The Seventh Biennial Ponyville Sex Contest

Chapters

Prologue
Coco Pommel -vs- Rainbow Dash (Ragabash)
Applejack -vs- Flitter (VitalSpark)
Colgate Minuette -vs- Fluttershy (Nocturnal Derp)
Apple Fritter -vs- Cloudchaser (Fimbulvinter)
Twilight Sparkle -vs- Cheerilee (Shrinky Frod)

Prologue

Everypony bowed as the regal sisters entered the marquee.

Princess Celestia made her way to the royal box, which offered the second best view of the stage area. Luna followed, yawning, unaccustomed to being awake in the middle of the day.

Celestia addressed the gathered ponies. "Please, take your seats everypony. Welcome to the seventh biennial Ponyville sex contest. A contest where the mares of this humble town compete in endurance and technique. My sister and I are honoured to have been asked this year to formally host the event which we have heard so much about. I shall now introduce to you the judge of this competition, the Princess of Love, my niece, Princess Cadence."

The now seated audience stomped their hooves in approval. Princess Cadence stood and the ponies simmered down to let her speak. "The rules are simple. Two ponies compete at a time; mare on mare. The first pony to whinny is out of the competition. There will be no magic unless both competitors are unicorn ponies. There will be no flight unless both competitors are pegasus ponies." She looked at her sister-in-law seated on the competitors' bench. "For the purposes of this year's contest, alicorns are considered to be both a unicorn and a pegasus."

Murmurs spread throughout the crowd. This was the first contest that an alicorn had competed in. The rule books had nothing to say about alicorn competitors. Twilight Sparkle's participation was proving quite controversial, but the committee had ruled it vital that Twilight Sparkle should be able to compete and have a chance to defend the title she'd won two years ago as a unicorn.

Despite being the defending champion, Twilight Sparkle wasn't even seeded #1 in the competition. Pundits had judged her wings to be more of a disadvantage than an advantage. They didn't think her dexterous enough to make good use of them in the contest, and they'd be an extra erogenous zone that could be taken advantage of by her opponents. Bookmakers and those in the know were predicting a victory for the fiercely competitive pegasus Rainbow Dash instead.

The judge continued. "Best of luck to all competitors, and may the best mare win!"

The audience erupted in a sea of hoof stomps again.

* * *

"Hi, my name is Spike and I'll be your official commentator for this competition." The little dragon stood on a small podium near the stage, which had been carefully positioned not to spoil the view of anypony who was watching.

In the stage area was a double bed, lined with sheets which would be changed between rounds for hygiene purposes, and with two pillows. No other props which a competitor might use for unfair advantage were on the stage. The tools to win this contest were hooves, muzzles, tails, wings, and horns, not dildos and vibrators. It was a contest to find out who had the best sexual technique, strength, energy, and endurance — not who had the best toys.

"And now," said the commentator, "it is my pleasure to introduce our first contestants..."

Author's Note

That's the boring bit out of the way...

Coco Pommel -vs- Rainbow Dash (Ragabash)

The little dragon watched the two mares take their places on the stage before announcing their names to the crowds. "… Coco Pommel and Rainbow Dash!"

Coco Pommel was starting to have second thoughts.

It had seemed like a good idea at first. After all, it wasn't every day that one gets the chance to take part in a sex contest. And who knew whether she'd be able to in two years. In the first place, she was only in Ponyville to visit her new employer Rarity and discuss some work-related things. It was her, who convinced her to stay longer and attend this event. And then, she even suggested that Coco joined as a contestant. It was a great opportunity, so she agreed, and thanks to Rarity's connection with the princesses, she was registered, even though it was normally restricted to Ponyville's residents. But then, thanks to Twilight Sparkle's rather new status as alicorn, she wasn't even the most irregular participant.

At the time, it had seemed like a good idea. What's the worst that can happen? That she loses and orgasms, while lots and lots of other ponies are watching. Not a big deal, not the end of the world.

However, now that her first fight was about to start, she wasn't so sure anymore. The reason was her opponent, whom many believe to be the most likely to win — for good reason: she was very athletic and competitive; she had the skills and the dedication to win nearly any physical contest.

Her attitude didn't help. Like Coco, she stood on one end of the big bed that would serve as their arena, but she oozed such confidence, she might as well have stood on top of a mountain, ready to sweep down on her, going for a kill. This was punctuated by the cockiest grin, the earth pony had ever seen. It was like she was trying to tell Coco that she had no chance and should give up.

Coco knew that. She was aware that she had no chance; that she would not only lose, but face a humiliatingly crushing defeat. Although it probably wasn't as humiliating when it was by the hooves of the one who would probably win the entire contest.

“In this match, Rainbow Dash, whom many already bill as the winner, will fight against Coco Pommel, who is actually from Manehattan, but was allowed to participate in this contest, by the grace of the princesses, because she is working under the amazing and gorgeous Rarity. But boy, I really wouldn't want to be in her place right now. Against Rainbow Dash, she has practically no chance at all.”

Spike's announcement didn't help at all.

Still, a part of her just couldn't give up. She had entered, so she should see it through the end.

“I won't go easy on you!” Rainbow Dash said. “So get ready to be trounced!”

Even considering her low chances, Coco didn't back away — the only thing she was ready for was to put up a fight.

“Alright, it seems that both contestants are on their place, so let's begin. Ready… fight!”

Before Coco could move a muscle, Rainbow tackled her and threw her down on the bed. Not wasting any time, the pegasus moved a front hoof between Coco's hind legs and furiously rubbed her crotch.

“Well, that was fast,” Spike commented. “The match has barely started and Rainbow Dash already has Coco Pommel under her mercy. It looks like this won't take long.”

Coco gasped. She was not prepared for this and the sheer speed of it all caught her off-guard. She tried to ignore the feeling of the hoof grinding against her teats and pussy, but it wasn't easy. Still, she couldn't give in just yet. At the very least, she should put up more of a fight.

The earth pony pulled her hind legs up and with a strong push of all fours, she managed to kick the other mare aside. As Dash landed on her back, Coco picked herself up and immediately went for her pussy. But before she could even touch it, the pegasus pulled her body away and Coco's hoof landed on the bedsheets.

“Seems that Coco Pommel wants to put up a fight,” Spike said. “It doesn't seem to have worked though.”

“Nice try, I'll give you that,” Rainbow Dash said with a grin. “But there is no way that you could beat me.”

After that, Rainbow didn't do anything. As if to dare, or even mock Coco, she just stood there, with the grin still plastered on her face. Coco didn't know what to do. If she tried to tackle her, the pegasus surely would get the better of her again. She was way too agile and fast for her.

Still, she tried anyway, dashing forward to her. Or at least, it seemed like that. As soon as Rainbow Dash began to meet her assault, Coco dived away and let herself fall on the bed. The other mare didn't seem to expect this, and she just ran by, fortunately without trampling on her, only stopping at the other end.

“What was that about?” Rainbow Dash asked confused.

Coco wasn't sure. She just thought that she had to do something, but didn't really know what exactly she tried to achieve. Maybe some kind of advantage, but she was too unskilled and Dash too good for that to work.

“Oh, Coco Pommel really put herself in a bad spot,” Spike commented. “Lying there like that, she is a really easy target. Even more than she was before.”

Sure enough, before Coco could stood up, Dash went between her hind legs with a quick movement and began to lick her. “Kya!” the earth pony shouted, as she felt the wet tongue against her lower lips. It was much harder to ignore, this time. She wanted to kick her away again, but the pegasus, much stronger than her, held her legs firmly in place with her hooves.

“It looks like Rainbow Dash really got her this time. Will this be the end for Coco Pommel or can she make a last stand?”

She really wanted to, but the more it went on, the weaker Coco got. Her opponent was good and it was hard, nearly impossible, to resist the tongue that moved up and down her, by now quite swollen, pussy lips. Fluids were trickling out of the slit, which Dash took as cue to move on. The earth pony moaned out loudly when she felt the tongue part the lips and enter the wet cave behind.

“I guess not. At least, she seems to enjoy it. And not just her, when I look at the audience.”

Indeed, she liked Dash's licking. Coco barely even cared about the contest anymore, as she got and more into it. She breathed heavily and moaned every time the tongue rubbed over the walls of her pussy. Looking around, she saw the audience staring at them. Some enjoyed the view in a very… physical way. Funny, Coco expected it to be more embarrassing. But now, she enjoyed giving them a little, if involuntary, show.

The closer she got to her limit, the louder her moans got. She moved her hips a little against her former opponent, who responded by downright burying her face in her rump and sticking her tongue deeper inside her.

Finally, it was too much for Coco. Letting out a final louder moan, she reached her climax, pleasure gripping her entire body. Her juices shot out of her pussy and made Dash back away from her. Not enough to avoid her face getting splashed by the clear fluid, though, although she didn't exactly mind that. Coco's body quivered while she came and even while her climax was slowly fading. Her breathing was still heavy when it was over and she recovered from the orgasm, while juices ran out of her pussy and stained the bed.

“And the winner is Rainbow Dash!” Spike shouted. “Well, that wasn't very surprising. Didn't expect Coco Pommel to be a squirter, though.”

Coco blushed as she stood up and saw all those ponies still staring at her. It turned out, it was a bit embarrassing to be seen like that, once she wasn't horny. Meanwhile, Rainbow Dash didn't even seem to be bothered by the fluids sticking to her face.

“Hey, you were pretty good,” the pegasus said.

“R-Really?” Coco couldn't really believe it, considering how badly she lost.

“Yeah. You have a nice pussy, and you're really fun to eat out.” She licked the juices around her lips. “And I fucking love squirters.”

“Oh...” Well, that was probably flattering too. In a way.

“Never mind your loss. There's no way you could beat me. Nopony can. And I'll make sure to win this contest. Just make sure that you'll watch, when I make all those other mares cum!”

Coco wasn't sure whether that was meant to make her feel better or whether Dash just wanted to brag. But she didn't feel so bad about losing. Now, she just looked forward to being a spectator, and seeing whether the pegasus could keep the promise she made.

Rainbow strode confidently backstage while Coco Pommel hobbled to the spectators' seats, making way for the next contenders. Spike put the microphone down and called out to a nearby marshal, "maybe somepony ought to change those sheets before the next mares start? Coco kinda made a bit of a mess."

Author's Note

This chapter contributed by Ragabash. If you liked it, then go look at his other stuff. Deal? Deal!

Next up: Applejack -vs- Flitter.

Applejack -vs- Flitter (VitalSpark)

Spike grabbed his microphone and introduced the next competitors. "Next up, we have Applejack, the earth pony that many consider to be a contender to win the entire contest, up against Flitter, a pegasus originally from Cloudsdale, but who made Ponyville her home five years ago."

Applejack stepped into the arena and Spike continued. "Applejack has strength on her side. Her experience rounding up animals has won her the Ponyville rodeo championships six times running, and she's picked up medals at the All-Equestria rodeo championships too." Applejack's face twitched at the mention of her participation in those particular games. It still hurt that she hadn't won a single blue ribbon. "But will her success in the rodeo ring translate to success in the bed? Will all that experience bucking make her better at--"

"Hkh-hmm!" Big Mac coughed. Spike looked round to see the large red stallion standing right behind him, looking down at the little dragon menacingly.

"I mean… I… I'm sure we all hope she does really well," Spike continued quietly, backing away from Applejack's brother.

Flitter walked nervously in from the side entrance. Spike put on his confident voice again. "Flitter might not be seeded as highly as her sister, but she may still prove to be a bit of a challenge for Applejack. She might not have the most wingpower of any pegasus in Ponyville…" Spike looked towards Thunderlane, who was sitting in the audience with his younger brother. "And she might not have the most speed…" He looked towards Rainbow Dash, who was still cleaning up her face. "But her flight dexterity and control are unrivalled." Flitter smiled with pride at the announcement. "Of course, as Applejack isn't a pegasus, flight will not be allowed in this round." Flitter suddenly looked deflated. Spike cleared his throat. "Let's hope she's as good on the ground as she is in the air. Anyway, let the round commence!"

In the spectator stands, a nervous Apple Bloom sat down next to one of her class mates. "That's mah sister up there," she whispered. "And my babysitter," whispered the grey pegasus colt beside her. Rumble scooted a little closer to the filly.

Elsewhere, bits were changing hands as ponies placed bets on the competitors. Most ponies had their money on Applejack, but several bets had been placed on Flitter, with ponies attracted by the long odds against her, and the potential for a big pay-off if she won.

Both competitors looked at Princess Cadence, who merely nodded her head silently. Applejack stood by one side of the bed, hat still on her head, and Flitter stood on the other. Applejack started circling the bed clockwise, with Flitter doing the same, not willing to come into direct conflict with her opponent straight away. Applejack stopped and moved the opposite way, and Flitter did the same, a bead of nervous sweat running from her brow and down her face.

Applejack stopped again. "Well come on, sugar cube, we can't do this all day." She started circling again. Flitter did too. Applejack sped up, and Flitter matched her speed.

Suddenly Applejack lunged across the bed, making a grab for the mare on the other side, but her hooves clutched the air as Flitter darted out of the way. Applejack's hat fell across her face and she lost sight of the pegasus. With a hoof, she brushed her hat aside and it fell to the floor. Where had Flitter gone?

Applejack felt two hooves on her flank and her head snapped round to see Flitter standing behind her, grasping it tight. She tried turning around, but Flitter clung on and stayed behind her. Flitter licked her lips and bent down towards Applejack's rump.

"Flitter takes a surprise early advantage," announced Spike. "It looks like this will be a two horse race after all!"

Applejack felt the pegasus's raspy tongue on her marehood and wondered how the mare had managed to hoodwink her already. She tried turning around again, but Flitter was holding on tight. Nopony could beat her with a lasso, but maybe at next year's rodeo, she'd have competition for the bucking bronco. Bucking! Why didn't I think of that earlier?! Then it dawned on Applejack that she couldn't just buck Flitter away — it would probably damn near kill her, and even if Applejack was comfortable with that, which she wasn't, she'd be sure to be disqualified. No, the only way she'd get rid of Flitter would be to shake her off.

And she'd have to do it soon, because she could feel herself starting to get wet from the pegasus's firm but gentle attention.

Applejack moved her hips from side to side, trying to shake Flitter off, but only succeeded in grinding her marehood against the pegasus's muzzle, with Flitter's nose rubbing against that sensitive spot between Applejack's pussy and plothole. Applejack drew breath sharply. No, no, this couldn't be happening! Applejack tried thinking unsexy thoughts. Mucking out the pig sty. Giving Granny Smith a hooficure! That seemed to help a little, but not enough — Flitter's mouth was relentless, her tongue flicking up and down Applejack's slit before sinking deep into her foalhole.

Applejack wriggled and managed to shake herself free from Flitter's face, but still the pegasus pony clung on to Applejack's flank with her hooves. How can I get her off before she gets me off?

Flitter tried to line her face up with Applejack's pussy again, but the mare moved too quickly, shaking her flank left and right. She went in again, but got butted in the face — literally — and nearly bit her tongue. She needed to find a better way to access Applejack's rear end without it being constantly moved away from her.

Having a great idea, Flitter jumped up, being careful to resist her natural urge to use her wings, twisted in the air, and landed on Applejack's back, her head over Applejack's tail end. She clung on as Applejack tried to buck her off. She used one hoof to reach back and unfasten her ribbon, her long mane falling free around her shoulders, then wound the ribbon around one hoof, and under Applejack's belly before clasping it with her other hoof to fasten herself to Applejack's back.

"Now, that was a surprise move," announced Spike. "Anyone who put a bet on Applejack, don't start counting your winnings just yet."

Now Applejack could kick all she wanted, but Flitter was securely on the earth pony's back. She bent her neck to deliver another sloppy kiss to Applejack's marehood only to discover a new problem — Applejack's tail was in the way, and she didn't have a hoof free to move it. Before she could think of a solution, Flitter had another problem: her own marehood was pressed up against the back of Applejack's neck, and Applejack was taking full advantage of this.

Applejack strained her neck, looking up to the roof of the tent and twisting her head from side to side. The back of her neck and her long blonde ponytail rubbed between Flitter's legs, stimulating her pussy.

Flitter blushed as she felt herself starting to get turned on by the tickling of Applejack's mane on her pussy lips. She felt Applejack's strong neck grinding against the length of her pussy, including her little pink clit. Flitter bit her lip and tried to concentrate on using her muzzle to shove Applejack's tail out of the way, but the mane against her pussy proved quite a distraction. Finally she managed to get her tongue into Applejack's pink slit and started working it up and down, seeking out Applejack's clit.

The two ponies were working themselves into a frenzy, Applejack using the back of her neck to rub Flitter's crotch, and Flitter using her mouth to lick and suck Applejack's pussy. Flitter felt her wings begin to involuntarily twitch. Applejack could feel herself start to get warm and tingly and knew she needed to find a way to get Flitter off her perch.

Without warning, Applejack fell hard onto the bed, rolling over, and finally freeing herself from Flitter's forceful oral fucking. Flitter's pink ribbon fluttered to the ground. Stunned by the sudden turn of events, Flitter lay supine on the bed, her wings outstretched beneath her. Applejack pounced on the mare, pinning her down to the bed with her powerful hooves.

"A nice move from Applejack," Spike said over the public address system. "She's giving us a demonstration of why she's one of the favourites to win this contest."

Realizing her vulnerable position, Flitter squirmed, trying to free herself from Applejack who had managed to hold her down by the wings firmly enough to stop her getting up, but gently enough to not cause any pain or discomfort. If anything, the hooves on her wings felt nice. It was almost as if Applejack had practised this a lot before. Flitter fluttered her wings, but it was no use — she was stuck.

Applejack smirked at the pegasus and lowered her head to Flitter's neck, kissing and nibbling it. Flitter felt something between her legs and looked down to see Applejack's back hoof rubbing her pussy. She shivered and tried to push Applejack's hoof away, but the earth pony was far too strong.

The hoof slipped between her pussy lips and Flitter felt it rubbing against her clit. Applejack doesn't waste time. She tried to squeeze her legs together, but Applejack's strong back legs kept them apart. Applejack kissed Flitter's cheek and gently bit her ear before whispering, "come now, pretty, you know you want to."

Applejack's mouth moved on to the base of Flitter's wings, delivering kisses and licks to all the most sensitive parts of them.

Flitter tried to roll her hips to the side, but it was no use — Applejack had her completely trapped. Applejack slid her hoof up and down Flitter's slit, pushing the end gently into her wet foalhole and fucking Flitter with just the tip of her hoof. Flitter sighed when it went in and moaned when Applejack started moving it slowing in and out. Flitter's front hooves grasped at the bedsheets beneath her, now resigned to what was going to happen — she was going to lose.

Flitter's breath became heavy and irregular. She gasped as Applejack's hoof found her clit again, flicking it up and down. Applejack leaned to her ear again and whispered, "come now, you're nearly there Ra-- I mean, Flitter. Why don't you cum for me?"

Flitter closed her eyes and started involuntarily bucking her hips against Applejack's hoof. Great, so I'm finally able to move, and this is what I do. But she couldn't help it; she was being driven crazy with pleasure and she knew there was no way to stop it. Her pussy felt a desire to be filled and she knew she needed Applejack's hoof to fill it. "O-oh! Don't stop!" she breathed quietly. What the buck did I just say?! Flitter's cheeks turned as pink as her ribbon.

Flitter couldn't help thinking about her sister, Cloudchaser. She was in this contest too. Would it be like this for her Ceecee? Would she, too, have to deal with the humiliation of her body betraying her to her rival? Flitter thought about her sister being in the same situation as she was.

Flitter's breathing became a heavy pant. Her heart raced. Her thighs started quivering. Her wing muscles pumped, but her wings were unable to move. She felt her pussy tingling, and the tingles started moving up her back and down her legs like electricity. "Good girl, just let it all go," Applejack purred into her ear. And so she did.

Flitter squealed as a wave of pleasure swept her body. The tingles reached her hooves, her ears, her nose… all of her extremities. She shivered as ripple after ripple of bliss washed over her and the tension that had been building up in her loins melted away into a soft warm fuzzy feeling.

And before she knew it, Flitter was free. Applejack had released her. Not that she was any more able to move now than when Applejack had been pinning her down — she was a quivering wreck. Slowly she caught her breath, and started to become aware of the world around her; the noise of the crowd, and the sound of the announcer.

"… And the winner of this round is Applejack!" said Spike, speaking into his microphone.

Apple Bloom threw her hooves around Rumble to hug him in celebration. "Your sister did good," said Rumble. He finally managed to pluck up the courage to ask what he'd been wanting to ask ever since he'd taken a seat next to Apple Bloom. "So," he asked in as casual a voice as he could manage, "are you competing in the junior division?"

Apple Bloom let go of Rumble and looked at him, her head hanging low. "No," she sighed, "they don't allow blank flanks. Something to do with 'em not wantin' us to discover our very special talent during the contest and end up with a, y'know, for a cutie mark."

"Oh," said Rumble, disappointed that he wouldn't get a chance to see the cute earth pony filly in the ring. "I'm sure you'd do just as well as your big sister. Better, maybe."

Apple Bloom beamed. "Really?!" she asked. The colt eagerly nodded. "Wanna see if I can do better?" she asked, fluttering her eyelids at him before walking off towards the exit.

Rumble sat in shocked silence for a moment. He looked up at his brother seeking permission to leave. Thunderlane, who had heard everything just nodded, and Rumble galloped after Apple Bloom as fast as his hooves could carry him.

Flitter pulled herself up off the bed and stepped away from the sticky patch of her own marecum. She saw Applejack sitting next to Rainbow Dash on the bench, laughing and joking with her. Another mare through to the next round. Still, I didn't make it easy for her. I can walk away with my head held high. And that's precisely what she did.

Author's Note

I did this one! I did this one!

I wanted to write the Applejack x Flitter round all along, but reluctantly assigned it to one of the other contributors. Luckily he pulled out, so I ended up being able to write it myself. :yay: ~yay!

Did you pay attention to what Apple Bloom was saying? I have plans for a foalcon spin-off, but I need more collaborators to get it started! PM me if you're interested in volunteering.

Anyway, next up: Colgate Minuette -vs- Fluttershy.

Colgate Minuette -vs- Fluttershy (Nocturnal Derp)

Spike seized the microphone as the next two contestants entered the stage area. “Up next we have Ponyville's resident dentist, Colgate Minuette, up against my good friend Fluttershy.” The yellow pegasus smiled at Spike as she walked towards the bed.

“Um... I-I'm not so sure about this,” Fluttershy squeaked at the start of the match.

Colgate didn't know if she wanted to make a move on the shy mare if she didn't have her head in the game. It would feel wrong. “Well Fluttershy, you could always resign. I won't lay a hoof on you if you don't want me to.” She tried to say this in a manner that wasn't taunting.

Fluttershy picked her head up a bit and looked over to the unicorn. “Ohh, I couldn't do that. I agreed, and these ponies would be so disappointed if I quit, but... they're all watching and I don't know if I could um... do that... in front of them.” Fluttershy hid behind her mane, trying to control her breathing instead of freaking out. It'd be much more embarrassing if she ran out now and too much trouble for her friends who would undoubtedly run after her.

“Well, maybe we could start slow. I won't jump you if you won't jump me,” Colgate replied. “Get on the bed and I'll start.”

Fluttershy seemed to like this alternative, and was glad she got paired with somepony who was willing to level with her. She looked up and smiled. “Okay, sounds good.” With a little more pep in her step she jumped up onto the bed, trotted a few paces to give Colgate room to jump up behind her, then turned to face her.

Colgate jumped up behind her, and decided to make her move then and there, figuring any procrastinating might lead to the canary mare backing out.

Her nervousness kicked in just as Colgate was approaching her but she tried not to let it show. Tried even harder when Colgate pressed her lips to her own. She squeaked but didn't pull away. She instead studied the feeling. Colgate's lips were smooth, soft and moist. She surprised herself by leaning into the gesture and allowing her eyes to close.

Colgate took this as a good sign, and pressed forward. She wanted to make this quick but wanted to go easy as to spare the mare any embarrassment. Gently but firmly she placed a forehoof and pushed on her. To her relief Fluttershy allowed her to push her into a sitting position while still maintaining their kiss. The fact she wasn't pulling away reassured her that this was okay.

Fluttershy allowed herself to be controlled by the unicorn for the time being, relishing in the experience. She'd nearly completely forgotten about the eyes that were on her. Was this normal? She'd also forgotten she was in a competition. Suddenly there was a gentle rubbing on her chest, that got lower and lower, to her warm belly and still, slowly lower. What was she doing? She was distracted for a moment by something new on her lips. Colgate's tongue prodded gently, almost like asking for permission.

Fluttershy wasn't ignorant: she knew what she wanted and almost happily obliged. She opened her maw, allowing Colgate's tongue inside which immediately found her own, and Fluttershy tasted it, ironically quite minty. For a few seconds she allowed Colgate to explore the caverns of her mouth unhindered, squeaking as it twirled around hers a few times, then pushed back gently with her own.

Colgate figured that if Fluttershy hadn't resigned by now, she wasn't going to. She slipped her forehoof the last couple inches down to the warm folds of Fluttershy's delicate flower, getting an immediate response in the form of a sharp intake of breath. Colgate allowed herself a smile. This was going to be easy.

Fluttershy's mind erupted in a explosion of color for just a brief moment and her wings sprung open. Her initial reflex was to pull away but her body kept her glued to the mare in front of her, allowing her to have her way. Being a virgin, she should have realized being in this contest was a bad idea. While she had touched herself there, she'd never had somepony else this close to her before. Fluttershy propped herself up on her haunches, wrapping her forelegs around Colgate's neck, deepening the kiss and allowing Colgate better access to her pussy. For a moment she thought this was what she wanted, until she remembered this was a competition.

Colgate drove forward with her sensual assault, pushing more against her while increasing the pressure on the yellow mare's now very slick crotch. She wrapped her free foreleg around her, lowering her to the ground gently. She wasn't going to be rough unless Fluttershy turned on her. Once Fluttershy's back was firmly to the bed she assumed her place over her, rubbing faster and broke the kiss, only to start nibbling on the pegasus's neck. She was even more pleased with herself when Fluttershy's wings visibly flexed and her back arched. Maybe it was time to end this, as much as she was enjoying her free ride, she had a contest to win. Colgate withdrew her hoof from her pussy and used it to support herself as she made her way further down the yellow furred body, nipping and nibbling down the mare's chest as she went ever so slowly along. She didn't want to startle Fluttershy.

“Oh come on!” Rainbow exclaimed in her seat. “She's just taking it! I mean... I didn't think she was going to win but she's just letting Colgate have her way with her!” Rainbow slapped a forehoof to her face and slumped in her seat.

“Now, Rainbow, you know more than I do that Fluttershy ain't really built for this. She's too darn subtle for this. I don't really think ya should have talked her into it.” Applejack turned to look at her blue friend.

“Yeah yeah...” Rainbow muttered. “Still...”

Fluttershy took in a breath of air now that she was able to think a little more clearly. She'd all but forgotten the crowd and was more focused on this wonderful new feeling. However she knew that the better this got the quicker she would lose. She certainly didn't want to disappoint everypony by just giving in like this. What else could she do though? She gasped as Colgate's lips found a nipple, and Colgate's tongue dance around it. She looked down and saw the cold white blue mane of her advisory, and her horn. Her horn... wasn't that... She remembered hearing something about a unicorn's horn. Was it against the rules to mess with it? No... only if they used magic. Nopony said anything about the other pony using it. Without much more consideration she reached down and took it in her hoof.

Colgate immediately froze in her tracks and her body stiffened. A weak gasp escaped her muzzle. She tried to look up but the pressure only increased as the grip on her horn held her in place. “F-Fluttershy!”

Fluttershy let go in an instant, worried she'd hurt her. “I-I'm so sorry! I didn't hurt you did I!?” Her cheeks lit up for a different reason.

“No...” Colgate looked up. She didn't want to lie to her. She'd feel wrong if she won by lying to her. “It felt amazing, just unexpected.” Colgate's face was half red with color at her arousal and embarrassment The arousal wasn't caused from that single moment alone however — she'd worked herself up toying with Fluttershy and was beginning to regret it. “I startled you, that's not fair. Go ahead and take it how you had it before, and we can continue.” Colgate's voice broke a bit. She wasn't sure if she'd be able to continue if Fluttershy messed with her horn for too long. Hers was much too sensitive and way too big a weakness to be exploited so early on in the contest. Fair was fair however.

“Y-you're sure?” Fluttershy squeaked, eying the blue horn that was glowing a bit.

“Yes.” Colgate lowered her head, closed her eyes and bit her lower lip in preparation for the contact. She wasn't disappointed. The soft hoof wrapped it's way back around her horn and she squeaked a bit. “R-ready?” She whimpered.

“Okay.” Fluttershy sounded much more determined now, and made good use of her new toy. It was okay if she wasn't hurting her. However she still felt the arousal but this only fueled her new found desire. Doing the only thing she thought to do at the moment, she began to rub it up and down, watching Colgate squirm over her, her forelegs struggling to support her.

Colgate could barely control her breathing, much less her thoughts. She had to figure a way out of this but nothing stayed for more than a moment. Little shocks spread through her body, radiating down from her head to her flanks. She tried to pull away a couple of times, but was too weak to accomplish much. Fluttershy was much stronger than she looked. While she was certain she could pull away if she wanted, the resulting friction would undoubtedly render her useless for all too long, and would give Fluttershy way too much time to take advantage of her. She wasn't given too much time to think as it seemed the yellow mare had a new idea.

Fluttershy figured that if Colgate touching her own pussy had felt so good, that doing the same to her would work just as well, especially with her apparent advantage. So with little hesitation she brought her hind leg in between Colgate's hind legs and rubbed her pussy ever so delicately, still afraid of hurting her. The reaction she got wasn't one of pain.

Colgate tensed up again, whimpered and moaned. “F-fuck.” She breathed. Things went from bad to worse. She wanted to return the favor and somehow regain ground but she couldn't use one of her forelegs for too long. If she did the other wouldn't be able to support her. She couldn't pull her horn free and was defenseless. She moaned again as the pressure on her crotch was increased, Fluttershy was getting more comfortable with her position and was pushing her hind leg harder against her now very swollen and very wet pussy. She had one idea.

In one last ditch effort to even the playing field she brought one of her forehooves down, pushing Fluttershy's hind leg that was assaulting her mare hood away long enough for her to bring one of her own forelegs between Fluttershy's, and brought her hips down quickly, almost slamming her pussy into Fluttershy's marehood.

Fluttershy gasped, her wings flexed to the point of pain and her back arched. It was all she could do to remember to hold on to her new found toy. She wasn't thinking about the awkward position she was in, or the ponies watching. All she was thinking about now was the pleasure radiating through her body, and this contest in which she had an unexplained desire to win all of a sudden.

Colgate moaned once more, and cursed realizing Fluttershy hadn't released her. At least now she had some means of fighting back. She suddenly wished she wouldn't have given Fluttershy any leeway in this bout and cursed herself again for underestimating her. All she had to do now however was out ride her. In an instant she began bucking her hips against Fluttershy's, sliding her marehood over the yellow mare's as best she could in her awkward position, her head still down with her horn still in the hooves of her opponent.

The juices from both mare's arousal served as more than enough lubricant for their grind which Fluttershy returned weakly at first, then with almost more force than Colgate. She used the horn for leverage, no longer concerned for hurting Colgate. It was obvious she was in no pain, or if she was, she liked it.

Colgate wanted to bring her forehooves up and take hold of Fluttershy's wings, suspecting that to be as big a weakness as a unicorn's horn was to their own body. However she couldn't quite reach with her head down the way it was. Even though she was on top she was still at a great disadvantage and felt the pressure building fast. She still attempted to ride her out, taking Fluttershy's hips in her hooves and driving into her as hard as she could, but it seemed to no avail.

Both mare's continued their instinctive sexual assault on one another, doing little to escape the clear signs of pleasure in the form of their moans and whimpers. However everypony could see early on who was clear to be the winner from this point. Colgate froze for brief periods of time, and her moans were noticeably louder and more drawn out. Eventually Colgate stopped all together and held on for dear life as the pressure and heat grew too such a great extent she could barely hold it. Fluttershy was relentless however, consumed in the heat of the moment and never let up.

Finally Colgate surrendered to her own instinct and desire. With one last cry her body exploded into a world of sweet release and bliss. She managed to hang on and ride out her orgasm as her juices covered Fluttershy's snatch, making the yellow mare arch again as she too lost control of her own body and she climaxed soon after, returning the favor.

As the last spasms of their orgasms rocked their bodies Fluttershy let go of Colgate's horn, letting her foreleg fall limp to her side as she struggled to catch her breath. Colgate straightened her hind legs and collapsed atop Fluttershy, too tired to catch herself. Fluttershy didn't seem to care.

After a minute Fluttershy became aware of her surroundings once more, and looked down at Colgate's head which rested on her chest. “Um... W-what happened?”

Up in the stands Rainbow and Applejack were out of their seats. “Did Fluttershy actually...”

“I think so, sugarcube,” and Applejack started laughing.

“Well...” Rainbow trailed off, speechless at the turn of events.

Colgate heard the soft voice and giggled, not even upset she'd lost. She looked up smiling at the Pegasus. “You won.”

“I-I did?” Fluttershy squeaked, half in surprise and half in shock. She felt too good to be embarrassed yet.

“Yup, you did.” Colgate picked her self up and backed away from Fluttershy, giving her some much needed space.

Fluttershy sat up and looked down at herself, covered in sweat and... cum. She felt sticky, her crotch was soaked and a musk lay heavy in the air. “O-Oh... my.” The realization of what it was finally caught up with her and her cheeks lit up. “Um... I think I need a bath.”

“We both do.” Colgate smiled and broke out laughing, leaving Fluttershy slightly confused but happy and proud of herself.

Spike returned to the announcer's spot, having conferred with Princess Cadence. “The winner is Fluttershy!”

He watched as Ponyville's dentist left the stage. “And to think I let that mare put her hooves in my mouth,” he mumbled.

Author's Note

This chapter was contributed by Nocturnal Derp, whose First to Whinny trilogy was one of the major inspirations for this collaboration, so go read it!

Next up: Apple Fritter -vs- Cloudchaser.

Apple Fritter -vs- Cloudchaser (Fimbulvinter)

There was a short delay as the sheets and pillows on the bed were changed once again. Spike took this time to get the crowd worked up for the next match.

"As always, we have a competition between two lovely mares. They are both eager and ready to screw each others brains out for your pleasure. In one corner, we have one of the cutest pegasi ever to soar the skies. Known for her skilled wing control, she even served a brief tour at the Wonderbolt's Academy training program. Put your hooves together for Cloudchaser!!!"

A lilac pegasus landed on the ground, waving to the crowd. She had dressed for the occasion in leg length purple socks, and her mane was specially styled for the event to ensure that it didn't get in the way of her muzzle. The crowd stomped their hooves, or in more than one case, just one hoof.

"Going up against Cloudchaser is some equally stiff competition. Three time winner of Equestria's best fritter fry off, this pony's talent with all things apple knows no bounds. While she doesn’t live within the town proper, she is a resident for tax purposes, and her grandfather did found the town, so the judges are allowing it. Give it up for… Apple Fritter!!!"

From the other side of the arena, a yellow earth pony walked in. With her mane pulled back in a pair of ponytails and thigh high white socks, she was cute as a button. Her eyes were locked on Cloudchaser and didn't waver for a second as the assembled ponies made their enthusiasm known.

In the centre of the stage, the bed was still being prepped, giving the two mares time to size each other up.

"Looks like we might have a slight delay, folks. But no matter, it seems that our competitors are already engaging in a little bit of pre-match trash talk!"

Cloudchaser walked forward slowly, eyes gauging Fritter's flanks and posture. "So, you're the pony my sister is shacking up with?" Cloudchaser said, her eyes narrowing on Apple Fritter’s body. "No matter. By the time I'm done with you, you're going to be screaming out my name."

Apple Fritter wasn't one to be daunted by words. After all, she was an Apple, and they preferred to do rather than say. "I know all the sweet spots on your body, Cloudy. I've enjoyed every one of them with your sister." Apple Fritter paused for a second to lick her lips. "She's tasty. You'll be begging me for another go once I'm done fucking your fritter."

Cloud Kicker switched her gaze to Apple Fritter's socks. "Fancy. Cashmere?"

Apple Fritter shook her head. "Wouldn’t you like to know? No matter, you’ll find out as I rub you out of this competit- "

Before they could say more, the ponies changing the sheets signaled that they were done.

"Mares and Gentlecolts, looks like we are ready to get underway with the next round. Competitors, remember that wingplay is fair game, but flying is banned. At any time that wings are in play, one hoof must always be on the ground. Keep it clean and let the next match in the Biennial Sex Contest begin."

Both mares climbed up onto the bed. Having just been changed, the sheets and pillows were perfect and crisp. Neither mare noticed though. Each only had eyes for their opponent.

"Screw her, Fritter!" A voice came from the competitor's rest tent "Fuck my sister!"

Apple Fritter's eyes waivered for just a second as she looked for the source of the voice.It proved to be a costly mistake.

Out of the corner of her eye, she saw a lilac blur speed towards her, and before she could react, she was knocked down to the ground while Cloudchaser stood above her and smirked. A hoof trailed down Fritter’s chest, making its way towards her nethers, and while her own socks may have been mink, Cloudchaser's were most certainly mode of very fuzzy, cashmere wool.

Apple Fritter squirmed as Cloudchaser slid the hoof between her legs. She tried to roll away or shove Cloudchaser away, but the pegasus had all the leverage. A moment later she felt lips on hers as Cloudchaser moved in for the kill.

Cloudchaser's fuzzy hoof massaged her nethers, rubbing lightly, but insistently, while she kissed Apple Fritter, who resisted for but a moment before melting into the kiss and returning it. Fritter's legs spread apart just a hair, giving Cloudchaser’s hoof free reign. Occasionally, Cloudchaser switched from rubbing her slit to brushing against her teats, the nubs hardening in response to the stimuli.

"Looks like Cloudchaser is off to an early lead!" Spike called from the announcer's box. "How long can Apple Fritter hold out under such an overpowering assault?"

Spike's words refocused Apple Fritter. She was in a competition, not in bed with Flitter; she had to fight back. I can't go out like this, she thought as Cloudchaser sloppily tongued her. She had to hold up the Apple Family honour, just as cousin Applejack had done in her round. Flitter had told her to fuck her sister, and that was exactly what she was going to do.

Gathering all of her legs together, she bucked upwards, sending Cloudchaser flying up into the air for a moment. Instinctively, Cloudchaser's wings spread open, locking into the flight position to steady herself as she came back down the stage; something that all pegasi had been taught to do since the day they learned to spread their wings.

The second her wings started to spread open, they were both engulfed in a blue magical glow and pinned back to her sides. Without her wings to guide her down, Cloudchaser fell down in a clumsy heap, sprawling out on the bed, defenseless and practically presenting herself to Apple Fritter; just as had been planned.

"Mmmm, no flying. You know the- AAAhhHHHH! rules." A mare's voice came from up at the judging stand.

Apple Fritter looked up. Looking down at her and Cloudchaser, Princess Cadance's horn was glowing as she ensured that the rules were followed. Every few seconds, she seemed to be squirming on her couch, gasping or moaning. Poking out from between her legs, Apple Fritter could just make out a blue mane and a white horn.

Looks like somepony else is enjoying themselves. Apple Fritter wasted no more time getting back to her hooves. Cloudchaser was still trying to scramble her way back out of the heap she had fallen into. Before she could get up again, Apple Fritter was behind her.

Fritter's fore hooves spread Cloudchaser’s rump apart, revealing her more intimate folds. The first signs of arousal were beginning to appear; the flushing of the tender flesh and drops of pre-cum lubricating the walls. Without hesitation, Apple Fritter leaned in and licked up from the base of Cloudchaser's clit right up to just below her dock.

She tasted so much like her sister, Apple Fritter closed her eyes and pretended that it was Flitter she was eating out. Her marefriend's pussy was warm and sweet, and her tongue explored inside, teasing and testing every nook and cranny. Mare juice covered her snout as she mashed her face against Cloudchaser's pussy, grinding hard.

In her current position, Cloudchaser couldn't get her hind legs free to stand up, and Apple Fritter clearly had an advantage over her when it came to eating carpet; her tongue seemed to know just how to please her in ways that none of her male lovers had ever even come close to, and Apple Fritter’s socks were tickling the nerves along her withers. She could already feel the tingling sensations that heralded the onset of climax. If she didn't escape soon, it would all be over.

It was time to play dirty.

Unfurling her wings again, Cloudchaser pushed them both straight down, lifting her body up off the ground and with the aid of her forelegs, she used them as a spring, cartwheeling up and pushing Apple Fritter onto her back again and sending them both sprawling.

But this time, Cloudchaser was ready for it. She had a plan; a little something she had learned during her all too brief tour serving with the Wonderbolts.

More like the Wonderbangs, she thought as she quickly twisted into position while Apple Fritter tried to recover. "Here's a little something Fleetfoot taught me behind the bike sheds," she whispered into Apple Fritter's ear. "The Academy wasn't all flying lesson; they made sure we had a few fucking lessons as well."

Before Apple Fritter could do anything, Cloudchaser grabbed her and spun them onto the bed. Rather than just wind up on top, she twisted until she had both her fore hooves under Apple Fritter's shoulders in a half nelson hold. With her hind legs, she twined between Apple Fritter's and spread them apart for the judges; not too much that she risked hurting Apple Fritter, but enough so that she couldn’t just wriggle free. She made sure that they were facing the judges box; she wanted them to see what was going to happen. Cadance was still watching intently, while her husband tenderly pleasured her. Celestia and Luna were also watching, while the two royal guards assigned to protect them today were busy trying to hide rising wingboners.

With her legs pinned, Apple Fritter was totally at her mercy as Cloudchaser's wings folded up and replaced her arms in holding Apple Fritter in place. They snaked down over her cutie marks and grazed the fluff of fur just above her…

"Eeepp!" Apple Fritter yelped as Cloudchaser's wing feathers teased her lips. It was a stretch, but Cloudchaser could just reach. With feather light strokes, Cloudchaser stroked her nipples and prodded her opening. Apple Fritter struggled, but she was held tight this time; Cloudchaser had her and she wasn't about to let go.

Juice slicked over Cloudchaser's wings as they went to town on Apple Fritter. Fleetfoot had been most diligent in her instruction in this position, and Cloudchaser could feel the signs coursing through Apple Fritter's body. Even still, she had one more trick up her sleeve.

Apple Fritter shuddered, trying hard to delay the onset of her climax, focusing on even breathing to carry her through, but Cloudchaser changed her technique and started to massage her clit and probe inside her vagina, treating her wingtips like crude dildos.

When she felt that Apple Fritter was just about on the cusp, Cloudchaser unleashed her final move. Nuzzling up against the back of Apple Fritters head, she lightly bit the tip of her ear; not hard enough to cause any pain, but just enough to send a sudden unexpected shock through her body.

"AAAAHHHHHHHHHHHH!!!" Apple Fritter's body twitched once, shuddering as pleasure worked its way outwards from her cunt. Cloudchaser felt a wave of warm fluid coat her legs, and she knew that she had victory. She released Apple Fritter at once, letting her slump down to the bed before scissoring her legs and pressing her cunt to Apple Fritter’s. Cloudchaser rode out Apple Fritter’s climax, humping her throbbing clit until Cloudchaser joined her in orgasmic bliss, throwing her head back and screaming in pleasure. The heat between them was incredible as their slick pussies slid over each other, twitching and spasming with every press.

Slowly, they both came down, panting and flushed with pleasure. As soon as she felt she was able, Cloudchaser looked up at Princess Cadance, who looked back down at her and nodded once to Spike.

"And we have a winner, mares and gentlecolts. Showing stunning versatility and a fine example of creative wing use, the winner of this round is Cloudchaser!" Around the area, ponies showed their enthusiasm while the service ponies in charge of changing the sheets ran out again, fresh linen clutched between their teeth.

Cloudchaser extended a hoof and helped Apple Fritter back up to her hooves. The earth pony looked downcast that she had lost.

“Don’t feel bad,” Cloudchaser said, leaning in close as they both walked towards the competitors tent. “I’d be willing to stage a rematch later on. Say, your house?”

Despite her disappointment, Apple Fritter smiled and gave a half hearted laugh. “You’re on, Cloudy. Now get out there and win this thing.”

Cloudchaser looked back at the stage. She’d only have a little while to get ready for her next match. Rainbow Dash would be tough competition, but she was all flash and no endurance.

Breaking away from Apple Fritter, she headed for the showers. A quick scrub and Rainbow Dash wouldn’t know what hit her…

Author's Note

This chapter was contributed by Fimbulvinter and edited by JumbledThought.

Cloudchaser vector by: quanno3.
Apple Fritter vector by: leopurofriki.
Background by: MLP Vector Club.

Next up: ???

Twilight Sparkle -vs- Cheerilee (Shrinky Frod)

Twilight vs Cheerilee (Shrinky Frod)

Spike picked up his glass and casually took a drink as the last preparations were made for the final match of Round One. Aloe and Lotus were changing the sheets and mattress out while Snips and Snails finished mopping up the floor from the various fluids that had collected since the last all-too-necessary cleaning. The little dragon at the announcer’s stand savored his tea, his overworked vocal cords relaxing while his emerald eyes scanned over the roster to confirm who the next match was.

Suddenly, those emeralds gained several carats, and shouts sounded from the audience in front of Spike’s booth as his tea found its way into their manes.Most were wearing something on their heads; it was only good sense given the tendency for bodily fluids to find their way into the air at the event. Still, most had their head protection angled towards the stage, not the announcer!

“Eheh, heh… heh,” Spike chuckled nervously, rubbing his spines sheepishly. “Right, sorry about that everypony! But I just realized it’s time for the match we’ve all been waiting for!”

Well, all except Spike.

The audience cheered, more than ready for the match. While the two colts on the stage quickly finished cleaning things up and the spa sisters tucked in the sheets on the new mattress, Spike regained his composure and sorted out his notes on the two competitors’ stats.

“Alright everypony, like I said, it’s time for the match we’ve all been waiting for! At the headboard, it’s Ponyville’s one and only hot-to-trot teacher, the Mulberry Mistress, the Teaching Tongue herself, Miss Cheerilee!”

The older mare came out onto the stage, tossing her mane flirtatiously as hooves thundered against the floor, particularly from the junior section of the audience. She’d come dressed, unlike most of the competitors, wearing a charcoal grey suit with a sinfully short skirt and pale grey, sheer stockings that ran down her shapely hind legs. She waved to the audience, giving a few lucky stallions and mares a saucy wink while Spike continued.

“A long-time resident of town, Miss Cheerilee was a favorite to win the third contest after strong showings in the first two, but withdrew on the eve of the finals with no explanation! Now, nearly ten years later, she’s returned just as suddenly trying to reclaim the glory she surrendered so long ago!”

“Ahem,” Cheerilee glared at Spike.

“Heh… well, uhm, maybe not so, so long ago?”

A few stallions in the audience chuckled, and more than a few mares, as Cheerilee rolled her eyes. Let them laugh; she certainly wasn’t the oldest mare who’d ever competed, or even that much older than the average.

“Moving on from how long it has or hasn’t been since Cheerilee took part in our biennial tournament,” Spike continued, “those who remember her past performance are no doubt anticipating how she handles one of Ponyville’s newest contestants! One of the favorites to take it all this year, it’s the Lavender Licker, the Horned Hedonist, reigning champion in every sense of the word… Princess… Twilight… Sparkle!”

The entire audience erupted into cheers and thunderous applause as Twilight teleported onto the stage at the footboard of the bed. She reared up and tossed her head, then spread her wings majestically to even greater acclaim from the audience. As she settled down, licking her lips sensuously and eyeing Cheerilee from nose to tail-tip, she raised an eyebrow curiously.

“I’m sorry to be the filly who reminds the teacher of the rules,” Twilight smirked, “but isn’t it cheating to wear something that covers your flanks?” Cheerilee smirked, reaching down and biting on the fabric of her suit. With a single jerk of her head, the fabric ripped at the specially concealed seams, revealing her nearly-naked body. The sheer stockings clinging to her hindquarters came up to just below her treasures, kept from falling as she moved by the lacy garter belt she wore.

Stallions in the audience whistled their appreciation as she tossed the ruined costume out into the crowd to be fought over for souvenirs. One charcoal grey mare in particular gasped as she recognized the second cutie mark subtly worked into Cheerilee’s underthings.

Good. She deserved to know she wasn’t the first one with those particular privileges.

Even better, Twilight’s wings trembled as she looked at the display that Cheerilee was making, fighting not to shoot out in response to what Cheerilee knew all too well was every faithful student’s fantasies made flesh.

“Oh, don’t worry,” Cheerilee nearly purred as she leaned in towards one of the mics on the stage. “I’m going to make sure you’re well disciplined for correcting teacher.”

“I’m the one who’ll be teaching all the lessons tonight,” Twilight shot back with a grin.

“It seems our two contestants are chomping at the bit to start!” Spike piped up nervously. “So let the Battle of the Brainy Babes begin!”

Somepony bucked the starting bell and… nothing happened.

Nothing physically, at least. On the surface, the two mares looked like a pair of particularly lifelike statues. Occasionally, Cheerilee would shiver, or Twilight’s wings would shudder as they considered a particularly pleasant attack and possible counters, but unlike any of the matches so far, neither mare seemed to be in a particular hurry to get in contact with the other.

Cheerilee knew she wasn’t the sexiest mare in Ponyville. She wasn’t the most experienced. She wasn’t even the most difficult to pleasure, an advantage that had seen her lose out in the finals twice to Granny Smith before she’d figured out the old biddy’s weak point in the third contest and knocked her out in the first round.

What Cheerilee had that no other pony in the contest had, with the possible exception of her opponent, was the understanding that sex wasn’t about applying part A to bit B and working it until something clicked. Ninety percent of sex was in the mind.

And when it came to getting into her opponents minds, knowing precisely what it would take to make them let down their guard, nopony beat Cheerilee. Especially not when it was as incredibly obvious as it was with Twilight!

Finally, Cheerilee drew herself up to her full height, glaring at Twilight with all the authority over a decade and a half in the classroom had taught her to muster.

“Miss Sparkle, what do you think you’re doing?” She demanded in a tone that somehow managed to blend command with condescension in a way that still made several of her students in the audience, current and former, tremble just to hear. For a brief moment, Twilight slid back towards her haunches, about to sit down instinctively.

Instead, she caught herself and changed direction, sitting on the bed with a sultry look.

“What’s the matter? Don’t you offer extra credit for your students?”

“This bout seems to have taken an unusual turn, ladies and gentlecolts,” Spike announced for the benefit of those in the cheap seats. “In all my years of announcing, I’ve never seen ponies getting into character like… oh sweet Celestia, is this what she was doing all those late nights at magic–“

A sudden glare from Twilight silenced Spike, who clapped a claw over his mouth before he could go any further. It was just the distraction that Cheerilee needed though; she pounced at the princess, forcing her down to the bed.

“Only the very naughty ones,” she purred, just loud enough for the mics to catch it before she kissed Twilight hotly.

Twilight moaned into the kiss, her wings finally spreading beneath her as she fought to get one of her legs between Cheerilee’s. Up in the royal viewing box, Luna leaned over towards her sister.

“Just how often hath Twilight enacted this fantasy, Sister?” She teased.

“Often enough,” Celestia responded with a cryptic, serene smile.

“Often enough that I couldn’t threaten to punish her without her blushing,” Cadance chimed in. “She can be a very naughty little filly when she wants to be.”

“And oh how she wants to be,” Celestia murmured under her breath, then blushed as she realized that she’d said it out loud.

Back on the stage, both mares were unaware of the discussion going on above.

“What’s the matter, Princess, afraid you’re going to get schooled?” Cheerilee taunted her as the kiss broke, nipping roughly at Twilight’s neck and keeping her legs close enough together to frustrate the alicorn’s efforts.

“Not really.” Twilight smirked, wrapping her legs around Cheerilee’s hips. “Just wondering when you’re going to actually teach me something!” She pulled her left wing in, flapping the right one back to lend herself a little extra muscle as she twisted and summoned every ounce of her earth-pony strength to wrest Cheerilee off her hooves. The two of them rolled over on the bed, leaving Twilight straddling the teacher’s hips as they bounced on the mattress.

“I think you’re ready for some advanced lessons,” Cheerilee shot back. She reached up, hooking her hooves over Twilight’s extended wings and stroking along the hypersensitive axilars. Twilight’s muzzle pressed against hers again, the princess’ tongue invading the teacher’s lips with an undeniable demand to control the situation. Cheerilee felt herself starting to heat up where their hips met, and wasn’t sure if she was feeling Twilight’s arousal or her own that moistened her nether’s lips. She pressed more firmly against Twilight’s wings, trying to force a reaction out of her, but got almost nothing.

Cheerilee scowled as she realized that Twilight had partially numbed them somehow. She could almost feel the princess’ smug satisfaction as Twilight began grinding their hips together, forcing an escalation as their most private parts slid slickly against each other. A moan escaped Cheerilee’s lips as Twilight broke their kiss, and she blushed at her own reaction.

Suddenly, Cheerilee tightened her grip on Twilight’s right wing, twisting it ever-so-slightly in the socket. Twilight gasped sharply, the smug look on her face evaporating into a flash of pain, pleasure, and shock. Cheerilee took full advantage of her distraction, twisting her wing back the other way and pushing her off of the bed. Twilight landed on the hard wooden floor with a squelch and a thud, stunned just long enough for Cheerilee to get off the bed herself.

“So, the naughty little princess likes to play rough?” Cheerilee taunted her, both of them breathing heavily as they started to circle each other. “Maybe she needs a good old fashioned spanking?”

“What, and get your hooves dirty?” Twilight countered. “You know you’d rather cane me.”

“I’ve got a yardstick back in the classroom with your name on it,” Cheerilee admitted. “But that’s for the third date.”

“Well, if this is the first, I should get detention more often.” A grin flashed across Twilight’s face before she rushed in, pressing her barrel against Cheerilee’s and leaning up to nip at her ear.

“She doesn’t deserve you,” the alicorn whispered.

Cheerilee was stunned; was Twilight just guessing? Had she noticed the tied scroll worked into the black lace of her garter belt too?

How much did she know?

Twilight pressed her newfound advantage, forcing Cheerilee down to the floor and standing over her.

“You gave her seven years,” she kept whispering, just quietly enough that none of the spectators would catch her words, but Cheerilee couldn’t avoid them. A nip at the teacher’s neck earned a moan that was half-pleasure, half-anguish. “Gave up your fun, your self and she never even admitted you were together.”

A blush crossed Cheerilee’s cheeks that had nothing to do with the hoof finding its way to her hot, desperate pussy. Even clopping herself to sleep for the last fortnight hadn’t completely deadened the physical need, the ache, to be touched by another pony. By a very special pony, one she’d caught in bed with another, much younger, mare just before the worst Hearts and Hooves Day of Cheerilee’s longer-than-she-cared-to-admit life.

The year since then without being touched had been torture, but it was nothing compared to knowing that Twilight somehow knew. Tears welled up in Cheerilee’s eyes as the hoof on her pussy started to move more quickly, skillfully stimulating thousands of nerves that were designed purely for pleasure.

“Just let the pain go,” Twilight whispered, nipping at Cheerilee lustily as she went straight for the teacher’s throbbing clit.

Sex was ninety percent in the mind. Both of them knew it. Twilight was very, very close to closing the final ten percent with her hoof. Unfortunately for Twilight, Cheerilee’s mind was second in Ponyville only to hers.

“No!” The earth pony snarled suddenly, twisting up and bringing her teeth down hard on the tip of Twilight’s horn. She gasped sharply, startled out of her attentions to Cheerilee’s vulva by the sudden throb of pain and pleasure that throbbed from the tip of her horn to the base of her brain and radiated out from there.

Cheerilee began working her tongue along the rough, spiral groove that ran from bony tip to fuzzy base, channeling magic and sensation straight into the alicorn’s incredibly evolved frontal cortex. It was a quirk of unicorn biology, one that allowed them to work miracles with their magic, but also one that gave them a giant, rock-hard erogenous zone right on their foreheads. Fluttershy had happened to discover it by mistake earlier in the day.

For Cheerilee, who not only knew about it, but about every single detail of its workings, it was her last lifeline.

“And it looks like the match is really heating up now!” Spike announced, filling the near-silence that existed now that the two mares were wrestling on the floor for dominance, words forgotten in the sexual melee. “Nopony, absolutely no pony, expected the defending champion to have a bout like this!”

The crowd cheered, hooves clopping against the floor, a few just clopping in general.

Twilight lowered her head further, trying to pull her horn out of Cheerilee’s muzzle, but the schoolteacher was able to lean forward, keeping it in her mouth due to her own flexibility and the alicorn’s greater length. Cheerilee’s eyes widened as she realized that the horn was just long enough for Twilight to lower her own muzzle between the middle-aged teacher’s flanks, sending jolts of pleasure through her body as the royal tongue descended to lap at her swollen lips.

It was time for the endurance portion of the contest now. Twilight was dripping onto the polished floor from the attention to her always-sensitive horn. She wrapped her forelegs around Cheerilee’s hips, shifting into position to keep up her oral assault on the delectable flesh in front of her. Cheerilee’s back ached from bending forward so far, but she knew that if she lost her grip on Twilight’s horn she’d lose any chance at winning the contest.

“Cum for me, Cheerilee,” Twilight panted between hungry licks, musky juices coating her muzzle. “Go on, let her go!”

Cheerilee bit down hard on the end of Twilight’s horn, fighting to try and push her over the edge sooner. Instead, Twilight returned the favor, nipping roughly at Cheerilee’s throbbing clit and tugging at it with skilled teeth and lips.

Cheerilee threw her head back and screamed as orgasm rocked through her, pleasure shooting up her spine and radiating through her body from nerves that were practically hardwired into the pleasure center of her brain. The crowd whooped and yelled excitedly as Twilight moved down to put on a show, devouring every drop of the fluids that leaked liberally from Cheerilee’s spasming sex, keeping the teacher writhing in bliss for nearly a minute before she finally collapsed, panting on the floor.

“So,” Twilight panted as she looked up from the sopping mess she’d made, grinning at Cheerilee, “how’d I do ma’am?”

Cheerilee lunged, grabbing her and kissing her deeply, passionately. She wrapped her pastern around Twilight’s horn, jerking at it roughly as the alicorn moaned and let herself go. Lavender fireworks erupted on the stage as Cheerilee brought Twilight to her own orgasm.

“A plus,” Cheerilee panted once they finally parted. “Thank you,” she mouthed silently.

“Meet me at the castle after the contest, and maybe we can have a rematch,” Twilight rumbled softly, kissing her again before she started to limp off to take her seat with the winners for the next round. “Without you trying to impress a pony who never deserved you.”

“Would somebody get a mop out here?” Spike sighed, glowing and sparkling behind his podium from where Twilight’s magical discharge had coated him with its light. “And maybe a magic suppressor for the next round,” he grumbled, trying in vain to put himself out.

Mayor Mare came back into the arena, taking her seat next to Octavia in the front row.

“So how did it go?” She asked the younger mare. Octavia glared at her, then looked forward stonily without a word.

“What’s wrong?” The Mayor frowned, not sure what had happened until she looked up at Cheerilee, still panting on the stage and wearing the garter belt she’d given her years ago.

The one that was suspiciously like a similar garment she’d given to Octavia not very long before.

“Tavi, I can expl-“

“That’s Octavia, Miss Mayor,” Octavia ground out through her teeth. “And you’d better be able to. From the couch.”

“I warned you she was a politician,” a blue-maned unicorn teased from Octavia’s other side. “Hot show though!”

“Shut up, Vinyl,” Octavia grumbled, glowering at the stage as Snips and Snails came out to clean up again, Spike still glowing like a green and purple Hearth’s Warming tree as he slapped at errant sparks of magic to try and put them out.

Author's Note

This chapter contributed by Shrinky Frod.

Sorry, this update has been a long time coming!

Next up: hmmm… we'll see.