Neonato Ranch - A Regression Story (Chapter 3)

This was a story I was commissioned to write - it features some themes that I don't often explore, and is primarily a slow-burn mental regression story. It's seven chapters long, I'll be posting the complete story over the next couple weeks.

Chapter 2 can be found here. 

Sleeping in pull-ups wasn’t as hard as Jeremy had expected. Comfort-wise, they weren’t so bad, fitting snugly and flexing in a way that was mostly like normal underwear.

The plastic sheet that had been added to his bed was a little harder to get used to, rustling and crinkling every time he rolled over, but even that wasn’t enough to keep his tired body from dozing into a deep sleep. He had comfortable dreams, and when he woke up, the bed was dry.

Of course, he thought, smiling as he sat up. It was just a one time thing. A freak incident on my first day, not a chronic issue.

Throwing off the covers, he stood out of bed, feeling his pull-ups sag around his waist. Frowning, he glanced down, inspected the padding, and found it sodden and soaked almost through.

Not quite a dry night, then. At least the pull up had done its job, though, and he hadn’t soaked the mattress and sheets.

Stripping out of the garment, he dropped it in the trash bin in his room, wrapped a towel from the dresser around his waist, and walked to get showered. After a quick rinse, a brush of his teeth, and checking to find that he didn’t really need to shave, he returned to get dressed.

At some point the day before, Billy or someone had gotten into his dresser and swapped out his boxers for pull-ups. The padding was lined up neatly.

Well, it’s to be expected. Making a mental note to ask where his boxers had been stored, he slipped on one of the pull-ups, put on pants, and left his room shirtless to go get breakfast.

No flapjacks that day. Billy was frying up eggs to order, with bacon on the side, crispy without quite being burnt. Jeremy helped himself, using an excessive amount of ketchup on the eggs, and needing prodigious use of a napkin to wipe off his face as he finished eating.

He noticed that the other hands were giving him funny looks, but brushed it off, until he realized that the waistband of his pullups were poking out. Pointing out that they were just temporary felt like too much of an admission, so he just ignored them, frowning down at his food.

There was no reason to care what they thought, but it still made him blush a little, making his cheeks warm. His crotch was warm, too, and-

Wait, am I peeing?

Jeremy looked down at himself, blinked, and quickly looked back up, pretending like nothing was the matter. The urine rushed into his pullup, flooding it and bringing the padding almost to capacity.

He’d have to change, when he went back to his room to finish getting dressed. No problem, even if it meant he might need to explain why there were two wet pullups in his trash can. In the meantime, he’d be more careful, more aware of how much he needed to go.

Standing, he squelched over to the sink, set down his used dishes, and walked back to his room to get changed and dressed for the day.

He never got the opportunity to put on a fresh pullup, because Karen was waiting for him.

“Oh, hey there,” she said, looking up from making the bed as Jeremy walked in. “Sleep alright?”

“Yeah, um… fine,” he said, eyes darting to the trash can, holding his first soggy pullup. “Do you need something?”

“I noticed your boots were a little too large, and not fitting properly,” Karen explained, gesturing to the floor where a pair of new rubber boots sat. “So I took you these out of storage. They’re a half size smaller, they should be more comfortable.”

“Aren’t those training boots?” he asked, looking at them.

“We didn’t have any leather ones in the shed,” Karen shrugged. “Put them on, see how they fit.”

He wanted to take off his pants and change his pullup, but he wasn’t going to do that while Karen was there. Crouching, he pulled on the boots one at a time, finding them a little more comfortable, just like she’d suggested.

As he stood, she tossed him a shirt from his closet. “Get that on, too. You’re late for starting your chores.”

“But…” he started to say.

“Is something wrong, Jerry?” she asked, raising an eyebrow. “Do you need to go potty first?”

“No!” Jeremy blurted, quickly buttoning up the shirt. “I’ll get right to that.” Tucking in his shirt and hitching up his pants, he tried to ignore the squelch of his pullup.

At least the choring was the same. Now that he’d done it once, things were easier, a familiar routine. Certainly, this time, he’d get it done in time to run back to the ranch house and change before riding practice.

Of course, faster didn’t mean fast. It was still a lot of work that took most of his concentration. The soggy pullup fell to the back of his mind as he built up a sweat sweeping, shoveling, raking, and generally keeping the barn in order. It wasn’t until he was a couple hours in and getting close to done that he felt the chafing that had begun to build. It was the sort of rash that he didn’t notice while it crept up on him, but once it had his attention, it was hard not to think about.

The rash wasn’t awful, but it was certainly uncomfortable, as though he’d been wearing something coarse that grated against his thighs, instead of just a wet pullup. He wasn’t sure why it was uncomfortable - he wasn’t really familiar with ‘diaper rash’ as a concept - he just knew that it would be a good idea to rinse off and get into something dry before it got any worse, even if that meant leaving his job early and coming back to finish it off.

Keeping in line with his terrible luck that week, though, something had to go wrong. As he hung up the tools and got ready to jog back to the ranch house, Karen wandered in. “Done already, Jerry?”

He shifted uncomfortably, both because his thighs felt a little raw, and because he knew he wouldn’t be any good at lying to Karen. “No, I just… needed some water.”

“There’s a cooler near the back, it’s always got water in it,” Karen said, pointing.

“Oh, uh… sure.” Spotting it, Jeremy walked that way, trying to limit how much his thighs rubbed against the pullup. “So what’s up?”

“I had a question,” Karen said. “Hold it, stop.”

Jeremy did so, glancing back at her. “Why?”

“Did you pull a muscle?” she asked. “You’re walking like something’s wrong.”

“Nothing’s wrong!” Jeremy squeaked, not wanting to admit to having had another accident.

She rolled her eyes, walking over. “It happens to the best of us. Here, show me where, and I’ll teach you a stretch to help… wait.” Realizing, she raised an eyebrow. “You didn’t pull a muscle, did you?”

“No,” he mumbled, looking down at the dirt.

Stepping up, she unbuttoned his trousers for him, letting them fall to the floor and exposing his sodden pullup. “Jerry! How long have you been this soggy?” she demanded.

Jeremy shuffled uncomfortably, blushing as he admitted, “Um… since breakfast?”

“Well, no wonder you’re uncomfortable, you’re going to rash something awful if you do that!” she said. “Here, you need to air out so it doesn’t get any worse. Sit down, I’ll help you.”

Feeling too awkward to do anything but obey, Jeremy plopped down on the ground, letting Karen pull off his shoes, pants, and finally the wet pullup. She helped put the boots back on, but that was it. “Now, you need to let that breathe for a couple hours, or you’ll just get all sweaty and make the rash worse,” she said, offering a hand to help him stand.

Jeremy got to his feet. “I… sorry.”

She sighed, sympathetically. “You don’t need to apologize, Jeremy, it’s not your fault that you’re having potty troubles.” Tilting her head, she considered for a moment before asking, “Do you need to go potty now?”

He started to shake his head, then considered how he felt and his eyes widened in surprise at how badly he needed to pee. Suddenly urgent, he said, “Yes!”

Taking his hand without question, Karen nodded. “Then lets get you to the potty.”

In just his shirt and his rubber boots, walking hand in hand with Karen, she walked him all the way back to the ranch house. It did feel nice to have some fresh air on his tender thighs, he had to admit, but that feeling was overtaken by embarrassment, and embarrassment was overtaken by his desire not to lose control.

They got inside, and she walked with him all the way into the bathroom, sitting Jeremy down on the toilet. “Can you do the rest?”

“I ca- yeah I can!” he exclaimed, annoyed. “I’m not, like, two.”

She shrugged. “Can you blame me for asking? Your track record isn’t great.”

He started to complain some more, then realized he’d started peeing in the middle of inventing an angry remark.

Karen just gave him an ‘I told you’ look, smirked, and said, “Be sure to wash your hands for twenty seconds, then finish up your chores before riding lessons.”

Jeremy blushed as she left, glad to have a little privacy once she’d walked away, almost missing the back half of her comment. She expects me to go to riding lessons like this?

It had to be something where she’d have clean pants and a fresh pullup for him. Airing out wouldn’t take that long.

Waiting a few extra moments to be sure he was really done, Jeremy got up, washed his hands, and walked half-naked back to the barn.

He had to be a little careful with the rest of his chores. Swinging in the breeze as he was, he didn’t want to accidentally get knocked somewhere sensitive. Going slow and steady, he finished setting out the hay, checked the clock on the wall, and-

“Dammit!” he swore, realizing he was late for riding lessons again.

Hurrying out of the barn, he jogged through the gate and into the pen, finding the whole group of hands already there, most of them already on horses. A couple of the girls giggled as he jogged up, leaning on his bare knees to catch his breath, but he pretended that it was just because he was late, and not for… other reasons.

“Finally decided to join us, Jerry?” Karen asked, glancing at him as she helped someone else adjust the straps on a saddle.

“Sorry,” Jeremy said, glancing around, looking for pants or at least a pull-up that Karen might have brought for him. “Um…”

“Um?” Karen looked over her shoulder at him. “What is it, Jerry?”

“Did you, uh… bring a change of pants for me?”

This time it was one of the guys who giggled, making him blush more.

“What for?” she asked. “You’ll really want to air out a while longer, Jerry, to help with your diaper rash.”

At that, everyone giggled.

“But-”

“I know best, Jerry. Now, wait patiently, and you can have a turn on the horsies just like everyone else.”

That left him dumbfounded, at a total loss for how to respond, and Karen went right back to her work, ignoring him.

There wasn’t much for him to do. Jerry stood off to the side, not feeling up to chit-chatting with the other hands while he was half naked. He felt ridiculous, exposed, constantly worried they were judging him, but most of the amusement seemed to come from finding him silly, not from thinking him pathetic. Whether that was comforting or not, Jeremy wasn’t sure.

On the one hand, it meant he didn’t have to worry that the girls just thought he was particularly small and unimpressive, but on the other, they probably weren’t thinking about him as a sexual prospect at all. That was off the table. He wore pull ups, he walked around without pants or underwear of any kind. At best, they probably thought of him as a slightly-larger-than-normal kid.

That… was uncomfortable to think about, so he tried to forget it, pacing in the yard while he waited for his turn to ride.

That came, eventually, as Karen walked Trigger over and nodded to him. “Alright, Jerry! It’s your turn to ride for a bit. Let me give you a hand up.”

He frowned, but accepted her hand, clambering up into the saddle. It turned out to be important that she was there for balance - he wanted to sit down gently and relax onto the saddle, given that there was nothing between his skin and the hard leather, and it took an extra hand for him to do that.

It was good to be in the saddle. Social awkwardness and embarrassment aside, he loved riding. With only a few days under his belt, he was by no means an expert, but it was fun, it was relaxing, it made him feel better when he was otherwise stressed out. His shirt flapped in the breeze a little as he was up on the saddle, free to trot around the yard.

He got to go about ten feet before Karen whistled, stopping him. He turned, frowning, and she raised a hand to get everyone’s attention. She pointed at Jeremy, next. “Alright, everyone take a look at Jeremy.”

Everyone did what she told them to, but nobody had any particular insights to offer.

“Something’s wrong,” Karen prompted, rolling her wrist in a ‘follow along’ gesture. “Who can tell me what it is?”

“He’s not wearing any underwear?” Someone proposed. Someone else giggled.

“That’s not it,” Karen shook her head. “It does have to do with his clothing, though.”

A few idle seconds passed. Nobody had any ideas.

She gave them another clue. “When you’re riding, you’re supposed to keep your clothes…”

“Tucked in,” one of the hands suggested.

“That’s right!” She smiled. “You can’t have your shirt getting caught on something, or loose, baggy pants that’ll get snagged on your saddle. Everything needs to be neat, and tucked, and tight. Now, look at Jerry’s shirt.”

Everyone did, Jeremy included. His shirt had nothing to tuck it into, and as such, was buffeting in the gentle breeze.

“Jerry, go ahead and take that shirt off, before you get yourself hurt,” Karen instructed.

“But…” he started to protest. “I mean…”

She gave him a withering look, and the protest died in his throat. Unbuttoning the shirt, he wadded it up and passed it down to her, completely naked save for his rubber beginner’s boots.

He felt ridiculous, but there wasn’t any more giggling than there had been a moment before. Mostly, the other students just got back to riding, or talking, or doing whatever they had been before he took off his last article of clothing.

Jeremy got back to riding, feeling the wind tickle his hair as he got up to a quick trot around the yard. Even with everything else going on, the riding was still okay.

…

He didn’t really unwind with the others that night. It felt awkward to approach them, seeing as they’d all seen him naked, even if they were still theoretically his ‘peers’.

Instead, he just retired to his room early. The pullup he’d put on after riding was wet. When did that happen? Stripping out of it, he tossed the old one in the trash, going for the drawer to get a clean, dry pair.

As he slipped them on, he examined the painting above the dresser, tilting his head as he puzzled at it. A young man on a horse - no, not even a young man. A boy, really. Tall, maybe, but still going through puberty, not quite as built out as he’d be in a few years.

It was a good painting, really conveying the youthful energy that it was going for, but something about it puzzled him.

He could have sworn that it was an adult a couple days before.

And it was hard to tell, but… Is the boy in the painting wearing a pullup?