironclad, Jenna had investigated it herself.

She’d even done some Internet research into diaper sales, of all things, to check that there hadn’t been some secret uptick. But by and large, they’d mostly stayed stable, with only slight increases which were probably new people moving into the city, perhaps with Littles who were already legally adopted from elsewhere. Or perhaps they were just for real babies, Jenna supposed, though she was quite sure that the ultra thick style she’d researched was only intended for one type of wearer.

Her research had led her onto some rather eye-catching pictures of Littles in diapers, and Jenna had to admit that - with there being no concern to herself - she had masturbated to a few, imagining a sort of BDSM situation of complete dominance by somebody else. It was dumb, and stupid, and gross, she knew… But sometimes, well, when she knew it really wasn’t happening to her personally, she’d bite her lip, and…

Goodness. Maybe she deserved to be in diap... No, what a silly idea.

Even as swamped with work as she was, with the endless tasks and tests which Mrs Perkins had set for her, she’d pick stressed adulthood over a nursery any day.

She could deal with an impossible boss, who only bothered her during work hours, mostly. But to have a… parent… A rule setter, in every aspect of her life… Bedtimes. Media limits. Supervision.

Well, in a sense she had some of that…

Her boss had gifted her a new, cheap apartment, closer to work. Though due to ongoing construction work, the power always went out at eight. She’d had also bought Jenna a huge TV and a computer second-hand from a family moving out, though Jenna wasn’t sure if Mrs Perkins knew that there were heavy-handed family controls set up on those. It was too embarrassing to ask to have them removed… Perhaps because she wasn’t entirely sure if the answer would be yes…

Perhaps that was why she had fingered herself over those photos while doing her diaper research, she hadn’t had access to porn for a while now...

And because Jenna had started to have doubts, even with the new law, she’d tried fishing for responses, and had carefully mentioned that she was a bit worried about ending up like her former co-workers, adopted by her former boss.

Mrs Perkins had hired a young Amazon girl downstairs to check up on Jenna regularly, as a precaution against her former boss trying anything. Jenna now had to check in with the college student every day the moment she arrived home, and then they’d go upstairs and check Jenna’s apartment for anything. The girl was quite thorough, and there was no way that Jenna could hide things in her own home… Her favourite, er, toys, were still in a rental lockup, at least until these awkward inspections passed. Her effective sitter would often just put the TV on something childish, set the remote up somewhere high, and then stick around for the night to ensure things were okay, right up until Jenna was in bed, her teeth brushed, her college-aged guardian having said good night, and the front door locked with the security systems enabled, which would trip if Jenna got out of bed in the middle of the night.

It might have been invasive, but she had so much work to do that she barely had time to consider it.

Mrs Perkins obviously didn’t believe that a Little could pull off the role’s responsibilities, and had been laying on more tasks and tests.

Jenna was often so exhausted that she actually fell asleep on those early nights. Though it did kind of miff her to sometimes hear the girl downstairs up late, talking on the phone out the window. The girl mentioned recently that she wanted to move into ‘real’ babysitting, and might have a job with Mrs Perkins. Jenna had rolled her eyes, and thought good luck with that. Her boss would need to leave the city to adopt. It wasn’t really Jenna’s problem, and she’d even helped Mrs Perkins pick out a changing table and crib from a catalogue, refining all the searches for her.

Thankfully Mrs Perkins couldn’t just ‘gift’ her a return to toddlerhood.

Jenna sighed, and now really did want to roll over, and go right back to sleep. The last thing Mrs Perkins had gifted her had been a strange spa retreat, for just the two of them. It was at least quite mature.

In fact…

Wait…

Jenna had gone to the spa, though that was the last thing she remembered. Frowning, she began to open her eyes, and found it tougher than expected.

She’d been asleep longer than she realised. Had there been an accident?

Well, the glass dome over her head wasn’t good. She definitely seemed to be in some sort of pod.

Oh, god, had there been a contamination leak or something?

Jenna felt so strange. Well-rested, though, and at least not hungry or anything.

She lifted her foot, feeling something strange there. Sure enough, there was something around her ankle. A metal band of some sort. She squinted, her eyes still foggy, with some sort of big white cloud in her vision blocking the way. After a moment her eyes began to focus, and she read her own name on the metal band. Only, it said Perkins, Jeni. They’d made some kind of mistake, thinking Jenna was Mrs Perkins’ girl. Or perhaps it had just been a way of easily identifying who she came in with.

Though, if they’d mixed up Jenna being an adopted Little, or goodness, had even thought she was the real thing, they might have put her in a -

Jenna blinked, and glanced down at what she’d thought was the white cloud in her groggy view.

That was in focus now. White, plastic, thick. Oh, now she understood how she had ‘imagined’ wearing a diaper so well...

Oh dear.

She gave it a poke, and felt her face immediately turn red at the crinkle, and how faintly she could only feel it through all the layering. Oh geeze, it was just like she imagined. Maybe even more embarrassing.

Well, thankfully it was all just a mistake. She could get this sorted out. There was that law, after all… And Jenna had gotten to find out what wearing a diaper was like, she supposed. Not worth the embarrassment of anybody else knowing about it though. Goodness, what if word of this got to the office? Everybody always seemed bemused by Jenna working there, smiling down at her as she hurried around, trying to keep up with the tasks. Even the Between-sized people saw Littles as ‘just the cutest.’ The other Littles had mostly ignored her, obviously thinking that she was much too involved with big people to be trusted.

Jenna frowned. She remembered hearing an office party about her, come to think of it. Had the accident been after they left the spa? Her memories grew vague after she entered there, and met a nurse, who had helped rub some kind of oil all over her… Jenna had blushed and said she didn’t need to get it everywhere, but the nurse had shushed her, saying it was necessary for the process. What kind of spa facility had it been anyway?

Yet she clearly recalled hearing people talk about how she was just so cute rushing about the office after that. They wouldn’t say that where Jenna could hear them would they? Well, they were Amazons, of course they would. One of the women there had even scoffed at the law, and cheerfully told Jemma how cute she’d look if only that silly law didn’t get in the way. She’d said it like it was a compliment...

Jemma had to admit she’d sized herself up in the mirror that afternoon, trying to imagine how she might look in the type of outfit the giant of a woman was probably thinking of. Goodness, nobody could ever see it though. Even if Jemma knew where to get such an outfit, which she didn’t. When the woman had heard that Mrs Perkins was adopting, however, she’d been rather excited, and said she was buying some outfits she had in mind, so Jemma supposed she’d get to see it soon.

Mrs Perkins.

Jemma snapped back to her current situation. The awkward mix up which had put her in some kind of chamber. The name tag on her ankle.

It almost seemed like… Well, no, the law was quite clear, only more traditional adoptions were allowed as well as births.

Jenna frowned, and tried to roll to her side. It was difficult in the thick diaper and on the plush padding. Goodness, wearing a diaper really was like she’d imagined, only somehow even more-

Wait. There was a whole grid of beds around her, as well as a few other long, round tubes like her own. It seemed like something she’d seen somewhere, in a movie or something…

There was a big window on the wall beyond her feet, and a few giants were peering in.

Jenna immediately tried to tug her short, white dress down over her diaper. Oh goodness, her diaper, she still wasn’t used to that. How long had they been standing there? Since she was sleeping? Had any looked at her.

It almost looked like… Wait, Jenna knew what kind of room this was. It was the kind of room for newborns in a hospital. The tube she was in was some kind of incubation chamber, for recent births who needed a little more observation. But why would see… Wait, she did remember some talk of Mrs Jenkins expecting soon, and some sort of baby shower. It was the same office party where they’d been talking about her. It had all been kind of muffled…

Jenna frowned, and glanced back to her ankle band again. She kicked her leg to spin it around, and saw a new birthday on it... 

Birthday…

It was… Goodness… It was nine months after they’d gone to that spa… Jenna had been rushing about, overworked, almost ready to throw in the towel and just go to one of those cities where she’d be diapered if she just wandered around unaccompanied at peak hour…

But no, this was all just a prank. A trick. There was no way to trick the law and pretend Jemma had somehow just been born. She…

She frowned. Mrs Perkins was entering the room at the far side, wearing a hospital gown, and looking a bit exhausted. There was the telltale sign that she’d recently been pregnant, though she was all smiles, and seemed to be on the mend…

“The procedure was a complete success,” a doctor was saying, accompanying her. “We can take her out of the incubation chamber now. These reverse pregnancies are going to be enormously popular.”

Jenna’s eyes widened, and she wriggled in a panic in her diaper. Her diaper.

If what he was saying was true… But it couldn’t be… Then again, the law had said births were allowed, and Jenna should have known that nothing would stop an Amazon finding a way to ‘adopt’ a Little who they had their eye on…

“Oh, Jen-Jen!” a big voice called.

She recoiled as Mrs Perkins appeared above the chamber, tapping on the glass.

She was quite sure she’d just wet her diaper a bit.

“Can you say thank you to the doctor, and hello to Mommy?”

Jenna found her jaw ajar, her mouth trying and failing to say… something…

Mrs Perkins suddenly grew cross.

“If you’re naughty, Mommy can always put you back in there.”

Jenna’s eyes widened. The diaper was definitely wet now...

“N-No. Thank you doctor. H-Hello… Mommy…”