A High-Tailed Bet

Story by draconicon on SoFurry

, , , , , , , , , , , , , , , , , ,

Fox and Falco have a rather extended bit of fun. A lost bet results in crossdressing and roleplay.

Commissioned by bbbuuu

If you want to get a commission for yourself, keep an eye on my journals and my twitter DraconiconWrite for updates on when I'm open.

If you're interested in supporting me, or just contributing more regularly - and cheaply - than commissions, consider visiting my Patreon at https://www.patreon.com/draconiconlibrary?ty=h for good rewards and better stories.

Enjoy.


A High-Tailed Bet

For bbbuuu

By Draconicon

Falco couldn't believe that they were actually going through with this little bet. Well, actually, he could, but only just. Fox had been getting more adventurous in bed, lately, and it was definitely paying off for him. All the stuff that they were getting to do together meant that he got to get off hard every time that they got going, and Fox kept finding new ways to make it interesting.

Bet the boss is just doing it so that he has an excuse to go through with it, he thought with a chuckle. Lose a bet, and suddenly, he doesn't have a choice. He has to go through with it. Fucking slut.

Not that he would ever say that to his boyfriend out of play. He cared too much for Fox for that, rivalry between the two of them notwithstanding. They were close enough that they were more than willing to go balls to the wall for one another on any serious issue, but as soon as they were just playing around...well, that was when things got interesting.

Beep.

Falco paused at the bottom of the Great Fox's gangplank, looking down at the communicator attached to his wrist. He tapped the button on top, and his partial grin grew to a face-splitting smirk.

"Oh ho ho, hello..."

Fox had just sent him a picture, and what a picture it was. His wingmate was all dressed up for the night, but not in anything like the usual jumpsuit or pants-jacket combo that he usually wore. No, that was all gone, replaced with a beautiful leather jacket over a skimpy little top, with a skirt that barely went to the thighs and leather boots that went up to the knees. A wig that made him look a little more feminine and a bow along the base of the tail completed the look. If Fox hadn't been a vixen, then he was a damn good sissy-boi.

"Mm-hmmm. Definitely glad I won this bet..."

He memorized the image and then minimized it. The last thing he needed was for Peppy or Slippy to see just what the pair of them were getting up to. This was a bet between the pair of them, no more, no less. And besides, Fox was pushing the boundaries, anyway. He didn't want to make his wingmate feel like he'd gotten outed as a pervert.

Still grinning his ass off, he walked off the gangplank and into Corneria City. Time to find his partner.

#

It didn't take long to find the public plaza where Fox was waiting to be picked up. The whole thing was as natural as they could make it. The bet had been that whoever shot down the most Venomian ships in the last engagement would do something sexy, silly, kinky for the other. Whatever Fox might have asked for, Falco was pretty sure that it wouldn't have been anything like this.

Look and act like a fangirl for the night, Falco had decided after he'd won. He had expected Fox to turn down the demand, and he would have allowed his boss to do just that. However, when Fox had gone along with it...

Well, it was safe to say that the pheasant had been stricken with a boner from hell. Still was, as a matter of fact, and he doubted that it was going down anytime soon. He'd just have to bury it in his fangirl a few times.

Various alien species called Corneria home, and he walked in and out among their ranks as he searched for his boyfriend. The fox was nowhere to be seen at first, but after circling the whole thing twice, he spotted that bow-marked tail right there in the middle of the plaza. He grinned, making a beeline for Fox.

He was about ten paces back when Fox turned around, and he was a little gob-smacked to see just how far Fox had taken it. He'd even painted his fur with a bit of makeup to really sell the illusion of being a female. No breasts, of course, as that would have been harder to make happen this quickly, but the face was perfectly that of a vixen.

Well, a vixen version of Fox, at least. If one really looked close, one could make out that little scar under the cheek, the little burn mark that was just under one ear after too close a hit on one of their dogfights. They were all definite signs that this was the right vixen, and not just someone that had managed to dress the same.

He and Fox met each other's eyes, and his wingmate blinked before falling into role. A rather ditzy-looking smile appeared on the other male's face, and Fox giggled as he clapped his hands to his cheeks.

"Oh, wow! Like, wow! It's Falco!" he said, his voice pitched up in imitation of a woman.

It was so ridiculous that it was all that Falco could do to keep from laughing. Even as Fox ran over to him, eyes wide as a fan's should be, he could still barely believe they were doing this. If he'd been in Fox's position, he would have been embarrassed as all hell to be in public in a skirt, in boots that had a heel more than big enough to make his ass pop. Yet, here was his partner, completely fine with it, getting into the role way more than he had to.

What did I do to deserve this guy?

"Oh, wow, I didn't think that you'd be coming into the city. Please, you've gotta let me show you the sights, or, or, just, uh...you know..."

Fox leaned in a bit closer, dragging Falco's hand around his hips. It took a second for him to realize that his boyfriend was pushing it just that little bit further than usual, making him grope the 'vixen' in public. Well, if that was what he wanted...

Falco curled his fingers that much more, and Fox yelped in surprise. He chuckled, pulling the 'vixen' around.

"Heh, Falco's always got time for his fans. Come on, girl."

"Oh? Y-you do?" Fox asked, blushing.

"You bet your ass, babe."

"Well, you got my ass now..."

"Heh, I saw it across the plaza. I always hit my target."

Wow, that was corny.

And it appeared Fox agreed, as 'she' rolled her eyes ever so slightly. That said, his wingmate didn't pull away, and seemed to push his ass that much further into his grip. Well, he wasn't going to complain about that.

They walked across the plaza to one of the bigger hotels just across the way. Falco was fine with all the eyes on them; he liked being a star, having people stare, seeing them appreciate him for what he was. That was just part and parcel with being a celebrity. Fox, on the other hand...

He could feel the stiffening muscles in those tight glutes, and he would have chuckled if it wasn't for the fact that he knew that it would only make matters worse. He dragged Fox a little closer.

"Heh, what's the matter, babe? Having second thoughts?"

"No way! Not when I get to have Falco to myself," the 'vixen' said, that voice going up even higher.

"You keep talking like that, and people are going to stare more. Act natural man," he whispered.

"I can't help it. People are staring."

"What are you afraid of?"

"Them seeing the panties, for one!"

"Oh ho ho, you went that far, huh?"

Fox groaned, then yelped as Falco slid his hand under that short skirt. Sure enough, there were the panties, a nice pink pair that cupped those cheeks nice and firmly. He followed the part of the cheeks, grinning as he found that the panties ran right up into the gap between the cheeks, and that it was all too easy to find the fox's pucker waiting between them. One feathery finger rubbed against it -

"Nnnngh..."

"What's the matter, hmm?" Falco whispered as they walked through the lobby of the hotel. "Afraid someone's gonna see you pitch a tent?"

"Falco, come on. This is - ah!"

The bird had just managed to sneak the tip of his finger past the edge of that hole, working it in, teasing that pucker by holding it open with a bit of silk. He smiled, pulling his hand back as they reached the front desk, leaving his partner stewing in his own need.

"Room for the next few hours," Falco said.

"I'm sorry, sir, we only put them out by the night."

"Yeah? Does the name Falco Lombardi open any doors?"

"...Strangely enough, it does, sir." The mole behind the desk nodded twice. "Let me get the paperwork ready. And you will be staying alone, or -"

"Hey, bud, does it look like I'm staying alone?" He pulled Fox over by the tail, resting his hand right on 'her' ass again, possessively as he could. "I got a fine piece of tail that wants to show me a good time. That's all that matters."

"Uh, yes, sir, very good, sir."

The whole situation was only getting more and more ridiculous, but Falco utterly loved it. The way that Fox was shifting from foot to foot, the way that his partner's tail was trying to dislodge his hand from that panty-covered ass, the way that Fox was clearly doing his best not to get noticed and recognized: it was all adding up to one hell of a pleasurable time. He kept rubbing those ass cheeks, on the verge of spanking them again when the mole finally handed over the paperwork.

"Here you are, sir."

"Yeah, yeah..."

Signing the stack in short order, he was given a room key and they were off. Fox kept trying to move ahead a little faster, and Falco kept pulling him back.

"Hehe, not so fast, babe."

"Come on. Just...faster..."

"What's the matter? Thought you wanted to show Falco the sights?" he teased.

"You bastard..."

And yet, there was no real complaint as they walked towards the hallway that would take them to the elevator, and from there to the suites at the top of the hotel. As embarrassed as Fox was, it was clear that his partner was more than slightly into the whole thing. Otherwise, why would he have agreed to the bet in the first place?

There were various eyes on them, mostly on him. Falco expected that. All members of the team were some level of celebrity, with Peppy being the least known and him and Fox vying for the position of most known. He imagined that just at that moment, Fox was wishing that he was in Peppy's shoes. Anyone that took too close a look at his face ran the risk of figuring out just who he was, and considering how much Fox was trying to keep a respectable image at the moment, that wouldn't help him much.

At the same time, he could feel the high level of sexual tension just pouring off of the fox. He was clearly interested, clearly needy, and the longer that their walk took, the clearer it was that Fox was getting turned on by this the same as he was. There was a slight bulge in the front of Fox's skirt, one that was steadily growing bigger and bigger as guests of the hotel looked at him and then looked on.

"Heh, you're going to give yourself away if you get any hornier," Falco whispered.

"Yeah? Bet you'd love it if I did."

"Bet you'd love it, too."

"Shut up."

"Heh, get a big boner that tells them you're a guy, and then get them looking at your face. Knowing that they've seen you somewhere before."

"Shut uuuuup."

"And then figuring out that you're not just some floozy, but that you're ready Fox McCloud. Not the pilot, but the slut."

There was such a groan from that tease that Falco actually did do a quick 360 to make sure that they hadn't been made as a couple. Much as it was fun teasing Fox about that, the last thing that they needed was for someone to think that his wingmate had gone soft. If that happened, then the contract bonuses would start going down, and then they'd need to pull off some big job to show that they weren't soft, after all.

Not worth the work, not for that kind of reward.

With one last close call with a fennec fox that looked at his wingmate as if she knew him, they reached the elevator. The metal doors closed, and they were sealed in the rising chamber. Fox let out a long, slow sigh of relief.

"Heh, better?" Falco asked.

"You...are...an absolute prick, you know that?"

"Yeah, but you enjoyed it."

"...Not the point."

"If I lifted the front of that skirt, would I see a tent?"

Fox fixed him with a stare, then slowly lifted the skirt himself. Falco went slightly wide-eyed at the sheer confidence in the display, and his eyes dropped down to the panties that he'd been feeling, but not seeing.

They were a soft red set, lacy around the edges but soft and not-quite-sheer in the middle. Sure enough, Fox's cock was up and hard, stiff and throbbing throughout, and he could see that there was just a hint of wetness at the very tip. He grinned to himself, his own shaft rising in his pants, pushing forward just a little bit.

Fox chuckled.

"Looks like I'm not the only one enjoying it, then," he said, dropping his skirt again.

"Not at all. You're rocking that, Fox."

"Yeah, well...you know what they say about foxes."

"Loose as fuck?"

Fox punched him in the shoulder for that, and Falco laughed. He had completely deserved that.

The elevator reached their floor and they stepped out, walking down the hall to the proper suite. One tap of the keycard and they were in, the door slipping shut behind them. A waterfall ran down the wall near the door, effectively muffling anything that might be done in the penthouse so that nobody outside could hear. Falco could imagine a number of useful things with that.

However, before he could say much, Fox groaned and reached down for the laces of his boots. The bird chuckled.

"Getting a little sore, there?"

"You ever try walking around in heels?"

"I'm the one that won the bet; I'm gonna say no."

"Smart-ass."

"Is it that bad?"

"Worse."

Falco shook his head, walking around his wingmate to check out the rest of the penthouse. There was a large bathroom right by the front door, one with a standing shower and a large bathtub. Jacuzzi, too, which meant that they'd have a little fun while cleaning up after they were done.

The main room was a simple affair, probably meant to be booked in advance so that they could get it all decorated according to the tastes of the person checking in. The couch looked comfortable, and there was a good holo-projector set up. Looked like a high-quality one, too, so if they wanted to get some porn later, it'd be a good show.

Chuckling to himself, he kept walking down the hall to the bedroom. It wasn't that long a hallway, and the bedroom itself was quite nice. A king-sized bed with proper cushions and pillows, rather than the bunks that they had to deal with on the Great Fox, made him wonder if it'd be a good idea to stay for the night rather than just for a couple of hours. The temptation was such that he almost gave into it right then and there.

He walked over to the bed, running his hand over the mattress and shaking his head slowly. It had been months since he'd seen a proper bed, and just feeling it under his hand made his back ache. He wanted to throw himself into it and start sleeping off all the days in a bad bunk, to forget about it for a while.

The soft groans of relief that came from further back in the room, however, pulled him back from that fantasy. Besides, there were quite a few other things that might be done tonight.

He turned around as Fox walked into the living room, the other pilot barefoot now and getting comfortable. He looked like he was about to pull off his skirt when Falco decided to step in.

"Hey, did I say that you could get undressed?"

"Well, considering what we're here for..."

"I didn't say that I wanted to start that right now. After all, you're supposed to be here as my fangirl, remember?"

"..." Fox's eyes narrowed. "You're not thinking what I think you're thinking."

"Oh, I might be."

"You seriously want me to go down and -"

"And keep acting the girl. Yep."

"...You prick."

"Gonna be down your throat in a minute."

His partner glared at him, but the sight of that slow-rising bulge was all the confirmation that Falco needed to know that he was going to get what he wanted. Fox had always been eager to go along with the more extreme stuff; he just needed that little push that took the choice away from him. Falco was more than eager to give him that push.

"Come on. On your knees."

"Nnngh..."

Slowly, Fox did as he was told, going down to one knee, then the other. He looked so...swishy, he supposed, in that skirt. It hugged his hips in such a delightful way, and it made it clear that he was built as a bottom. That ass was just begging for someone to come up behind it, spank it, smash it, use it. Falco groped himself through his pants as his partner knelt, chuckling to himself.

"You look good on your knees. I'm going to have to keep you there for a while."

"Falco, I swear to god -"

"Ah ah. Is that how a fangirl would talk?"

Flabbergasted face aside, he was still enjoying seeing Fox on his knees so much. There was something inherently satisfying about it, particularly with the way that the other man was already spluttering with confusion and exasperation. Having that bit of power, knowing he could fluster his partner so much, was always intoxicating.

He tapped Fox on the lips, silencing him. With his other hand, he played with his zipper, on the verge of pulling his cock out.

"If you want to play, then play. What would a fangirl say?"

"...Like, oh, my, god. Falco, you're gonna let me play with your dick, right? I've been dreaming about it for so long."

He couldn't tell if that response was funnier or more arousing, but either way, it kept his dick hard and put a smile on his face. Fox looked like he was about ready to spit venom, but considering that he was still on his knees, still staring right at the bird's bulge, that didn't mean squad. Fox might have been the leader of the group, but when you hit his buttons the right way, he was as big a whore as you liked.

Still fondling himself, Falco pulled his partner forward, grinding him against his crotch. One grind, two, three, thrusting along his face, and Fox groaned lustfully. The first time it was a bit masculine, but the second and third times, definitely more feminine. He was getting into the role now that he had some encouragement.

Let's see if he can keep that going...

The bird grinned as he slowly pulled his zipper down, finally letting his cock out. Going commando always meant that he had something to show off, and this was no exception. His wingmate's eyes immediately went to his cock, and Falco swayed his hips from side to side, showing the large rod off.

"Yeah, you like it, girl?"

"Mmmph. It's, like, so hot."

"You want to suck on it, don't ya? Well, show Falco what you can do with his joystick."

He grabbed for Fox's head again, but it wasn't needed this time. The pilot leaned in, his mouth open, and that warm mouth wrapped around the head of his cock with all the eagerness that he could have ever wanted. The bird groaned, his toes curling in his boots as he felt that tongue working down along the underside of his shaft, steadily creeping towards the base. It was always a trip feeling his wingmate doing this, just because of the shape of that muzzle and how damn hungry Fox always was for this.

Groaning under his breath, he rested his hand on Fox's head, slowly encouraging him further and further down. Bit by bit, slippery lick by bobbing bounce, they finally made it to the base. He groaned under his breath again, feeling the head of his cock popping into Fox's throat. Just as tight and wet as ever, but seeing him all dressed up like this, looking like a vixen, looking more like the sub and slut than usual, was just doing something for him.

With his cock throbbing like crazy, he slowly pulled back, dragging it over Fox's tongue, tilting his hips slightly so that he brushed against the roof of the fox's mouth. Just that little bit of a tease, making sure that he got that taste all through the muzzle, and then he slammed forward again, grinding his cock on Fox's tongue, working it deeper.

In, out, in, out, each thrust another little tease for the both of them. Fox was moaning, and Falco was grunting and spitting out teases as best he could.

"Heh, you like that, huh? You like getting a star's cock?"

"Mmmph..."

"Yeah, you know. Good girl. Keep on sucking, and you'll get a star's cum, too."

Fox didn't stop sucking, though he did occasionally glare at the teasing. There was something about that helpless face which only made it better, though, and he kept thrusting, kept fucking, kept pushing his luck that little bit more.

Fuck...fuck, he looks so hot like this...

He could feel his load bubbling up, and the decision whether to cum or hold back was upon him. Much as he would have loved to jam his cock down Fox's throat and blow the first load of the night, there was something else that he wanted even more. Something that he hadn't had for a little while, something that he needed.

Pulling out and panting, he stared down at the 'vixen' kneeling before him. Fox was panting, too, his mouth connected to the bird's cock with a long string of drool. The pair of them groaned together, neither quite able to believe just how horned up the other ways. Who would have thought that Fox would love crossdressing so much?

"Turn around."

"Huh?"

"Turn around. I want your ass. Now."

They were both grinning, slightly ruining the illusion of the 'fangirl', but Fox did as he was told. That skirt flipped up, just over the base of the tail, and he had a perfect view of that hot pair of ass cheeks. The sheer pleasure of seeing that ass, seeing the panties that were barely covering the cheeks properly, knowing that he was about to have that muscular rump pressed firmly against his cock...

Fuck, it was hot.

Gripping the edge of the lacy panties, he slowly dragged them down. Not all the way, just enough to expose the gap between the cheeks, to let him see that waiting pucker. He licked his lips at the thought of just how much he was going to enjoy this, and Fox swayed his hips. There was just enough extra there that he could just about imagine that this was a real vixen rather than his wingmate, a real fangirl instead of his boyfriend.

"Mmmph...I'm going to pound the living shit out of you."

"Heh, says you."

"You think I won't?"

"I think you'll break before I do."

SMACK!

A quick spank drew a sharp yelp from the 'vixen', and Falco yanked that ass back against his cock. The way that the skirt drew attention to it, framed it, and the way that the panties were pulled down just enough to show that hole made it all the easier to imagine his boyfriend as his girlfriend, and he smirked as he gripped 'her' hips all the harder.

"Let's just cut to the chase, huh, Fox? No fangirl comes on to their idol without begging to be fucked."

"Mmmph..."

"And you know you miss my cock."

He smacked his dick against that pretty little pucker, rubbing the dripping head against the slightly wrinkled flesh. It puckered, alright, puckered and twitched against the tip of his cock, and Fox groaned under him, confirming his guess. The pilot had been waiting for it for a while, since the pair of them didn't get the chance to get up to much beyond handjobs and oral on the ship - Peppy and Slippy were too annoying and interrupted too often to get into a scene - and this was a rare time for them to really indulge.

He knew that he could push it further, make Fox say things that would get the other man blushing harder than ever. He could have pushed it, made Fox act like the bimbo all through the night, acted like the dick-hungry airhead that they both knew that he really wasn't. It would have been easy to turn the scene that way...

But he didn't. He wanted to fuck, and that was exactly what he was going to do.

Spitting on the 'vixen's' hole, he rubbed his cock against it a few times, smearing pre-cum and spit around before slowly sinking in. Fox groaned under him, arching his back as he always did, and the bird grinned as he felt that slow entrance. The way that the rim gripped around his tip, the way that the hot inner walls clenched before pulling on him, the way that Fox shivered with each new inch sliding in: they were all familiar, and all contributed to making him stiffer and stiffer still.

He took it slow, making sure to enjoy every little sensation that he could get out of his partner. In for a bit, then pulling back, then in a bit further, drawing a moan from his slut. In almost halfway, adjusting his position so that he could grind on that prostate on the way back out, then sliding right back over it again. Fox mewled happily under him, shivering, biting his lips, showing just how into it he was.

Falco reached around, gripping his boyfriend's cock through his panties, feeling just how wet and full of pre-cum they were. Dripping easily, soaking his fingers with pre-cum, giving him just another reminder of how needy his 'vixen' could get as soon as he got his cock into 'her'. He smiled, pulling back slowly, feeling those inner walls clenching around him again, feeling them trying to drag him back in.

POP!

But he dragged his cock all the way out, instead, making it bounce up and down in the open air. Fox gasped, his hole open, but slowly closing again, tightening without something to hold it open.

"Mmmph...you bastard..."

"Oh, I'm sorry. Do you want it back?"

"You know the fucking answer to that."

"Then shake that ass for me. Show me you want it."

As his partner did just that, swaying his ass back and forth, making the cheeks shake just enough to look appealing, Falco grinned. No matter how many times they went through this, no matter how much of this was a 'bet', they both knew that they were here for the fun of it. Fox liked being pushed around, and he liked to do the pushing. It worked out well for the both of them, and it meant that he got some fucking hot shows. He stroked his cock to the sight of that swaying ass, licking his beak.

"Yeah, that's some prime ass, Fox..."

"Mmmph...you going to put your dick back in or what?"

"Hehe, patience..."

It was fun to tease. He could have taken all night to tease his little slut, but at the same time, he was just as eager as Fox was, deep down. That hole was calling to him, and he was going to answer.

With one hard thrust, he buried his cock inside his partner again, and this time, he set to fucking the 'vixen' good and rough. Fox yelped, falling against the floor, face-down, ass-up, and they got right to it. In, out, in, out, roughly ramming against each other, feathery crotch and furred ass meeting again and again and again. Each time that they came together, it was announced with a loud clap, and then they came apart, spit and pre-cum linking them together as it oozed from Fox's asshole.

In, out, in, out, each time slamming in that much harder, coming together with force and frenzy. He could feel that tightness gripping him, muscles trained in all kinds of exercises milking his cock for everything that it was worth. Forward, back, forward, back, his balls swinging forward and gently tapping his lover's pair through the panties, a scant reminder that he was fucking a male rather than a female.

Fuck, you're always getting hotter...

He could hear the soft grunts and the faint 'spluts' of pre-cum hitting the inside of Fox's panties, and he knew that his partner was as close to cumming as he was. He picked up the pace, throwing in a spank here and there to make Fox tense up, to feel that tightness get that little bit tighter. It milked his cock like nothing else could, and he groaned loudly.

"Almost...there..."

"Give it to me, Falco. Give me that load."

"Mmmph...gonna...do that..."

"Give it to me!"

With one last thrust, Falco buried his cock deep. His balls pulled up and he moaned as he let loose, his cock pulsing as he came. One shot, two, three, before it started tapering off a bit. His balls kept churning, his cock kept pulsing, and he shivered from head to toe as he felt the sheer pleasure of blowing his load inside of that sexy foxy butt.

It clenched around him, milking him of everything that he had, and eventually, he slumped backwards, popping his cock free. It was quite the sight left behind, a slight gape - just enough to see that the rim wasn't going to immediately close - and some of that load slowly oozing out.

"Mmmph...that's hot," he muttered.

"You like the view?"

"Heh, you know I do."

"Good, because I didn't finish yet. Get your beak in there, Falco."

"Oh, now you're calling the shots?"

"Unless you can keep on fucking me, yeah, I am."

He chuckled. So much for getting Fox to break on his dick. Then again, that only happened about half the time. The rest of the time, his boss was good enough to outlast him, and that meant that the roles started switching. If he was going to get the chance to fuck again, then he needed to get Fox off at least once.

"Alright, man. Come here and take a seat. I'll get you off."

"You better," Fox said, the pair of them going to the bedroom for round two.

The End

Summary: Fox and Falco have a rather extended bit of fun. A lost bet results in crossdressing and roleplay.

Tags: M/M, Fox McCloud, Falco Lombardi, rule 34, boyfriends, crossdressing, embarrassment, oral, blowjob, anal, skirt, panties, teasing, roleplay, Starfox, orgasm, cum, creampie,