A Long, Hard Detention

by Holocron

Rating: mature
Tags: Profanity, Non-consensual, Random, Twilight Sparkle, Anthro, My Little Pony: Friendship is Magic, Alternate Universe, Porn, Sex, Fetish, Spike
Length: 3067

Twilight Sparkle, a troublesome student, attends detention with the very busty Miss Barb.

Twilight Sparkle is among one of the best, brightest, and most talented among the senior students in Canterlot High School. But, she has a major attitude and ego problem. As well as this, most staff can't even put up with her, and many students have already succumb to her. Now serving in detention, one of her teachers, the dragoness, Miss Barb, will try to do something about this troublesome alicorn. Unfortunately, Twilight may be more than she can handle.

This is a Commission for Tailsic.
Derpibooru: 3192042

Published 2023-09-23 23:10:01 UTC
Last updated 2023-09-23 23:10:01 UTC

How to Deal with Prudish Teachers

Canterlot High School, a prestigious institution of higher learning; where only the best and brightest attend. But unfortunately, there is a third group who make their way into this school, the well connected. These are students who may have talent, or a desire to learn, but many are simply the children of nobles and royalty, whose connections have allowed them to come to this school, where they would’ve been otherwise denied. Twilight Sparkle, a rather infamous name, is a bit of an enigma in this school.

Since her arrival, she was nothing but a smug, cocky brat. Thanks to her connections with the Princess, she could get away with just about everything. But what frustrated teachers the most, was that this student was more than some spoiled bitch, she had talent. Achieving marks in her class higher than any on record, Twilight spent the last four years overachieving and out shining her peers, but this didn’t change the fact she was completely insufferable. So much so, that few teachers lasted with her, and would even just give her a passing grade, whether she even showed up to class or not.

But this did not make Twilight immune to some degree of disciplinary actions. The Princess herself had given the faculty the right to punish the mare in terms of detentions and such. Though this did little to curve the cocky mare’s behavior. If anything, she only seemed to purposefully put herself in detention, just to toy with whatever teacher was doomed to supervise her. For today’s staff condemned to put up with this senior student, Miss Barb, a dragoness who had numerous issues with Twilight in the past.

Sitting in the empty classroom, Twilight, dressed in an extra small black skirt, that revealed some skin tight black leggings; as well as an even tighter looking button up white shirt that better showed off her large, round cleavage, was busy licking and suckling along a lolipop. Barb, dressed in somewhat more modest clothes, or what could pass as modest for a dragoness of her figure. A more straight down black skirt that hugged her fat ass, and large thigh tight legging. But it was her tits, a massive, round shape of perky breasts that was the boner material of every male student, and the envy of every female student.

“Looks like you’re stuck with me again.” Twilight playful chuckled, mocking the dragoness as she licked along the lollipop. “Why don’t we cut the crap and you just let me go? Everyone else does it.”

“Well, I’m not everyone else.” Barb hissed, glaring angrily at the mare. “I don’t give a fuck if you’re an alicorn, or even Princess Celestia’s bastard daughter, you’ve been a pain in this prestigious school since coming here.”

“You’re right. You’re not everyone else.” Twilight laughed, staring more at Barb’s chest. “I don’t even think Celestia has tits like yours.” Barb blushed, and hissed angrily at the mare. “Ha! What’s wrong? Couldn’t find anything to cover up those huge milkers?”

“You’re one to talk.” Barb replied, giving into Twilight’s taunts. Taking a yardstick, she pointed at the mare’s tits. “You’ve always dressed like a little slut, but once you turned eighteen, you’ve done nothing but fuck your way around the school. You’re nothing but some pampered whore.”

“Fuck you, you fat titted prude!” Twilight snapped, seemingly taking offense to the dragoness’ words. “Besides, I’m quite proud of what I got.” She spread her legs a little, sighing a breath of comfort as she did so. “Not my fault, everyone else around here wants this.”

Barb’s eyes went wide with confusion and anger. Though it was mostly under the desk, she could see it, Twilight’s cock. It was a monster, a massive girth of meaty, bitch breaking, pussy destroying of a dick. And even as only maybe a little under half of it was poking out from under the desk, it was enough to show off just how terrifying it was. Even the precum that was oozing out the blunt tip was testament to how much cum must be stored in her huge balls. Barb’s gaze only lasted a moment, where she shook her head and brought her attention back to Twilight’s face.

“Why can’t you understand, that what you say and what you do is fucking inappropriate!” Barb snapped, shouting at the mare. “You really think you can just flaunt some big dick, and bimbo boobs around to get your way?”

“Oh? Saw something you like down there?” Twilight asked, laughing and mocking the dragoness as she was licking along the lollipop. “Maybe what you need is to take that stick out of your ass, and let me shove my cock right in there.” She smirked as she glared at the teacher. “I bet you’ll love it.”

Never before had Barb felt a strong urge to strike this bitch with something. And while she gripped the yardstick in her claws, almost to the point of snapping it, she struggled to restrain and compose herself. She hated this mare, having had to deal with her these last few years, and now that she was older, she felt her eyes drift a little back and forth to this cock. Twilight was a bitch, a massive pain to the teacher, but she was a sexy mare, and this dick, it was bigger than anything Barb had ever seen. And though this thought lingered for a fraction of a moment, she couldn’t help but be curious if such a thing could even safely fuck someone.

“Hey, Barb.” Twilight commented, sticking the lollipop in her mouth as she looked at the teacher. When Barb’s eyes met with hers again, the alicorn pointed a finger towards her face. “My face is right here. Or do you wanna continue this conversation with my cock?” Barb said nothing, only angrily blushing as she pretended, in vain, to not look at this dick. Running her hand over it slowly, the mare laughed. “Maybe you just need something to get that bitchy attitude out of you? I know, how about I show you what you’re missing?”

Before Barb could reply, Twilight got up from her seat, even shoving the desk out of her way as she swayed her way over to the dragoness. The teacher stuttered nervously, backing up until her ass pressed against the nearby desk. Licking her lips, Twilight took this chance and lunged at the teacher, groping at her huge boobs. Barb gasped out in shock, and was about to shout something angry and vicious at the mare, but Twilight then shoved her mouth over hers, letting her tongue slip in and overwhelm Barb’s. The dragoness’ body tensed up, and yet her tits felt so soft. The alicorn couldn’t help herself as she all but tore off the teacher’s top, letting these massive tits bounce free of their cloth restraints.

“Fuck, you got some nice tits.” Twilight hummed, groping and teasing at Barb’s nipples. “Oh? And you’re even moaning? I bet you love it, you slutty teacher!”

“Get…the fuck…off…me…” Barb protested, trying to fight back as she was being so violently molested, but Twilight’s skilled touch was seemingly draining her strength as she felt so weak against the alicorn. “Don’t…don’t touch me…there…”

“Don’t touch you where?” Twilight teased, taunting and mocking the dragoness as she was grabbing and groping both breasts, tugging and teasing the nipples to draw out more and more forced moans. “Or maybe you meant here?” Reaching down with one of her hands, she started rubbing along the moist lips of Barb’s pussy. “Oh fuck, you’re so fucking wet?! Bet you must love this.”

“It’s not…like that…” Barb replied, trying to fight off Twilight, but was feeling too weak as the mare was toying with her. “J-just…stop this…”

“Aww, are you begging?” Twilight laughed, releasing Barb, only to grab her by the hips, pulling her closer to her. “Don’t worry, slut. I’ll make you feel really good.” Before the dragoness could do anything, the alicorn turned her around and pushed her over the desk, making her bend over it. “Now, let’s get rid of these.” Tearing off Barb’s panties, she laughed.

Grasping at her cock, Twilight pressed and prodded it against Barb’s moist pussy. The dragoness winced, shivered, but didn’t move as she felt as the alicorn was teasing her soft entrance. She whimpered, feeling as she was unknowingly fidgeting from the feeling of this cockhead pressing against her lower lips. But Twilight didn’t thrust forward, didn’t even try to put an inch of her massive cock in her teacher. She only reached down, groping at Barb’s round ass as she held herself in place.

“Beg for it.” Twilight commented, almost ordering Barb as she glared at her. “Tell me how much you want it, and I’ll fuck the prude shit out of your slutty pussy.” Barb hesitated, not wanting to admit anything. “Oh? Still playing tough?” Igniting her horn, she grabbed at the yardstick that the teacher had dropped. “Maybe you need more motivation?” Taking the yardstick, she struck hard against Barb’s ass.

The dragoness screamed out as she nearly came from the feeling. The way Twilight had teased and molested her, though she hated it, it felt good, sending unwanted ripples of pleasure throughout her body. Again and again, Twilight struck her teacher’s ass, making Barb pant and scream out, struggling to hold back the moans they echoed in her voice. The alicorn only continued to tease and taunt her teacher, but not thrusting forward, only rubbing her oozing cockhead against this dragoness’ moist fuck hole.

“Come on, you slut. Say it!” Twilight hissed, feeling as her own pent up feelings were becoming too much to handle. “Scream it out! Tell me how much you want this cock!”

“... … …” Barb whimpered, shame and embarrassment washed over her face, feeling only hatred and yet pleasure under her anger. But even then, her voice only came out as a whisper. “I…I want it…”

“What was that?” Twilight asked again, smacking Barb’s ass again, leaving more red marks with the yardstick. “I said scream it, not whimper like a bitch. Fucking say it!”

“I want it!” Barb shouted, feeling herself fall into the depravity being forced upon her. “Just shove that fat cock in my-” She gasped as she felt the sudden thrust of Twilight’s cock inside her.

The alicorn bottomed out in the dragoness, savoring the feeling of shoving her full length in this extra tight pussy. Even Twilight couldn’t help but moan a little from the feeling. Barb’s pussy was so tight, it was one of the best feelings she had felt, and it felt as if she was bottomless. Maybe it was something unique about dragons, but it felt as though Barb didn’t have a cervix. Twilight’s cock had rammed itself in the initial thrust all the way into the womb, causing her flexible belly to bulge out in the shape of this dick.

“Oh fuck?! Are all dragons like this?” Twilight asked, only to see Barb’s eyes were rolling back from the orgasm she just experienced. “Oh well, might as well not hold back.” Nearly pulling out, she fucked hard and deep again.

Twilight felt her cock being squeezed by the inner folds of Barb’s pussy walls. This fuck canal was just perfect, stroking and milking her length for seemingly everything it had. She loved it, causing her to flap her wings eagerly as she was thrusting. Twilight’s balls slapped hard against the back of Barb’s thighs, the sound mixing with the sloppy sounds of this pussy being stretched and dominated by this alicorn’s cock. The dragoness was panting and moaning, feeling as if she was losing herself to the pleasure.

“Oh shit, this is the tightest pussy I’ve ever fucked!” Twilight laughed, taunting Barb on and on. “But maybe you’ll love this!” Reaching around, she groped at the dragoness’ tits.

As soon as she got her hands on these massive, soft mounds, Twilight pinched, teased, and tugged at the nipples, making Barb moan more and more from the pleasure. They were just so big, so soft, she was gonna need to slap her cock between these tits some other time. Right now, she wanted to let out all her frustration over this bitchy teacher by fucking up her pussy. Her mind teemed with all manner of thoughts and fantasies.

Would she keep this affair a secret? Pretend to still be bitchy with Barb, only to fuck her slutty brains out during detention now? Or would she keep this dragoness as a pet, bring her home, and keep her as her favorite cockwarmer? Or maybe she would use her connections and masturbate while watching some of her favorite royal guards gangbang this dragon? The ideas and temptations, it was all so much for the alicorn to handle. Maybe she would do more than one? A mix? Or even all of them?

“Gotta say, you got the best pussy I’ve fucked in a long time.” Twilight taunted, hammering her cock in and out of Barb’s pussy. “Even better than that fashion slut, Rarity. You even got way bigger and softer tits than her.” Barb only moaned, feeling as the alicorn hugged herself closer to it, allowing her to thrust more and more upwards. “Come on, slut. Tell me how much you like it.”

“Fuck…you…” Barb moaned, her mind still resisting a little, but her body had been broken and submitted to this cock. “Fuck…you…and your…massive…dick…”

“Well, this massive dick is about to really fuck you up!” Twilight groaned, tugging at Barb’s nipples forward, making the dragoness moan out, shivering as she was spilling all her glistening fuck juices all down her thighs and pooling on the floor. “Oh yeah, that’s the sound I want to hear. A slut moaning while I milk her.” She continued to grope and tease the nipples, tugging at them as if she were milking a cow.

Barb’s mind was being fucked into a sloppy mess. There was no going back from this, she was going to be Twilight’s slut. Her body was now at this bitchy alicorn’s mercy. No doubt she was already coming up with all manner of ideas on how to torment her. Fuck her every day, and make her little more than some cock craved whore. And yet, part of her didn’t seem to mind that. As Twilight’s pet slut, Barb wouldn’t need to worry so much, and the pleasure hammering in and out of her body was driving her mad with euphoria.

This was it, this was the end of this proud, prudish teacher. To be fucked and broken by this alicorn’s cock. The feeling of…of happiness was rippling through her. Barb’s mind could barely resist as she was getting closer and closer to another orgasm. From the way Twilight’s cock was throbbing and swelling in her pussy, and how it felt to have her heavy balls slap against her thighs, she was feeling as though she would be flooded with cum.

“I’m getting there, I’m gonna blow my fat nut right in your slutty hole.” Twilight teased, picking up her humping speed. “Keep moaning, and I’ll make sure to stuff you, with every…last…drop…”

Twilight grunted and panted between her words. The desk Barb’s body was being pushed against was violently shaking as she was getting closer and closer to cumming the mind breaking orgasm that sealed her fate. Twilight’s dick was throbbing, getting closer and closer to the climax that would finally break her, making her this alicorn’s newest slut pet. The mare was huffing as she could feel her cum filled, heavy balls tighten against her body. Her cock was swelling and throbbing. It was going to cum, very, very soon.

“Fuck, Barb. I’m about to cum.” Twilight grunted, mocking the dragoness as she was now tugging at the teacher’s huge boobs. “Maybe I should just fuck you full of cum.” She leaned in to whisper seductively in her ears. “But I wanna hear you beg for it.” Barb tried to resist, but the way she was moaning, she was about to cum. “Come on, you bitch. Fucking beg to be fucked up by my cock. Admit it. You’re just my cum slut!”

Barb only moaned, her pussy wrapping tightly around this dick as she was feeling herself cumming over and over again on its girth length. Twilight only continued to laugh, fucking faster and faster as she was getting ready to blow her load. For her, she didn’t care if Barb admitted it or not. If anything, she enjoyed the resistance, it only made her want to break her pussy more. Hammering harder and harder, Twilight was about to cum in her teacher’s pussy. Just like every other fuckhole that she craved before, this alicorn was claiming Barb’s pussy as her own toy.

“Here it cum, slut.” Twilight laughed, tugging at Barb’s tits to make her moan. “Scream like a whore while I knock you up!”

As soon as Twilight shouted this, she bottomed out, hilting in Barb’s pussy, which caused a massive belly bulge. This was only expanded as the mare released her cum in the teacher’s pussy. She gasped out, moaning a breathless scream as the alicorn’s cum flooded her pussy. Her womb not only expanded outwards, but her belly bulged to further and further degrees until it was nothing more than a bloated mess. Barb’s legs tightened as she came from this feeling, her tongue dangled from out her mouth as she moaned and felt herself going limp.

Releasing the dragoness, Twilight laughed as Barb collapsed on the floor, to which her cock slipped out and fired off another heavy load of hot spunk all over her twitching body. She stared at her conquest. The biggest prude with the biggest tits was now so full of cum, how her eyes were rolled back and tongue lay in this pool of fuck juices and cum. Twilight couldn’t help but smirk down at her, having added a new cum slut to her collection.

“Now then…” Twilight commented, sitting on the desk. Taking out her phone, she took a few moments to take several pictures of Barb laying there, covered in and leaking out cum. Adding those photos to her vast galleries, she scrolled through to see the faces of other students and faculty. “Who…is…next?”