Schoolhouse Fun

by TheCloppyComedian

Rating: mature
Tags: My Little Pony: Friendship is Magic, Fetish, Cutie Mark Crusaders, Porn, Sex, Cheerilee
Length: 4357

Sweetie and Cheerilee get more ponies involved in their affair...

Apple Bloom and Scootaloo are wondering why they don't see Sweetie Belle as much anymore. So, they decide to do a little digging and are completely shocked...and pleasured...by everything they find.

WARNING: This contains foalcon, f/f/f/f sex, and bondage. If you aren't a fan of these things, than this won't be for you. Otherwise, I hope you enjoy it! Also, I'm disabling the ratings because I'd like to actually hear your feedback via the comment section.

Published 2020-01-19 14:20:01 UTC
Last updated 2020-01-21 14:07:27 UTC

The Crusaders Dig

Apple Bloom had called a special meeting between herself and Scootaloo. The orange Pegasus didn’t quite know why one of her best friends had scheduled such an exchange without inviting Sweetie Belle. She was also a little confused as to the secrecy with which the olive colored filly had demanded that the meeting take place. In fact, Apple’s whispers had sounded angrily harsh when she made her request. It had nearly frightened Scootaloo, and she had stared after her friend as she trotted away, wondering just what had seemed to put Apple Bloom so firmly on edge.

They met at the Crusader Headquarters, which was the name they had come up with for their small treehouse. The Cutie Mark Crusaders had become a global phenomenon in the year since Princess Twilight had ascended to the throne of Equestria. They had been specially featured in her ceremony as examples of young ponies who thrived on the magic of friendship. The trust and bond they shared with the ruler was impeccably strong, and they knew better than to betray her. They had gone on tours of the country with her, speaking with colts and fillies and urging them to fight for their friendships. Now it appeared as if their own was fraying.

Apple Bloom peeked out the door and looked to make sure that Sweetie wasn’t there before shutting it and locking it tight. It had four deadbolts on it, because the Crusaders kept a lot of confidential files and they didn’t want anypony breaking in and stealing them. It could be embarrassing for a blank flank to have their personal details revealed to ponies who had not been charged with helping them. Until a client reached their potential and their cutie mark was revealed, their files were kept locked away in the Crusaders’ trusted care.

But all the same, it was odd to hold secret meetings, and Scootaloo wasn’t a fan of leaving their friend out. “Alright, Apple Bloom,” she said gruffly when the other filly turned to face her, “what the hell is this all about?”

“Haven’t ya been noticin’?

“Noticing what?”

“Sweetie Belle’s…strange behavior lately.”

Scootaloo looked at the floor, then back at Apple. She had noticed that Sweetie wasn’t eating lunch with them as much anymore, and she never seemed to be able to attend their weekly Crusader meeting. She always had some excuse, like needing to do her homework, or attend one of her sister’s fashion events. But her dodgy ways were growing thin, as her last excuse involved something regarding a fire hose, a dog, and a peanut butter & jelly sandwich. Apparently, Apple had begun observing the same things Scootaloo had.

“Yeah, I guess,” Scootaloo said, “but that doesn’t mean anything.”

“Oh, it doesn’t?” Apple asked, “what about her and Cheerilee?”

“What about them?”

“Oh, for Twilight’s sake, Scootaloo!” Apple Bloom squeaked angrily, “you’re about as clueless as a bucket of rocks! Come on, mare, open your eyes!”

Scootaloo didn’t appreciate the comparison to common boulders, and gave her friend a nasty look. “There’s no need to resort to name calling, Apple Bloom. Just say what you need to say so I can leave! I don’t much feel like hanging out with somepony who’s only aspiration in the last thirty seconds has been to insult me!”

Apple took a breath and realized she had taken things a bit too far. “Alright, I’m sorry, Scoot,” she said, “but you have to admit, Sweetie’s been actin’ powerful peculiar lately. I mean, she’s never with us anymore, but she’s always with our teacher!”

“I’ve seen them around town together,” Scootaloo admitted as her own temper cooled off, “but that doesn’t mean that they’re up to anything. I swear, Apple Bloom, it sounds like you’re accusing Sweetie of doing something wrong.”

“I ain’t accusin’ nopony of nothin, yet,” Apple responded, “I’m merely observin’ that Sweetie’s behavior’s been odd for the past couple of weeks. I move that we, as her friends and as Crusaders, dig around and find out just what she’s been up to.”

“I don’t know, Apple,” Scootaloo said nervously, “it would be violating her privacy, and that’s not what good friends do.”

“Oh, for cryin’ out loud, Scoot!” Apple exclaimed, “it could save her from trouble! As far as I’m concerned, a good friend always looks out for her other friends. That’s what we’re doin’!”

Scootaloo took a moment to ponder and weigh the pros and cons of her decision, before finally relenting with a nod. She felt terrible about digging around into Sweetie’s personal life, because she knew they had no right to do such things. But Apple Bloom saw it in a different fashion, and in the end, the olive filly’s judgment won out. After all, Scootaloo reasoned, we’ll be protecting her by doing so…won’t we?

The next day, the Crusaders went to work. They hid out in the bushes right outside their school’s front door, waiting for any sign of activity from either Sweetie Belle or Cheerilee. Their teacher had requested that their friend stay after class. To the other foals, some of whom snickered on their way out the door, that meant Sweetie had gotten into trouble in some way. What they didn’t know was that the school had become something of a sexual dungeon for the lovers, and they would often stay for hours after the school closed. The desks would rattle with their passionate lovemaking, and their screams would be contained thanks to the soundproofing job that had been recently done.

Scootaloo and Apple Bloom popped up out of the bushes after two hours of waiting, when they realized that the prickly branches were a terrible hiding spot. They had little barbs all over their bodies, and they took a few minutes to help each other remove them. It wasn’t an easy task, but they managed to get them out. When they finished, they noticed that little red sores dotted their bare flanks from their shoulders down to their cutie marks. It was an annoyance, certainly, and Scootaloo was beginning to seriously second guess her earlier decision.

“Sometimes, I wish I’d never agreed to this!” She spat softly.

“Shut up!” Apple retorted, “and look inside the classroom!”

When Scootaloo looked, she was shocked at what she saw. Cheerilee had on a black outfit that ended just above her haunches. Dangling in between her legs was something that the small orange pony had seen on plenty of stallions, though she didn’t quite know what it was called. She noted that it seemed to be plastic, with black straps that reached up and over her teacher’s rather sizeable rump.

Underneath Cheerilee lay their friend, also dressed in black, but wearing a mask. She held a burning candle in one hoof and a whip in the other. She seemed to be cowering before Cheerilee, frightened of whatever was about to happen. As the Crusaders looked on in horror, Cheerilee plunged her stallion part deep into Sweetie’s filly parts. They could tell that their friend was screaming, though they couldn’t hear it, and tears filled their eyes. Whatever was going on in there, Sweetie was getting hurt, and they couldn’t take it anymore.

“Apple, we’ve gotta stop Cheerilee!” Scootaloo yelled.

Apple Bloom nodded, and the two fillies burst from their hiding spot and crashed through the doorway of the school. “STOP!” They screamed.

Very Friendly Fillies

“What…what the hell are you two doing here?!” Sweetie Belle shouted when she finally caught her breath. To say that she was shocked by the sudden appearance of her very best friends would have been an incredibly severe understatement. Her anger at their materialization would have suffered the same fate, as rage began boiling up inside her small body. She and her mate were in the midst of a rather beautifully sadistic sexual game when Scootaloo and Apple Bloom decided to pop in for a visit. But through her vitriol, she also saw two friends with looks of major concern on their faces.

Scootaloo spoke up. “We’re here to make sure that SHE…” here, the young Pegasus pointed an accusatory hoof at Cheerilee, “…doesn’t hurt you anymore!”

“Yeah!” Apple Bloom squeaked, “we saw her puttin’ that thing into yer privates! We’re gonna save ya, Sweetie Belle!”

Sweetie’s anger melted away as she realized that her friends had nothing but good intentions. They legitimately thought that Cheerilee was attempting to harm her. They didn’t understand the exchange of love and devotion happening in the classroom. They were simply ignorant to the fact that there were things happening in the world of which they knew nothing about, and they didn’t have parents to teach them. With Scootaloo’s folks being halfway around the world, and Apple’s residing in two graves within Ponyville’s cemetery, it was understandable that they wouldn’t quite get what she and her lover were doing.

She smiled and got down off the desk, disrobing in the process. Considering the fact that ponies didn’t normally wear clothes, this should have been no big deal. But Sweetie got a certain thrill from taking her submission outfit off and trotting over to hug her friends. She was so thankful that she had them in her life, and she knew that, if she were to really fall into danger, they would come running fearlessly. She backed away from the hug and gave them each a gratuitous look.

“Thank you,” she said, “for being such wonderful friends.”

“Yer right welcome,” Apple said, “now, what do we do with Cheerilee?!”

“Yeah,” Scootaloo said, “after all, she was the one who-“

Sweetie hushed them both with a gentle hoof to the mouth and explained that she had asked Cheerilee to do these things to her. When her friends gave confused looks, she furthered the explanation, saying that it was a fun game that she was playing with their teacher.

“A game?” Apple asked, “what kind of game?”

“Well…a game of love,” Sweetie said genuinely.

“Wait, wait, wait,” Scootaloo said, “you and Ms. Cheerilee…love each other?”

“Like, Princess Twilight and that stallion she’s datin’, love?” Apple asked.

Sweetie nodded. “Yep!” She squeaked with pride, “Cheerilee is my mate, and this is something that we do to show our affection for each other. See, Cheerilee is dominant in our sexual relationship. She’s the bigger pony, after all.”

“What’s a sexual relationship?” Apple asked, eyes wide.

Sweetie blushed heavily. She had completely forgotten that her friends didn’t know anything about sex or penises or vaginas. But she quickly shook her head, removed the blush, and stepped forward. Her eyes narrowed to beautiful green slits as she wound her body around Apple, ending up right back at her nose. “Would you like me to show you?” She asked huskily.

Cheerilee immediately broke into a grin. She had always fantasized about watching fillies mate, and now she would get the chance to. She had heard stories from other fillyphiles in the school system about what they had seen. They told her that there were times when moaning could be heard coming from the filly’s restroom, and they would creak open the door to find two or three young ponies “testing the waters” of their sexuality. Their back legs would be opened, revealing gorgeous pink flowers that were quickly bereft of all their juices via lashing tongues. Masturbation came quickly to the teachers, both male and female, and they would have to hide their doings from their colleagues.

But Cheerilee was both principal and teacher, and the only ponies she had to answer to were those of the EEA. If Chancellor Neighsay or one of the residents of Ponyville were to suddenly barge in, then she would have a major problem. But as far as she was concerned, the ritual between the mature fillies in front of her was going to be the highlight of her night. She thought she was getting a filly threesome, but Scootaloo backed away, frightened at the prospect. Thankfully, she was right there to scoop the young Pegasus into a tender embrace, kissing her cheek in the process.

Apple Bloom had nodded her small head at Sweetie, and the white filly pulled her into a kiss. Their hearts beat rapidly as Sweetie became instinctively dominant and Apple allowed her to explore as she needed to. She cleaned the inside of her friend’s maw gently, and then licked around her lips for good measure. A rather cliché strand of saliva passed between them as they broke apart, and Sweetie shoved Apple over onto a desk before getting on top of her.

“You’re a good bitch, aren’t you?” She growled.

Apple nodded, not understanding why. She hated the B-word that had snuck out of Sweetie’s mouth, yet she loved it at the same time. She found that the sweat that now popped out of her pores only increased the closer that Sweetie moved her gorgeous face towards her. The dominant filly smiled wickedly as she kissed around Apple’s neck, moving lower and lower until she finally reached Apple’s sensitive body parts. She suckled on the tender nipples that greeted her, causing Apple to moan deeply.

“Oh, Sweetie…”

“Sh…” Sweetie said, “…enjoy it, my Apple Bloom.”

She began swirling her tongue in agonizingly beautiful circles around the prone filly’s vulva and slit. She noted that Apple’s clit was especially puffed out and ready for action, and she made a mental note to give her both cunnilingus and pussy-to-pussy sex. She moved her oral action across the very vagina that graced her eyes, and she thought Apple’s responsive groans were some of the most amazing she had ever heard, and she mated with Cheerilee on a regular basis. But sharing this tender moment with somepony she held so dear drove her forward, and she dove directly into Apple’s pussy.

Her licks and sucks caused Apple to begin howling and screaming as pleasure shot through every pore of her small body. It was as if Sweetie had an electric prod filled with the greatest adrenaline rush known to ponykind and she was constantly shocking her with it. It felt itchy, but Apple didn’t want to scratch. She wanted the itch. She NEEDED the itch. “Oh, Sweetie!” She cried, “please, don’t stop! Oh, that feels amazing! Oh! Oh! Oh!”

“Don’t you DARE cum yet!” Sweetie suddenly commanded.

She had stopped her oral administration and gotten on top of Apple, grinding their bodies together in a lovely display of affection and power. She held Apple’s hooves down with her own and began to slowly rub their vaginas together. Both fillies now felt the absolute pleasure of doing it with their best friend, and the mental link they shared had solidified itself. They knew they could never recant this night, no matter how much they tried. Their cries echoed across the room, but never a sound made it outside into the clear Ponyville night.

“YES! YES!” Apple Bloom screamed as Sweetie became more violent with her thrusts, “MORE! MORE! PLEASE! OH, MY FUCKIN’ TWILIGHT, THIS FEELS GOOD! OH, SHIT! OH, OH! MORE, SWEETIE! MORE!”

“OH, APPLE BLOOM!” Sweetie cried right back, “YOU FUCKING WHORE! TAKE MY VAGINA! TAKE IT, BITCH! TAKE IT! TAKE IT!”

“I’M TAKIN’ IT! I’M TAKIN’ IT! OH, YOU FEEL GOOD! UGH! OH! YES!”

Sweetie then turned on some afterburners and began to absolutely smack their bodies together. Every single time they made contact, a new sensation of both pain and pleasure passed through them. They loved it, and they felt closer than they ever had before. Apple, in particular, found herself shocked at the immense feelings that coursed through her system. But through the shock, a new level of love and respect for her best friend emerged. This was special, and she knew it.

Suddenly, Sweetie flipped Apple onto her belly and mounted her. She began thrusting faster than ever before, and it didn’t take long before Apple felt something building in her nether regions. She didn’t know what it was, but she screamed that she wanted it to keep growing. Sweetie happily obliged to her friend’s first orgasm, wailing harder and harder, wanting to hurt and pleasure her. Soon, the two ponies couldn’t take anything else and their bodies unloaded with a beautiful volley of delicious looking liquid. The scream that accompanied the orgasm nearly shattered the windows of the classroom, and Sweetie immediately clambered off of Apple Bloom and cuddled her close in a hug.

Apple caught her breath as her sexual high left her. “WOW!” She said emphatically, “I’ve never felt nothin’ like that before! Is that a…sexual relationship?”

Cheerilee and Sweetie both nodded. “Yep, that was sex,” the teacher said, “and I’m so happy I got to watch your first time, Apple Bloom! You did exceptionally well, and I know Sweetie Belle enjoyed it. I’ve never heard her scream so beautifully before. Now…it’s Scootaloo’s turn.”

A Hooves On Education

After Sweetie Belle and Apple Bloom finished their passionate session, Cheerilee turned to Scootaloo with a rather warm smile. But that warmth was belied by something that the young Pegasus found rather deadly: deception. She had never known her teacher to lie to her before, but it appeared as if there were a first time for everything. From the moment that Cheerilee had proclaimed that it was Scootaloo’s “turn,” the filly had felt uncomfortable. She noted the rather large plastic stallion’s part still dangling in between her teacher’s back legs.

“My turn?” Scootaloo asked nervously.

“Yes, darling,” Cheerilee cooed, “it’s your turn to experience everything Apple Bloom just experienced. Only this is far more…penetrative.”

She chuckled a bit, and Scootaloo felt shivers permeate her spine. She had never been frightened of her beloved instructor before. Cheerilee had always been so kind and tender with her pupils. Even when they needed to be disciplined, she would exact punishment quickly and then explain just why she had done so. She always greeted them with a smile and cheerful well wishes for the day ahead. Every one of the small ponies adored her, including Scootaloo. So why was it that this wonderful pony had turned into something that hid behind a façade of smiles? Why was she keeping her true intentions hidden from the filly?

“Ms. Cheerilee?” Scootaloo asked, before being hushed by a hoof to the mouth.

“No formalities, dear,” Cheerilee said, pulling her hoof away, “you can call me Cheerilee, and I think it’s time you got a proper sexual education.”

“You mean…what they were doing?” Scootaloo asked, pointing to her breathless friends.

Cheerilee nodded, and then positioned herself over the small filly so that her faux penis landed right at her nose. Scootaloo had no idea what she was supposed to do, but Cheerilee softly encouraged her to begin administering oral sex. “Suck it,” she commanded simply, “and feel every inch in your mouth. It’s so big…I think you might just choke on it.”

“Choke?!” Scootaloo asked with scared eyes, “but won’t that kill me?! If I can’t breathe-“

“Breathe through your nostrils, my dear,” Cheerilee said with love and lust in her voice, “now, begin.”

Scootaloo, seeing no way out of this predicament, slowly took the tip into her mouth and began running her tongue around it. As she got used to the feeling of the plastic brushing through her maw, she became more courageous. She felt her fears begin to gradually fade as she lessened the distance between her lips and the hilt. She still had no idea what she was sucking, nor why she was doing so, but she felt as if she wanted more. For some reason, pleasing her teacher sent a thrill through her body the likes of which she had never felt before. She suddenly wanted to do everything her teacher asked, no matter how depraved things got.

“You’re doing so well, Scootaloo,” Cheerilee praised.

She raised one of her hooves and began to slowly touch herself as the filly sucked. The combination of viewing the rather magnificent blowjob and her own masturbation caused the pink mare to let out deep moans of satisfaction. She noted that Scootaloo’s ears pricked up when she began, but the filly didn’t stop. Instead, her sucking became harder and harder and Cheerilee’s hoof went faster.

“Oh…oh, don’t stop, Scootaloo,” Cheerilee moaned, “mm…that’s my filly…oh, yes…oh, yes!”

She was on the verge of climaxing when she suddenly stopped, wanting very much to penetrate the young pony beneath her. She pulled her fake appendage out of Scootaloo’s mouth, leaving the Pegasus whimpering. She had been enjoying the blowjob as well, and to have it suddenly removed left her feeling empty. “Oh, come on, Cheerilee!” Scootaloo complained, “I wanted to go all the way to the back!”

Cheerilee smiled, excited at seeing Scootaloo in such an amplified fashion. The tomboyish filly was well known for getting into scrapes and for her love of adrenaline, but she had been quivering when the proceedings began. It made Cheerilee feel fulfilled to see her so agreeable to the circumstances. It was almost like watching her solve a new math problem or ace a test. You beautiful filly, she said, before turning and looking at Apple Bloom and her beloved Sweetie Belle, you’re all beautiful fillies.

Then, Cheerilee brightened as an idea rushed through her mind. “Oh, Sweetie Belle? Apple Bloom? Would you join us, please?”

The two other fillies immediately perked up and rushed over to where their friends were. They looked down at Scootaloo, sitting with a pout, and then back up at their teacher. In their minds, they knew what was coming, and they wanted every single part of it. They had viewed Scootaloo’s vagina before, when she had accidentally moved her tail in the wrong direction, and they could attest to its beauty. Now it seemed that Cheerilee wanted them all to experience it together.

“Sweetie, baby,” Cheerilee said to her mate, “I’m gonna fuck Scootaloo. Would you be so kind as to tie her up?”

“YES!” Sweetie cried in excitement and used her magic to drag some rope over to the desk. She whispered to Scootaloo that this was all normal, and manipulated her onto her back. Her back legs were spread apart, and Sweetie gently applied the rope to them, tying two small knots to hold her in place. She then did the same thing with her forelegs, and Scootaloo was splayed out in front for all to see.

“You’re so beautiful, Scoot!” Sweetie complimented, “I mean, just…wow!”

“Yeah,” Apple Bloom affirmed, “you’ve got one of the purtiest little private areas I’ve ever seen! I can’t wait to watch Cheerilee fuck you…whatever that means.”

Sweetie kissed Apple on the cheek, and whispered the meaning of the word. Apple’s eyes widened as her heart began beating faster. She knew that she wanted to watch the events unfold, but she didn’t realize that she wanted it that badly. She must have let out a silent cry of anticipation, for Sweetie began making out with her severely. The two fillies fell over each other as they kissed and moaned, and then looked over and locked eyes with their teacher.

Cheerilee, very much stimulated by the two, looked down at her small plaything. She smiled and bent down to kiss her, burying her tongue in between Scootaloo’s small lips. The orange Pegasus immediately relaxed under her teacher’s gentle love. She was no longer fearful. She wanted to be Cheerilee’s…no…she NEEDED to be Cheerilee’s. She whimpered as the kiss broke and silently begged her teacher to continue. Her wide eyes now pled with Cheerilee, and the pink mare was happy to oblige them. She gently maneuvered her strap-on into position before slowly plowing her way into the filly.

Scootaloo screamed in pain as she felt something in her nether region for the first time. Her breaths were rapid as her teacher began silently pumping in and out of her. A few seconds of agony passed before pleasure slammed into her like a freight train. She began grunting and moaning under her teacher, who bent over and began increasing the speed of her thrusts. Back and forth pumped Cheerilee’s magnificent rump, driving the toy further and further into the student.

For Sweetie’s part, she left Apple Bloom in a wide-eyed stare and began administering oral to Cheerilee’s exposed vagina. The teacher began howling in pleasure as she felt her mate’s small tongue do its work. Her mind exploded with absolute love and affection for the three fillies that she had in her care, and her thrusts became even more violent. Scootaloo begged her for more, because the orange pony was about to experience her very first orgasm. Cheerilee counted it among one of her greatest honors to be able to administer it.

“YES, YES, CHEERILEE!” Scootaloo screamed with reckless abandon as she felt the penis tug on her insides, “I LOVE IT! MORE, PLEASE MORE! OH, FUCK ME, CHEERILEE! FUCK ME!”

“You’re such a good filly, Scoot!” Cheerilee cried as she felt her own orgasm coming, “OH, TWILIGHT DAMNIT, LICK ME, SWEETIE BELLE! OH, SHIT! OH, SHIT! OH, OH, OH! MORE! MORE! MORE! THAT’S THE SPOT! OH, SCOOTALOO! OH, SWEETIE BELLE!”

The mind numbing pleasure from having sex with one filly while being given sex from another’s tongue caused the teacher to go over the edge. She screamed as she dumped a gorgeous trail of silvery liquid onto Sweetie’s nose. Once she came down from things, she noticed that she had stopped thrusting and Scootaloo was waiting patiently. With a wicked smile, she shoved her tongue down the filly’s throat and began wailing away. Scootaloo screamed into her mouth as her first orgasm shook her small body. Her cum was thick and coated the faux penis rather completely. She removed it and allowed the other two fillies to suckle and lick to their heart’s content.

“Oh, my Twilight, she tastes so good!” Apple exclaimed, “I mean, I ain’t never really tasted this stuff before, but I want more!”

“You’re supposed to like it,” Cheerilee explained, “after all, it came from somepony you love and cherish.”

“Yeah,” Apple said, “I guess it did.”