Adventures in Sissysitting - Chapter 2 (Patreon)

"Where do you think you're going?"

Paris rolled her eyes, stopping to glare down at the horny little sissy. "Where do you think?" she sneered. "I'm going to go change in the bathroom." It was obvious... He didn't think she was going to strip down right here, in front of him, did he?!

"No, I don't think so," he shook his head, clearly enjoying what tiny shred power he'd been able to gain. 

"Well, what else am I supposed to do?" she asked, wanting to make him say it, to admit to what he wanted. "I'm not going to strip down in the middle of the living room, or in your mom's room, or..."

"Just do it here." Her plan, such as it was, seemed to have back-fired... He'd had no problem with it, not sounding ashamed at all. "You already saw me naked, after all. It's only fair."

"Yeah," she teased, "but it isn't like there was anything there to look at." She felt a bit bad about it, seeing him blush, though just until he refused to budge. "You are such a pervert!" she grumbled. "No wonder your Mommy keeps you in diapers! What, are you curious to see what a girl looks like naked? I can't imagine you've ever had any other chance..."

Part of her felt like she was betraying Darius, but she was sure he'd understand... He'd probably beat Ash up if she told him about this. She didn't want that, exactly; a spanking, on the other hand, might be fun to watch.

"Fine," she slid off the top of her cheerleading uniform, tossing it aside, leaving her standing there in her bra. "Is that what you wanted?"

She could see him squirming, a hint of discomfort on his face, making her smirk, imagining what was happening under his diaper, as his body and the chastity device fought for dominance, the latter clearly winning. She definitely didn't feel bad for him now... He'd asked for this. She reached for her skirt, starting to wiggle it down, only to have Ash shake his head at her.

"That, too," he pointed at her chest.

He really did want her naked... She'd hoped she could avoid that. "Oh, wow," she mocked. "You want me to be your first pair of boobies, other than your Mommy's? I hate to break it to you, but you're not getting any milk out of mine, you gross..."

She froze as she unhooked her bra, the reveal getting the exact opposite reaction as what she was anticipating: he laughed. Her cheeks turned pink, and she felt like she was shrinking, becoming even smaller than him. "Nobody's getting anything out of those," he commented. "They're barely any bigger than mine without your bra!"

"Shut up!" Her bra was doing a lot of the heavy lifting, she knew, which she had already been self-conscious about... And it was only fair, really, considering she'd just made fun of the size of his equipment... But hearing it now, coming from this pathetic sissy, gave it an extra sting, tears stinging her eyes, much to her horror.

Angry and embarrassed, she tore off her skirt - and the bloomers, when he made her, keeping her from at least having her panties hidden from him - and pulled on the maid's dress. Sure enough, the hem of it stopped high enough for the majority of her lacy, white panties to be on display, while the bodice, made for the slightly scrawnier Ash, pushed her breasts down even further, crushing out the last bit of cleavage she could normally count on.

"Are you the flattest cheerleader on the squad?" Ash mused. "I bet even the freshmen are..."

"What do I need to do?" Paris interrupted, not wanting him to finish that thought, though, of course, she knew where it was going, and that he was right, much to her chagrin. She had been at peace with the idea of Darius finding her here in the maid dress... Now, however, after being made to take off her bra, she was desperate to finish the chores so she could get into her own clothes again before he arrived.

"Today is dusting day," he told her. "The whole house... Are you sure you can reach everything?"

"I'm taller than you, you little twerp!" she snapped. That was one thing he couldn't take away from her... Any other time, she might have worn heels, to give her a bit more of an edge there, but coming straight from practice, she hadn't had time. He toddled out to show her where the cleaning supplies were, then planted himself on the floor in the living room, watching.

It certainly was degrading, walking around in the tiny dress, knowing her underwear was on display, and that the diapered sissy boy sitting there, pretending to do his homework, had made her do this, that he'd managed to take control from her, when it had been so obvious that she was the more mature person here. Her panties were showing the whole time, but she heard him snicker every time she had to get up on her tiptoes, the stretching motion leaving even more of them than usual visible.

With her longer legs, and lack of a diaper between them, she was positive she could outrun him, if it came to that; nevertheless, she didn't want to alert him to anything unusual, so she took her time, working her way over to where her purse, and the bathroom key beside it, were, only speeding up when she felt her bladder starting to ache, signalling that her time was quickly running out.

"You missed that shelf," he pointed out, when she skipped one, moving on to a lamp that was nearer to the coffee table.

"I'll go back to it," she replied curtly. "I'm already doing your chores, you should be happy with that... Don't tell me how to do them, too."

"Whatever," he shrugged.

She dusted off the lampshade, creeping closer and closer to the coffee table, only to find... The key wasn't there. She barely suppressed a curse, shooting a glare at Ash, who didn't even bother to hide his leering. She hadn't seen him stop by that table when he came in, however... And, now that she thought about it, the key hadn't been there when she'd gone to get her phone, either...

What happened to it?! She peered into her purse, trying to dredge up a nonexistent memory of dropping the key into it, then pushing it aside to see if she'd accidentally pushed it underneath. When she didn't see it either place, she knelt down, looking under the table, heartbeat quickening, sweaty hand closing tighter around her feather duster.

This was bad for now, obviously, since she wasn't sure how much longer her bladder could hold out... It wasn't going to reflect well on her babysitting skills, either, though, for her to have lost the bathroom key her first time here. Ash's mom surely had a spare somewhere, but she wanted the woman to think she was responsible...

She bit her bottom lip, barely suppressing a groan, not wanting Ash to hear her in distress. "You don't have to dust the floor, you know," he called.

"I-I'm gonna go dust another room," she said, scurrying away, off to his mother's room. She'd hoped, faintly, there would be another bathroom there, though, of course, that defeated the purpose of locking the main one. She didn't want to snoop around too much, to give the woman any reason to suspect Paris had stolen from her, but this was the most logical place for a spare key to be...

"N-No," she whimpered, bouncing in place, glad Ash was a few rooms away. It was taking every ounce of her strength not to let her urine start trickling out... It was absolutely worth it, however, knowing her white panties wouldn't hide even the smallest accident...

There was a drawer in the bedside table that was promising; unfortunately, like so many other things in this house, it was locked. "You have to be kidding me," she huffed, tugging at it uselessly. She hadn't found any other keys that might go to it, either. "Junk drawer," she suddenly thought out loud. That might be a good place to keep a key...

She shuffled quickly out of the bedroom, down the hall, to the kitchen, tearing open drawers, finding wash cloths, utensils, container lids... "Come on, come on..." she begged, squirming desperately, praying that she was right, that this wasn't another dead end...

"You don't have to dust the insides of the drawers," Ash said.

Paris, bent over, bottom in the air as she dug through one of the lower drawers, jumped, not having known the boy was there... Then gasped, spinning around, nibbling at her lip, tugging on the skirt of the maid dress as she pressed her legs together, shuffling in place. He couldn't have seen... She'd been fast enough, right?

"I-I just want to be thorough," she gulped. "W-Wouldn't want you to get in trouble for doing a bad job..."

He eyed her suspiciously, looking her up and down, Paris squeezing her thighs closer in to one another, barely stopping a gasp as she felt wetness there. It had only been a spurt, enough to make a wet spot, nothing more... Or so she'd thought. 

"Then you should come finish the living room before running all around random rooms in the house," he suggested. "You're going to forget what you did and didn't do..."

"Maybe you would," she leapt on the opportunity to tease him, to feel like she had some control over the situation again. "I know exactly what..."

"What's that?" he pointed. 

"N-Nothing!" she replied automatically, before looking down, seeing a trickle of yellow running down her legs, betraying her. This couldn't be happening... She couldn't be peeing herself in front of him, of all people!

"If you needed a diaper, you should have just told me. I've seen mom do it enough, I could have helped."

"No, you couldn't have!" she stomped her foot. "I-I'm not going to be put into a diaper by a..."

Before she could even finish her sentence, her bladder spasmed again, soaking her underwear further, a fresh dribble of pee starting to leak onto her inner thighs... And, as she gawked at herself in disbelief, she heard the click of a camera shutter, and saw Ash taking a picture.

"Erase that right now!" she demanded, reaching for his phone. He easily moved out of her way, then waddled out of the room, leaving her stuck there, struggling not to wet herself any further.

Even knowing he had evidence of her accident, part of her was glad he'd left her alone, that she had privacy... Until he returned, carrying a trio of cloth diapers and a pair of pink plastic pants, laying them out on the kitchen floor. "A-Ash, no!" she whimpered, unable to call upon any of her babysitter's authority in the moment, standing there in a pair of dripping undies. "I-I'm not gonna..."

"I already have the text written up to sent to mom," he informed her. "All I have to do is hit send, and she'll get to see that the babysitter she hired doesn't even know how to keep her own pants dry, much less look after her sweet little son..."

"You are such a brat," she growled... But she didn't know what else to do. Reluctantly, she plopped down onto the diapers, gasping as her backside landed, making her feel like she was sitting on a pillow. "N-No!" she squealed, her tone instantly changing as he bent forward, hands closing around the waistband of her panties, not wanting to lose them, to have to sit, bare-bottomed, on his diapers...

He yanked them down, and, almost immediately, she felt her bladder cramp again, a stream of urine pouring out onto the waiting diaper, ensuring she was going to be soggy from the start. He set the soaked underwear aside, opening up the bottle of baby powder and starting to sprinkle it onto her, the smell taking Paris back to earlier that afternoon, to his own diaper change, to how powerful she'd felt, watching that... Now she was the one being diapered, and there was nothing she could do about it...

He pulled the three layers of cloth up between her legs, the cheerleader whimpering as she pushed her thighs together, hardly able to make the bulky padding budge, which did not bode well for trying to keep her diapers dry... Of course, it was already far too late for that. She covered her face in humiliation as he pinned the diapers into place, pulling the plastic pants up her legs, letting them snap into place.

"Come on," he said after a few moments, offering his hand. "You still have work to do."

Still dribbling into her new, infantile, undergarments, Paris quietly took his hand, letting herself be helped up. The diapers were so big, it was hard to walk, and the wetness just seemed to make them heavier, adding even more challenge to it. She toddled behind him, stomach churning, as he took her to get supplies to clean up the little puddle she'd made, then led her back to the living room to continue dusting.

She was, perhaps, a bit in shock, still trying to process everything that had happened as she slowly did Ash's chores, her wet diaper mostly on display under the maid dress, until she looked at the clock on the wall, and realized how late it had gotten.

Darius's practice had to be over by now... He could be on his way here right now! As bad as the maid outfit would have been by itself, that was nothing compared to how she looked now! "A-Ash," she gulped, hating how hard it was to look him in the eye, now that he'd diapered her. "C-Can I go clean in your room now?" She'd left her phone there, when she'd been undressing... If she could get to that, she could text Darius, tell him not to show up, promising to explain everything later.

"What for?" he asked. "Are you looking for this?" He held up her phone long enough for her to recognize it before setting it back down among his homework.

"Give that back right now!" she squealed. "That's mine!"

"You can have it back," he promised. "But not for free..."

Paris rolled her eyes. "What more do you want from me?! I'm already doing your chores, you saw me naked, you put me in a diaper..." She couldn't imagine anything worse... Until he led her to the bathroom, using the missing key to unlock it. "You had it!" her eyes widened, seeing him open the door. No wonder she hadn't been able to find it! He'd known where it was all along!

"You shouldn't leave important things like this just lying around," he chuckled. "That's not very responsible of you... Now, you stand over there in the corner for a minute..."

She blushed as she did what she was told, nose in the corner like a naughty little girl, listening to him doing something behind her, the water running, not daring to look until he told her to, "Turn around," when she was faced with his grinning face as he held up the bulging enema bag.

"No!" she shook her head. "No, no, no!"

"Then I'm keeping your phone," he put it simply. "And I'm telling my mom everything."

After a little time in the thick, hot diapers, Paris had been sure she'd be so relieved to get out of them... But, as Ash slid them down, she just wanted to burst into tears. Feeling the hose slip into her backside didn't help matters, either, nor did the sudden rush of water gushing into her, flowing fast and free as she squeaked and squirmed miserably. The bag had looked so big, so full of water, she was positive she couldn't hold it all... Unfortunately, Ash wasn't satisfied until it was empty, giving it a squeeze a few times to get every bit out, the extra water pressure only making Paris squawk louder, bouncing frantically in place, desperate for relief.

It shouldn't have been a surprise, really, when Ash pulled the diapers back up. The toilet was right there, inches away, but Paris had always known, deep down, that she wasn't going to get out of this that easily. "Pl-Please, no," she shook her head, wrapping her arms around her bloated, churning tummy. "I-I don't wanna..."

And that was all the further she could go. Involuntarily, she bent forward, face red as her body began to expel everything out into her waiting pants, the diaper bulging outwards, trying to contain it all, Ash watching gleefully as his babysitting filled her diaper.

"Oh, my God!" he clapped his hands. "I can't believe you did it!"

"Sh-Shut up," she sniffled, shaking her head, unable to believe it herself, wiggling her backside in disgust. She couldn't think of anything more infantile than this... But, between the feeling, the smell, the sight of the huge lump in her diaper in the mirror, there was no getting around what she'd done. "Y-You do it all the time!" There was a reason that enema bag was there, after all...

"Yeah," he admitted, "but I go in the toilet. I've never done... that... in my diaper. You must be a real baby, pooping your diapers like that! Even more of one than me!"

"I-It's not my fault!" Paris fidgeted, nose wrinkling as she felt the contents of her diaper shift and squelch. "C-Can I go get changed now?" She really couldn't let herself be seen by Darius like this... It would be fun to watch her boyfriend see Ash in all his sissy glory, but not if she was standing by in a messy diaper herself, looking like even more of a baby.

"I don't know," Ash pretended to think about it.

"I did what you wanted!" she growled.

"That wasn't to get changed, though, that was for your phone," he reminded her.

She sighed, exhausted. "Then give me that," she held out her hand. She could stop Darius from showing up, anyway... But she needed to get out of this stinky diaper as soon as possible, too.

"No," he shook his head. "I'm not sure you've earned it."

"Ash!" she stomped her foot, feeling more like a little sister, begging her big brother to help her out with something she was too small to do on her own, than a babysitter, or the sexy cheerleader she'd been when she first showed up in this house. "Look at me! What more do you want?!" He stroked his chin, acting like he was really pondering the question. "Ash! You stupid little sissy, just tell me what you want!" she exploded. "I don't have all night you pathetic..."

"I'm pathetic?" he broke in, raising an eyebrow.

"Yes! Look at you! You're the one who needs diapers, and you let your mom treat you this way, and..."

"And you let me do the same to you," he shrugged. "Isn't that more pathetic?"

She sputtered, wanting to deny it so very badly. "W-Well... At least I'm not in chastity!" she said finally.

"That's right," he nodded. "You're not... That's a very good point, Paris. Come on... Why don't you enjoy yourself?" She knew she'd made a mistake right away, before he took her hand and led her back to his nursery, to one of his giant, oversized stuffed animals. She shook her head, nose wrinkled. "Do you not want your phone back? Do you want your boyfriend to come over and find you like this?"

She swallowed, the image of that running through her head... Along with the imagine of the same thing happening while she was in the midst of this. "I-I could..." she tried to think of an alternative. With his chastity device on, she couldn't exactly offer him anything in terms of that... It was degrading enough even considering the idea of giving him a blowjob at all, much less in exchange for a diaper change, but, if that had been on the table, she couldn't say she wouldn't have suggested it.

"I-I'll do your homework for you?" she tried. "F-For the rest of the year?"

"I'd like to actually pass my classes, diaper bimbo," he sneered.

"Hey!" she pouted. "I'm smart! And I don't need these diapers, unlike you!"

He raised an eyebrow. "I know Barry... I know you have him do your homework for you," he informed her. "What were your grades like before then?" She squirmed, not wanting to answer. "I could always talk to him, get him to stop... But if your grades start slipping again, you'll lose your spot on the cheerleading squad, won't you?"

Could he really do that? He was a nerd, so he probably did know Barry... "Pl-Please, don't," she sniffed. Being a cheerleader gave her a certain amount of protection... The squad wasn't going to let other people make fun of her too much, because it reflected badly on them. If she lost that, what did she have? Darius... If he didn't decide that her being a cheerleader was what made their relationship so hot. She didn't think he'd ever so much as looked at her before she'd made the squad...

"Then tell me what you are," he crossed his arms.

She stared down at the floor. "I-I'm an empty-headed little diaper bimbo," she confessed.

"Yes, you are," he agreed. "All you're good for is bouncing around, shaking your pom-poms, and using your diapers. Isn't that right?" Mortified, she nodded. "Good girl... Now, show me how much you love your diapers."

With no other alternative in sight, Paris straddled the leg of the huge teddy bear, nose crinkling as she felt her backside sink into the mushy mass in her diaper, and started to hump and grind, knowing that Ash was recording the whole thing, giving him even more ammo to use against her. He was going to own her after this... That sad little diaper sissy was going to be able to make her do anything he wanted...

She closed her eyes, trying to pretend she wasn't there, that she didn't smell her own diaper, or feel the mess inside it. It was impossible to ignore, though, no matter how much she tried to convince herself she was with Darius instead, every little squish reminding her of standing there in the bathroom, right next to the toilet, and pooping her pants, Ash watching the whole time... She forced herself to rub harder against the toy, frantic to get off before her boyfriend walked in the door and saw her this way... It was difficult to imagine anything less sexy than this, but, eventually, she felt a warmth building in her, urging her to go faster, harder, moaning and squelching all the way...

She told herself it was worth it, when, after her loud, shuddering orgasm, she got her phone back, and immediately texted Darius, keeping him from finding out how she'd been spending her afternoon. Ash even helped her change, which was nice, other than him putting her back into diapers, then putting her to work rinsing out her diaper, making her run in through the washer.

"I don't mess my diapers," he told her, again, "so mom will know right away something is up if you don't get it clean, and then I'll have to tell her the whole story..."

At least she was able to wash her underwear at the same time. She couldn't wait to get back to them, but Ash wouldn't let her have them until the diaper was dry, too, and ready to be added back to the stack...

"There!" As bulky as it was, it had taken several dryer cycles, but, finally, it was done. She tossed it at him, glancing nervously at the clock, knowing his mother would be back any minute now. 

He turned it over in his hands, examining it. "There are still stains," he said after a minute or two.

"I did the best I could," she whined. "Come on..."

"No," he shook his head. "Not good enough... Mom can't see these. So I guess you'll have to wear it instead... And, in exchange, I'll just keep your panties."

"You perv," she shook her head. 

He shrugged. "You certainly don't deserve them after what you did to this poor diaper."

"Yes, I do!" she pouted. "I'm a big girl! I deserve big girl panties!"

But they weren't what she got. A single diaper wasn't nearly as bad as three, though, under her cheerleading uniform, it still felt wrong... She was certain Ash's mother would notice the extra bulk right away, and she knew, if that happened, Ash would be happy to spill the beans, tell the woman all about the day they'd had. 

Thankfully, if she saw it, the woman didn't say anything about it. "Did you two have fun today?"

"Yeah, Mommy!" Ash bounced up and down, while Paris blushed, tugging at the hem of her skirt. "Can she babysit me again?"

"She seems like a very responsible young lady," his mother said. "I'd love to have her again, if she'd interested... Maybe I'll even make her your regular sitter. What do you think about that?"

Paris's eyes darted over to Ash, the expression on his face making it clear what her answer should be. She squirmed in place, feeling a nervous trickle of wetness into her diaper. "S-Sure," she lied. "I-I'd love that." She'd love keeping Ash from showing his mother, and the school, the pictures and videos he'd taken of her... She could tell them all about his sissy lifestyle, but he was already a loser; she had so much further to fall than him. As pathetic as he was, he was right that it was even more pathetic that she'd somehow managed to end up totally at his mercy. "I-I'd be happy to come sit for Ash a-any time..."