Extracurricular Activities

by SFC Ponycron

Rating: mature
Tags: Twilight Sparkle, Cheerilee, Big Macintosh, Anthro, My Little Pony: Friendship is Magic, Romance, Sex
Length: 1654

A scholar, a schoolteacher, and a farmhand. These are their stories, their fantasies, their fun times, and their wacky, sexy hijinx!

Twilight Sparkle, the Scholar. Cheerilee, the Schoolteacher. Big Macintosh, the quiet Farmhand.

These three names are constants throughout Ponyville. A deeper look reveals that these three individuals actually know each other very well. Intimately well. An even deeper look reveals that such intimate knowledge of each other is anything but what is deemed vanilla.

Join Twilight Sparkle, Cheerilee, and Big Macintosh as they indulge in such intimacies, and the conversations that ignite such curiosities and adventures.

*---*---*

What started as a Sexty Minute Pony Stories prompt is now going to be yet another miniseries here on FIMfiction.

Published 2015-08-19 21:30:02 UTC
Last updated 2015-08-19 21:30:02 UTC

Chapter One -- Two ponies sneak into a classroom... (Part One) [MacCheeriLight]

“I can’t believe I’m so late!”

Cheerilee made it to her destination, panting heavily. She looked up and smiled at Big Macintosh, breathing evenly, a ghost of a grin on his face.

“You wanna sneak in with me?” she asked.

He waggled an eyebrow and brought his face down to her ear.

“Eeyup,” he whispered, sending chills down her spine. Shaking away the growing desire, Cheerilee put her hand on the doorknob, quietly turning it and easing it open painstakingly slowly. She looked up and saw the bell and slipped her other hand up against the door, catching it as it fell and preventing it from ringing. She cast a quick glance at her tall lover and pressed a finger to her lips as she opened the door just enough to slide between the door and the jamb.

Without waiting for Macintosh, she slipped past the main desk and found the stairwell leading to her classroom. As she reached the bottom of the stairs, she glanced around and made sure that no one was around. She looked up the stairs and saw Big Mac heading towards her, already halfway down the stairs. He was wearing a simple white shirt with a black tie and black pants, the tie undone and hanging around his neck, the top two buttons of his shirt undone, revealing a chiseled chest underneath a thin red coat. Her eyes roved lower and she licked her lips at the sight of the straining tent at the crotch of his pants.

“Come on,” she whispered urgently. Big Mac nodded and followed wordlessly as she walked down an aisle of desks. Once she reached the front row, she turned and winked at him, patting the top of the desk immediately beside her.

“Sit,” she said, hooking a finger on her lower lip teasingly.

Mac chuckled but shook his head. Instead, he tilted his head upward, glancing past her. She raised an eyebrow and turned around, following his gaze to the teacher’s desk. She grinned and slowly slid her hooked finger along her lip.

“Naughty boy,” she said with a nod. Without answering, he walked past her and hopped up on the desk and leaned back casually, the tent in his pants glaringly obvious and presented to Cheerilee.

She sashayed slowly towards him, and he took the time to take in the sultry shamelessness in his lover. She had her two-toned pink hair in high pigtails, her shirt was closed by a single button just below the valley of her breasts, and her gray skirt with red, black and white tartan was much too short to be even remotely considered wholesome.

As she knelt down in front of him, she spread his legs and undid his pants. Without waiting, she slipped his underwear off his stallionhood, and her eyes grew dark with lust as it popped free, just the sight of his ready length already making her wet. Wasting no time, she ran her tongue underneath his shaft, cupping his balls in one hand, her other hand reach down and shifting her panties aside to play with herself.

As her tongue reached the tip of his penis, he ran his fingers through her hair and gently gripped the back of her head, guiding her mouth down on him. He groaned and threw his head back as she moaned around him, and gasped in surprise when she went down further, attempting to take the entirety of his member in one go. She stayed there for a few seconds before she lifted her head free of his penis with a loud gasp, followed by a devilish smile.

“You like that?” she asked as she pumped him slowly.

“...Eeyup,” he gasped.

*SWISH* *SMACK*

Cheerilee whirled around to see a stern-looking mare wearing a black blouse, a plain light-brown jacket with matching skirt and a pair of half-moon glasses. In her hand was a metre-stick, still slightly bent against the top of the desk closest to her. Her eyes were half-open with disgust.

“H-He-He-Headmistress Twilight!” Cheerilee gasped in surprise.

“That’s Headmistress Sparkle, Miss Cheerilee,” she snapped disapprovingly. “Not only are you late for your advanced private tutoring session with me, what do I see when I enter my classroom than you giving fellatio to Mister Macintosh? On my desk, no less!”

Big Mac opened his mouth to say something but was cut off by a slash of wood as Twilight wielded the metre stick like a sword, pointing it at the dumbstruck stallion. “I’ll have none of it, Mister Macintosh!” She strode purposefully towards the pair. “I’ve half a mind to expel the both of you right now.”

“B-b-but...”

“Indeed, Miss Cheerilee,” Twilight interrupted, looking down her nose at Cheerilee and lifting up the hem of the one-third-skirt with the tip of the metre stick. “And your panties are barely covering it.” She narrowed her eyes even further. “I should bend you over the desk and give you lines.”

“M-Miss Twi-Twilight, please...”

“That’s Headmistress Sparkle,” Twilight interrupted loudly. She glared at Big Mac. “Off my desk. Now.” He scrambled off the desk and did up his pants. Twilight turned down to Cheerilee. “You, lift up your skirt and bend over the desk.”

Shaking, Cheerilee stood up, lifted her skirt ashamedly and looked at the desk in fear.

“I said bend over!” Twilight shouted, slamming her free hand on the desktop.

With a fearful nod, Cheerilee bent over, pressing her breasts against the cool wood of the desktop. As Twilight lifted her hand and moved behind Cheerilee, the earth pony took note of a small slip of paper, the writing she recognized as Twilight’s and just big enough to read.

Just to recap, it said, the safe word is ‘molasses’.

“Are you ready?”

“Y-y-yes, Miss Twilight--”

*SWISH* *SMACK*

Cheerilee yelped in surprise and pain as the metre stick lashed at her ass.

“I’m sorry! I’m sorry!” she cried out hurriedly.

“Are. You. Ready?” Twilight asked again, emphasizing every word.

“Yes, Headmistress Sparkle,” Cheerilee said shakily.

“Your line is 'I will not be late and suck off my classmates in class',” Twilight said expressionlessly. She turned to Big Macintosh. “Mister Macintosh, seeing as it is your first offense, you will sit in my chair and watch how I punish my students as a warning to yourself.”

Big Macintosh needed no further bidding. He scrambled to the teacher’s wheeled chair and sat ramrod straight.

“Do not take your eyes off Miss Cheerilee,” Twilight ordered. “Miss Cheerilee, you will repeat your line ten times. Go.”

“I will not be late and suck off my classmates in class,” Cheerilee recited.

*SWISH* *SMACK*

“Ahh!”

“Nine more,” Twilight said unsympathetically. “Go.”

“I will not be late and suck off my classmates in class.”

*SWISH* *SMACK*

“Ahh! Please...”

“Eight more, Miss Cheerilee.” She looked over to see Cheerilee turning to her. With the tip of the metre stick, Twilight gently moved her head to face Big Macintosh. “Eight. More. Continue.”

“I will not be late and suck off my classmates in class--”

*SWISH* *SMACK*

“Ah, Goddess!”

“Seven more, Miss Cheerilee,” Twilight said. Without moving her head, her gaze rested on Cheerilee’s red, raw flank, her nether lips sopping wet and glistening. She imperceptibly licked her lips.

“I will not be late and suck off my classmates in class.”

As the metre stick lashed against Cheerilee’s ass a fourth time and then a fifth, Big Mac couldn’t help but stare at her lover in total awe. Her eyes were rolled back in ecstasy, and every swish of the metre stick against her rump left her squealing with pleasure. He took in a slow, stuttering breath as he watched Cheerilee accept her ‘punishment’.

“Mister Macintosh,” Twilight called out gently. He looked up in surprise.

She nodded at the bulge in his pants. “I can see you have a problem there. Feel free to deal with it as you see fit. She still has three more lines to recite. Maybe it will help her remember what she’s reciting if she sees why she’s bent over my desk in the first place.”

As Big Mac met Twilight’s eyes, he could see her eyes go misty with lust for the briefest of moments before hardening with clarity again. Unable to control his hormones, he undid his pants again and stroked himself as he watched Cheerilee accept her punishment with equal parts surprise, awe, and lust.

*SWISH* *SMACK*

“I will not be late and suck off my classmates in class.”

“Two more, Miss Cheerilee, and I will let you go.”

“Please, Headmistress, let me...”

Twilight let out an exasperated sigh. “If you must, Miss Cheerilee,” she said, feigning annoyance.

Cheerilee slipped her hand between her legs, furiously rubbing her already-hard nub.

“I will not be late and...hahh...suck off my classmates in...” She tensed up and squeaked. “...Class.”

*SWISH* *SMACK*

“Oh, Goddess!”

“One more, Miss Cheerilee,” Twilight snapped.

“I will not be...” She let out a stuttering breath. “...Late and...” She writhed on the desktop. “...Suck off my classmates...”

Big Macintosh watched as Cheerilee’s body tensed tightly in impending orgasm, Twilight already raising her arm and ready to administer the final punishment.

“...In class.”

*SWISH* *SMACK*

Cheerilee screamed in ecstasy as the final blow from the metre stick brought her to her climax. Twilight looked down at Cheerilee, feigning indifference, before setting her eyes on him.

“Mister Macintosh, though I have foregone punishment on your part, there is still the matter of informing your immediate family about this grievous breach of etiquette and protocol.” She smiled devilishly, lifting up her skirt with a free hand and revealing her own wet nethers, a trail already streaming down the inside of her thigh. “Although, I can forego that as well, if you were to do what I ask of you...”

Author's Note

Hope you enjoyed! Comments and concrit are welcome.