Taking Losing Bets

“That's such a stupid bet. Why would I do that?” protests an indignant Thunderlane towards a smug Soarin. The dark gray pegasus flaps his wings as he tilts his head back, then tucks them back in with a frown.

“It's only stupid if you plan to lose, and if you plan to lose, why would you even argue with me in the first place?” Soarin retorts as he holds up the pony cheerleader costume, shaking it to emphasize the stakes.

Thunderlane snorts, looking away for a moment as he thinks, then his eyes turn back towards the outfit before the rest of his head follows. “F... fine. You're on, but when I win, I don't want you backing out of your own stupid id—”

“Good!” Soarin interrupts loudly. “So, the bet is for the whole costume, except pom poms, cause who wants to carry those things around?” The pale-blue pegasus shows off each piece of clothing before putting them back in a nearby locker, then shutting it with a loud, metallic clank, sending an echo through the empty locker room. He then turns and grins widely at Thunderlane before continuing, “And you have to leave it on for the entire day, walking around in public where everypony can see you.”

“Whatever, just hurry up and finish cleaning so we can go.”

Soarin gives him a nod and gets back to cleaning the small locker room, “So, where do you wanna eat tonight?”

* * *

The next day, both pegasi find themselves cheering amidst a loud crowd of ponies in stadium stands, each shouting for the two teams in the field. It's a buckball competition between the School of Friendship and the School of Magic, and their bet is on who will walk away victorious. Thunderlane looks over at Soarin with a wide grin as the half-time bell sounds with his team leading by one. Soarin looks back at him, but doesn't seem at all bothered, giving him a small nod.

The cheer squad for the School of Friendship is impressive, and even ponies of the opposing team seem caught up in the celebration. Unfortunately for the team itself, fatigue is setting in, and it begins to show on the field. By the end of the match, the School of Magic scores one final goal, ending five to four.

Soarin chuckles and then cheers for the winning team, then looks over at Thunderlane with the widest grin of satisfaction. He had won the bet.

Thunderlane stares back nervously, swallowing his pride and dignity as he accepts his defeat. A small part of him hoped beyond hope that any second now, Soarin would laugh at him and tell him it was all just a joke. He doesn't really have to—

“Alright, let's get to the locker room and dress up the losing mare,” Soarin teases as he hops up off the stands and takes flight, hovering in place to wait for Thunderlane to follow.

Thunderlane's ears droop as he hears the word 'mare,' unable to believe that he's just accepting such a demeaning label without protest. He did lose fair and square, after all. In his mind, he curses his stubborn pride, which both got him into this mess to begin with and will now lead to him seeing it through.

With a sigh of resignation, Thunderlane hops into the air and flies next to Soarin, then the two of them make their way towards the locker room to find a spare outfit. It'd take a while for the teams to make their way there, leaving plenty of time for them to get what they need and leave.

Within the locker room, Soarin happily trots inside with his head held high, excited about what's to come. Thunderlane follows with his head down, trotting a little slower and quieter, dreading his punishment. Soarin chooses an unused locker and pulls it open, revealing his prize. Piece by piece, he pulls out a cheerleader outfit, tossing them at Thunderlane. A violet sequin vest, a frilly purple-and-aqua skirt, and lastly a pair of violet panties. The gray pegasus watches them all fall to the ground in front of him, then Soarin turns towards him expectantly as he shuts the locker.

“Alright, haha, it was funny, but you can tell me you were just kidding now,” Thunderlane says as one last line of defense. The way Soarin laughs at him extinguishes the last vestige of hope he had to renege on his deal.

“Didn't you add something about not backing out of it if I lost?” Soarin asks, although he already knows the answer—both of them do. The pale-blue pegasus nods towards the clothes crumpled in a pile on the floor. “Go ahead, then. Dress up for me.”

Thunderlane looks over the clothes, then picks up the vest and stares at it, holding it out towards Soarin after a few moments. “This is too small, though. It's made for teens.”

“Guess you'd better suck in that gut then, huh?”

Soarin was entirely unsympathetic. Their previous argument had gotten pretty heated over something as stupid as a no-stakes buckball match, and now it was time to get some payback for the annoyance. Thunderlane stops objecting and slowly slips on the tight vest, indeed needing to suck in a bit in order to zip it up. Luckily, the threads were partially inlaid with magic to increase the natural sparkle effect, so perhaps it wouldn't burst open when he relaxed his body into it. So far it seems to be holding.

“See? Easy stuff,” Soarin adds unhelpfully as Thunderlane looks over himself. Next came the frilly skirt. At no point in his life had Thunderlane even thought about cross-dressing. He blushes deeply and pants lightly in embarrassment as he looks over the skirt, wondering how he was supposed to put it on. “Want some help with that?” asks Soarin with a chuckle.

“Don't even think about it,” Thunderlane says quietly and coldly, deciding to just attempt to put it on however he could. Once it was on, he spun it around until it looked right, and his blush grew even darker. “I hate you so much.”

“C'mon, you look great. Like a real cheer mare,” Soarin says in mock support, looking over the thoroughly-degraded Thunderlane. “Only one thing left.”

With a dejected sigh, Thunderlane picks up the tight panties, then gulps. These would definitely leave nothing to the imagination. He turns away from Soarin as his embarrassment grew to unsustainable levels. There was no way he could look at his face as he did this. Slowly and carefully, he slips the panties on around his hinds, sliding them up until they pressed into his sack. Tucking them inside, he continues pulling them up, the fabric wrapping around his sheath and at ending just under his dock. He could feel it rubbing firmly against his tailhole and squeezing his genitals uncomfortably tight. With great effort, he manages to tuck his sheath and balls inside just enough that the edges of the panties hugged around them instead of crushing them, though movement was now nearly impossible. Without looking at Soarin, he stutters out, “S-so, how's that? Good enough?”

Soarin begins to blush as he looks over his friend, completely caught off-guard by how it makes him feel. His heart speeds up and he gulps down a bit of nervousness before he answers, “Looks fine. Uh, yeah, that's fine how it is. Walk around town like that and consider the deal done.”

The tight clothing accentuated his natural curves, making him look more feminine, though it was still obvious he was a stallion. The skirt teased at hiding his male bits, and from some angles you couldn't even see them. Best of all was the tight panties that covered his anus completely, but showed its outline clearly through the fabric, as well as hugged his orbs against his body and almost completely hid his sheath. Soarin was staring silently for an uncomfortable amount of time, to the point that Thunderlane raised his voice when he wouldn't answer.

“Huh, what?” Soarin asks as he blinks away the image of his friend's rear.

“I said, what parts of town do I have to walk around in before I can take this off?” Thunderlane asks with his head lowered. He stole glances now and then at Soarin, still avoiding direct eye contact, his face completely flushed red.

“Oh, uh, hmm. The main square, I guess? Just walk through public, I'll tell you when you're done,” Soarin adds with a nod to himself. Was this still a good idea? he wonders to himself.

Thunderlane looks directly at him and stands up straight. “Wait, you're gonna follow me around?”

“Well yeah, I have to make sure you actually do it. What if you just hid somewhere and then told me you did it?”

The thought had crossed his mind, but he still feels offended by the accusation. “I always do what I say I'll do. You know that!” the flustered pegasus yells louder than he intended, a mixture of insult and embarrassment flooding his mind. “Let's just get this over with; I wanna get this off,” Thunderlane says in frustration as he begins to trot briskly towards the exit, then slows down to readjusts his panties before walking away.

Soarin follows closely behind, watching his friend's hips sway back and forth as he walks. Before long, he has to avert his gaze and think about something else, as his sheath starts to plump in arousal.

After a short flight, they find themselves on the edge of Ponyville's main square. With a carefully maneuvered landing, Thunderlane manages to plant his hooves on the ground gracefully. Soarin lands beside him, still slightly flushed, but his friend was fairing far worse. Thunderlane had his head just about as close to the ground as it could go, glancing around to see if anypony had seen him yet. “Even if... no one sees me, this still counts, just so we're clear.”

“Quite a few ponies are still at the stadium, but not everyone. Go ahead, strut your stuff like a sexy mare,” Soarin teases and gives Thunderlane a light smack on the ass with his wing to get him walking. Thunderlane yelps quietly, turning with frustrated anger to stare at his friend for a moment. He contemplates yelling something at him, but that would just draw attention.

Timidly, Thunderlane begins walking toward the central area of Ponyville where at least one pony was sure to see him. Maybe they'd get as embarrassed as he was and run off? he hopes to himself, still looking all around for the first sign of life. Unfortunately for him, he didn't need to wait long. A mare with a pale-green body and two-tone streaked orange mane, the first pony to trot near them since they landed, turns and looks in his direction before staring forward, then looks back in bewilderment. She is more confused than anything, and nearly walks into a wall while staring at him. Thunderlane sighs and keeps moving at his steady pace.

Soarin follows at his side, although he had noticeably lagged behind a bit to watch Thunderlane walk. The outfit really suits him nicely... too nicely, he thought to himself as he bit his lower lip, watching his friend sway his hips from side to side with each step. The panties had fallen down just enough to show the top part of his anal ring, perfectly teasing the edge of his hole, but keeping it covered with fabric. His orbs were still perfectly visible around the edges of the panties, but hugged tightly against his body, and his sheath was practically invisible. His mouth salivated slightly, and he bit his lip harder to break his trance. Am I... getting turned on by Thunderlane? he questions himself, and in that moment of awareness realizes his stallionhood had drooped down a bit, dangling and swinging from side to side with his strut. Still soft and small, but visible to anyone looking for it.

“This is so humiliating. Everypony's gonna think I'm a freak now,” whines Thunderlane as a few more ponies pass by him on either side. One laughs openly, while the other two just stop and stare, mouths agape. The stallion's face couldn't possibly get any more red than it already was, huffing and whining as he tries to disappear inside himself.

“Looking good, Thunderlane!” shouts a nearby stallion, followed by his laughter. If he wasn't so focused on vanishing, he might have recognized the voice, but in his current state it was all he could do not to pass out. “You wear those better than I could,” chimes in a mare. “Lift that tail higher!” shouts another stallion, “Show off more!”

Thunderlane glances from face to face, all staring in his direction. How many were there now? He wasn't even sure. There was a haze at the edge of his vision, and his breathing grew louder in his own ears. Everypony is staring right at him. They're all laughing at him, and mocking him. His life is over. It's over!

With a shout of frustration, he begins to gallop straight forward. He doesn't even know or care where, just away from here. Somewhere no one can see him. Escape, escape, escape!” pounds through his mind over and over, drowning out all the sounds around him.

Soarin follows behind, shouting at him, “Thunderlane, stop! It's fine, we can just stop! Hey!” It was no use. The pegasus is in a full sprint and shows no signs of slowing down. Soarin jumps into the air to follow behind him, waiting for him to slow down. He was already through the center of town, and soon passed through the edge of town, and found himself in the nearby woods, still running. At last, Soarin decides to stop him physically, landing directly in front of him and grabbing him.

Thunderlane crashes into Soarin and they fall to the ground. The impact snaps him out of his panicked state, his breathing still erratic and desperately trying to fill his body with air. Glancing all around, he realizes he had escaped, closes his eyes, and he collapses flatly on the ground, still panting like mad.

“Thunderlane! I'm sorry, I shouldn't have done all that! It sounded funny, but I didn't know you'd panic so much!” Soarin yells as he hugs his friend, panting and holding him close to his chest. They were quiet for several minutes as they each calmed down.

Thunderlane's breathing returns to normal before he speaks again, whining softly, “I'm such an idiot. I should've just told you to suck feathers, but... but....” His thought goes nowhere, and he just whines again against Soarin who hugs him tighter.

“Yeah, it's... yeah,” Soarin similarly trails off into nothing, and once again they're left in silence for a couple minutes as they think to themselves. The pale-blue pegasus pushes his friend out of his arms to look at his face and offers him a dumb grin. “That was really stupid of us both, heh.”

As if reassured the world didn't come crashing down, Thunderlane gives a single laugh in response, wiping his eyes with the back of his hoof. “I guess we should explain things later,” he says as he looks down at himself, then blushes once again.

Soarin follows his gaze, as both of them had completely forgotten he was still in the cheerleader outfit. His face flushes and he huffs quietly, looking over the wonderful sight. The tight panties that were too small for Thunderlane had adjusted to his movements. They now barely hung on, his sheath fully hanging out of the front and his sack hanging out of one side, caught in the tight grip of the fabric. The frilly skirt had mostly stayed in place, covering most of his sheath from this angle. His vest hadn't moved at all. “You know....”

Thunderlane looks up sheepishly as Soarin spoke, noticing that he wasn't the only one embarrassed, though he wasn't sure why. “Yeah?”

Soarin looks up at his eyes and then quickly looks away, letting out a fake cough. “You uh... look... really good.”

Thunderlane scoffs and punches him in the arm. “Idiot, you didn't waste any time teasing me again.”

“No, I...” Soarin rubs his arm idly as he stares back over at Thunderlane, giving him a nervous grin. “I mean it. I wasn't the only one staring, either.”

“I know, I saw. Everypony in town was pointing and laughing.”

Soarin waits a moment, then spoke again, “Is that all you saw?”

“Should I have seen something else?” he asks impatiently, his embarrassment being replaced with annoyance as he grows defensive.

“Uh... maybe I should just,” Soarin begins as he moves out of his hug, standing on his hooves. He then gives a nervous laugh as he turns to the side and lifts a hind, showing off his partial erection as it hangs limply below him. “I wasn't the only one staring... for other reasons, I mean.”

Thunderlane wasn't sure what to think. They often teased each other, and weren't even shy about their stallionhoods after sharing a locker room for so long, but this was much different.; it was completely personal. Soarin was thinking about him, and it turned him on. “Oh, uh... I. I, uh,” he makes noises to fill the air with sound in the otherwise uncomfortable silence, but has no idea how to respond.

“Could you, uh... feel free to say no this time, alright? But could you maybe, stand up, and fix your outfit for me?” Soarin manages to ask just above a whisper, his heart pounding loudly in his chest.

The stunned stallion sitting on the ground stares at him, his random noises coming to an end. He thinks to himself, Soarin thinks I'm sexy. Wait, he thinks I'm hot? He's actually got a boner from seeing me! He's not just teasing! A wave of new power that he'd never experienced before washes over him. Never in his life had he been in such a position, and it filled him with confidence.

Giving a nod, he stands up and turns to the side, then adjusts his panties back to normal, pulling them tightly around his stallionhood and over his tailhole. Everything was a little dirtier this time from sitting on the ground, but it still looks decent enough. Once in place, he stares at Soarin with a lewd grin, teasing the chance to see him once more. “You like what you see, big guy?” he says in a sarcastic feminine tone, wiggling his hips.

Rather than scoff and laugh it off, Soarin allows himself to become fully engaged. “You look so good, Thunderlane. Like really, really good.”

Thunderlane blushes, once again feeling something he'd never felt before. He was the target of lust, but also in control: the seducer. With this in mind, he returns a lidded stare, then spins around just enough to tease what's under his tail, shaking his hips from side to side. His tail holds the skirt up, and the panties slowly slip down until part of his ponut is visible again, the tight fabric perfectly outlining everything else hidden underneath.

Soarin's cock grows beneath him, soon flopping down to the full soft length. Thunderlane watches and huffs, each of them getting swept up more and more in the moment until they let themselves go completely. The pale-blue pegasus flaps his wings once in excitement and leaves them extended as he moves swiftly toward Thunderlane. Once near him, he hesitates only once before allowing his snout to press under his friend's tail.

Thunderlane shivers, his own wings extending out and vibrating softly in delight as he feels the warm breath wash over his sensitive area, even through the panties. After a few hot breaths bathe him, a slick tongue follows, licking over the thin, tight fabric. Each wonder if the other is fine with this, but neither of them say anything, so they continue.

Lick after lick begins to wet his panties directly over his tailhole, until the fabric is soaked in saliva. Thunderlane's cock attempts to expand, but is caught and held mostly in place by the strong and tight panties, acting as a makeshift chastity cage. He huffs in a mixture of frustration and pleasure, leaning his chest down and lifting his ass higher to encourage access under his tail.

Soarin bites the panties and slides them down just beneath the anal ring of his friend, the fabric pushing up against his ponut to make it stick out further than it otherwise would, then continues his licking, this time directly on the sensual flesh. The ring clenches and winks at his first few licks, and he can hear Thunderlane let out a girly gasp, but he relaxes back down and allows deeper access as the pressure from the licks increase. Soon enough, his tongue presses through and is greeted by his hot anal walls, his ring hugging him tightly.

“Ahh, fuck,” Thunderlane gasps. He'd never done anything like this before, not even with toys. Soarin's tongue had taken his anal virginity, and he was more than happy for it. Pressing back even harder, he welcomes the hot digit into his depths.

Soarin eagerly accepts the offer, plunging his tongue deeper and placing his hooves on either of Thunderlane's flanks to support himself. One of his hooves runs beneath Thunderlane's tail, then moves firmly up his rear to pin his tail up tightly. The firm pulling allows even better access to his tailhole, and feels quite wonderful to Thunderlane himself.

After several minutes, Soarin finally pulls away, his tongue mostly numb. “That was... too good. I've always wanted to try it, maybe not with you, but— I mean, not that I didn't want to with you, I just mean it could have been someone else. I wasn't fantasizing about you when I thought I should try—” he blurts out thought after useless thought, then stops himself abruptly.

Thunderlane was too lust-drunk to really notice how stupid his friend sounded, instead wiggling his hips from side to side. “Alright, that felt really good... so let's see how that cock feels.”

Soarin is taken aback by the blunt statement, but as he stares at Thunderlane's confident and happy face, there is no doubt left in his mind that he should go through with it. With a nod, he mounts Thunderlane, moving his forelegs up his sides until he can wrap around the front of his chest. His tip kisses the anal ring of the other stallion, still drooling out saliva from the tongue treatment, leaving him slick and loosened up.

Slowly, he pushes forward, and Thunderlane grits his teeth, his confidence wavering as reality sets in. “Oh, fuck, that's ahh— bigger than I expected,” he states through grunts of pain as his hole stretches.

Still determined to see this through, Soarin leans his head down next to Thunderlane's ears, speaking in a soft tone of encouragement. “You can do this, just relax. I'll go really, really slow, and won't move until you tell me to. Okay?”

Thudnderlane doesn't answer, but gives a nod, focusing on his expanding tailhole and how much it hurts. Still, he attempts to relax, breathing slowly and deeply, trying to force his anal muscles to relax even though they are clenching against his will. After what feels like minutes of nothing pass, he feels the cock head slip through his ring and penetrate inside, stopping immediately after entering, causing him to buck forward in surprise and pain. “Ahhh, it's too big!”

“Want me to take it out?” Soarin asks, already pulling back to tug himself free, but Thunderlane shakes his head quickly.

“No- no, it's fine. It's fine, I just... I need a minute.” His legs shake as he pants, attempting to relax and catch his breath to recover from the ordeal. He wants this badly, even if he's unsure why. He just knows for certain he wants this, and will get it.

Soarin's tip throbs inside of the tight tailhole, leaking a steady supply of slick precum as he waits patiently. Even without moving, everything about this moment excites him beyond belief, and he has absolutely no trouble remaining as solid as a rock. At last, the nod comes from below, and he pushes forward ever so slightly.

There is less resistance now, and Thunderlane is surprised. “Oh, you're moving in, right? Why's it so much easier?”

“The tip is much bigger than the shaft. Everything should be easier now,” Soarin responds helpfully, grunting softly into his friend's ear in pleasure. He soon reaches the maximum depth he can from this position, then pulls himself out to his tip to slide back inside again, beginning his rhythmic thrusting. Very slowly, his speed builds, and soon he's huffing and moaning into Thunderlane's ear. “You feel... ahh, so fucking good.”

Thunderlane responds with moans of his own, and over time they become more feminine as Soarin grinds across his love button. Eventually he says something, but Soarin can't quite make it out, so he speaks again more loudly, “Call me your mare again.”

Soarin grunts as he hears what's asked of him, unable to believe it, but it turns him on in ways he never imagined as he picks up the pace and speaks loudly into his friend's ear. “My sexy mare. Hnff, my pretty pony princess, you like being rutted?”

Thunderlane moans openly and leans his chest flatter to the ground, lifting his ass higher as his cries become even more feminine. “Yes! I love being your mare! I love feeling you inside of me!”

Soarin gets into the spirit of the playful and sexy banter, hugging his friend tighter in his arms as he builds up even more speed and lust-driven roughness. “Moan louder then, my slutty mare. I want to hear you sc—”

Before he can finish speaking, Thunderlane squeals in pleasure as his legs nearly give out, cum spurting through his tight panties as he reaches his climax. His cock manages to grow to only slightly while pressed firmly against the fabric. As his seed lubricates the panties, his cock slips out, and the rest of his seed spurts uselessly to the ground beneath him.

Soarin is surprised by the sudden orgasm, but also pushed beyond his own limit by the display of his new mare cumming just from being rutted by him. He blows passed the point of no return and slams himself as deep as he can, planting his cock firmly as he releases rope after rope of thick seed into the clenching walls of Thunderlane. Each of them flap their wings as they finish cumming, and then Thunderlane nearly collapses to the ground in exhaustion, but manages to stay standing on shaky legs.

“Oh... oh Celestia. That was... that. Hah, fuck.,” Thunderlane pants out as he attempts to recover. Soarin isn't fairing any better, fully collapsing on Thunderlane's back and resting as his cock stays buried inside, leaking small amounts of leftover cum and pre into his body.

“Yeah,” is all he adds as he pants along, trying to catch his breath.

Thunderlane allows himself to fall to the ground, resting flat on his belly in the dirt with the other pegasus on his back. He lets out a grunt as Soarin pulls his softening cock free, a lewd wet 'splort' can be heard as his tip is pulled from the clenching wet hole, a trail of cum following behind. His cock then presses limply against his tailhole and panties as he rests against him once more, giving him a tight hug.

“We're uh... gonna have to clean these clothes,” Thunderlane says with a tired laugh, then adds, “and we're gonna have to do this again.”

Soarin chuckles on his back, the force making him bounce up and down on his friend's body. “What, dress you up for town?”

“No... but... I'll dress up for you, Soarin.”

Soarin kisses Thunderlane's neck, and lets out a happy hum. “I'd love that a whole lot.”