Published: October 24th 2021, 2:00:03 pm
A Halloween-themed continuation of this short story series, commissioned by an anonymous Patron.
"Do you know what today is, Joshy?" Miss Autumn cooed down at him as she changed his diaper.
"Umm..." Josh furrowed his brow, staring up at her, thinking his very hardest. It always felt harder to do that once he got to her classroom... At one time, it had taken being put into diapers, seeing his behavior chart, hanging on the wall next to the 'real' students', to get him in that headspace, but, by now, all it took was coming into the building, seeing Miss Autumn's face, spotting a diaper...
That last one was particularly tricky now, as evidenced by the fact that, at the start of one of their sessions, he was getting his diaper changed, not losing his underwear to have one put on. It was so easy for him to fall into that mindset now, he caught himself doing it at work now and then, especially on those rare occasions when he had to restock the baby section, and was surrounded by things that reminded him of how he spent his Monday, Wednesday, and Friday afternoons. It wasn't uncommon for him to catch himself sucking his thumb there, without thinking... Or worse.
And it didn't always take that visual stimulus, either; sometimes, the thought of what a baby he knew he was, deep down, would enter his head unbidden, especially on the days when he had 'class', and, if he wasn't careful, that could lead to some small accidents. He'd known what the solution was for a while, but he'd been too embarrassed to commit to it until Miss Autumn suggested it.
"Again?" she'd said, not sounding mad, or disappointed, simply surprised, when she found a wet spot in his undies one day. "You know, Joshy, maybe you ought to start wearing your diapers all the time, not only here... Just in case."
Josh had wanted to protest that he didn't need them, that he wasn't really a baby, but it felt unconvincing as he laid there, having a diaper taped on his bottom, and even more-so after he spent a while playing, his body taking over and helping his wet and mess it without so much as a second thought from his conscious brain.
He'd had a bit of doubt then, as he remembered this had all started out because he thought Miss Autumn was cute, and he'd been curious to see the inside of the preschool. Never, when Autumn had extended the original invitation, had he imagined it would end up this way, with him wearing baby diapers most of the time, to keep from leaking onto his pants while he was at work, and potentially causing a far more humiliating situation for himself. Things were maybe going too far... But, when it came time for his next class, despite his determination to take a break, at the very least, he'd wound up right back at the school, not wanting to let Miss Autumn down.
Which had led, ultimately, to today, and his futile attempts to deduce what was special about it. He was relatively certain it wasn't the anniversary of his first time here, thinking it had happened a little later in the year. The year was starting to wind down, however, and it was possible he'd lost track of time... "No, ma'am," he shook his head, happy to admit his ignorance, confident Miss Autumn wouldn't get mad at him.
"Well, today," she smiled, sliding a fresh diaper under him, "is Halloween! Isn't that exciting?"
"It is?" he asked, tilting his head, seeing now why he hadn't been able to come up with the correct answer. "But that was..."
"Yes, I know it was over the weekend," she pulled the front of the diaper up, taping it snugly into place, Josh as impressed as ever at how quick and efficient she was. Now that he did it himself at home, it seemed like even more of a feat... He had a fair amount of experience himself, yet he was nowhere near as fast, or as good. Then again, no matter how much he had, she had way more, having done this for so many kids for however long she'd been here... "We didn't have class over the weekend, though, did we?"
Josh shook his head. He'd known it was Halloween, of course, having had to hang up - then take down - the signs for it at work, and help put together the seasonal section of the store. And Miss Autumn had decorated her classroom, too, with some friendly-looking paper spiders and fluffy 'cobwebs' in the corners of the room, jack-o-lantern shaped fairy lights strung around, and a full-sized plastic jack-o-lantern sitting on her desk. He had noticed it was all still up, too, although he'd attributed that to Miss Autumn just not having time to take it all down. And it was like at work, where it had to be removed right away so they could immediately start to get ready for Christmas.
"So, today is your Halloween," she declared. "And I found the perfect costume for you!"
Josh sat up in his new diaper, his curiosity piqued. It had been quite a while since he'd worn any costume... He hadn't gone to any Halloween parties this year, and even when he had, he'd felt too awkward to get all dressed up, content to show up in his street clothes and give a shrug if anyone asked where his costume was. He had stolen a few glances at the costumes at the store this year, however, blushing as he saw how cute some of them were, and wondered how well they'd hide his padding...
Miss Autumn unbuttoned Josh's shirt, getting it off him and setting it aside with his pants, then helped him down off the changing table, leading him over to her little closet, where she kept, mostly, supplies. When she opened it up today, on the other hand, he immediately saw what she had in mind, his cheeks warming slightly, watching her slide it off the hanger, unzipping it and opening it up for him to step into.
"Come on," she urged. "Get in, Joshy!"
He'd expected a kids' costume, obviously - what else would she put him in? - yet he'd still been surprised to see how childish it was. It was, for all intents and purposes, a green, fluffy footed sleeper, complete with snaps in the crotch. It was quite cozy, and the feet of it were nice and padded, making it feel almost like he was wearing slippers. It had a long, swinging tail, however, one that took a bit of getting used to, with cloth spikes running up it, and his spine, and, as a finishing touch, Miss Autumn tugged the hood up, letting him see the googly eyes on top, and the cloth teeth lining part of the opening.
"Oh, no!" she chuckled. "How did such a fearsome beast find its way into my classroom?"
He giggled, too, despite himself. It did feel very silly, but he would have felt silly no matter what the costume was... He was certain the bulge of his diaper was obvious beneath the crotch of the sleeper; both of them were already quite aware that he was wearing it, though, so why should he care? Plus, even if that was his imagination, the snaps in the crotch made it clear that, at the very least, this was designed for someone who might need a quick change.
He lifted his foot, listening to the muffled crinkle of his diaper, then slammed it down, the soft padding keeping him from making too much noise. It was still fun anyway, stomping through the classroom like a dinosaur, while Miss Autumn ran from him in faux fear, all the way up to her desk.
"Will you spare me if I give you some candy?" she asked, doing her best to hide her smile as he toddled towards her. He paused for a moment, then nodded, and she lifted the top off of her plastic jack-o-lantern, and let out a gasp of manufactured shock. "Oh, no!" she declared dramatically. "I'm all out! Whatever will I do?"
Josh didn't have an answer for that, wasn't sure what he was meant to do, where this game was going. There was a time, back when he'd first come here, and hadn't known exactly why the cute young woman was inviting him to meet her in her empty classroom, where he might have thought that was an invitation for something naughty, for him to declare that there was another way she could earn her 'freedom' from the mighty dinosaur roaming her room... But, after nearly a year of being diapered by her, treated like any of the other toddlers she looked after, that didn't even enter his mind. "I dunno," he said instead, pausing and staring at the empty pumpkin.
"You don't?" Miss Autumn raised her eyebrow. "You can't think of any way that you might be able to get candy on Halloween?"
Josh's eyes widened as he stared up at her, wiggling his bottom, his diaper crackling, his tail swinging. "T-Trick or treat?" he squeaked. What could she mean?! She wouldn't take him out like this, would she?! Even if she did, Halloween was over, so there was no guarantee the other houses in the area would have any candy to give him, if they bothered to answer their doors at all...
"Exactly!" she beamed. "Such a clever dinosaur... Now, why don't you take this?" She handed him the plastic jack-o-lantern, walking across the room to the door, turning back to beckon him onwards. "Come on, Joshy!"
He swallowed, glancing down at the pumpkin, and his costume, then up at her. He had no reason not to trust her, and yet... This was certainly the most scary thing he'd experienced this Halloween season, being faced with a choice like this. There had been so many chances for Autumn to expose him, if she'd wanted, and she hadn't, so he shouldn't have been worried that she was going to do it now, but the idea of being taken trick or treating like this made it hard for his mind not to go there.
If that was what Miss Autumn wanted him to do, though... She must have a good reason, a good plan. It was a big leap of faith, and he could definitely feel his diaper warming as he took a step forward, towards her... But he still took that step regardless, and the next...
"Good boy," she smiled at him, patting him on the back, the tail preventing her from giving him the diaper pats he was used to. "Now, let's see here... Where should we start?" She guided him out of the door, Josh feeling sweat trickling down his forehead as they moved away from the comfort and security of her classroom, the place he was used to doing this, turning down the hall, back towards the entrance...
"I know!" she exclaimed. "Doesn't this look like a nice place?"
She stopped short of the door outside, turning him to face another door, one he had seen before, of course, had walked past every time he came here, yet had never been in. "Go on," she gave him a gentle push towards it. "You know how to trick or treat, don't you?"
He frowned, looking up at her in confusion, then, pumpkin tucked in one arm, lifted his hand to knock. Almost immediately, the door swung open, another pretty young woman standing on the other side. Josh swallowed, gaze falling, heart pounding. By now, plenty of people had seen him with diapers under his normal street clothes, but, as far as he knew, none of them knew about them... Autumn was the only person who had ever seen him like this, however, diapered and dressed like a toddler.
"Hello, there," the woman knelt down. "Aren't you cute? Is there something I can help you with, sweetie?"
Josh kept staring downwards, the hollow insides of the pumpkin filling up his field of vision. "Go on," Miss Autumn repeated, her hand returning to his back, rubbing it soothingly. "You know what to do."
He wriggled, attempting to lift his chin to look at the other woman, failing. He did managed to squeak out an uncertain, "T-Trick or t-treat?" though, and, almost instantly, he saw a whole handful of candy being dumped into his waiting pumpkin.
"Of course!" the woman grinned. "How could I resist a big, bad dinosaur like you?"
"Go on," Miss Autumn reminded, while Josh stared at his haul in disbelief. "What do you say, Joshy?"
He'd already said the thing, so he was confused at first, before realization hit him. "Th-Thank you," he blushed, glancing back up at the other woman at last.
"Happy Halloween," she told him, patting him on the head before closing her door.
"Look at that!" Miss Autumn exclaimed. "What a good job you did!"
"Th-Thanks," Josh blushed.
"There's still lots of room in that pumpkin, though, isn't there?" she asked, and he had to nod. "Good thing there are plenty of other places to go here, then, isn't it?"
He looked down the hall, at all the classroom doors, shut tight, waiting for him to knock on them. He assumed it was the other teachers behind them, but perhaps they were Miss Autumn's friends, people she knew wouldn't make fun of Josh, or judge him... Either way, as scary as that first door had been, it had been wonderful, getting to be his real self in front of someone other than Autumn... By the end of the hallway, he had a feeling all that fear would have worn off. That, he recognized, must have been the lesson Miss Autumn was trying to teach him today... And what better lesson was there for Halloween than learning to deal with things that were spooky, in order to get something nice?
"Yeah," he agreed, taking a tentative, toddling step towards the next door, not even having to be prompted this time to give it a knock. "Trick or treat!"