Spitfire Loses a Bet

by mlpfunfictionwriter

Rating: teen
Tags: Random, Slice of Life, Alternate Universe, My Little Pony: Friendship is Magic, Soarin, Comedy, Spitfire
Length: 4891

Soarin's had enough of Spitfire's ego and decides to knock her down a few pegs, nothing a old fashioned wedgie session can't cure. How long will the yellow pegasus hold out? Read to find the answer!

Soarin's had enough of Spitfire's ego and decides to knock her down a few pegs, nothing a old fashioned wedgie session can't cure. How long will the yellow pegasus hold out? Read to find the answer! Read more if your into humiliation type stuff.
Cover art is credited to WaniLeviathan

Contains Wedgies and spankings

Published 2016-02-23 06:20:01 UTC
Last updated 2016-02-23 06:20:01 UTC

Chapter 1

It was another great day in the wonderful land of Equestria. The birds were singing, the sun was shining, and there was a cool breeze in the air. All of these things meant that today was going to be a great day except… there was no way that could be possible. Especially not for a certain blue maned pegasus that was currently in the middle of an intense training workout. Nope, today was going to be just as rough and frustrating as it always was. After all, today was the worst day of the week and no amount of nice weather could ever change that.

Man, I hate Mondays. Soarin sulked inwardly as he zipped through his specialized obstacle course.

Soarin never liked Mondays. Not only was Monday the most hated day of the week because it signified the end of the weekend and the beginning of another work filled week but it also meant that Soarin had to go do flight training with the rest of the Wonderbolts. It wasn't that he didn't like flying or his teammates for that matter. On the contrary Soarin loved to fly and his teams of flyers were some of the best friends he could ask for. It was just that he wasn't as easily motivated as everyone else was when it came to training especially after a full weekend of partying and pranking. Oh yes, Soarin was a huge prankster and everyone respected and revered his pranking prowess if only to keep themselves from becoming the next victim to his antics.

When he wasn't trying to uphold the high standard of professionalism expected of a prestigious acrobatic flyer, Soarin could often be found pulling pranks with his friends. From light hearted simple pranks to complex pranks created for extreme prank wars, Soarin did it all. The grey pegasus athlete was undoubtedly the best prankster in Equestria… well he liked to think so at least. Soarin smirked as he remembered that just a couple of weeks ago he had declared himself the team's prank King and had pranked almost everyone on the team in some way. Lucky for them, it was never anything major. He had gotten everyone except for Spitfire, his old childhood friend. He was going to spare her at first but that all changed when she got promoted to captain of the Wonderbolts after their old Captain retired.

Now Soarin had known Spitfire his entire life. They were good friends. Best friends even. He was the one who'd given her the idea to become a Wonderbolt when they were just a little older than foals. A lot had changed since then. Now Soarin was a great flyer. In fact, Soarin was gifted with excellent flying skills from birth while Spitfire had to undergo hours of physical training just to keep up with him in flight. Soarin was still the fastest flyer on the team and could easily out maneuver any of the others, even Spitfire. He just didn't have the right motivation or even the slightest desire to lead. He much rather let someone else fit the role of a leader. Let them bear the weight of responsibility, all he wanted to do was have fun. Lucky for him, Spitfire fit the bill perfectly.

At first Soarin was happy for his friend and congratulated her with the rest of the team. He was happy to see her finally reach the goal she had worked so hard for but it wasn't long before he started to see something change in her. As time went on, Spitfire became more and more obsessed with winning. Now she did anything she could to win, whether that meant pushing her team past their limits or just trading them off for better athletes. It didn't matter to her anymore as long as it meant a victory.

Spitfire, being the leader she was, made sure that every member of the Wonderbolts team was in prime condition both physically and mentally. In order to keep the Wonderbolts in shape, she implemented rigorous training programs specifically designed to challenge each individual Wonderbolt so they would get as much training as they possibly could within a relatively short period of time. Unfortunately, because Spitfire often pushed her team past their limits the obstacle courses had caused some pretty bad injuries to a few members of the team. She, of course, blamed the injuries on incompetent flying on the injured individual's behalf. One of those injured individuals included her second in command and most trusted friend. Sure, Soarin healed after about a week but it still caused some serious strain on their relationship. She didn't seem to care about the team anymore, just winning. No one knew why she was being such a huge jerk to her own teammates. But what they did know was that it had to stop. Her attempting to trade himself off for Rainbow Dash last month was the last straw. Something would have to be done about her 'highness' one way or another. And as the self-anointed prank King he was just the pony who could do it. And he would use his most powerful prank to do it. The wedgie bet.

In Soarin's eyes she had directly insulted his honor by attempting to trade him and you just don't do that to your second in command. Even worse was how high and mighty Spitfire was acting lately in addition to her desire for victory. Someone had to take her down a peg and Soarin knew exactly what to do. He would get her back. And he would do it on a Monday just to spite the odds. "Just you wait Spitfire, Soarin's got your number" he said with a light chuckle under his breath. It had been two weeks of planning, training, ranting, and scheming but now he was finally ready to strike.

As the blue maned pegasus continued to train in his personally designed obstacle course he started to slow down and gently coast around the numerous obstacles surrounding him. Despite his position on the team and blatant skill, Soarin was still subject to the intense training program that Spifire had created. Sometimes Soarin felt like she made examples out of him while they were training on purpose just to annoy him. And today was no different.

"Soarin what are you doing?! Get your head in the game!" Spitfire yelled with a slight smirk from across the field getting everyone's attention on the grey wonderbolt.

Soarin snuck a quick glance at the yellow mare. She wore the same outfit that he and everyone else was wearing. A blue and yellow hoodie with matching sweatpants that bore the exact same design as the Wonderbolts performance costume. The only real difference was that instead of spandex, this outfit was made of cotton. Their blue and yellow sweat suits weren't nearly as tight as the uniforms they wore when performing. This was because the team wanted to practice in comfortable clothes that didn't pinch or squeak when making sudden movements. Not to mention the fact that nopony wanted to stop their training just to pick out the spandex fabric that magically decided to wedge itself between their flanks during routines.

"Don't worry I got this!" Soarin yelled back as he started to pick up speed once again.

"You better, we have to perform at the annual air show in two weeks and I don't want to give off a bad impression for the fans. And then we have the annual race against the Griffon Kingdom's best flyers and I swear if we lose to them so..help...me" Spitfire said in a very threatening voice as she made her way over to the grey Wonderbolt.

Spitfire decided to kick himself into gear. "You want to be 'impressed' let me make you 'impressed'"

In an instant Soarin was flying twice as fast as he normally did. He zipped through the obstacles like they weren't even there. To the other Wonderbolts who were watching there was no doubt, he'd just flown as fast as Spitfire. When he finished he turned around to take a look at their 'fastest' flyer who was currently staring at him in disbelief.

"How did..i don't even..what?" Spitfire stumbled through her list of words completely confused.

Soarin gently coasted over to a nearby cloud. "Like I said, I got this." He said with a deep-set smirk.

Spitfire just stood on a cloud staring at Soarin in complete shock. Around her, the other Wonderbolts started to mutter under their breaths.

"Wow, I had no idea Soarin was that fast"

"Has he been holding back this whole time?"

"Do you think he was faster than Spitfire?"

"I don't know but he was going pretty fast!"

Quickly Spitfire tried to regain control of the situation. She tried coughing loudly to get everyone's attention. "Well I think that wraps it up for practice today. We should all get some rest." She took Soarin aside and whispered in his ear. "As for you Soarin, you seem to have made a lot of progress recently. Good job. While I can't say I'm not impressed, that doesn't change the fact that if you still had that much energy left then you were definitely not giving it your best. In fact maybe you should continue your training session until you learn to put in some real effort during practice."

Soarin saw his chance and went for it. "Well if you think you can do better then be my guest ma'am. Perhaps in a race?" He said it just loud enough for the others to hear him.

For the second time in two minutes Spitfire was speechless. A few moments passed before the properly censored words came to her. "What did you just say to me Soarin?!"

Soarin bowed in mock reverence. "Oh great leader, I do believe I just challenged you to a race to see which of us is faster."

Spitfire noticed that the other Wonderbolts were now surrounding the two of them and listening intently for her next words. Never the one to back down from a challenge, she didn't have any choice but to agree. "Fine we'll race on the track. What are the stakes?"

The rest of the wonderbolts cheered and waited to hear what Soarin had to say.

Soarin paused to give off the impression that he was thinking on the spot. "I got it! The winner gets to give the loser a couple of wedgies in front of the entire team."

The shocked crowd of Wonderbolts gasped in unison and a few of the mares blushed at the thought of seeing one of their superiors getting a wedgie by the other. Spitfire was the most shocked out of the crowd though. She tried to say something but she was having a hard time finding the right words.

"I..you can't…THAT'S RIDICULOUS! Are you crazy Soarin!"

Soarin raised his brow at her as he spoke, "What's the matter ma'am? Don't think you have what it takes to match your second in command? It's alright, not everyone can be this spectacular at flying."

Spitfire gritted her teeth, she couldn't stand his taunting. He was such a child sometimes. Finally she couldn't take his self promoted praise anymore. She frowned slightly, giving him an icy cold stare that made the grey wonderbolt more than a little nervous for his life. "Gee Soarin, I wasn't aware the self-anointed prank King was in such a hurry to get his tighty whities hiked up his plot. Fine, you're on! Even if you have gotten faster, you're still not fast enough to beat me! It's time to put you in your place. I hope you're wearing clean underwear." She said with an evil grin.

Soarin gulped noticing her newfound confidence and nodded. The two wonderbolts hoof-bumped to acknowledge the bet and flew over to the race track. He'd been training for a whole week now to prepare for this race but now he wasn't too sure he'd done enough training. Get it together Soarin! He berated himself. You've got this! Remember this isn't just for your prank. This is for the team.

Fleetfoot stood off to the side with a yellow flag in her hooves. She waved it a few times before starting the race.

"On your mark…get set...Go!"

In a burst of intense speed both flyers rocketed forward hoping to get the lead on the other. Five laps passed and the two wonderbolts were still neck and neck with one another. Four more laps passed and Spitfire started to gain the lead as they came up to the final lap.

"Give it up Soarin." Spitfire said in a strained yet triumphant voice. "I'm the fastest!"

"Not…today aggh!" Soarin screamed as he pushed himself harder than he'd pushed himself all year in a last ditch effort to pull off a victory. His efforts were successful, giving him a clear lead at the last second.

The rest of the Wonderbolts were silent for a few moments and then burst into an overwhelming applause. Soarin landed by cloud and nearly collapsed from exhaustion. He'd done it. He'd actually beaten Spitfire in a full out race. Spitfire landed next to him but she actually did collapse. She took in a few deep breaths before sighing in frustration.

"I can't believe you beat me…How could you possibly beat me. You haven't done that since we were foals. I don't suppose you would settle for a draw?" She said in a pleading voice.

"Not a…chance…" Soarin muttered in between pants.

The team continued to cheer and congratulate the winner. After given some time to recuperate, Soarin decided to make good on his deal. The rest of the Wonderbolts gathered around the two lead flyers in a small semi-circle. Most of them

"Alright everyone we all know that for the past couple of weeks our leader has been pushing us really hard. But to show that she isn't all that bad, Spitfire will be willingly listening to my commands and hopefully be able to entertain us for the next hour." A loud cheer rang out amongst the crowd of professional athletes.

Spitfire's eyes widened. "You can't be serious!"

Soarin chuckled, "Of course not. Your panties will probably rip way before then."

Spitfire gave him a pleading look. Her cheeks were starting to turn pink as she blushed furiously. "Please don't do this. I'll do anything just…please."

"Sorry Spits. My hooves are tied, we made the bet and I can't go back on my word. Besides, you don't don't want to back on your word, do you? Now be a good girl and face away from the crowd." Soarin had her right where he wanted her. She wouldn't go back on her word no matter what the situation was. He knew it and she knew it.

Soarin was right, she could back out now. Not after giving her word in front of the team and using a hoof-bump to sign the deal. What would it say about her? How would her teammates view her? In retrospect probably no better than how they would view her after this spectacle. Either way she had to make a choice. Spitfire's ears flattened but she did what she was told. Very slowly she faced herself away from the crowd of whooping pegasai. Soarin examined his captain's flanks as he prepared to pants her. They were so big and round. If there was one thing he really loved about Spitfire, it was that she had a nice plot.

Most of the team would agree, though never within hearing distance of Spitfire, that the way their captain had been treating them was wrong. What was happening to her now seemed to be a fitting end for the yellow pegasus pony. Almost like poetic justice. Soarin waited for the cheers of his fellow teammates to die down before giving them a big toothy grin.

"Now let's all see what type of underwear our captain likes to wear."

And with that Soarin unceremoniously yanked his captain's pants down to her ankles. Spitfire could suddenly feel a draft as her cerulean thong with yellow frills was revealed to the world. The same national colors of the Wonderbolts. A few seconds passed followed by inevitable waves of laughter and cat calls. The entire team burst into a fit of giggles, snorts, and chuckles as they viewed the specific type of underwear that their captain was wearing.

The blue and yellow thong was deeply wedged between the yellow pegasus pony's firm plot cheeks. Had any of her teammates been able to see her face they would have seen a dark red blush beginning to burn through her cheeks.

Soarin couldn't control himself. "Hahaha! Wow Spits" He said as he struggled to regain composure. "You sure know how to pick em! How about you give us a little jiggle!"

Spitfire hung her head in defeat as she spoke, "S-shut up and get it over with Soarin" She tried to sound strong but Soarin could hear the embarrassment in her voice.

"As you wish" He said with a wave of a hoof and a curt bow. "But not before getting to do this!"

Spitfire wondered what he meant by that but it wasn't long before she found out. The stallion quickly wrapped his foreleg around her torso trapping her in place. SMACK. A muffled slap rang out as Soarin swatted the mare's right flank with his free hoof. The yellow mare swung her head back in surprise at the stinging sensation. A second slap shortly followed after the first one. Spitfire yelped in pain as she felt the first spanking she'd received since her years as a filly. Spitfire felt the stinging bite behind each slap of her friend's hoof as it struck across her flank. She grit her teeth hoping that her torment might end soon.

"What do you say guys? A few slaps to the rear before we get started?" The crowds applauded in approval. Nodding in return, Soarin turned back to his captain's smarting derriere. SMACK. SMACK. SMACK. For over a minute the stallion continued to swat his friend's sore plot until her golden yellow backside started to give off a light pinkish color. Throughout the whole ordeal Spitfire resisted the urge to cry out. Instead she bit into her hoof to keep from crying out. Soarin noticed and grinned at her resolve, she was one tough mare.

With each agonizing slap all Spitfire could think about was how her entire team was watching Soarin turn her yellow flank pink. She couldn't tell which was worse. Tears started to well up in her eyes from all the pain and humiliation as she just stood there and endured the degrading spanking that Soarin was giving her.

Soarin finally let go of her and Spitfire collapsed to the floor rubbing her sore haunches with her forelegs hoping to relieve some of the pain. Had this really just happened? Did Soarin really just give her a spanking in front of the Wonderbolts? Could this all be some kind of sick dream? The burning sensation in her rear assured her that it wasn't. She decided to sneak a look behind her but as soon as she did she wished she hadn't. Most of the team seemed to be enjoying the show. Most were grinning and laughing while a few others just stood there completely stunned at what they were watching.

Only a few of them looked as concerned as Fleetfoot who was currently standing in the back of the group with a deep red blush burning through her cheeks. To her dismay some of the males and even some of the females seemed to have gotten quite 'excited' from the show. She looked back at the ground in front of her too embarrassed and ashamed that she had let something like that happen to her. She just wanted to crawl under a rock and die.

There was nothing anypony could do. Spitfire considered getting up and ending the spectacle but then changed her mind. She couldn't do that. She had openly agreed to this challenge and now she had to accept the consequences or risk being seen as a liar and a coward. There was no other way to get around it. She had to go through with it now. She only hoped that afterward she might still possess some fragment of her dignity and be able to move on with her life. She only wanted this to end. Unfortunately, that would not be the case today.

Seeing the great position she had left herself in from her collapse, Soarin mentally prepared himself for his next move. He was going to knock his leader down a few pegs, declare himself prank King, and get a little revenge for the team all at the same time. Sometimes life was good…other times life was great! He crouched down behind the yellow mare that laid sprawled out before him and wrapped his hooves through the leg holes of her thong. Still recovering on the ground, the Wonderbolt Captain never stood a chance. Spitfire's eyes bolted open as she felt her most intimate piece of clothing being touched by her best friend's hooves.

"Ready, lift off!" Soarin shouted as he launched upwards from his crouched position and reared up on his back legs lifting the poor pegasus back onto her hooves by her underwear. The thong shot itself deep into the yellow mare's toned haunches as the cotton underwear reached up about a foot above her. Spifire gasped in a blend of shock and pain as the blue and yellow fabric cut into her plot crack causing a terrible burning sensation in her butt. The face she bore was one that Soarin had seen many times in his lifetime. She stood stiffly and awkwardly on the ground. Her brows were furrowed into a set of bulging eyes that stared absently off into the distance. Her mouth was dropped in a way that could only express deep surprise and even horror at her situation. It was obvious now. Spitfire was a wedgie virgin.

"What's the matter? You act like you've never received a wedgie before?" Soarin asked cockily, now knowing his friend's secret. She didn't reply but he knew her answer.

Soarin slowly pulled on her thong to make her face the crowd once again. Awkwardly Spitfire followed his lead and reluctantly faced her teammates. He gave a small tug on her thong again and she grimaced as the soft fabric wedged itself deeper into her hindquarters.

"Your very first wedgie this must be a real treat for you, it definitely is for us! How does it feel Spits?"

The yellow mare craned her neck back and half glared half grimaced at the grey stallion who was currently holding her up by her panties.

"P-please!" Spitfire managed to squeak out. Her voice sounded weak and desperate which was very different from her usual confident take charge voice. Soarin liked that.

"Whats that? You want more huh? Ok if you insist!"

"What?! I didn't mean it like—!" She was immediately cut off as Soarin quickly jerked her intimate article of clothing up to his chest lifting the mare's rear legs off the ground by an inch or two leaving her backside dangling. The Wonderbolts leader struggled desperately to touch the ground with her hooves but her efforts were futile. The crowd laughed as they watched her rear legs stretching and kicking in vain to touch the floor. Soarin opened his wings and started lifting a few feet off the ground taking Spitfire's underwear with him. With each flap of his wings Spitfire's thong dug deeper into her private parts.

Spit fire groaned as her two other hooves left the ground leaving her totally suspended in the air by her blue and yellow undies. The pain in her crotch increased as her extra weight caused the cotton fabric to dig deeper into her butt. Spitfire ground her teeth together and moaned under her breath as Soarin continued to parade his trophy to the crowd of onlookers. The blue maned pegasus looked down at his victim and smirked.

"You know a couple of years ago if somepony would have said that one day I would be giving you a wedgie I would have called them insane but here we are."

"Sh-shut up Soarin" Spitfire stammered back.

"Aw, don't be like that. Hmm, you don't seem to be having any fun. What if I do this?"

Soarin lowered her back to the ground. Spitfire sighed heavily in relief. She had never been so happy to be on the ground in all her life. But the moment didn't last. Soarin quickly launched her into the air by the elastic of her thong making her squeal in surprise and pain. He was using a lot more force than before. Soarin stood with his forelegs outstretched holding his leader in the air by her undies giving him a great view of her bum.

Spitfire didn't notice or if she did she didn't say anything. She just hung there by her panties waiting for the inevitable. The yellow mare's head hung in shame as she swayed back and forth on her thong as if it were a swing. A smile slowly crept onto Soarin's face as he examined just how hot her tanned buns looked as he gently swung her back and forth by her own underwear.

"Here we go!"

Soarin chuckled as Spitfire grunted and groaned with every bounce of her thong. The mare's butt jiggled slightly and her hooves instinctively dropped to her crotch as the underwear sunk itself inside 'there' for the first time. She lost her composure after that.

Spitfire shook her head violently but she couldn't move. She felt completely stunned by the frontal wedgie she was getting.

Spitfire hung her head in shame as she begged, "P-please I c-can't take t-this anymore! Please s-stop! Oww!"

Even if he was the one giving it, Soarin could feel the strength and power of the wedgie in each bounce. The constant bouncing was starting to stretch the cotton thong past its limits and it started to creak under the strain. Hearing the sound and not wanting to rip the underwear, Soarin quickly put Spitfire down. He looked at her butt in amazement at how deep her thong had buried itself within her nether regions. The thong itself had grown larger than before and it gave Soarin one last idea.

"Alright everyone, here goes the last wedgie for today!"

He pulled Spitfire's thong up past her back and up to her shoulders.

"Please, these are one of my favorite pairs! You're going to stretch them out if you continue!" Spitfire pleaded.

Soarin laughed, "Yeah that's kind of the point."

He stopped for a second before continuing to pull on the thong bringing the blue and yellow undies up to her ears. Here it was, the final piece to his plan.

"Arg! It's too much! You're going to rip me in half!" Spitfire screamed.

"Nonsense, I bet right about now you're starting to taste cotton huh Spits?" He taunted obnoxiously.

Soarin leaned in and whispered in her ear, "Oh and Spitfire. Nopony tries to trade off the prank King and gets away with it"

Spitfire's eyes lit up in realization but it was far too late for her. A few more hard tugs and Spitfire was able to see the cotton fabric just as Soarin fastened the colorful thong over her forehead. Her humiliation was complete now. Soarin held it there for a few seconds and gave the crowd a good look before letting go of the humiliated mare. Spitfire immediately pried her underwear off of her forehead. The colorful thong flew off and smacked against her flanks making her jump slightly before collapsing to the ground. Her overstretched thong stuck out of her but awkwardly

"Alright guys that's it!" Soarin said loudly with a huge smile on his face. "The bet is over!" The crowd cheered and applauded their new hero as Fleetfoot and a few others came to help Spitfire up. One of the ponies to walk over to her was Soarin. The other wonderbolts backed away cautiously from the grey stallion.

"Ugh! My plot feels like it's on fire!" Spitfire moaned as she tried to pick out her devastating wedgie.

"You want some pliers for that Spits? Maybe now you'll start treating us like teammates now instead of like trash."

The yellow mare slowly stood up and used one hoof to rub her sore flank. "Yeah I get it. I've been a real plot hole lately. But did you really have to do all this? I won't be able to sit straight for a week now!"

"Don't worry it'll pass, trust me. I've received my fair share of unwanted wedgies. It happens to everypony at some point in their life"

"Yeah, I guess you're right. Still you better watch your back for a while Soarin. I won't be forgetting this."

"Trust me, I'm counting on it"

As the grey stallion flew off he left the humiliated mare gazing up at him intently.

She smiled slightly to herself as she watched him go.

"Oh I am sooo getting you back Soarin!" she said through her smile.