Out of His League (Patreon)

A short story commission for an anonymous Patron. This is a little more sexually explicit than most of my stories... Nothing too bad, but just a warning for anyone that might not be interested in that.

"Well, then, big boy?" the woman smiled seductively. "What did you have in mind now?"

Colt blinked, paused, something not feeling quite right, although he couldn't put his finger on what that could be. If anything, he thought, everything was going perfect... It must be, looking at the woman sitting there on his bed, waiting expectedly. 

She was definitely one of the most beautiful women he'd ever seen, at least in real life... And, the longer he stared, the more he started to think she'd put up a stiff competition against movie stars and models, too. She was incredible, with her long, blonde hair, her delicate features... And her body, stuffed into the tiny dress she was wearing, the neckline plunging so low he could hardly believe it was staying up, over her ample breasts... It ended awfully high, too, the whole thing barely more fabric than was used in most shirts, her slender legs spread just enough to be inviting, without actually showing him anything, though the implication was more than enough.

And yet... A slight frown crossed his face as he tried to remember who she was, where he'd met her... How he could have gotten her here, to his room. He didn't think he was bad looking - he'd had a girlfriend, Bria, for quite a while, until recently, and slept with a few other women, too, before the break-up - but this woman was not Bria. She was so far out of his league, she might as well be playing a different sport altogether.

Right now, however... What did it matter how he got here? The point was that he had, by some miracle, so why not enjoy it? Maybe, now that he was officially out from under Bria's thumb, he'd gained the confidence he needed to bag even bigger game... Maybe, now that he was single, this was his league after all.

"Everything all right?" she asked, adjusting her pose on the bed, legs shifting, giving him the briefest glimpse of black lace under her miniscule white dress.

"Yeah," he shook his head, grinning. "Yeah, of course. So, what do you think?"

She turned her head, taking in the room. "I like it," she nodded. "Simple, not too fancy."

"Well, yeah, I'm not an interior decorator or anything," he smirked. "I have more important things to do with my time than make my bedroom all prissy... All I really need is this." He patted the bed, his hand achingly close to her bare leg... And then, right next to it, touching her smooth, silky skin as she opened her legs further, bumping one against his fingers, inviting him to run them upwards...

"I guess that's true," she said. "If you know how to use it."

"You'd better believe I do," he bragged. "Why don't I show you?"

He slid his hand further up her leg, under her dress, his other hand mirroring the action on her other leg, both wrapping around the waistband of her underwear. He gave her a moment, waiting to make sure she didn't change her mind, or say no, then pulled them down, pausing only to knock her heels loose so he could get the panties off her feet, setting them aside, a part of him wondering if he'd be able to find some way to hide them, to keep them as a trophy of his conquest... Not that anyone would ever believe him if he told them how gorgeous she was.

"Are you wet?" One hand made its way back to her leg, tracing her tibia towards the hem of her dress once more.

"I don't know," she purred, gently scooping his hand up, moving it to his own crotch instead. "Are you?"

"Oh, yeah, baby," he fumbled with his belt. "And that's not all..."

"Well, don't keep me in suspense," she teased. "Show me."

"Y-Yeah." He wanted to, of course... There seemed to be something wrong with his belt, however, one part catching on another, making it more difficult to undo... His movements became more frantic, not wanting to keep her - or, more importantly, himself - waiting any longer than he had to...

"Hey," she put a finger under his chin as he dared to look away from her, to peer down and see what was going on. "You're not nervous, are you? This isn't your first time or something, right?"

"No way," he snorted, denying them both, although only one was technically untrue. No real macho man was going to admit to being anxious now, to worrying that, if he didn't pick it up, she would realize her mistake, that she should be with someone far hotter than him...

"I didn't think so," she smiled, the look on her face emboldening him, washing away whatever hesitance he had left. Automatically, he could feel his hands working, the buckle finally coming loose, the zipper on his pants quickly following. 

"Oh, my," she put a hand to her mouth as his pants fell to the floor, leaving him in just his boxers. "I knew I made the right choice with you."

His blood really started pumping now, the last of his nerves long forgotten as he started to crawl up onto the bed, over top of her. "Are you sure you're ready for this?" he asked, reaching down.

"I've been waiting my whole life for it," she moaned.

It felt so good, so much better than it ever had before... Forget Bria, forget any of those other women he'd cheated on her with, this was the real deal... He, he recognized now, had been waiting for this for his whole life, too... He simply hadn't known it.

"Oh, yes!" he could hear her squealing out, encouraging him to keep it up, thrusting his hips harder. 

He had to... It wasn't just a matter of pleasure now, or of pride... He had to convince her with this that he was the only man for her. He wasn't sure he could go back to anyone else, that he'd ever be satisfied with anything less...

He watched her back arched, heard her moan out his name in ecstasy, feeling it all coming to a head for him, too. "I love you so much," he mumbled, half delirious from everything he was feeling, something it had taken him months, if not a full year, to say to Bria, and truly mean it to anywhere even slightly approaching this degree...

She didn't answer, and, for a split second, he wondered if he'd gone too far, if he'd sounded too desperate and scared her off... He looked down at her, gasping, climax about to hit...

But it wasn't her anymore. He was no longer straddling some Playboy cover model of a woman, scantily clad and sprawling across his bed... His legs were spread over an oversized, fluffy teddy bear, staring back at him with empty, black eyes, mocking him.

It was strangely appropriate, though, despite how adult the act was that he had thought he was doing, because that wasn't the only thing that was not how it had seemed. He could hear a crinkling accompanying his every movement, a warmth surrounding every part of his crotch, not just one... He glanced down further, cheeks burning as he saw something big and bulky and covered in plastic there...

A diaper. He was wearing a diaper... One that was, from the look of it, indeed, wet, like he'd told the woman... And not only in the way he'd meant. "N-No," he shook his head, but it was already too late.

With a moan, his body spasmed, sending waves of pleasure from the tips of his curling toes to the top of his head, not caring what he was wearing, what he'd been humping... Mortifying, even knowing all that, this was still the best, most intense, orgasm he'd ever felt.

But that was only because of how it had started... If he'd known the truth all along, it wouldn't have been that good... Would it? He couldn't actually like doing this, certainly not more than he liked real sex...

He leaned against the bear, panting, confused, blushing beet red... Until he heard a slow round of applause starting from behind him. He turned, scrambling with the covers on his bed, trying to pull them up, to cover the humiliating, infantile garment he was wearing, as if that was the worst part about what whoever was there may have just seen...

"That was quite the performance," Bria smiled, rising up from a chair on the other side of the room. "Did you have fun? It definitely looked like you did..."

"N-No, I... I-I didn't..." he shook his head, attempting to deny it... Knowing that a peek inside his diaper would be all it took to betray him.

That was exactly what she did, curling a finger around the plastic waistband of his diaper, the same way he'd done with the woman's panties, peeling them back, peering inside. "That's what I thought," she gave him a pat through the padding.

"Wh-What are you..?" he shook his head, trying to move past that, to work out what had happened here. His fuzzy memories were starting to clear up, and he did recall getting a text from Bria, asking if she could come over, to talk things over... Thinking harder, he recalled her arriving, pulling a pendant with a swirl pattern out of her purse.

"What's that for?" he'd asked, rolling his eyes. "What, are you a hypnotist now?"

"Don't worry," she chuckled, seeing his expression grow more and more horrified, realizing none of that had been real, that the woman had never been there at all.... That his ex-girlfriend really was a hypnotist. "You did very well, 'big boy'... And I hope you did have fun. Because, after that... Nothing else is going to satisfy you. The only way you're going to get to feel that again is just like this... In a soggy diaper, with your new best friend."

"B-Bria!" he shook his head, tears starting to fill his eyes. "I-I didn't... I-I'm sorry! Y-You don't have to...!"

"I already did," she informed him. "It's over, Colt. I wasn't able to do it in time to save our relationship... But at least now I know you won't be cheating on anyone else. Don't worry... I left you the rest of the pack of diapers right by your dresser, there... Go wild."

"B-But..." he sniffled, watching her strut towards the door, squirming on the bed, his brain hardly able to process, much less accept, that she'd turned him into a diaper-wearing, plushy-humping loser... And yet, as he tried to stand up, to run out and beg her to change her mind, his diaper rubbed against the bear's leg between his thighs, and he just couldn't help himself, even as he saw the satisfied grin cross her lips, seeing waht she'd reduced him to, before walking out of his life forever...