A Wilde Time
Request for CharlesDragon
Story by 2BIT
Tails (c) Sega; Nick Wilde (c) Disney


Toon Town, a wondrous place where toons from all media could gather and mingle. Many even chose to live there, but as the entertainment industry expanded, a lot of these characters had to live in other towns, even a place built for toons had a limited amount of space. Still, the original Toon Town was a popular location for toon-related events, conventions, celebrations and what have you. Today, there was a special convention being held just for fox toons to gather and meet. Ever since a fox portrayed Robin Hood in a classic Disney film, there had been no shortage of jobs for toon foxes. It was certainly interesting for them all to gather and meet up, to be able to get autographs from their foxy heroes, and to generally have a good time. As the first fox of video games, Miles "Tails" Prower was pretty busy. He had to do a few interviews about upcoming games, his thoughts about the movie, and sign a few autographs here and there. He really wanted to get away from it though, fame was more Sonic's thing, he was happier in the background. Eventually, the fans had moved on to another famous fox though, and Tails went to grab himself an ice cream and relax. He was surprised to find Nick Wilde running the ice cream vendor, selling "Pawpcicles." "Hey, two-tail. You look like you could use something sweet." Nick smiled, offering a popsicle. Tails nodded, smiling as he took the treat. "Kinda missing my girlfriend right now... Hardly get to see Cream these days with how busy I am..." he said, taking out a picture of his rabbit girlfriend and looking at it. He let Nick see as well, and the other fox grinned. "So, I'm not the only fox who's into rabbits, hehe..." he said, lifting his wallet and showing off a picture of himself and Judy Hopps together. Tails blushed lightly and nodded. "Guess so... Cream's just so sweet and pure." he chuckled. Nick nodded, pocketing his wallet. "I suppose Judy's kinda like that... in a butt-kicking sorta way. Don't tell her I said that." he murmured with a blush of his own. They both sighed wistfully at the same time. They were each thinking about how lonely their hotel rooms would be during the convention. Nick glanced at Tails and leaned against the ice cream vendor cart, resting his head in his hands. "Wanna spend the night in my hotel room, pal?" he asked. Tails looked at him with a bit of surprise. "Well, uh... S-sure, it'll be good to have someone to stay with. Thank you?" he said a bit shyly. Nick gave a soft chuckle. "Don't be nervous. It'll be a good time." he said, clicking his tongue.

So, that night, Tails accompanied Nick back to his room, the pair of them having some laughs as they swapped stories about their misadventures with their rabbit girlfriends. "And so I said, 'Chief Bogo? More like Chief Yo-yo!' ...Out of earshot, of course." Nick opened the door to let Tails in as he wrapped up a little story. The two-tailed vulpine looked around and quickly noticed that there was only one big bed. He didn't bring it up right away, though. It'd be more of an issue if it were a small bed, after all. It wasn't like they'd necessarily have to cuddle up to sleep in it. Nick found a chair by the dresser and plopped down in it, leaving Tails the bed to sit on. "I can't usually get such nice accommodations. I hope you're comfy." Nick smiled. Tails nodded. "It's very nice. Sooo... What do you wanna do now?" he asked, hanging his legs off the edge of the bed and watching Nick curiously. The taller fox was busy unfastening his necktie. "Hmm, well, how'd you like to have a little fun, seeing as we're away from our girls?" he asked, his tone playful and to the point. Tails blushed. He wasn't too surprised, considering he'd asked him to his hotel room. "S-sure...I mean, you think the girls would mind?" he asked nervously. Nick chuckled and tossed his tie around Tails' neck playfully. "They don't have to know... Or maybe they'd like to meet up sometime, hm?" he smirked, "But I do tend to prefer a girl, so how would you feel about being one for me?" he asked, reaching for his suitcase and opening it to reveal a collection of...dresses! Tails blushed deeper. He had worn a dress once or twice for some of the old Sonic cartoons, so it wasn't like he'd never done it before....

Tails took a look at the pretty girl's clothes that Nick had brought with him, trying to decide which to wear. "You planned this, huh? Inviting someone up to your room..." he said, his blush not going away. Nick shrugged. "Well, if I'm making you uncomfortable we don't have to do this, two-tail..." he stated. Tails looked at him with a cute smile. "No, it's fine! Not the first time I've...worn a dress..." he said bashfully. He finally picked out an outfit, and started to the bathroom to try it on. "I do hope it fits." Nick smirked, slowly starting to unbutton his shirt, already picturing how Tails would look as a girl. It didn't feel like much of a stretch to his mind...and that's part of the reason he specifically had what he thought would be Tails' size. He had hoped to run into the famous twin-tailed fox boy on this trip. He'd admired Tails' cute, sort of feminine build for years now. He sat with his shirt unbuttoned as he waited for Tails to change. The other fox had taken off his shoes and gloves, and then held a bra up to his chest with a blush. "Do I need this...?" he questioned. Well, he could stuff it with his own socks, they were pretty fresh and didn't smell. After giving himself some small boobs, Tails turned his attention to the dress itself. There was also a matching pair of shoes, some cute flat heels that might be slightly tight on his feet, but would complete the look. There was just one option in Nick's bag that Tails wasn't going to fiddle with. "Yeahhh, no makeup. I'd just mess it up, anyway..." he murmured before glancing in the mirror with a deep blush. He looked quite lovely in the bright yellow dress, though his tails held up the bottom of the dress a bit more than they should. He wondered what Nick would think...well, it was time to find out!

Nick was lying on the bed with his shirt open, his hands resting under his head as he hummed softly, waiting for Tails to come out and join him. As he heard the door open, he turned on the bed, leaving himself in a rather sultry pose as Tails stepped out. Nick licked his lips as he laid eyes on the lovely vixen stepping before him. Tails blushed, brushing the wrinkles out of the yellow dress as he emerged, and cutely twirled so Nick could get a good look at the outfit on him. "W-what do you think?" he asked shyly. Nick smiled and patted the bed beside himself. "Such a pretty girl you are... Why don't you join me up here?" he asked, winking at "her." Tails smiled cutely and climbed up onto the bed, sitting next to the other fox. They'd think of Tails as a girl for the night, despite the fact his body was still the same under those clothes. Nick sat up himself, crawling to Tails' feet and gently rubbing them, admiring her in those yellow flat heel shoes. "Indulge me for a few seconds... I promise I'll make you feel very nice when I'm done..." he whispered. Tails wasn't sure what he was doing until she saw Nick slowly lick his tongue against one of those heels. Tails chuckled softly. "She" was wearing a dress, so who was she to judge. Nick gently licked and sniffed at each shoe for a few seconds before slipping those shoes off, kissing the other fox's feet. "You have very soft feet, two-tail..." he cooed, taking a moment to lick at Tails' toes. She giggled ticklishly, blushing hard as Nick played with her feet. He didn't spend much more than half a minute teasing her toes with his tongue before he gently slipped her shoes back on. "Sorry if that made you uncomfortable at all... Carrots found it strange the first time, hehe." Nick said bashfully. Tails looked at him, and could see that his tip was peeking out of its sheath after that. She blushed and took his hand. "I'm glad to help you enjoy yourself..." she smiled.

Nick sat beside Tails on the bed again, hugging "her" close and giving her a kiss. Tails accepted the kiss, moaning cutely as Nick's tongue slipped into her mouth, his hands running down the back of her dress and mischievously fondling her two tails that poked out from under it. "Ohh..." Tails gasped softly as the kiss broke, looking into Nick's eyes and blushing yet again. The other fox smirked and winked at her. "I am gonna show you one wild night... I'm gonna take your cute foxhole from every angle..." he whispered, making Tails' face turn redder as he kissed her cheek, "So, care to get me ready, two-tail?" he asked playfully. Tails nodded slowly. "Sure, Nick, you sly fox..." she said, nuzzling his nose for a moment before she started to lower herself between his legs. Nick smirked, watching the crossdressing fox move. Tails really did seem like a girl with that outfit... Nick loved how she'd stuffed the bra to simulate breasts. He reached down to pet her head as Tails found his sheath, his tip already emerging. Tails shivered slightly. He could tell Nick was different from him down there...where Mobians had more human-looking cocks, Nick was endowed with a feral, knotted shaft. Tails blushed realizing he would knot her before the night was through. Still, she lowered her head, and gave Nick's tip a few quick licks. This made him purr excitedly. "That's it, sweetie... Get me nice and wet for you..." he whispered. As Tails continued licking, Nick's foxhood grew quickly, rising from its hiding place. Tails' tongue slid up from base to tip, getting a feel for his length. Her tongue felt Nick's knot as it emerged, and her heart fluttered. It was so big... The whole package, really. Tails' ears folded as she felt a bit of embarrassment to realize that this was getting her...him aroused, too. A bulge was starting to form in the dress, betraying his disguise. Once Nick was at full mast, Tails briefly took his length into his mouth, gasping softly over it as he coated it with saliva. Nick scratched behind his ear until Tails pulled back. "Good girl... Now, are you ready to take me for a ride?" Nick asked with a grin, lying back with his open shirt revealing most of his reddish-furred chest. Tails looked at him cutely, nodding.

Tails climbed over Nick, lifting the bottom of "her" dress as "she" positioned herself over his hard, feral cock. Nick smiled, admiring Tails' beauty in that dress, even though his own dick was poking out from under it now, messing with the illusion. It was fine, though. "Mmm, take your time, cowgirl. Ride me at your own pace." he winked, making Tails blush shyly. He placed his hands on Nick's chest and rubbed gently as he started to lower his rear end, shivering as he felt that tip poke his entrance. "I-I'm scared... I've never done th-this..." he whispered. Nick took one of Tails' hands in his, gazing up into the other fox's eyes compassionately. "Just gotta take the plunge. Trust me...you'll be fine." he promised. Tails nodded, and lowered himself down, gasping as Nick's hard shaft began to penetrate his ass! It hurt at first, and he whimpered, tears welling in his eyes. Nick reached up to wipe those tears for him. "I hate to see a pretty girl cry..." he cooed, coaxing a sheepish laugh out of Tails. Nick held him for a moment, letting Tails rest and adjust to the feeling of a cock inside him. Then, he laid back and let Tails continue. The girlish fox slowly began to move up and down, riding on his shaft. He seemed still in pain at first, but soon he let out his first soft moan. Nick smiled warmly to hear that, and took hold of Tails' waist, starting to thrust himself upwards a bit, making it a real ride for Tails! The cowgirl gasped, his head tilting back as he bounced on Nick's length, each motion loosening his ass up more, and making his cute fox dick bounce along with the momentum! Nick panted softly, his partner's cute moans like music to him as he watched Tails ride him while wearing that dress, looking very much like a vixen in heat. He soon sat up, and started to work his shirt completely off. "I'd say we're warmed up..." he huffed, "Now I wanna be on top..." he grinned with a sexy growl. Tails looked at him with a deep blush. "O-okay, Nick... I'm ready... t-take me!" he said in a girlish voice.

Leaving the dress on, Nick lowered Tails onto his back, admiring the twin-tailed cutie as he laid back, tails draped over the mattress under him, and legs spread open for the other vulpine, keeping the bottom of the dress spread open, too. Nick licked his lips as he held Tails' waist and pushed back into him, eyes locked on the cute baby blues of his vixen as he took him in the missionary position. Tails grabbed the bedsheets under him, gasping softly, each thrust of Nick's dick causing jolts of pleasure to fill his body now that his tight hole was loosened up. Nick's hands slid up that cute dress, feeling Tails' girlish figure. "Mmm, you're such a cutie... I can't wait to stuff your foxhole with my knot..." he whispered, leaning over Tails and playfully kissing his nose. The submissive fox let out a moan as that cock pushed deeper into him, that big knot starting to tap at his hole and beg for entry with each thrust. Tails blushed deeply. He'd never been knotted before. Wouldn't it be as though Nick was claiming him, making him his...something? He couldn't think too hard about it as Nick sped up his thrusts, his tongue licking at Tails' neck while his hands rubbed down his sides and... fingers wrapped around his neglected shaft! Tails' eyes widened. "O-ohh!! N-nick!! Ahhh, y-you're so good! Y-you're making me so w-wet!" he panted girlishly, his tip indeed starting to leak small amounts of precum. Nick chuckled softly and started to slow his pace. "Let's not race to end this too soon... Once I knot you we're done for the night..." he huffed. Since Tails didn't have a knot, Nick felt it necessary to point that out. Purring cutely, Tails hugged the other fox and nuzzled him. "Yeah, take as long as you want..." he cooed, seeming to really enjoy Nick's touch. Nick smirked and stroked Tails' hair gently. "How about we try a real fox-on-fox position?" he whispered, giving a flirty wink.

Tails was soon on his hands and knees atop the bed, his ass held up for Nick to admire. The bottom of the dress was held open by his two tails, allowing for a perfect view of that cute, yellowy-orange furred bottom. Nick smirked, lightly rubbing those butt cheeks in his hands before sliding his cock back inside, ready to pound that ass doggy-style. Tails let out a soft, feminine moan as Nick slid deep into him. "Ahhh... K-keep going you fox stud..." he gasped, flattening his ears and blushing deeply as he talked like a slutty vixen in heat. Nick wrapped his arms around the fox under him and started to thrust, able to pound into Tails at a pretty good pace now that he was well and truly loosened up. He felt the twin tails of the girlish fox gently wrap around him as he humped that lovely ass, those tight walls massaging his shaft and making him moan himself. Nick smirked playfully, his hands sliding up and grabbing at the fake boobs that Tails had stuffed for him. "Not bad...you sure you're not a girl for real?" he joked, rubbing and playing with the stuffed bra cups through the dress, imagining he was groping real breasts. Tails huffed lustfully from his thrusts, and his face reddened bashfully as he felt Nick playing with his chest. For tonight, he basically was a girl...his ass being fucked like it was a lady's love tunnel. He gripped the sheets under him and let out a slightly louder moan, goading Nick into speeding up his thrusts. That knot kept pounding at his entrance, begging to tie them together. "Y-yes! Ahh! I-I'm your girl, Nick! M-make me yours!" he panted, lifting his head and gasping in lust as the fox cock inside him struck a sensitive spot! Nick nuzzled and licked Tails' neck, seeming quite pleased with himself. "Alright, two-tail... I think I'm r-ready to fill you... Let's get you on your b-back so I can look you in the eyes..." he huffed, kissing Tails' cheek.

Tails laid back on the mattress again, his cute butt lifted quickly so that Nick could slide back inside him once more. The dress was quite wrinkled and sloppily hanging on his body, but neither cared much as they moaned, Nick's long dick thrusting deeper and deeper into him, his knot fighting for entry. Nick looked Tails right in the eyes, a wide grin on his face as he watched the other fox blush and pant and gasp in lust. He grabbed the "breasts" of Tails' outfit again, leaning in close so their noses touched. "Once I knot you we're stuck for the night... You want it, cutie?" he huffed. Tails hugged him tightly, his sweet blue eyes meeting Nick's gaze as their faces drew closer. "I n-need it... Please, N-nick..." he gasped, their lips meeting in a gentle kiss. Nick held him down, moaning into the kiss as he made a powerful thrust, then another... Tails broke the kiss with a loud, lustful cry as he felt the knot stretch him open, popping inside and tying the foxes together! Their voices filled the room with moans as Nick began to shoot his load, his pent-up cum pumping and pumping into Tails' behind, the knot keeping it from leaking and making sure to stuff him nicely! Tails' eyes rolled up, and with several pants of satisfaction, he came as well, his own seed squirting up all over his dress and mussing up Nick's fur a bit as well. They kissed again, and Nick began to hold him more gently as both of them expelled their loads, beginning to pass into the lovely feeling of afterglow. Tails nuzzled the other fox, blushing deeply. "Our secret..." he whispered. Nick nodded. "Sure, two-tail... I wouldn't want you to feel embarrassed about this, heh..." he said softly, cuddling his adorable little buddy.

There would be no pulling out for some time. They'd be sleeping in each other's arms. In order for Tails to be comfortable, Nick helped to remove the dress, the pair of them resting in the bed naked while the cum soaked dress was tossed to the floor. They laid awake for a bit, cuddling closely. It felt strange to have Nick's dick stuck inside him like this, if only because he'd never been knotted before. It wasn't unpleasant though. Still, as Tails nuzzled into Nick's chest fur, the other fox had a mildly apologetic look. He felt just a slight bit selfish. But...they still had some more days at this convention. Nick smiled and whispered into Tails' ear. "So, tomorrow night... I'll be the girl, 'kay?" he cooed, giving Tails a wink as he looked up at him. Tails blushed and gave Nick a smile. "I'll look forward to it, you 'Wilde' fox..." he chuckled. Nick nodded and started to blush. "This could be the start of a beautiful friendship... G'night, two-tail..." he purred, kissing Tails' forehead before they both began to drift to sleep.

End