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 Notes:

This chapter contributed by Shrinky Frod.

Sorry, this update has been a long time coming!

Next up: hmmm… we'll see.