Hitting on the Babysitter - Chapter 3 (Patreon)

Joseph knew that he should look away, that watching Anita swimming was only making things worse, but he couldn't help himself... You would have thought he'd never seen a girl wearing so little in real life, the way he was gawking, although he was married, had gotten his wife pregnant, so of course he had.

Then again, judging by the ever-worsening state of his diaper, you also would have thought that nobody had ever bothered to potty train him, either. Every time he caught himself staring at her chest, barely contained in her tiny bikini, there was another trickle into his increasingly soaked diaper. He was positive Anita would know what that meant, since she surely was the one who had done this to him, that she'd be disgusted - yet probably not surprised - to discover how drenched his diaper was when she got out of the pool.

As it turned out, she didn't even have to wait that long. "Oh, Jojo," she sighed, peering over at him as she came up from over the water. "Did you get too close, silly? Did I splash you?"

He wasn't certain what she was talking about, at first, frowning and fidgeting, until he glanced down. He let out a squeak, stomach churning at the sight of the wet spot on the front of his shorts. Had he seriously leaked through his diaper?! "Y-Yeah," he nodded, glad for the excuse she'd handed him, even though he hadn't moved from his spot after being dragged out to the poolside.

"Poor thing," Anita shook her head, with a hint of what might have been a knowing smirk at the corner of her mouth. "Well, I suppose that's the risk you take when you hang out by the water without a swimsuit on. I can't believe your Mommy doesn't have any swim diapers for you!"

Joseph blushed, unsure how to respond. He wanted to say he didn't need those, but she'd already changed him out of a wet Pull-Up, and, any minute now, she was bound to discover that his diaper was very wet, too. At this rate, it seemed like, if he was going to go in the pool, he would need a swim diaper, as mortifying as that was to consider.

"I'll tell you what," Anita said. "Next time I babysit for you and your sister, maybe I'll bring you some, okay? Then you can splash around with me, and I can teach you how to doggy paddle!"

He really had to bite his tongue to keep from blurting out that of course he could dog paddle, that it was one of the first things you learned when it came to swimming, so obviously he knew how to do at least that, given that he did own a pool. Being a smart aleck right now was not going to help matters, though.

The babysitter almost looked disappointed, for a moment, that he didn't rise to her bait. She quickly shook it off, however. "I guess we probably ought to head back in soon, huh? I know your sister's asleep, but we shouldn't leave her alone where we can't hear her if she gets up and starts to cry for too long."

"Y-Yeah," he agreed, shimmying up a little closer to the pool. She was going to get suspicious if she saw there was no other water around him. She likely would anyway, if she checked him... Maybe he could find a way to postpone that, keep her from seeing what he'd done. 

"Hold it right there, mister!" she warned. "I don't want you slipping and falling in!"

"I won't!" he promised. "I-It just looks so fun..."

She smiled, floating up on her back. "It is," she teased. "You're going to enjoy it so much when you're a bit older... Uh-oh, did I splash you again?"

Did she actually believe that was what was happening? Or was she playing with him? He could feel the wetness spreading across his shorts after she pointed it out, looked down in time to see it expanding slightly, definitely looking like someone peeing their pants... If she was being serious, he was glad that was giving him the benefit on the doubt, yet, if that was the case... Did that mean she wasn't the reason he was wetting himself? Was his body doing that on its own?!

"Y-Yeah," he fibbed anxiously.

"Sorry, buddy," Anita told him. "All right, we'll go get you into some dry pants."

"N-No!" his eyes widened, knowing that, as soon as she did that, she'd find how soggy his diaper was. "I-I'm okay... You can swim a little longer..."

She chuckled. "How sweet and thoughtful of you. If you insist."

He tore his eyes away from her, knowing that was his only hope, trying to find a way to position himself to get the wet spot as much in the sun as possible, to give it the biggest chance to go away. The leak didn't seem too awful just yet, but if it had started, it was only going to get worse the more he used his diaper.

So it was not a good sign for him when Anita climbed out of the pool and dried herself off with a towel... And then didn't put her clothes back on. "I'm still a bit wet," she explained. "I'll get dressed after I dry off completely. What about you, Jojo?"

"H-Huh?" he blinked, looking at her again, towel over her shoulders, her mostly naked form right in front of him now.

"Are you all..?" she began to ask, before tilting her head downwards. "What's going on, Jojo?" she crossed her arms. "I know I didn't splash you this time... I'm not wet enough for that anymore."

Joseph swallowed a curse, nose wrinkling as he realized that, of course, he was dribbling into his drenched diaper once more, the flow only growing stronger when she reached down, gave his padding a squeeze. "Jojo!" she scolded. "I know this isn't my fault! I would have had to dump half the pool in here to get this so soggy! Did you lie to me and let me believe your wet pants were my fault, young man?!"

"I-I..." Joseph whimpered, biting his bottom lip and trying to squeeze his thighs together as he felt the warm trickling making its way down his inner thighs, not stopping this time.

Anita let out a sigh. "You're wetter than I am, and I just got out of the pool! Honestly... It hasn't been that long, Jojo! If you had to go to the potty this badly, you should have told me!"

"I-I'm sorry," he sniffed. He was still certain she had to be behind all this, that she had to be... If she wasn't... Well... That would be so much worse, so much more humiliating...

"Well, you can't go inside like that," she shook her head. "You'll drip all over the carpet! Wait right here!"

He didn't feel like he had a choice, even if he wasn't sure what she was doing, walking inside and leaving him there, until she returned with a changing mat, a box of wipes, a bottle of powder... And two diapers.

"W-Wait, why do you have two?" he whined.

"Because one is obviously not enough," she informed him matter-of-factly, spreading the mat out on the ground. "Now get over here so I can change you."

"H-Here?!" he squealed.

"I don't want to have to clean up your puddles inside the house," she told him, giving the mat a pat. "Come on... Don't make me come over there and get you."

He pouted, squirming. "B-But..."

With a huff, she stood back up, marching over to him, grabbing him by the wrist. He should have been able to resist, to stop her from taking him anywhere, yet he was no match for her as she dragged him to the mat, easily brushing aside his hands to tug his shorts down, exposing his leaky diaper, right in the back yard. He groaned, looking to his privacy fence, praying it was tall enough to keep anyone from seeing this.

"I'm going to have a talk with your Mommy about this," Anita threatened as she pushed him down onto the mat, then onto his back, ripping open his diaper and starting to wipe him off. "I'm starting to think you ought to be in these all the time!"

"N-No!" he yelped, terrified... But, shamefully, also looking over at her, kneeling beside him in her bikini, feeling a rush of excitement that, as usual, turned into a spurt of pee, dribbling out into his open diaper.

"Jojo!" Anita gasped. "You're only proving my point, little man!"

"I-I can't help it!" he sulked.

"I know," she cooed. "And that's why you belong in some big, thick, fluffy diapers."

And that was exactly where she put him, taping him into the pair of diapers, the bulk of the two together almost feeling like it had, somehow, more than doubled, making it a struggle to keep up with his sitter's shorter gait as she led him back into the house, waddling along behind her, carrying his wet shorts and diaper, being led to the laundry room to drop off the former, then, shamefully, back into Kelli's nursery to put the latter into her diaper genie.

"Since you fibbed about it being my fault," Anita said when he was done, while she washed his hands for him in the bathroom, "you can wait in the corner while I get your supper ready for you."

His nose scrunched, recalling her threat regarding his supper. When he opened his mouth to protest, however, she pushed a pacifier into it, and he found himself starting to suck on it instinctively, the desire to do so suddenly overwhelming his need to speak entirely. He sniffled, staring at himself in the mirror as Anita dried his hands off, seeing his double diaper bulging beneath his t-shirt, his sitter having not offered any pants to cover it, and his paci, bobbing up and down in his mouth, keeping him from being able to ask for any on his own.

True to her word, she led him by the hand to the dining room, straight over to the corner, leaving him there with a sharp swat to the backside. It took him a few minutes to work up the courage to look away, to see what exactly she was doing, as he heard her opening and closing cabinets the next room over in the kitchen... But, even when he was ready to do so, he realized he couldn't. He felt frozen in his spot, trapped in time-out, a naughty little toddler completely under the thumb of his pretty, older babysitter...

But she wasn't older than him! She was so much younger, so much smaller... Which only made the control she had over him - or, rather, his inability to do anything about it - all the more pathetic. How could he have let her do this to him?! He was an adult, and she was practically a child herself, barely old enough to not need her own babysitter, much less be one for him...

"All right," she said, her voice breaking through his self-pity. "Have you have time to think about what you did, young man?" He nodded meekly, eyes widening in surprise to find he could move again, apparently. "Then let's get you fed and into bed."

He turned around, gasping into his pacifier as he saw a high chair waiting at the table. It was clearly Kelli's, with all the same scuffs and stains, except it was large enough for him to sit in... And not disassembled in the attic, in case they had another baby eventually, since Kelli had graduated to a booster seat months ago.

He, apparently, had not, though, as he was helped into the seat, meekly sitting there, letting her snap the tray into place, setting a huge bowl of baby food on it. She tied a bib around his neck, then popped out his pacifier, setting it next to the bowl, and picking up the spoon. "I-I can..." he kicked his feet, watching unhappily as she dipped the plastic spoon into the mush.

She ignored him, bending down to offer it to him. "Here comes the airplane!" she teased. He tried his hardest not to look, but with her bending down in front of him, right behind the spoon, still in only her bikini, it was impossible not to see her cleavage, not to feel himself begin to wet his fresh double diaper.

"Ugh!" he gagged as the baby food touched his tongue, sending it dribbling down his chin, onto his bib. "That's disgusting!"

"Don't be silly," she said, scraping some of it off his chin with the spoon. "This is what babies like you need to grow up big and strong. You're not getting out of this chair until you swallow every bite."

It was no wonder Kelli had been so fussy about eating when she was smaller, he thought, struggling to choke down the stuff. He was sure it couldn't get any worse than this, any more humiliating...

And then he heard the front door open, the sound of Elaine's laughter. He shifted in the high chair, hoping that meant that she'd come to her senses, but when she poked her head into the dining room, the man who had picked her up was right there with her, looking like he'd had a far better night than Joseph.

"Back already?" Anita asked. "Sorry, I'll have him in bed soon, he was just being a bit of a brat."

"No problem," Elaine giggled. "We're back early... We couldn't help ourselves. Don't mind us."

It was hard not to, though, as they vanished into the house, and, moments afterwards, Joseph could hear the bedsprings - his bedsprings - creaking, the sounds of heavy breathing, of moaning... He might as well have been in the room with them. He whimpered, squirming in his diapers, in his high chair, helpless to do anything about it as his babysitter spoon-fed him his supper of baby food, then, when that was finally over, led him back to Kelli's nursery.

To his shock and horror, there was a second crib there, on the other side of the room from Kelli's, a bigger one, sized perfectly for him. "No," he groaned behind his pacifier, the only thing he could do as Anita removed his t-shirt and put him into a set of baby blue PJs over his diapers and tucked him in nice and tight, the covers feeling like they were trapping him inside just as much as the bars, once Kelli pulled them up and locked them into place.

"Night-night, Jojo," she winked at him. "I hope you had as much fun tonight as I did..."

______________________________________

Joseph woke with a start, absolutely soaked, though it took him a few moments to gain enough consciousness to realize that he was back in his own bed, Elaine beside him, and that the wetness was coming purely from the layer of sweat his body was coated in rather than a soggy diaper. He let out a sigh of relief, leaning back into his pillows. Had it all been a dream? It felt so vivid, so real...

He was able to convince himself that was all it had been pretty easily; there was only one crib in Kelli's room, after all, her hair chair still in the attic, in pieces, her diapers all normal sized, far too small for him. He couldn't remember what Elaine and he had done on their date, no, but they may have just had a few too many drinks while they were out. 

Even so, he couldn't help feeling a pang of anxiety the next time they had a date night and he heard the doorbell ring, checking the camera to see Anita there, grinning through the video feed in a way that made him positive she knew it was him watching.

"D-Did you hire Anita again?" he asked quietly.

"Of course I did," Elaine told him. "I know you think she was too strict, but that's just what you need, sweetie." Joseph's eyes widened, his heart thumping faster and faster as she continued to speak... And especially as she reached down to give his bottom a pat, and he felt her hand land on the diaper he was suddenly wearing again, beneath the shorts and t-shirt his nice clothes had transformed into, heard it crinkle. "She even said she was going to bring you some swim diapers this time! Isn't that nice of her? Be sure to say thank you... Now, run along and answer the door, Jojo. Mommy has to finish getting ready for her date."