Adventures in Sissysitting - Chapter 1 (Patreon)

The start of a new (probably fairly short) story commission for Mashugana.

"Well, don't you look cute?"

Paris blushed modestly, but couldn't stop herself from giving a little spin, her cheerleading skirt flying up to show off the bloomers underneath, before glancing down, admiring all the work her push-up bra, and the extra padding, was doing for her cleavage in the top. "Oh, I don't know," she giggled. "I'd planned on changing, but practice ran long, so..."

"No, no, it's fine, don't worry about that," Ms. Carter assured her. "As long as you're comfortable babysitting in it, I don't mind what you wear."

"Great," Paris smiled. "So... Where is she? Is she down for a nap?"

The woman hesitated. "I told you this was something of a special case, right?" Paris nodded. "Maybe I should have been a little more open about it, but I really did need a sitter... You know what? It'll be easier if I show you."

"O...kay..." Paris stayed in the doorway for a moment, the words ringing alarm bells in her mind, calling up all the lectures she'd gotten from her parents about how to stay safe, to avoid getting kidnapped... Surely they didn't apply here, though. This was just a normal house, somewhere she'd even been before, with someone she knew, vaguely, anyway...

She followed Ms. Carter into the house, down the hall, well past the living room, the only place Paris had really been, for a study group, years ago. Thinking of that, she decided to break the silence, and hopefully assuage her nerves, which, logically she knew were being overly sensitive. "Not that I'm complaining about getting a job myself, but... What's Ash up to? Why isn't he doing this?"

Ms. Carter chuckled. "You'll see," she promised, stopping in front of one of the doors. "Now, Paris, dear, I want you to keep an open mind for me. Can you do that?"

"I... Sure," Paris agreed, reminding herself of the more than generous rate she'd been promised for the job. "I can do that."

Ms. Carter opened up the door, swinging it open into an explosion of pink. The walls were a bright, bubblegum pink, the fluffy carpet a slightly darker shade, the furniture inside varying versions of the same color. As Paris would have guessed, considering all the requirements Ms. Carter had laid out for things she had to be willing to do to take this job, the furniture itself was pretty typical for a nursery, with a crib, a changing table, a high chair...

Except that it was all far too big. Big enough that Paris could see herself fitting into any of it, having it make her feel as small as any toddler. She shifted her weight, sneakers digging into the soft carpet, something about that thought making her stomach churn... Until she saw the form lying in the crib move, sit up in a mass of pink ruffles and bows.

"Mommy," a familiar voice - though one that sounded higher, more pitiful, now than she was used to - emerged. "Can I get up now?"

"Oh, my God!" Paris couldn't stop herself from squealing, recognizing the person behind the bars, even dressed this way. "Ash?!"

He turned, saw her standing next to his mother, his cheeks turning the same color as everything else in his room. "Mommy!" he gasped, eyes darting around the crib, searching for something to hide behind. "Wh-Why is she here?!"

"I told you," Ms. Carter cooed, striding over to her son, lowering the side of the crib. "I have an important meeting this evening, so I had to get you a sitter. That's why you had your enema early today."

Paris's hands shot up to her mouth, snickering, watching the boy get more and more uncomfortable. It wasn't only from the talk of enemas, although that did help... As Ms. Carter took Ash's hand, helped him out of the crib, the cheerleader saw what else he was wearing, even more humiliating than the dress, which she wouldn't have thought was possible.

A diaper. The biggest diaper Paris had ever seen, both because it was big enough to fit Ash - who was pretty scrawny for a high school senior, as they both were - but also in sheer bulk. They had to be layer after layer of soft cloth, wrapped in a pair of - of course - pink, translucent, plastic pants, barely obscured by the short hem of the floofy dress. On his feet, he was wearing lacy ankle socks, and shiny, pink Mary Janes, the very picture of a perfect sissy baby.

"Wh-Why her, Mommy?" he whimpered, trying to hide behind the woman, not helped at all by the size of his dress, and diaper. All it did was make him look more like a silly little girl, thinking that if he couldn't see someone, they couldn't see him.

"She was available," his mother informed him. "And she came very highly recommended." Without another word, with no regard for his dignity or privacy, she slid her hands into his plastic pants, giving the diapers underneath a squeeze. "Ash!" she scolded. "Already?!"

He blushed again, trying to push his legs together, only to be thwarted by the thickness of his diapers. "I-I'm sorry, Mommy," he mumbled. "I-I couldn't help it..."

"Of course you couldn't," she sighed. "That's why we're here, isn't it? Oh, well... It'll give me a chance to show Paris what she needs to do. Up onto the table."

"M-Mommy!" his eyes went wide.

"She's your babysitter," Ms. Carter reminded him. "She's going to have to see it eventually. Now, march yourself over to the changing table... Or do you need to fetch the hairbrush?"

"No, ma'am," Ash shook his head, then reluctantly slumped his way over, towards the changing table. There was a stool beside it to help him climb up onto it, lying down, whining while his mother collected supplies from the shelves below him, until, finally, she pushed a large, pink pacifier into his mouth.

"That's better," Ms. Carter commented. "We don't need him interrupting."

"Nope," Paris stifled a giggle. This was all about him, but it was clear that his input was completely unnecessary. 

"Now, I tend to go with three layers," Ms. Carter set three cloth diapers down on the table, next to her son. "That's up to you, ultimately... As much as he wets, however, I've found that's a good compromise, so you're not changing him every twenty minutes."

Ash gave a muffled protest from behind the paci, but neither of the women understood him, so they simply exchanged a knowing look and pressed on. "The plastic panties are very important, too," Ms. Carter lectured. "He might complain that they're too hot... Without them, no matter how many diapers he has on, he will leak all over everything. You can make him clean it up, of course... It's just easier to keep them on him at all times, though, no matter what he says."

"Okay," Paris nodded, watching Ms. Carter slide what she'd just been talking about down Ash's wiggling legs.

"Someone your age probably isn't used to cloth diapers," Ms. Carter said, Paris shaking her head. "They aren't as intimidating as they seem. For Ash here, they make the most sense, because he'd go through so many disposables, if I let him wear those instead... As long as you pin them nice and tight, they aren't that much different."

"I'm sure I'll get used to it," Paris told her. "Wait, what's that?!"

She couldn't help it, pointing into Ash's diaper as Ms. Carter opened it up, at the predictably pink contraption wrapped around the boy's privates. He groaned behind the pacifier, closing his eyes.

"You don't need to worry about it," Ms. Carter smiled. "That's his chastity device... He was being very naughty, which is what landed him here in the first place. That takes care of all that. I'll be taking the key with me, so there's no way he's going to get out of it."

Paris giggled while Ms. Carter wiped the mortified Ash clean, tossing the diapers into a pail, slipping the new ones under his bottom. "Make sure to use plenty of powder," she instructed. "And don't hesitate to use the rash cream if it looks like he needs it."

In no time, Ash was pinned into a fresh trio of diapers, his plastic pants put back into place. His mother sat him down in the middle of the floor to play with dolls while she showed Paris the rest of the house.

"This is the bathroom," she unlocked the door and flipped on the light, Paris smirking at the sight of the enema bag, draped over the shower curtain rod, recalling what Ms. Carter had said earlier, imagining Ash bent over, having the tube pushed into his pathetic little bottom... "I should be home before Ash's bedtime, so he has no reason to be in here. You can use it, of course, but I ask that you leave it locked, to keep him from trying anything."

"No problem," Paris promised. She wouldn't have minded stopping in there now, since she'd rushed there straight after practice, trying to keep from being late, but she could wait until the tour was done.

"He only uses it for when I give him baths, or brushing his teeth, or his daily enema," the woman continued. "I've already done the last one for the day, so you won't have to worry about any messy diapers. If you start sitting more often, you might need to deal with that at some point... For your first time, though, I thought it would be best to keep it as simple as possible."

"Thank you," Paris said. As funny as it would be to see him mess himself, she didn't like cleaning up real babies when they did that... How much worse would it be when it was coming from a fully grown - no matter how shrimpy - guy? 

Ms. Carter smiled, nodded, locked the door, then handed over the key. Paris moved to slip it into her pocket, before remembering that she was in her cheerleading uniform, which didn't have any pockets. She kept ahold of it until they passed the living room, when she set it down on the coffee table next to where she'd put her purse. She didn't want to delay the tour long enough to open up her purse, put it inside, but she made a mental note to do that later, or find somewhere even safer to keep it.

"Here's his dinner," Ms. Carter opened up the fridge, showing off a large bowl of unappetizing, multi-colored mush. "He'll whine about it, but if it gets too bad, feel free to take his diapers down and use one of those spoons over there on him, because he knows better." She nodded at a set of large, wooden spoons. "There are some leftovers you can help yourself to, or, if you'd like, you can make something new... Whatever you'd like."

"Thank you," Paris smiled politely. 

"That's really all you should need," Ms. Carter said. "He has chores to do, though I won't make you worry about them; he knows what they are, and if he doesn't do them, that's on him, not you. It should be pretty simple... I'll let you know if I'm running late, and need you to put him to bed, but I don't think that will happen. If this works out, and you become his regular sitter, I can teach you to do all that another time."

As weird as it was, Paris meant it when she chirped, "I hope that happens!" She couldn't wait to tell all her friends at school about this... And she was getting paid way better than she would at any other babysitting job, or even at a 'real' job, like her her parents kept pushing her to try to get. 

"Me, too," Ms. Carter smiled. "I think you're going to be perfect, dear."

Paris watched her leave, waving goodbye out the front window, then sauntered her way back to Ash's nursery, finding him still sitting on the floor, playing with his dolls. "Wow," she taunted, "you really are a little sissy, aren't you?"

"N-No," he shook his head.

"Oh, please," Paris bent forward, making sure her cleavage was practically pouring out of her low-cut top as she stared down at him, watching his gaze, seeing him swallow, imagining what was happening in his diaper, thanks to the chastity device. "You're sitting here, in a diaper, playing with your dollies... You're eighteen, aren't you?"

He stared down at the floor. "N-Nineteen," he mumbled.

"Nineteen?!" she snickered, chest bouncing as she laughed at him. "And you let your Mommy do this to you? No wonder you've never had a girlfriend! That is so sad... I can't believe you ever even considered asking Kellie out."

"H-How did you know about that?" he squirmed in place. "Sh-She said..."

"We're cheerleaders," she smirked. "We talk. How did a pathetic little baby like you think any cheerleader would want to go out with you? I can't wait to tell her all about this..."

"No!" he shook his head. "Please, don't!"

Her eyes glimmered as another, even more evil, idea occurred to her. "You know what else I should do? Just as a good babysitter? I ought to call up Darius right now, and have him come over..."

"N-No," Ash paled, clearly thinking of Paris's boyfriend, the big, tough football player who already bullied him, being here, in his house.

"It's for your own good!" Paris told him. "I bet you don't have any idea what to do with a girl, even if one agreed to date you... So, why don't we show you?"

She really liked this plan, so, while Ash begged her to stop, she hopped up, hurrying out to the living room, grabbing her phone and flouncing back, too smug to look too closely at the table next to her purse.

"Hey, Dar," she wound a lock of her hair around her finger, giggling suggestively while Ash wriggled on the floor beneath her. He was still at practice, unfortunately, so she'd gotten his voicemail. "I miss you, baby... I know I said we couldn't get together today because I was babysitting, but..." She stared down at Ash maliciously, debating how much to spoil now, before deciding it would be better to leave most of unsaid, to get as pure a reaction from Darius as possible when he showed up. "I have a surprise for you," she left it, simply. "I think you're really gonna like it... And, even if you don't we can have some fun together. I'll text you the address, okay? See you soon!"

"Y-You're not s'posed to have boys over," Ash pouted. "I-I know Mommy doesn't let any of my sitters..."

"Who cares?" Paris cut him off, finding the pacifier where he'd left it, shoving it back into his mouth. "I don't care about some stupid rules. I'm in charge here, I can do whatever I want. Listen to you... She isn't even here, and you're still calling her 'Mommy'... You deserve this... And you are way too big of a chicken to tattle on me to your Mommy. Besides, she knows I'm an adult, and you're just a pathetic little diaper-wetting baby, so she'll believe me, no matter what. So you are going to sit there, and piddle your Pampers, while Darius and I screw in front of you, and in your Mommy's bed, and... Well, anywhere we want."

He glared up at her, a glint of defiance in his eyes... But not nearly enough to worry about, not after everything she'd seen, and heard. What could he possibly do to her at this point?

"Now, why don't you go ahead and get started on your chores?" Paris suggested. "I need to go get ready for Darius. Just keep sucking on your paci like a good baby... The practice might do you some good. Darius isn't gay, but he might let you practice on him. You'll need it... No girl is going to go out with you after I tell the whole school about this."

She spun around, letting her skirt fly up, teasing him with another glimpse of her bloomers, but, as she made her way towards the door, she heard Ash's voice again. "Y-You're not s'posed to have boys over," he repeated. "I-I know Mommy doesn't let any of my sitters..."

"Why is your pacifier not in?" she turned back around, hands on her hips. "I..."

But it was still there, the shield covering most of his mouth, bobbing up and down slightly as he sucked... And then she heard her own voice. "Who cares? I don't care about some stupid rules. I'm in charge here, I can do whatever I want."

He slid his phone back out from under the poof of his diaper, pushing stop on the recording as he removed the paci. "How do you think Mommy is going to like to hear that?" he asked. "I ignored her rules, and look where it landed me... Not to mention the rest of what you said you were going to do in her house... And what you were going to let your boyfriend do to her poor, innocent son..."

Paris's face turned red. "Y-Yeah, well..." she started. "I-I'm not... Just give me that!" She leapt forward, grabbing for the phone, but he slipped it back under his diaper. She shoved him, trying to get him off it, to no avail. She was taller than him, though not by that much, and, in terms of weight, he was probably the same size, if not a bit heavier. "Are you going to sit there all night?" she asked, frustrated, after a few moments.

"Maybe," he shrugged. "I have my diapers on... I don't need to move. And then I can let Mommy hear all about what you think about doing the job she's paying you for... I bet she won't invite you back, then... She might not even pay you for tonight. Or I could always send it to her now. She can't have gotten too far yet..."

Part of Paris was positive he was bluffing... The rest knew she couldn't risk it. She really might be stuck working at some stupid fast food place if she lost this job, and Ms. Carter ruined her reputation with the other families she sat for. She wouldn't have done any of the things she'd threatened anywhere else, in any houses with real children in them... But she hadn't said where she was, who she was sitting; as far as any of her clients knew, she was saying all of that to an actual kid.

"Fine," she shook her head. "Fine! What do you want? I'll call Darius back and tell him not to come, a-and..."

Ash pushed himself to his feet, snatching up the phone before she could try to grab it, toddling over to his closet. He opened it up, taking out a hanger with a pink, lacy maid's outfit on it, holding it out.

"What?" she rolled her eyes, staring at it. "Do you want me to wear this, you perv?" It had clearly been made especially for him, and with his diapers in mind. It would likely fit her, but, since she was taller than him, and in far less bulky underwear, it would put what she did have on under her cheerleading skirt and bloomers on full display.

"Yes," he replied. "You're going to wear this, and do all my chores for me."

She glared at him, nostrils flared... Then took the dress. "Fine," she huffed. "Whatever." It could have been worse, she told herself. She had no idea what the chores were, but maybe she'd be able to finish them before Darius arrived, since Ash, stupidly, hadn't made her cancel his visit. If not, she could always claim the outfit was part of the 'surprise'... He'd probably like it, too, and, unlike Ash, with his chastity device and his diapers, he could do something about it.

That dumb little baby, Paris smirked, looking at Ash. He thought he'd outsmarted her, but he was nowhere close... And, when Darius got there, there was no way he was going to be able to keep his phone away from both of them. She was going to make sure he regretted this. Though, first, once her chores took her near the living room, she was going to grab the bathroom key and make a stop there, because her bladder was really starting to beg for relief...