Published: October 25th 2023, 12:00:14 pm
One of the entries to the Community Story contest that didn't win, but was sponsored to be turned into a story anyway by an anonymous Patron. Set in the Dollhouse universe.
Ms. Barlow had always hated Halloween. It had started well before she'd gotten her job at the Dollhouse, and, if anything, it had helped motivate her to take it, having seen exactly how immature young women behaved on the holiday, even some of the most well-behaved ones she knew, going out and flouncing around in their tiny, skimpy costumes, usually drinking too much...
There was certainly a part of her that wished the Dollhouse would have banned celebrating it at all, bringing back those memories for their girls, but she had to admit that the Headmistress had come up with a decent compromise, giving the students only the most cute, innocent costumes to choose from, enacting strict punishments on the ones who tried to get around those rules by modifying the costumes the school provided or making their own. It was generally a busy night, at least with the newer students... The ones who had been around a while usually knew better. She suspected they may by egging the others on, telling them that the teachers didn't pay that much attention, or that the rules were actually more lax for the night, though in her experience, if the girls were the type to do that sort of thing, they'd do it regardless.
Ms. Barlow herself, of course, never participated. Most of the teachers didn't, and seeing which ones did was another useful tool, showing her which of them may not be totally suited for their role, who might be better off as a student. The only proper thing for an authority figure to do, in her opinion, was to wear their regular clothes as they chaperoned, like the adults they were.
So she had not been pleased - to say the least - when the new Headmistress had made announced her stance on the matter. "It's Halloween!" she'd said at the staff meeting. "I think for one night a year, maybe we can take it easy on them, and have some fun ourselves. So, I'm making costumes mandatory... For everyone who attends the party, including all of you."
"Ma'am," Ms. Barlow had to grit her teeth to force herself to call the woman that. It was difficult, at times, to remind herself that she was a woman at all, not a girl like their students... In terms of age, she would fit right in among them, and, frankly, it seemed, at times, like she would in terms of maturity as well. The only real distinguishing factor between them sometimes was the Headmistress's expensive taste in clothes, and even that was only evident because the students had to wear their uniforms... More than one of them had been sent here for exactly that reason. She had been disappointed when the former Headmistress had stepped down, moved on to another opportunity, but not nearly as much as she had been when she'd met the replacement. At first, she'd thought it might be beneficial, that the students would be extra humiliated, knowing someone their age was in charge of their re-education. Now, she wasn't so sure. "In my experience, I just don't think it's good for our students to see us..."
"Don't be so stuck up, Ms. Barlow," the Headmistress rolled her eyes. "It's Halloween! It's all right to look silly for one night!"
If the woman had been anyone else, Ms. Barlow would have taken her over her knee right then and there. As it was, all she could do was stay quiet, afraid of what she might say if she didn't. She might be a full decade - perhaps even a bit more - younger than the previous Headmistress, but she was still Ms. Barlow's boss.
Ms. Barlow never forgot about the proclamation, the exchange ringing through her mind whenever she saw the woman from then on, though she did keep putting off the indignity of going off to some costume shop to find herself something to wear. When she did, finally, it had been picked through quite thoroughly, crawling with young women who would have been better off under her care at school. She had to leave before she started calling in an extraction crew for everyone there, without having seen a single thing that she would have been caught dead in herself.
So she held on to hope that the Headmistress, instead, would change her mind, see reason after a couple more weeks looking after the students. On Halloween morning, however, an e-mail went out reminding the teachers about the requirement, and Ms. Barlow reluctantly went to the Seamstress, who was, of course, able to make her exactly what she needed.
She disliked the thought of wearing one of the school uniforms, but was it really any worse than any other costume? She could talk herself into it being acceptable this way, having the Seamstress take it in, adjust it, turn it into something sexy and flattering on her more mature form, something to remind the students of how childish they were in comparison to her, how, even in one of their uniforms, there was no question that she was an adult.
And, to further emphasize that, she added some extra supplies to the diaper bag she always carried as a chaperone to these sorts of things. She could see the students taking too much advantage of the relaxed costume rules, or thinking they could joke with her - or about her - if they saw her in costume, and she wasn't going to stand for any of that.
The Seamstress sent a student by Ms. Barlow's office later that day, the girl meekly handing over the package, pausing. "Do you have something to say, young lady?" Ms. Barlow snapped.
"H-Happy Halloween, ma'am!" the girl stammered, hurrying away.
Ms. Barlow sighed, closing her door so she could get changed. The Seamstress had done good work, she had to admit, and she was confident it would do the trick, but, regardless, she was still apprehensive when she heard another knock on her door, the idea of allowing anyone to see her this way leaving a sour taste in her mouth as she adjusted her dress, feeling a slight blush in her cheeks. "Come in!" she yelled.
To her surprise, it was the Headmistress, in her designer dress and fancy heels, looking no different than she had when Ms. Barlow had seen her in the halls earlier that day. "Oh, good!" the Headmistress smiled, looking her up and down, giggling after a moment. "I was worried you weren't going to participate."
"I follow the rules," Ms. Barlow informed her coldly. "What about you?"
"What?" the younger woman blinked. "Oh, this? I didn't have time to come up with a costume, but, honestly, there are enough chaperones as it is... I'll probably just say a few words to everyone and then duck out, so I'm technically not breaking the rules. I'm very glad you're participating, though, I was a little worried with what you said at the meeting, and everyone told me you don't tend to go in for this sort of thing, but..."
Ms. Barlow's eyes narrowed. Had the Headmistress ever intended to do it herself, or was this just a convenient excuse to get out of spending her night chaperoning the party? Either way, on today of all days, it was easier than ever to see the girl like any one of her students, in costume as what she thought of as a grown-up.
"Oh, sweetie," she purred, grabbing the Headmistress by the arm, the girl's eyes widening in surprise. "I don't think you paid attention to your own rules... Costumes are mandatory for everyone. Don't worry, though... I'm sure we can find you something."
She picked up her diaper bag, feeling the younger woman start to writhe desperately in her grip. "You wouldn't dare!" she shrieked... Until Ms. Barlow took a pacifier from the bag, shoving it into her mouth, inflating it to silence her protests.
It was probably a good thing Ms. Barlow had so much of the faculty busy worrying about their own costumes, making it easy for her to drag the woman off to the Nursery. "Hmm, let's see," she mused. "A onesie would be traditional, and adorable, but it just doesn't seem right for you... Oh, I know."
The Headmistress squealed behind her pacifier as Ms. Barlow laid out a bib, bonnet, mittens and booties, all in matching pink, finishing them off with an extra thick diaper from her bag, spreading them out on the changing table. It felt like second nature, stripping the girl out of her expensive clothes, taping her into a nice, big diaper...
It suited her quite well, if Ms. Barlow said so herself. She really did look like the other students, all pouty and blushy, pawing angrily at her pacifier, glaring at Ms. Barlow. "I'm going to take these silly things to the incinerator," Ms. Barlow smirked, holding aloft the Headmistress's former outfit, the girl whining, grabbing for them, too short to reach them in her booties rather than her heels, Ms. Barlow easily able to keep them away from her as she left, locking the woman into the Nursery room, watching her for a minute as she stomped around helplessly.
Would anyone recognize her like this? Would anyone even suspect her true identity at all, much less enough to believe her if she attempted to tell them the truth, rather than assuming she was a typical Nursery student, willing to say anything at all to try to be promoted out of there?
They wouldn't, Ms. Barlow was confident, after the suppository she slipped into the girl's bottom when she returned took effect, following it up with a second, just to be safe, and a pat to her bottom as she begged for her to stop through her paci. "Aww, it's okay," Ms. Barlow cooed at her, before lifting the whimpering woman into a stroller, bending over her nice and close as she buckled her in, pulling the restraints snug against her diaper. "It's all right to look silly for one night, right?"
She was almost disappointed she couldn't see the Headmistress's face as she pushed the stroller through the halls, as they got closer and closer to the party, and the other teachers chaperoning it, and the students the Headmistress had been punishing, and condemning to just this sort of punishment. She had no doubt it was delicious... Which was why she made sure to wheel her all around the party, letting everyone get a good look at her as she thrashed futilely in the stroller, her tummy churning.
Ms. Barlow had given enough girls suppositories to be able to time it just right, to end the woman's humiliating trip with her right in front of the rest of the chaperones, once the students had gotten their turn to coo at her and tickle her tummy, making her squirm in embarrassment and discomfort.
"And who is this?" one of the teachers asked, kneeling down in front of the stroller. "Is this a costume, or a punishment?"
"A little of both," Ms. Barlow smirked. "What she was wearing was totally inappropriate for this party, and she'd been on the verge of getting sent to the Nursery anyway, so I decided it would be best to give her a look at what she was going to be missing because of her bad behavior first."
She peered into the stroller, seeing the Headmistress's face red as she wriggled desperately. Was she more mad at her employees for not recognizing her, or more mortified at what Ms. Barlow was certain must be happening inside of her right about now, at the pressure rapidly building. She must be fighting so hard not to let go, knowing that, regardless of any resemblance they might notice, once she'd filled her diaper in front of them, nobody would ever think she could possibly be the Headmistress. And even if they did, there was no way she could go back to any position of authority after doing that in the middle of the Halloween party.
Too bad for her that Ms. Barlow's timing was impeccable. There was a tiny, muffled squeal, one all of the teachers were familiar with, all of their eyes turning towards her diaper to see it begin to swell. She held her mittened hands over her crotch in a futile attempt to hide it, but Ms. Barlow grabbed them, fastening them to a pair of restraints built into the inner sides of the stroller.
"Now, now," she lectured. "None of that... You're going to have to get used to people watching. You're such a cutie, I'm sure your new Mommy or Daddy will want to show off how precious you look when you poop your Pampers. Don't worry, though... Once the Nursery is done training you, you won't even have to think about it. It will be second nature."
The Headmistress stared up at her, tears glistening in her eyes. Ms. Barlow would have loved to take her on another pass through the party, but the lesson seemed to have sunk in enough already. "Could one of you take her down to the Nursery for me?" she asked. "It's past her new bedtime. Be sure to play a nice video for her to help her get to sleep." The Headmistress struggled in her stroller, knowing, of course, exactly what that meant, but there was nothing she could do about it now.
Ms. Barlow went to check on her after the party was over, after a few spankings, and a few demotions. She took particular joy in demoting a student who had managed to cling to big girl panties her whole time here straight back to diapers for having the nerve to try to dress up like her, running around, talking in a snooty voice... She might have let it go for the spirit of the holiday if the girl hadn't thought it clever to threaten to spank Ms. Barlow for being out of dress code, not wearing the proper tights with the uniform she had on.
The Headmistress stirred at the sound of Ms. Barlow coming into the room, blushing as she saw who it was. She was in a crib, wearing a sleeper, an extra-thick overnight diaper underneath it, her eyes looking a bit dazed, her paci bobbing up and down in her mouth. One session wouldn't be enough to completely brainwash her, of course...
It would be enough to leave her disoriented, confused, even less capable of convincing anyone that she didn't belong there. Any good worker here would laugh off her silly story in an instant, perhaps threaten to spank her if she kept it up too much... If anyone did start to get suspicious when she kept going, began to wonder if maybe it wasn't a coincidence that she'd wound up there the same night the Headmistress went missing... Well, by then, it would almost certainly be too late.
Hopefully, Ms. Barlow thought, giving the seat of the Headmistress's diaper a satisfied pat before heading back out, the next Headmistress they got would be more suitable for the job. And, if not... Well, she'd find a way to deal with her, too.