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Hitting on the Babysitter - Chapter 2
🕑 Added 2023-07-29 12:00:03 +0000 UTC"W-Wait, what?" Joseph shook his head, pulling away as Anita reached for his hand, staring down at himself again. This whole thing was so insane... It didn't make any sense. "N-No, I don't wear diapers!" he whined.
But... He didn't wear Pull-Ups, either, did he? Yet, there, around his waist, designs faded, sagging slightly, was definitely a Pull-Up... And, as far as he knew, Elaine wasn't cheating on him, didn't have another boyfriend, though that hadn't stopped her from following some guy out of the house, away from him, leaving him all alone with the hot babysitter.
"Excuse me?" Anita raised an eyebrow, crossing her arms. "You're telling me no, Jojo?"
"Yes!" he fumed, bending down to yank up his shorts, hiding the training pants, which help him feel a tiny bit more authoritative. "You're my employee for the night, and you work for me, and..."
Anita scoffed. "You're paying me," she agreed. "That doesn't mean you're in charge. I don't take orders from little boys who can't keep their pants dry."
"I'm not a little boy!" Joseph insisted, hating how much it sounded like whining as he attempted to get the girl to listen to him, to hear what he was saying... To not do what she'd threatened.
She grabbed for him again, faster this time, and helped along by the fact that she wasn't aiming for his hand... Her grip tightened around his arm, clamping down like a steel trap, giving him a yank that surprised him with its power, nearly dragging him off his feet, forcing him to follow from the entryway into the living room, where she sat down in one of the armchairs and pulled him over her lap.
"What are you doing?" he demanded. This couldn't possibly be comfortable for her... He was so much bigger than her, his knees practically reached the floor.
"Oh, I think you know," she said, reaching over to the end table by the chair, picking up a large, wooden hairbrush, one that Joseph could have sworn wasn't there before, was relatively certain hadn't been in his house at all until now.
"N-No!" he squealed, cheeks burning as he felt a squirt of warmth into the squishy padding of his Pull-Up, which only made it more humiliating. There was no reason for him to be scared at all, much less to that degree... Anita was small enough that there was no way she'd really be able to hurt him.
"Your Mommy told me I could," Anita claimed. "I didn't think I'd have to do it so soon, but..."
She finished her sentence with a swing of the brush, any response Joseph could have come up with to it immediately forgotten as the sound of the wooden surface smacking against the soft plastic of his Pull-Ups beneath the shorts echoed through the room. His eyes widened, growing wet, his mouth opening, letting out a whimper of shock and pain.
"You made me do this, Jojo," Anita scolded. "If you could have just behaved yourself and listened to me... Or, you know, not been a gross weirdo and hit on me to begin with..." She whacked the brush against him again, before sliding down his shorts, letting them fall down to puddle around his knees.
"N-No!" he sniffled, more embarrassed at having his trainers exposed, though losing any layer of protection did scare him a bit, even if he doubted the shorts had made that much of a difference. "I-I'm sorry!"
Anita giggled, pausing for a moment to rub his padded rear with the brush. "Are you?" she wondered. "That was only two spanks... I'm not sure that's enough..."
"I-It is!" he nodded.
"I wouldn't think it should be," she mused. "Not for a big, strong boy like you."
"I-I'm not!" he told her, cringing as he spoke the words, recalling how, mere minutes earlier, he'd so vehemently denied it. "I-I'm a little boy!"
"You really must be," Anita agreed, "to crumble so quickly..."
He blushed, knowing it was pretty pathetic. But it had hurt, more than he ever would have imagined, and he was truly scared to discover how much worse it would be without his shorts... And if she was willing to take off his shorts, what was to stop her from doing the same with his Pull-Up? That sent a bolt of fear straight down his spine, more tears welling up in his eyes at the thought of that than from the pair of spanks he'd been given.
"Poor baby," she shook her head, setting the brush down and wiping away his tears. "You're all bark and no bite, huh?"
"N-No," he protested, confident that wasn't normally true, though it was hard to claim it wasn't now.
"Are you going to let me put you in a diaper, where you belong?" she inquired.
"B-But I don't!" he groaned. "I-I don't wear diapers!"
To his surprise, she accepted that response. "You don't, do you?" He shook his head. "Not during the day, only at night... You've been having so, so many accidents lately, though, you have to see why your Mommy told me that if it kept happening, she might have to put you back in them all the time again."
"B-But..." he tried again, brain struggling, failing, to come up with what to say afterwards. He'd love to say he didn't have accident, yet he was in a soggy Pull-Up, had made it soggier moments ago without meaning to... That was definitely an accident, so he couldn't truthfully tell her they didn't happen...
"So you have a choice, Jojo," she continued. "You can let me put you in a diaper now, without making a fuss, or I can finish spanking you and then do it. Which would you prefer?"
He pouted, so upset and mortified that those were his choice, that there were none that would keep him out of diapers. If those were what he had to pick from, however, there was really only one answer. "Y-You can diaper me."
Anita grinned. "Yes, I know I can," she purred, stroking his hair. "I'm glad you do, too, now." She helped him up off of her lap, taking him by the hand. His hand twitched, but he meekly made it stay there, let hers close around it as he shuffled behind her, shorts around his ankles, not knowing where they were going until they stopped in front of Kelli's door.
"W-Wait, no," he finally resisted again. "N-Not here... Not in front of her..."
"Your sister is sleeping," she said. "And if you don't throw a tantrum, she'll stay that way."
He opened his mouth, but Anita had already opened the door, pulling him into the room. He almost didn't dare breathe as she dragged him to the changing table, bending down to pick up one of Kelli's diapers.
Was that her plan? To put him in one of those? He felt a wave of relief, however small. There was no way that would fit him... They were for his daughter, not him, and he was so much bigger than her... The very thought of it was ridiculous! He wasn't going to be diapered, after all... A small comfort, relatively speaking, but he'd take whatever victory he could find today.
"Up you go!" she ordered, patting the surface of the changing table. He dutifully climbed up onto it, proud of how stable it felt beneath him. Clearly, he'd done a good job assembling it. He didn't have long to pat himself on the back before he had to concentrate on staying calm as he felt Anita's hand moving to his Pull-Up, ripping open the sides. It had been a long time since any woman other than Elaine had seen him naked, and as inappropriate as this was, he couldn't trust his body not to react, especially once she took out a baby wipe, started to clean him up.
"Does that feel nice?" she cooed.
"Wh-What?" he gasped, biting his lip, staring down at himself to double check that nothing was happening. "N-No!"
"No?" she smirked. "You preferred being in soggy pants? No wonder you've been peeing yourself so often!" She tossed the Pull-Up and wipes away, slid the diaper underneath him.
Immediately, he knew something was wrong. He could feel the padding - so much thicker than the trainers, the plastic so much louder as he squirmed on top of it - under his whole backside, could see it stretched out in front of him... There was no way this was the same kind of diaper Kelli wore...
"We'll get you powdered up," Anita said in a sing-songy voice, shaking the bottle of baby powder over him. "And pull this up and over..." The sound of the tape being opened was so familiar, and yet, at the same time, so incredibly terrifying as he stared, open-mouthed, watching her stretch the side of the diaper up and around him, saw it envelop him, easily wrapping around him, reaching the landing strip.
Seeing the front of the diaper now, half fastened over his crotch, there was no doubt that, as impossible as it seemed, it was one of Kelli's diapers. He'd seen so many of them, had changed her into, and out of, them countless times... And now, it was on him, fitting him just as well as they fit her... "N-No," he whimpered again, shaking his head in disbelief while Anita unfolded the other side of the diaper, taking her time adjusting it, and him, to get the perfect fit before tugging it up and over, pushing its tape into place, sealing him into the soft, cozy embrace of the diaper.
"There we go!" she brushed her hands off, then put them on her hips proudly. "All done!" He sat up, stunned, the diaper crinkling as it followed him. "You're all ready for bed!"
He whined, looking over at the window, at the sunlight creeping in around the heavy curtains. "I'm only playing," she giggled. "You don't have to go to bed yet." She pulled his shorts up his legs, over his diaper. They had to strain a bit to contain the bulk, which almost made it more embarrassing once she helped him off the changing table, seeing how obvious the bulge was, how much he could see the waistband peeking out before he adjusted the hem of his t-shirt. He might as well not have the shorts on at all... Anyone who saw him would know what he was wearing under there.
They crinkled and crackled with every step as she led him back out of Kelli's room, his gait turned into an undeniable waddle as he struggled to get used to the thickness of the padding while he followed her through the house obediently... Until she reached for the back door.
"W-Wait, we're going outside?" he squeaked, cheeks burning at the thought of going outside in this outfit... And at the warmth he felt spreading through his diaper already in response. He sniffled, squeezing his thighs together in shame and desperation, stopping the flow, yet unable to escape the consequences of what he'd already done as it continued to soak into the padding.
"Just into the back yard," she promised. "You said you had a pool, didn't you?"
"W-Well, yeah," he admitted. He had a privacy fence up around it, too, but that didn't mean he wanted to run around outside in a diaper.
"I love swimming," she told him. "So we're going to go play there. I mean... I will. I suppose you can't, because I just diapered you, and you can't wear a diaper in the pool." She giggled. "Clearly, I can't trust you to go without one, though, so you didn't leave me any choice, sweetie."
She pushed open the door, dragging him out, leaving him standing there awkwardly as she reached for her tank top, lifting it up. He couldn't help watching, gawking, as she exposed even more of her flesh to him, and the light of the slowly setting sun, revealing the bikini top she was already wearing underneath.
"Your Mommy told me about the pool, so I was prepared," she told him, tossing her shirt onto a beach chair, moving on to her skirt, wiggling out of it. "What do you think, Jojo? Do you like my swimsuit?"
Joseph gulped, nodded. It really did look incredible on her... He couldn't keep himself from staring at her body, a part of him wanting to do something more, despite being married... The rest of him remembered what she'd just done to him, what he looked like right now, how he'd have no more of a chance with her than any of her charges, after she'd diapered him like one of them.
"Oh!" she moaned as she walked down the steps into the water. "That is incredible! It feels so good, Jojo!"
He squirmed uncomfortably, certain she was toying with him now, like a cat who had caught a mouse. She had to know how that sounded when she said it that way, how she looked as she dove under, came back up, bare flesh glistening with water. She probably also knew how it was making him feel... And how every impure thought he had about her was accompanied by another spurt of pee into his diaper, a fresh reminder of his place in this 'relationship,' such as it was.
He wasn't a handsome older man to her, someone she might be able to tempt into having an affair with her... He wasn't even an adult at all. He was a silly little boy, and nothing more, one who couldn't even keep his pants dry for five minutes after she'd changed him.
"Wow," she said. "This puts me in such a better mood... I'll tell you what, Jojo. If you can keep your diaper dry until I get out, I'll let you stay up late tonight, and you can have a nice, grown-up meal with me... Just like your Mommy is having with her date."
Joseph blushed, fidgeted, embarrassed by how much he wanted that, despite knowing it was already out of his grasp. "A-And if I can't?" he asked nervously.
She grinned at him in a way that made him positive she knew what he'd done, that this was a promise more than a possibility. "Then I think somebody ought to go to bed early," she told him. "And I bet we could find some of your sister's baby food to feed you... Anyone who wets their pants again so soon, after telling his sitter he didn't need them more than once, doesn't really deserve anything more than that, don't you agree, Jojo?"
He nodded meekly; that was certainly how it felt, anyway, standing there, dribbling helplessly into one of his daughter's diapers as he gawked at the much younger babysitter. This really probably was what he deserved... And he had little doubt that she was going to follow through and make sure that he got it.
