Holly & Elizabeth - Chapter 10 (Patreon)

It might not have been Elizabeth's best decision, but it was one that had amused her at the time. Perhaps she'd had a few too many sips of wine as she was scrolling through her dating apps, giggling to herself and squirming hornily in her bed as she imagined each of these people she'd been matched up with in full baby mode, sucking their thumbs and staring up at her in disbelief as they realized she was the one who had manipulated them into their pitiful new lives of early bedtimes and dirty diapers.

There were always plenty to choose from, and it was almost as much fun to look at their profiles, fantasize about her potentials ways in, and how she could make her scheme work with each of them, as it was to actually enact those plans. She had a soft spot for women, and they were usually who she picked, though not always. Every once in a while, she'd get the taste for doing it to a guy...

And tonight was one of those nights. They definitely could be fun, in their own way, and it was a great way to keep things fresh. She was pretty petite, pretty flat-chested, and while she had clothes that would help her disguise both of those, embracing them did typically help get her victims to underestimate her, to see her as hardly better than a little kid next to them, someone they needed to look after, to protect, up until she had them in her trap...

With men, however, most of the time that wasn't necessary. Her normal victim was on the scrawnier side, nerdy and not particularly physically strong, since it made it easier to find a caretaker who could overpower them if need be, and even they always seemed to automatically fall into that protector role when they were with her, no matter how mature she made herself look. Not that she minded; she encouraged it, if anything. The more helpless they saw her as, the more funny it was when they wound up diapered.

That was the train of thought that, along with just a bit too much alcohol, led her to Drew. He was definitively not one of her usual victims... And that was what made him so attractive to her. Purely from his profile picture, she could see that he was big and strong and athletic, someone who could probably pick her up with one hand without breaking a sweat...

He was probably also, she assumed, glancing over his profile, not too bright. That was how it tended to go with these sorts of guys, and there were several spelling and grammar mistakes in his About Me section to support that hypothesis. He'd likely been too busy playing sports to concentrate on classes, and from all the trophies she saw in the background of one of his photos, he must have been beneficial enough for the school that the teachers were required to let him pass anyway so he could keep making the place look good.

She knew these types of people existed, of course, and the idea of choosing one intrigued her, but it had always seemed like playing with fire. If anything went wrong, if somehow he suspected her of being up to something, there wouldn't be much she could do to defend herself against someone so much bigger and stronger than her... She really would be as helpless as she wanted her victims to think she was.

If nothing did go wrong, however, if she pulled it off - and she was coming off a long line of successes that were bolstering her ego - then it would be so much sweeter. To take someone like this and turn him into a sweet, simpering little sissy baby... She writhed in bed, rubbing her thighs together, grinning, setting her wine glass down on her bedside table to free up one hand to slide between her legs as she continued to look through his pictures, thinking about what she could do to him...

She had some sweet dreams that night about it, about seeing this hulking meathead prancing around in a tiny, frilly dress and huge, crinkling diapers, lisping as he begged to be allowed to use his potty chair, bursting into tears when he had it pointed out to him that he had, in fact, already started to pee himself, so there was no use... In the harsh, sobering light of the morning, though, she knew that it was probably for the best that she not go through with it...

So it was quite the surprise when she looked at her phone and saw the notification that she'd gotten a reply to the message she'd sent, a message she couldn't remember sending until she tapped through. She blushed as she read it, telling herself that the reason it was so messy and misspelled was that she'd been attempting to imitate his profile, making it seem like they were equals so he wouldn't be scared away, but, really, the more likely explanation was that she'd been drunk and hadn't realized what she was doing... And there was obviously at least some truth to that, since she'd been at least inebriated enough to have no memory of sending it in the first place.

'Hell, yeah, we should meet,' he'd written back. 'Just give me a time and place, hot stuff.'

She probably should have ghosted him, or blocked him altogether, written it off as a delightful fantasy that could never come to be... But her dream about it had been too good, and his cockiness only proved to her that he deserved to be brought down to size. And who better to do it than her?

If anything, he was even larger in real life than she'd seemed in his pictures, looming over her as they greeted one another in the fancy, expensive restaurant she'd chosen, the rational part of her hoping that would scare him off, or that he would complain it was a bit too much for a first date, and she'd have a justification to call it off. 

Instead, all he'd said was, 'Sounds good!', and he had, indeed, shown up, a few minutes early, even. "You must be Elizabeth," he grinned, holding out his hand. "So nice to see you in person!"

She took his hand, a tingle running through her at how thoroughly his hand wrapped around hers, how strong his grip felt. There was a hint of fear to it, but mostly she was thinking back to her dream. The bigger they are, the harder they fall... And he had a long way to fall, clearly.

There were plenty of ways she could have went about that... She didn't want to let him get away, now that she had him, however, didn't know when she'd come across another specimen quite like him, so she'd gone with one of the riskier approaches. He might have been too proud, and thus too embarrassed to keep letting her come over to his place if she started to drug him to begin wetting the bed, and he was too aware of his own hotness for her to talk him into being the first one to try wearing diapers.

That worked for some other guys... She could say she'd seen it online, that it was kind of cute, and she was curious, and half the time they'd practically jump at the chance to give it a shot, to prove how willing they were to do what she wanted, to keep her from dumping them and moving on to somebody else... When she dropped hints about that to Drew, though, they didn't phase him in the slightest. "Hey, you gotta do what you gotta do," he'd replied. "I've been having fun, but if you aren't and you think it's time to move on, it's all good."

The implication, at least in Elizabeth's mind, was that he'd have no problem finding another date. And that was probably true, to be honest... That meant she didn't have nearly as much leverage on him, however, so to get what she wanted, she might need to make a sacrifice or two.

"I have a confession to make," she told him one night. "I know I've been acting a little weird lately... It isn't because I want to break up... But I'm worried that if I tell you, you might."

"I doubt it," he scoffed.

She stared down at her feet. "I wouldn't be so sure... I've been keeping a secret from you, and I just don't know if we're going to be able to keep this up if I don't share it..."

"A secret, huh?" he raised an eyebrow with a smirk. "What is it, some kind of fetish?"

She blushed, shifting on the couch, surprised that he'd gotten it in one guess. He could be surprisingly perceptive for someone she'd assumed would have had no reason to develop that skill. "Well... Yeah, actually."

"Lay it on me," he said. "I've seen lots of freaky stuff online, so I doubt whatever you're into is going to shock me."

"We'll see," she shrugged archly, almost taking it as a challenge. 

The next day, she showed up to his place in a plaid skirt, a button-up shirt, and a sweater, with a hair band and Mary Janes, looking sweet and innocent. He chuckled when he opened the door for her. "That's it?" he asked. "I thought it was usually guys who had a schoolgirl uniform thing, but if you want to dress up like that..."

"What are you talking about, Daddy?" she pouted, staring up at him, giving him a tiny shove to make herself seem even weaker compared to him than she really was. "Of course I'm wearing my uniform! I just got back from school!"

"Oh, you did, huh?" he nodded, quickly catching on and starting to play along. "Did you have a good day?"

"No!" Elizabeth stomped her foot. "Daddy, it was awful!"

"It was?" he asked. "Do you want to tell me about it?"

She looked down at her feet, digging the toe of her shoe into the floor. "Not really..." she fibbed.

"Well, I think you probably should," he smiled. "Come on, sweetie." He took her by the hand, leading her to the couch and sitting down, giving his lap a pat. As much as she would have liked to sit there, she knew she couldn't, not yet.

"You remember that one teacher?" she asked him, continuing to stand in front of him, pretending to be bashful. "Mr. Wilkins?"

"Sure," he replied gamely. "What about him?"

"He did it again!" she whined. "He always accuses me of cheating, and I promise, Daddy, I don't! I would never cheat!"

"Of course not," he agreed with a bemused grin. "My little girl wouldn't do that."

"Nuh-uh," she shook her head. "But he wouldn't believe me, and so he... He bent me over his desk, Daddy, and he spanked me! He spanked me right in front of everyone!"

"Oh, spanking!" he exclaimed. "You thought that was going to weird me out?"

"Daddy!" she sulked, crossing her arms. "You're not supposed to break character!"

"Sorry," he laughed, patting her on the head, the condescension of the gesture both exactly what the situation called for, and exactly what she needed to further her resolve to get her plan rolling. "He spanked you, huh?"

"Yeah," she started to reach back to rub her backside, only to stop herself short. "A-And he sent home a note that you or Mommy has to sign... I-I know that Mommy usually does this sort of thing, Daddy, but she doesn't listen to me the way you do, Daddy... She thinks I really am just a big, naughty cheater, and if she sees this, she'll probably say I deserve it, and ground me... So, Daddy... C-Could you sign it, and keep it a secret from her?"

He raised an eyebrow, watching her squirm in front of him. "I don't know, sweetie," he told her. "I don't like keeping secrets from her like that..."

"I bet," her eyes twinkled as she reached out, starting to unbuckle his belt, "I could find a way to make it up to you if you did..."

"Really?" he smirked. "What did you have in mind?"

It was not something she normally did, but in this case, she was happy to show him, crawling up onto his lap, straddling him, grinding against him, acting like she couldn't help herself. She assumed he had to have felt it then, or heard the crinkling, but it wasn't until he tried to pull her in further up his leg, closer to him, and his hand cupping around it, that he said anything.

"Wh-What are you wearing?" he panted.

"No, Daddy!" Elizabeth pretending to be embarrassed, even as she began to writhe harder against his crotch. "D-Don't look!"

But she grabbed his hand anyway, guiding it to the hem of her skirt, holding it there until she could tell it was right on the edge, then letting go, allowing him to lift it up at just the right moment, to see that the thing that she'd been humping him in, and that he'd clearly been getting plenty of pleasure from, was, in fact, a diaper.

"I'm sorry, Daddy," she told him, leaning against his chest as he finished up, catching his breath. "I should have told you before... When that mean Mr. Wilkins was spanking me, I had an accident, so he put me in these... H-He said he expects me to wear them every day from now on... But that's no fair! I don't need them, Daddy! I swear!" She led his hand to her diaper again, sliding it down the crinkly, padded surface, letting it feel the dry section before moving it down to where she was warm and squishy, and very obviously wet. "You believe me," she blinked innocently into his eyes, "don't you?"

He paused for a second or two, then leaned forward, kissing her on the forehead. "Of course I do, sweetie. But... If that's what your teacher wants, I think it might be a good idea to give it a try... Just so you don't get in any more trouble."

"But Daddy!" she whined, bouncing in place on his lap. "Well... Maybe you're right..."

It was quite the pathetic display... Which was, of course, the whole point. She was, without him knowing, leading by example, playing the part of the horny little baby who couldn't help humping her stuffed animals, or a pillow, or whatever was nearby, any time she wet her diaper, always eager to find some excuse to give him a handjob, or grind on him in her soggy diapers in exchange for the most minor of favors...

Or, in some cases, not so minor. It had been one of the first things that came up right after their initial playtime, as they talked about where they were going to go from there. "You don't do... anything else... in them, do you?" he'd asked, giving her damp padding a squeeze. "This isn't so bad, but I'm not so sure about..."

"No!" she'd shaken her head. "I mean... Not if you don't want me to..."

There was no way she was going to do that... But that didn't mean she didn't want to introduce him to it, because, if everything went well, he was going to be doing a lot of it. She gave him a little more time to get used to the basics, then, one day, showed up with a full pot-full of oatmeal in the seat of her diaper.

"Daddy," she sniffed as she trudged into his apartment in her uniform. "I-I don't want you to be mad at me..."

"What happened this time, sweetie?" he smiled. "What did Mr. Wilkins do today?"

"W-Well," she wiped her eyes, "I told him I hadta go potty, like, twenty times, and he just kept telling the whole class about how I was wearing diapers, so there was no reason for me to leave class, and they were all laughing at me, and..."

"Did you wet yourself again?" he asked. "I'm not mad, Elizabeth, but I'm starting to think..."

She gulped and shook her head. "N-No, Daddy... N-Not quite..." She turned around and lifted her skirt, showing off the clearly lumpy rear.

"Elizabeth!" It was hard to tell if he was in character or not anymore, though the disgust was obvious in his voice. "You didn't..."

"I didn't mean to, Daddy! I couldn't help it!" she pouted, the feeling of humiliation starting to wash over her. She knew she hadn't really, of course, but just having him think that she had, that she would do such a thing, was almost as bad, especially while she was still standing there, diaper sagging with a heavy load of mush.

"I told you, I'm not sure..." he shook his head.

"But Daddy!" she whined. "You hafta help me! If Mommy sees, she's never going to let me out of diapers! She's going to think Mr. Wilkins was right about everything! You can't let that happen!"

"I don't..." he scooted away from her.

"I'll make it up to you, Daddy," she promised, kneeling down in front of him, opening his fly wide, then opening her mouth even wider, not having to pretend to be impressed by his size, the way she often did at the start of her relationships with other guys... If she wasn't going in the opposite direction, and shaming him for how tiny it was instead. There had been a part of her, at the beginning of this, that had hoped that would be the case for him, that all those big muscles had been to compensate for the size of what was in his pants, since that would have given her the perfect opportunity to manipulate him without having to stoop to this level herself, yet she was still convinced it would be all for the better in the long run.

It was so mortifying, so degrading, blowing him in exchange for a change out of her messy diaper, whether that mess was real or not... But it was only fair that she experience it at least once, when she knew that was what she wanted him to have to do in perpetuity. The hotness of thinking of him in this position, in a prissy, girly little dress and full diaper, was more than enough to get her through. And she'd refused to do that at all up until now, to make this time even more special for him...

He definitely seemed to appreciate it, too, enough so that, when he was finished, he got out her changing pad and was ready to get her cleaned up. He chuckled in relief when he saw what was really in her diaper, giving her thigh a smack. "What a naughty girl!" he scolded playfully.

"Me?" she giggled. "Never!"

And all the while, she'd been looking for the perfect caretaker for him, someone just as strong, who was more than a match for him... At last, she came across a female bodybuilder turned Mistress who she was able to talk into helping her, who found the idea of her own sissy baby intriguing, especially after Elizabeth told her about all the things she did with Drew, but in reverse, saying that he was the baby of their relationship.

"You know," she suggested one day, certain she had her hooks into him far enough now, "this is a lot of fun... But aren't you curious about what it's like from the other side?"

"The other side?" he frowned. "What do you mean?"

"I mean, like... What if I was the Daddy?" she shrugged nonchalantly. "I bet I could find you a cute dress, and some diapers that fit... Aren't you curious about what that's like? We could even make up some oatmeal, and I could get a strap-on... You thought that was hot, didn't you?"

"Sure," he admitted. "But that doesn't mean..."

"Come on!" she pouted. "You won't try it for me, just once?"

"We'll see," was the best she could get out of him, but she was getting impatient by that point - as was her ace in the hole - and she was confident she could make it work, so she set everything into motion, showing up to his place the next time in one of her suits, with a frilly pink party dress and diapers for him.

"I couldn't find a school uniform in your size," she told him. Really, she wanted him to know that he was even lower than she had been when they were roleplaying, that, while she'd been acting like a schoolgirl, he was just a toddler...

"That's all right," he smiled. "Because we're not going to need it..."

"H-Hey!" she gasped as he grabbed her by the wrist, dragging her over his lap. "What are you doing?!" she demanded, feet kicking helplessly.

"Sorry, Elizabeth," he told her, "I don't think I can do the whole role reversal thing... But, to make it up to you, I want to let you live out your own fantasy... And that's why Daddy has to spank you, sweetie. I know you want to be a grown-up, but you have to wear your uniform to school! What is this?" He lifted the back of her skirt, giving her wiggling bottom a pat. "And you aren't even wearing your diapers? What a naughty girl!"

"Drew!" she squealed, squirming frantically. "Don't you...! Ouch!" She squealed as his hand smacked hard against her backside, Elizabeth's heart pounding as she realized that she'd miscalculated... And that there was nothing she could do about it now. He spanked her silly, ignoring her protests altogether, but the real surprise came as he was taping her into her diaper, and she felt him slip something into her bottom. "Wh-What was that?!" she whimpered.

"Don't worry about it," he cooed into her ear. "The idea is still a little gross, but I know you want to try it for real, so I'll see if I can deal with it."

"Drew!" she groaned. "You can't do this!"

"I already did, baby girl," he smiled. "And don't be rude... Little girls like you don't address their Daddies by their first names."

And so, when the Mistress Elizabeth had contacted showed up, in full dominatrix gear, it was Elizabeth herself who was diapered and quivering in the living room while a very confused Drew answered the door. "Sorry," he frowned. "I think you must have the wrong..."

Elizabeth ducked her head, cheeks burning, while the woman peered around Drew and spotted her. "No, I don't think so," she said, pushing past him. "I think we had a little misunderstanding... But that's all right."

Elizabeth nibbled her bottom lip, peering up bashfully at the massive woman towering over her, feeling very tiny and childish in comparison. "N-No," she shook her head frantically. "N-No, it's him! Not me! L-Look, I have a dress for him, and..."

She groaned as a cramp hit her, arms wrapping around her aching tummy. "I was told there was a little girl here who loves her diapers, but is embarrassed to admit it," the woman lifted Elizabeth's chin with one finger when she attempted to glance away. "And it looks like I've found her."

"What's going on, Elizabeth?" Drew demanded. "Who is this?"

"Not now!" Elizabeth whined. "I-I mean, I don't know! T-Tell her to get out of here!" The cramps were coming fast and furious now, and she knew she was right on the verge of losing the battle. "Now!" she stomped her foot.

"Not until I hear some kind of explanation," he replied sternly... But all Elizabeth could do was bend her knees and helplessly begin to fill her diaper, right in front of both of them.

"This is definitely the little girl I'm looking for," the woman sneered, as Elizabeth grunted and groaned, feeling her diaper swelling with warm mush, so much mushier and stinkier and grosser than her oatmeal. "And she's told me all about how she likes to earn a diaper change after she does this..."

Elizabeth watched in horror, still messing herself, while the woman pulled a strap-on out of her bag of tricks. "Sorry," the woman said as she fastened the harness onto herself, "I'm not interrupting, am I?"

"Oh, no," Drew shook his head, glaring at Elizabeth and reaching for his belt. "We can share this time... And then she's all yours.

"No!" Elizabeth whimpered. "You can't let her have me! You don't know what she's going to do to me!"

"But I have a feeling you do, don't you?" he asked, looking over at the dress she'd brought for him. "And that you deserve every bit of it..."

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

That had been a tricky one to get away from, almost as bad as one of the Nannies, and when she finally had, Elizabeth had hoped she'd never see the Mistress, or Drew, ever again... And now, here Drew was, smiling down at her, seeing her once more in a dirty diaper, and all she could do was pray that he somehow wouldn't recognize her, knowing that, if he did, there was nothing she could do about him blowing her cover... Or, if it was what he wanted instead, getting any more revenge on her for what she'd tried to do to him.