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This "Three Word Prompt" commission was written for Kio Redsen. Their three words were "Pokemon, Crossdressing, Pegging." and the story contains M/F sex between consenting adults; a pokemon and their anthro trainer. :3

Aces Wild

Cinderace giggled and blushed as he pulled the dress up over his head and wiggled his arms down the sleeves. The pokemon wasn't accustomed to dressing himself at all, never mind in lady's clothing, but the silky pink garment he'd found stuffed right at the back of his trainer's closet while... exploring it had somehow seemed irresistible to the rabbit pokemon. He tugged and teased it down over his slender body with relative ease, and though it was a more than a little big for his four and a half foot frame, falling down well below his knees and sitting rather baggily on his lean figure, the pokemon gasped as he looked into the closet door's mirror and saw himself. Turning on the spot, Cinderace squealed happily as the skirt portion of the dress flared out and rippled around his legs. He stopped with his back to the mirror, looked around, and giggled as he saw a bulge where his tail was interrupting the otherwise smooth lines of the material, but also a little hole there at the back of the dress not too far away from where his tail was currently resting. It took just a little wiggling and squirming to poke his own tuft of a tail through where his trainer's tail would normally have emerged, and Cinderace wiggled his hips from side to side to admire the now much better fit of admittedly still oversized garment.

His eyes travelled with the motion of his hips, of his firm rump outlined by the dress as he arched his back slightly to emphasise those curves. Again he giggled, but this time there was a slight bashfulness to the sound, and a growing rosiness to the pokemon's cheeks. He shivered as he kept on watching himself, and curiously wondered what it was about this dress that he liked so much. It was making him all tingly, making him feel warm and ever so pleasant inside. Maybe it was the way the silky fabric felt against his fur. Maybe it was the novelty of being dressed in human clothes. Or perhaps it was the actual sight of himself. Maybe there was something deep inside Cinderace that enjoyed seeing himself all dressed up like that, though before today he'd never had any other experience of clothing with which to test that theory. Whatever the reason though, the outcome was the same.

The pokemon gasped, and blushed as he felt a very particular kind of stirring between his legs, and he trembled slightly as he turned back towards the mirror. Cinderace watched his reflection as slowly but surely something began to poke through the fabric at the front of the dress, where it hung over his crotch. He huffed and giggled at the sight of his erection swelling and starting to tent the front of his new and now suddenly even more appealing clothing, and before he really knew what he was doing the pokemon found himself reaching out, wrapping a paw around his swelling shaft through the fabric of the dress, and squeezing.

"A-ahh..."

Cinderace was no stranger to masturbation, but the feeling from that single touch not just of his hand but of the fabric of the dress wrapped around his rapidly growing erection was something much more than he was used to from even his most energetic self-pleasuring efforts. His hips rocked forwards, and he giggled again, groaning happily at how wonderful it both felt and looked as his cock twitched and pushed against the fabric now tightly wrapped around its length. Letting go of his erection for a moment, the rabbit pokemon reached down and grasped at the hem of his dress with both paws. He lifted it, and squealed with excitement at how naughty it felt to show off his bare erection as the pink material was lifted away from it. Was this why humans wore clothes? So they could tease themselves and one another knowing that there was a naked body underneath them? Cinderace didn't know if that was a reasonable thought, but in that moment he couldn't help but think of his trainer, picturing the plump border collie in this very dress, lifting it just as he was to reveal her own intimate reaches.

Shuddering, panting slightly at the intensity of his own fantasies, the rabbit pokemon took one more look at his bouncing, twitching cock as he showed it off to himself in the mirror, then forced himself to look away by turning around on the spot once again. Instead he lifted the rear of his dress, and moaned louder still in awe at how it was possible for his own body to excite him as much as it was right now, just by playing a quick game of peekaboo with it behind the fabric of the dress. His rump swayed, tight, firm cheeks hypnotically rocking from side to side. Cinderace whimpered, gurgled, and a few seconds later gasped in bashful longing as he felt his cock twitch once again, and with his swaying hips putting the dress' entire lower half into motion felt the silky fabric just teasingly grazing at the very tip of his dripping, tender shaft.

Still admiring himself, still excited and enthralled by the potent combination of these clothes and his body within them, Cinderace bent further forwards until he could barely peer up over his shoulder and down his back to continue admiring himself in the mirror. His hands stretched out behind him, and he placed his fingertips upon his cheeks, keeping the lower portion of his dress bunched up but still playing its pivotal role in letting him expose what was normally always visible. The pokemon whimpered as he spread himself, trembling, panting, giggling and moaning as he watched not just his ass sway in the mirror, but with his legs spread further and further apart watched his white furred balls jiggle with the pink of the front of his dress still hanging down and still caressing the tip of his cock every now and then in the background. So badly he wished he had someone to share this with. Someone with whom he could show off what he had learned, what he had discovered about himself today. He...

"O-oh my god, Cinder?!"

With a squeal the pokemon tumbled forward face-first onto the bedroom floor, dress still tucked up around his ass and hands momentarily still grasping at his spread cheeks. He rolled himself upright, but with legs splayed out, his torso still wrapped up in that silky pink dress and the bulge of his erection now poking up through the dress' delicate material once again there was absolutely no hiding what he had been caught doing. All he could do was blush and try to cover the tent of his arousal with his hands as he saw his trainer standing in the bedroom doorway, wide eyed and with a hand pressed to her muzzle.

The pokemon momentarily had visions of his pokeball being emptied out and deactivated as he was released from his trainer's care, or simply being recalled to his ball, placed in deep storage in some computer mainframe and never let out again. Before he could depress himself too much with how badly he'd screwed up though, he heard something that shocked him back to reality. A loud, sudden snort of laughter. His eyes widened almost as much as Nyla's own, and in that moment he realised that his trainer's hand over her muzzle wasn't an act of shock, but one to conceal her mirth.

"Holy shit, Cinder, is that the godawful dress my aunt got me a couple of Christmases ago?? I thought I'd binned that thing. Though, wow, I'm glad I didn't. It suits you."

The collie giggled once again as she padded into the room, and dropped down to her knees in front of her still brightly blushing but at least less stressed looking pokemon partner. Her eyes darted down towards Cinderace's crotch, then back up again to the pokemon's face. She grinned. He blushed deeper still.

"So... have you done this before?"

The pokemon shook his head. Nyla raised an eyebrow. He pouted and shook his head harder, and she smirked with a shrug.

"Okay, if you say so. But... you sure looked uh, comfortable there."

Cinderace's cheeks glowed crimson, and as his eyes turned downward bashfully, it wasn't long before he felt his trainer's left hand cupping his face, guiding his gaze back up to meet hers again.

"Hey. Kidding aside... you know I'm not mad, right? If you wanna dress up in human clothes... ladies human clothes, and... enjoy yourself? That's okay, Cinder. You're a grown pokemon with needs just like any other creature. Just, next time maybe give me a head's up so I can either leave you to it, or join in."

The border collie winked playfully to her pokemon to make it clear that she was kidding, but that didn't seem to register with him, either due to how flustered and embarrassed he already was or just a disconnect between anthro and pokemon body language. Whatever the reason though, the outcome was the same. Cinderace's already rosy cheeks burned hotter and brighter beneath his fluffy white fur, and before Nyla could say anything to clarify, he lifted his hands out of the way of his tented, dress covered crotch, then used those hands to lift his dress, and flash his trainer the sight of his exposed, throbbing cock.

"O-oh, god, Cinder..."

Nyla gasped bashfully, half wanting to tell him that she had been joking, and that while flattered she really wasn't attracted to pokemon the way she knew that some trainers were. And yet as the pokemon sat there, red faced and trembling, nibbling bashfully on his bottom lip while he showed his cock off to her from under the cover of that oh so pink, pretty, feminine dress, she felt something. A twinge, a flicker of something within her loins that as she focused on it and looked at the pokemon more turned to a spark, which turned to an ember, which turned to a flame and soon to a roaring, scorching inferno inside of her.

She swallowed thickly as the pokemon whimpered nervously, but hopefully as he showed off to her and his trainer didn't immediately flee. Nyla looked up again, tearing her eyes rather agonisingly away from Cinderace's cock, and smiled bashfully back to her pokemon.

"So... do you wanna fuck me in that cute dress of yours, or... do you wanna bend over again, like you were when I got here?"

*******

A shrill squeal echoed around the bedroom as Cinderace felt his trainer's hands grasp at his hips, and press the glistening, slippery strap-on deep into his ass. The rabbit pokemon had never used a sex toy before, and had never even considered the idea that a lady could use one to fuck a guy. Now though, as he knelt upon the collie's bed with his hands clutching desperately at handfuls of bedding and his cute pink dress bunched up around his ass, the pokemon was getting a crash course in a great many things he had never experienced before today.

"Oh, god, Cinder... I dunno if it's the dress or whether you just like it in the ass, but... f-fuck, squeak for me again, just like that!"

Nyla moaned as she felt her thighs begin to slap against Cinderace's firm rear end, breathless with pleasure of her own as the other end of the toy strapped to her midsection teased and pleasured the depths of her pussy in tandem with her pokemon's backside. She leaned down over the pokemon, giggling as she heard him gasp and moan at the feeling of her bare chest pressing against the soft pink material of his dress rather than bare fur. His gasps turned to moans however, and then to more of those squeals that set her loins ablaze as she began to fuck him in a shorter, sharper series of true doggystyle humps. As she knelt over the pokemon, able to encircle his four-foot-six frame with her five-foot-five body, Nyla lifted one hand from where they were supporting the weight and momentum of her thrusting, and curled up around Cinderace's chest. She kissed the pokemon on the back of his neck as she ran her hand up and down his dress' loose front, no cleavage to fill it out even if it hadn't been too big for the pokemon. He didn't seem to care in the slightest about the poor fit though, and when she moaned teasingly to him, his cries of elated pleasure intensified by another couple of degrees.

"You're so cute in that dress of yours. I see why you were admiring yourself. So soft and... mmh... g-god, yes... fuckable."

Another minute or so later and Cinderace was on his back, legs bent way back as Nyla lay over him with the pokemon's ankles resting by her shoulders, and her strap-on ever more urgently pounding deep into the pokemon's rump. By that point the pokemon's echoing and near constant squeals of pleasure were close to being matched by Nyla's own yelps and barks and panting cries of pleasure as each thrust send the toy within herself grazing against her g-spot while the harness which held the double ended dildo to her crotch rubbed teasingly against her engorged and aching clit. Collie and pokemon cried out to one another as their faces rested mere inches apart, Nyla occasionally bowing her head a little lower to kiss Cinderace on the muzzle but for the most part drawing back just far enough to watch his feature contorting in ecstasy, and show him her own wide eyed bliss at the same time. The rabbit pokemon's hands grasped at handfuls of fur upon Nyla's back as over and over again she seemed to find another gear, a way to pound him harder, faster, to alter the angle of her thrusts just enough to strike at some new sweet spot that Cinderace hadn't known existed until the very moment it erupted with bliss within him.

Just as both Nyla and Cinderace's cries were reaching a fever pitch though, orgasm barrelling towards the pair of brand new lovers faster than they could really process how they'd ended up in this unexpected but undeniably glorious situation, the border collie pulled back from the squealing, shuddering, bliss-stricken pokemon beneath her. He tried to cry out, to beg her in whatever way he could not to stop, but even as her glistening strap-on slipped from his ass, Cinderace felt Nyla's hands on his feet. He wailed bashfully but happily as she scooted back along the bed to its edge and rose shakily to her feet while pulling him along with her, bunching up his loose fitting dress so much that most of his fluffy white belly was now in view. The collie pulled Cinderace down until his buttocks were just barely resting on the edge of the sheets, and then with her own plump body standing upright, she not only reached down to guide her rubber cock back into the pokemon's ass, but extended her other hand at the same time and wrapped it around Cinderace's cock.

"G-gonna cum..."

She panted hungrily as she drove herself back into Cinderace's rear and began to fuck him with reckless, fevered abandon.

"...mmnhhgonnafuckingcum, C-Cinder. So... please..."

She begged as she humped urgently at the cute, dress-clad pokemon's tight and welcoming ass while stroking him, jerking him off in an equally giddy frenzy.

"...please, Cinder! Cum with me!"

Neither pokemon nor trainer could have held back more than a few moments even if they'd wanted to, but the almost instantaneous wailing that rang out as collie and rabbit alike careened over the brink was a tastement to their desire for one another and everything they had so recently learned they were able to share. It took almost all of Nyla's focus just to keep her on her feet, shuddering, convulsing, jerking forward as waves of pleasure crashed through her pussy while it milked her end of the strap-on. What energy she didn't use simply remaining upright and keeping her toy buried deep inside of Cinderace though was spent drinking in the sight of her pokemon's squealing, flushed and utterly joyous face as she jerked his cock throughout his own climax and watched the fire type writhe and thrash as he absolutely coated his belly and the bunched up front of Nyla's dress with eruption after copious eruption of hot, glistening cum.

Their climaxes were drawn out by their sheer longing to continue sharing one another's pleasure, Nyla fighting with everything she had to keep cumming as long as Cinderace did while the pokemon strained himself to do the very same for her. There came a point however where neither trainer nor pokemon had the stamina to continue no matter their will, and with a final giddy groan Nyla hefted herself back onto the bed, wrapped her arms under Cinderace's practically limp figure, and cuddled him close as she rolled over onto her back, leaving the pokemon's head nestled gently against her breasts.

"O-oh... Cinder... that was... that was so, so fucking... fuck!"

The collie gasped happily as the rabbit pokemon nuzzled against her breast, and she felt his lips kissing ever so gently at her nipple; not trying to excite her spent body, just to show her a little more of his adoration for its own sake. While Nyla craned her neck up briefly to peck Cinderace between the ears though, as fatigued as she was she couldn't help but take one more moment to admire how cute and naughty all at once he continued to look in that bunched up, ill fitting pink dress. Nor could she help herself as her head sank back to the bed and she simply cuddled her dear pokemon even closer to her bare body, his rear end still wrapped around one end of the strap on as the other lingered within her still wet, dripping depths. A soft giggle escaped her, and she whispered playfully to Cinderace as they lay together, revelling in their afterglow.

"Hey, Cinder...?"

The pokemon raised his head slowly, wearily towards his trainer.

"Later today... wanna see the suitcase where I keep the rest of the dresses I know I'm never gonna wear?"

By Jeeves

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