Cheerilee's Parent Teacher Conference

by Clopficsinthecomments

Rating: mature
Tags: Comedy, Filthy Rich, Sex, Cheerilee, My Little Pony: Friendship is Magic, Romance
Length: 4491

Cheerilee is having her parent teacher conferences for the year - a combination of additional funding needs and her strong biological urges may lead to a 'conference' of a different kind.

Cheerilee was almost through a long evening of meeting with Ponyville's parents. It was no easy task.

Aside from the usual bickering from parents about how their foal deserved better grades, how homework was too difficult, or how the curriculum went too far one way or another in the current pony political spectrum, Cheerilee was dealing with her own problems as well.

She usually didn't get a second seasonal heat, but she was right in throes of one now. The medication she'd taken to dim her burning, passionate, need was only halfway effective at best... and it was wearing off.

To top all of that, her last parent-teacher conference of the night was Filthy Rich, a pony she had hoped to petition for a charitable donation to the school to revamp their under-budget and failing musical program. Will Cheerilee be able to withstand her burning desire and get through the final parent teacher conference without incident?

NOPE.

A quick-fic based on a derpibooru pic NSFW: #1568354

Contains: M/F, Anal, your favorite pony teacher getting railed

Published 2017-10-23 23:00:06 UTC
Last updated 2017-10-23 23:00:06 UTC

Extra-curricular Activity

A quick fic based on a derpibooru picture NSFW: #1568354... short and to the point. Enjoy!

Cheerilee groaned as she put aside the clipboard with the notes from the previous meeting. She would never be able to show it to anypony else: in and around the countless notes about apples, apple-related cooking recipes, and apple anecdotes (she really needed to tell AJ that Granny Smith was perhaps not the best Apple-family member to attend parent-teacher night)... it was covered in sexually explicit doodles of Big Mac and 'little' big mac. That she had managed to draw big throbbing cocks, spurting cocks, twitching cocks... all while staring at Granny Smith's wrinkled face only showed just how sexually frustrated she was.

Tearing the sheet into a thousand pieces with a moan, she slammed her head onto her desk. Reaching down below to her groin she removed the ice pack she had placed there moments before Granny Smith had entered the classroom only 10 minutes earlier. Already it had gone from ice cold to red hot. She could feel the heat radiating off of her swollen marehood, the sweaty musk having seeped onto the seat of her chair as her slick lips began to drool.

She slammed her head against the desk again and groaned twice as loud. "I swear, this is the last time I ever take a late season vacation to Neighvada... all that extra sun probably triggered this second heat..." she growled as she idly stroked her teats, trying to avoid touching her nether lips (she knew it would only serve to stimulate her further).

She pulled her head up slowly as she looked at her schedule. "OK Cheer, just one more conference to go." Cheerilee said to herself. "Then you can head home and draw a nice long bath... pull out Mr. Happy and think about that big red stallion and shove that fat piece of silicon up your we-" A knock on the door shook Cheerilee out of her fantasy.

"H-hello?" She asked, flustered, while straightening up and trying to adjust herself. Her sweating brow and throbbing wet groin feeling painfully noticeable.

The door opened and Filthy Rich poked his head into the classroom with a smile. "Hello Ms. Cheerilee! I was a few minutes early so I was wondering if you were free... would love to help get you off early tonight." He said with a smile as he stepped into the room.

Cheerilee's mind instantly snapped to the phraseology and she murmured "I bet you'd like to get me off...:

"Hmm? Did you say something?" Said as he reached over the teacher's desk to take Cheerilee's hoof and give it a quick, polite kiss.

"N-no! N-nothing!" Cheerilee chuckled nervously, quickly pulling the kissed hoof back and wiping it on her other arm, conscious that it had just been playing with her slick teats, and hoping that Filthy hadn't gotten any of her juices in his mouth.

Filthy's nostrils flared wide as he pulled back and looked at Cheerilee as a whole. "You smell... incredible Cheerilee." Filthy took a deep snort of the musky air.

Sweating nervously and fanning herself, Cheerilee laughed nervously. "H-h-ha really? T-thank you... I'm sure it's just your imagination."

Filthy exhaled. "No, I dare say that is the loveliest perfume I've ever smelled. You'll need to give me the name sometime so I can get some for Diamond Tiara." He chuckled as he walked toward the desks.

Cheerilee shook her head, happy to have dodged that bullet but needing to refocus. She'd forgotten that she had scheduled Filthy Rich as her last interview of the evening. She'd hoped to convince him to donate some additional funds to the school to help support their underfunded musical program and had tried to slot him in last to have the additional time to... work him - she imagined the older stallion's hoof kiss earlier turning into a long lick going up her arm an-...

Cheerilee blinked and shook her head violently. 'No Cheer! Bad Cheer!' she thought to herself. 'No lewd thoughts! Think of the kids and the musical program! Don't mess this up for them!'

Filthy Rich had found the desk he was looking for in the meantime. "Is Diamond still sitting here, Ms Cheerilee?"

Cheerilee looked nervously up at the stallion she had just been imagining ravishing her with his tongue. "H-hm? O-oh yes!"

Filthy chuckled, "probably still sitting next to Silver Spoon as well, after all these years. Are you OK Ms. Cheerilee? You seem a bit flushed."

Cheerilee *eeped*, pulling her hoof up from below the desk before it could absent-mindedly reach her marehood. Something was very wrong! She was rapidly losing her senses... the medication! She tried to use her remaining mental focus to think about the suppressant she'd taken that morning... her memory strained through the haze as she remembered reading the directions... 'good for up to 12 hours'... she checked the clock.

'Oh no.' Her rational fore-brain thought.

"Ms. Cheerilee?" The handsome, strong, powerful, virile, potent, sexy stallion in the room asked her.

'NO!'

She had to get out of here, before it was too late. She stood up, feeling the rush of wetness fall from her rear to the seat she'd just vacated, as she'd been sitting in a pool of her own juices. She couldn't do this.

"I-I'm s-so s-sorry Mr. Rich, I'm afraid..." Cheerilee mumbled out, her mind racing as her nostrils caught Filthy Rich's scent and called to her... he was always such a kind parent, even if misguided... he was wealthy, well-groomed, intelligent... he would make a great father for her fo-

"Ms. Cheerilee?" Filthy asked with a raised eyebrow.

'NO Cheer!' You need to get out of here!

"I-I'm af-afraid I'll need to r-re" She reached shakily for the door... then her head began to clear. What if... what if she could do both?

'NO Cheer you can't!'

But, what if she could? Seduce Mr. Rich to make a little donation and quench her thirst... no big deal right?

'No Cheer... you're not thinking Clearly.... stop stop sto-' Her rational mind was finally overwhelmed by the powerful, surging biological urges she was experiencing. Taking her hoof off of the doorknob, she reached up to the deadbolt and locked the classroom door.

"Ahem. I'll need to request that you remain seated." Cheerilee adopted a sultry look as she began to walk toward Filthy rich.

Filthy sighed and smirked, "lay it on me Ms. Cheerilee, what's Diamond Tiara done this time? Please tell me she hasn't gone back to bullying again..."

Cheerilee giggled girlishly. Having walked up to the desk where Mr. Rich sat. She tittered as she leaned in over the desktop close to Filthy, grasping his tie. "Oh I'll lay it on you, Mr. Rich."

Filthy Rich nervously chuckled, then tried to fill the silence. Something had been tickling his nose since he'd entered the room, some sort of mixture of vanilla and spice. He'd thought it was Cheerilee's perfume, but things were only getting thicker and thicker. It was as if he could drink the scent on the air.

"W-well... between you and I... I've separated with her mother Spoiled Rich. She has been completely intolerable. I'd worried that the divorce might have impacted Diamond Tiara..." Filthy Rich stammered as Cheerilee continued to lean into his personal space.

"Hmmm?" Cheerilee hummed, her lidded eyes just across from Filthy's.

"H-has she been bullying anypony?" Filthy gulped.

"Hmm... noo..." Cheerilee whispered, her snout almost brushing Filthy's.

Something was wrong. Filthy could feel his head getting cloudy... the smell was overwhelming now.

"Bad grades?"

Cheerilee shook her head, her bangs tickling Filthy's nose.

"Acting out?" He whispered.

Cheerilee giggled at this last one and grasped Filthy's face with her hooves. "You know Filthy... sometimes when little fillies or colts act out, its not their fault at all." She began to lean in closer, now basically nuzzling Filthy.

Filthy Rich took a deep gulp as he felt Cheerilee stroke his neck with her snout... heard her inhale with a snuffling gasp to smell him... "I-it's not?"

Cheerilee put her mouth close to his ear, wrapping her hoof around his tie to hold him in place before whispering, "nope... usually its just hormones."

Filthy could swear she had licked his earlobe as she finished her sultry statement. He turned toward her, fully expecting to plant a deep french kiss onto his daughter's teacher and satisfy the lust that had been burning brighter and brighter over the past few minutes. Instead he found nothing but air.

Cheerilee had pulled back over to the other side of the desk, pretending to focus on her clipboard while holding a pencil in her hoof as she went on, teasing him. "Yes. Hormones. Diamond Tiara is getting to that age you know."

Filthy was furious! Cheerilee had worked him up like crazy and was now just backing away as if nothing had happened? The stallion urges in his body were throbbing including his erection, now halfway out of his sheath under the desk. He gripped the edges of the desk in anger.

Cheerilee seemed not to notice. "Yes, yes. Hormones can make anypony do the craziest things or lose all sort of control. Even a 22 year-old single mare school teacher on her heat." She chuckled gesturing at herself with the pencil end before pointing it at Filthy, "or an older divorced stallion on a dry spell."

Filthy's eyes went wide... Cheerilee was on her heat? That explained the smell! He had t-

"Oopsie!" Cheerilee dropped the pencil, which rolled under the desk. Quick as a flash, Cheerilee had ducked under the desk to retrieve it.

Filthy swallowed, as he knew exactly what Cheerilee would be seeing down there... he stared forward, only seeing the pink and cream colored tail of the sexy, young school teacher as her body explored underneath.

He heard another giggle from under the desk before Cheerilee went on. "Yes indeed Mr. Rich... we're taught all about dealing with hormones when getting our education degrees..." Filthy felt a hot breath on his almost fully erect stallionhood.

"R-really?" Filthy asked his mind racing but failing to keep up with the pace of the situation as it developed.

"Yes, really..." He heard and felt a deep sniff near his stallionhood's flare. "For instance, when little colts are starting to go through puberty and getting inadvertent erections in class... even big, THROBBING hard-ons... its best not to call attention to it so they don't get self-conscious... just let them hide it under the desk."

"O-oh?" Filthy groaned, shifting in his seat as he felt her breath tickle his sensitive glans.

"Yes... don't call attention." She chuckled, her tail swishing back and forth in Filthy's view. "Of course... I do support unconventional teaching methods..."

Filthy felt a long lick starting at the base of his shaft and pulling all the way up to his head before something warm and wet engulfed his cock head. He groaned aloud as his shaft reached its full throbbing extension under the lashing tongue and suckling muzzle of Ms. Cheerilee. He began to try to get up, but instantly the sucking stopped.

Cheerilee popped her head back above the desk.

"Ah, please stay seated Mr. Rich... I was actually thinking there might be another problem to discuss other than hormones." Cheerilee turned and looked at the chalkboard.

Filthy Rich was beside himself, his eyes bulging at the sockets as he gripped the desk so hard he was sure it would crack. Under the table his cock bounced off the underside of the desk, throbbing with impatience and dripping pre-cum and saliva... Cheerilee was such a... a... COCKTEASE!

Cheerilee sultrily murmured while looking away from Filthy Rich, standing in front of the desk with her rear facing Filthy's breathless face, "I wonder... maybe the problem is a visibility issue?"

Filthy could only stammer out... "What?"

"Yes..." Cheerilee chuckled, swishing her tail from side to side, tantalizingly revealing her soaked marehood to Filthy Rich. "What you see can be a big issue, you know."

He gasped as he saw her fat heart-shaped clitoris winking periodically in and out, splurting drooling strands of mare-juice down to the floor below... could this really be happening to him? Such a beautiful young-adult aged mare? He felt like a teenage-colt again.

"I wonder if Diamond has trouble seeing my lessons from here... let me try to get her point of view." Cheerilee backed up onto the desk, putting her beautiful rear end on the wooden desktop in front of filthy. She was sitting up now, clearly not looking at the chalkboard, but instead back over her should to see Filthy's reaction to the show she was giving him as she flagged her tail completely up and out of the way so he would see every inch of her.

Filthy looked with his mouth agape in awe at Cheerilee's swollen labia, pressed apart by her large, throbbing clit, revealing the twisting, clenching muscles in her love tunnel. A constant stream of slick juice ran down the desk to trickle over the edge and fall into his lap, dripping onto the base of his shaft. Every other moment, Cheerilee would wink heavily with a spasm, letting loose a small spurt of cum that would splash into his face. He was drowning in her pheromones now.

"Hmm... not quite the angle yet." Cheerilee moaned, scooting her butt further and further back, the action squeezing her butt even more blatantly (if that was possible) into Filthy's face. "Tell me Filthy... do you like what YOU see?"

Filthy groaned as he looked on the 22-year old mare's fat but taut ponut, just beneath her flagging dock, the twisting depths of Cheerilee's cunt begging to be dominated. The warm breath exhaled from his groan spread over Cheerilee's exposed and swollen love-button causing her to wink, spraying him with marecum.

Cheerilee groaned and pressed back further.

"Sweet Celes-mfhia" Filthy Rich groaned before he was muffled as his nose was pressed up against the young teacher's rosebud, perfectly positioning his tongue to lash into Cheerilee's marehood.

"Oh CELESTIA Mr. Rich!" Cheerilee moaned out, thrusting back into the desired sensation.

Filthy lashed his thick tongue in and out of Cheerilee, licking at her twisting and pulsing clit, making her throw her head back as she came almost immediately. Filthy reached forward with his hooves to slap her tight rump as she spasmed on his muzzle.

"Buck YESSSsssss.... FILTHY!" Cheerilee screamed as she came with abandon. "Take me now! RUT ME SENSELESS!" She yelled.

Filthy'd had enough. He exploded from his seat, knocking his daughter's desk aside and throwing Cheerilee forward through the classroom, knocking the neatly arranged chairs and desks aside. Cheerilee was pushed up against her teacher's desk, her forehooves splaying across her blotter and knocking piles of paper and pens aside.

Cheerilee looked back over her should with some fear at the stallion's sudden outburst and the look on Filthy's face as he extricated himself from the mess of student desks he had knocked about the room. His face was one of pure biological focus and intensity as he stalked toward her. All Cheerilee could do was wince and splay her ears back against her head in fear.

"N-n-now Mr. Rich... be gentle... it's been a little w-w-WHILE!" She squeaked out as Filthy ignored her plea and pinned her forehooves on her desk with his own.

"Y-you little cocktease, I'll teach you not to play with older stallions." Filthy breathed into her ear, nipping the tip passionately before sticking his rear hooves inside hers, kicking her two rear legs outwards so that she was splayed wide open and at his mercy.

Instinctively she began to tuck her tail to shield herself from his passionate aggression, before Filthy leaned forward and gripped a chunk of Cheerilee's mane in his teeth and yanked. "I'm going to buck your sweet little ass until you beg, Cheerilee..." he grunted through the mouthful of hair.

Cheerilee felt her biology override her again as she was dominated by the older stallion. "Unnnf.... YES! BUCK ME!" She moaned as she flagged up her tail.

Immediately she felt Filthy's shaft against her mare parts. He reached back to smush his cockhead up and down against her open, grasping vagina slathering it in her slick juices.

"Let me show you why the mares called me Filthy Rich." He growled into her ear.

Cheerilee tensed as she felt his thick flare against her tight rosebud. She stiffened up immediately. She'd seen him under the desk. He was nowhere near as long as Big Mac, but Filthy might have him beat in the girth department. "W-wait... I've n-never..."

Filthy pulled at her mane again and pressed down her forehooves, pinning her and dominating her utterly.

Cheerilee grunted in pain and pleasure as she felt Filthy's girth press against her tight ponut, slowly spreading it.

"Buck me, you're HUGE!" Cheerilee grunted through strained teeth as he slowly invaded her sphinctre.

Filthy began small thrusts against her ass, until suddenly it slipped in with a tiny squelch.

Cheerilee tried to stand bolt upright at the strange sensation of a thick sausage sliding deep into her anus, but Filthy kept her pinned to her desk.

"F-fuck!" She moaned out, as Filthy began to piston in and out of her, his free hoof playing with her pussy. The thick cock slid into her, inch after inch, but try as he might, her ass was far too tight to let his medial ring slide into her ass.

Minute after minute went by of the brown stallion slamming into her tight pink puckered asshole, the most obscene squelching sounds only being overshadowed by the squeaking of the desk as it slid across the classroom under the pressure of Filthy's powerful thrusts, the slapping of Filthy's heavy testicles against her open marehood, and the screaming throes of some mare.

Wait... that was her! She was the one screaming in pleasure?

She hadn't realized it but she had at some point started loving getting railed in the ass.

"Unf, unf, unf..." she squeaked out, feeling the sweaty stallion's breath against her ears from his heavy exertion, "yes... yesssss Filthy.... buck my tight little ass!"

She felt him bite down on her mane again, yanking back just as his balls slapped against her winking clit. In that moment Cheerilee came harder than she ever had before.

"Oh my goooooOOooodnesssss....." she moaned out, as her juices gushed out from her and her legs gave out, as she slunk to the floor, her ass disconnecting from Filthy's cock with a pop.

She crawled forward on the floor, completely disheveled, her breath ragged and her body covered in sweat, but her marehood burning worse than ever before... she looked back over her shoulder at Filthy.

He was breathing heavily, using a wet wipe from the dispenser on the teacher's desk to clean his brow before wiping his cock, cleaning it from its recent anal adventure. Had it always been that big and thick? Maybe it was in the 'Big Mac' category after all..

"And just where do you think you're going Ms. Cheerilee?" Filthy growled, his refreshed and clean cock already drooling with pre-cum for her... "MY little lesson isn't finished yet."

Cheerilee whimpered and spread her rear-legs, flagging her tail to the side to permit Filthy's return. He stalked right over to her and mounted her with no hesitation.

Cheerilee's eyes rolled back into her head and she orgasmed instantly as Filthy Rich's cock slipped into her marehood. It had been waiting so long to finally be filled with hot, throbbing, COCK that it happily rewarded her with a flood of orgasmic chemicals, melting her already fragile brain.

"BUCK, you're a tight little mare, Cheerilee... did you just cum on my cock?" Filthy chuckled as he continued sliding into her.

"Ungghhh..... yessssss....." Cheerilee groaned, her tongue lolling out of her mouth. She could feel her clitoris, more swollen than it had ever been before, tortured as it had been all day with this teasing as it throbbed and clenched against the thick brown shaft sliding into her.

"I bet you're as tight as your little students, aren't you, you horny little schoolteacher? Maybe I should stop, maybe you're too young and innocent for this..." He growled at her, nipping her ear as he began to thrust his hips.

"Mmmmffff.... pleassssseee FIlthy!" She groaned, hating to be teased.

"What was that Cheerilee? I told you you'd need to beg for it you little cocktease..." he stopped thrusting, and began to pull out of her.

"Ngggg.... NoooOOooo.... pleasseeee Filthy... I want it..." Cheerilee moaned, her brain totally aswim in dopamine, but instinctively begging to be fucked, her pussy suckling at Filthy's cock.

"What do you want, Ms. Cheerilee?" Filthy teased, pulling his cockhead out so that only the tip was kissing her open, clenching cunt.

"I WANT YOU TO FILL ME UP, YOU STUD!" Cheerilee shouted her eyes clenched in embarrassment as her body's needs took over her mouth.

Filthy obliged her.

In one swift thrust her plowed deep into the school teacher, getting right up to his medial ring before the tightness of her cunt slowed his entry. Not bothering to stop, he pulled his hips back for a second thrust, and then a third... a fourth.

Cheerilee was mewling in little squeaks as she slid across the floor from the constant thrusting, her hooves unable to find sufficient purchase to prevent sliding across the linoleum. Finally, she came up against the wall, her arms and head being smashed against them as the older stallion continued to try to force more of his thick shaft into her much smaller cavity.

"BUUUUCK!" Filthy let out a might roar as his thick medial ring finally slipped past Cheerilee's abused labia, and he slid the remaining inches of his cock into her wet, velvety sleeve.

His hilt slammed into her thick and bulbous clit, instantly causing Cheerilee to orgasm as she was filled to the brink.

"Filthy! I'm... I'm cummmMmmMiinnnng...." She squeaked out in bursts as she continued to be bumped into the wall, knocking hand-drawn pictures by her students down from their thumb-tacked spots.

Filthy continued thrusting, even as the younger mare spurted and clenched all around him. He could feel his own orgasm rapidly approaching as his flare grew and grew, lodging himself squarely against the schoolteacher's cervix.

"Inside or outside?" He growled as he yanked Cheerilee's tail with his teeth. It was a meaningless question... he knew at this moment that he was lodged within her.

Cheerilee came again, harder even than when she was being bucked in the ass. "INSSSSIDDDE!!!!" She moaned, her eyes rolling back and her tongue drooling as she was plastered into the wall. Her tail tried to wrap around her stallion but was unable (seeing as it was trapped in his mouth) only adding to the overload of sensations. She felt her clitoris throbbing in a convulsive, continuous wink, as it tried to open itself as much as possible to his shaft... meanwhile, deep inside her, her vagina had clenched powerfully around his thick flare, providing the purchase against which it could pull him in closer to her cervix.

Finally, Filthy let loose a mighty bellow and unloaded into the little school teacher. Spurt after spurt came out of his cock in thick blasts, each accompanied with a small thrust and a whinny from the older stallion. He hadn't ejaculated this hard since he was a young colt - he couldn't believe how many spurts he was unloading into her womb.

"Buck me!" He groaned, as he felt a few more convulsions ripple out of him, before he finally felt finished.

Disappointingly, he felt his stallionhood go soft almost immediately. That wasn't like the old days, he sighed. Ah well... don't look a gift-horse in the mouth... at least he'd still had enough to go one round.

Cheerilee felt Filthy withdrawing from her quickly, the thick sausage becoming smaller and smaller and withdrawing sloppily from her cunt, even as it tried desperately to clench him and keep him locked to her. Finally, she felt it slide from her body like a wet noodle, and barely registered the sound of his juices splattering out of her and onto the linoleum tile below.

Filthy released the young schoolteacher's tail and backed away from her. With his weight no longer pinning her against the wall, she slid down into an exhausted pile of pony, oblivious to the fact that she was laying in a pool of their juices.

Quickly, his mind came back to its senses... WHAT THE HELL HAD HE JUST DONE.

"Oh my Celestia... Ch-cheerilee?" He stammered. "Wh-what did we do!?"

Cheerilee waved exhaustedly from her little pile while still breathing heavily. "Huf- huf-, don't worry... huf- huf-... birth control... huf- huf-... on heat... huf- huf-... our little secret..." she hadn't even bothered to look up from where she was curled up on the floor.

"Oh thank goodness... but... LOOK AT THE TIME! We've been at it for an hour... Diamond Tiara will be waiting for me... I'm so sorry... I need to go!" He grabbed his bag and began to go toward the door, his limp cock still dripping juices.

"W-wait!" Cheerilee propped herself up on to one hoof and looked across the floor at him... "y-you were... huf- great!"

Filthy blushed, and smiled back. "So were you Ms. Cheerilee, it was a lovely evening..."

Cheerilee smiled back, "huf- th-thank you... ah... music program... donation... please..." she breathed out, trying to get to her hooves as a small river of cum trickled out of her swollen marehood and down her leg.

"Consider it done! I have to go!" Filthy waved and rushed out the door, barely managing to unlock it.

Cheerilee sat there breathlessly for a few minutes, surveying the disaster that was her classroom, now a complete mess of papers, disheveled desks and chairs, covered in juices and stinking of smelly, sweaty, passionate heat-sex.

Then she pumped her hoof in triumph.

'TAKE THAT, FORE-BRAIN, I KNEW I COULD DO IT!' She thought to herself in triumph, she wouldn't even need to take that bath with Mr. Happy now!

She stood up gingerly, and set to cleaning up the classroom. Her foals were her first priority after-all.

Author's Note

Just a fun little fic while I write some longer stuff in the Anon universe.

Not sure why I picked Cheerilee, but I saw the picture on derpibooru and just decided to go with it. She's such a sweet-heart and gives out a really innocent vibe...

Perfect for my brand of pony-corrupted-by-biological-heat-impulse clop...

I tried to do a lot more foreplay in this one, and it was quite fun... let me know if you liked it!

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