Detention

by Gypsy Writefag

Rating: mature
Tags: Anon, My Little Pony: Friendship is Magic, Porn, Sex, Cheerilee, Human
Length: 3452

You get sent to detention by Cheerilee.

Cheerilee sends you to detention even though you're not a student at Ponyville. Even though you try your best, there's no escaping it. And maybe that's for the better.

Contains: human on pony, foalcon, and futamare on guy.

The first story I ever wrote for this fandom!

Published 2019-11-09 04:00:01 UTC
Last updated 2019-11-09 04:00:01 UTC

Detention

You are Anon. And you are in detention alongside Sweetie Belle. You're not really sure why you're here though. Sweetie Belle cursed at Cheerilee, so naturally she got the detention deal. All you did was laugh at her joke and try to defend her. It's not like you go to school anyway.

"All right you two, let's get this started." Cheerilee sounds stern. It's actually quite intimidating. "You're going to be doing these tests in total silence while I review papers. Not one word from either of you."

You sigh and look down at the paper.

No, fuck this. You are Anon, and you are not doing this stupid shit. So you stand up and turn around and walk towards the door.

"Anon! What do you think you're doing?!"

"Leaving"

"You get right back to your seat this instant, young man!"

Her voice and tone reminds you of your mother scolding you. Waves of embarrassment course through your body. It makes you start shaking and you feel like an idiot.

"O-of course, ma'am"

It's the only thing you can utter as you scamper back to your seat. Sweetie Belle stares at you in disbelief the entire way. A blush is covering your face as you sit back down in your seat. Cheerliee eyes you cautiously until you pick up the pencil and look at the paper. When the embarrassment and blush slowly fades other emotions begin anew. You realize how attractive it was to be put in your place. Something about Cheerilee scolding you was enjoyable. And she was quite the beautiful mare. Well educated and kind, too. After pretending to look at the paper for a little while, you sneak a glance at her. She's absorbed in her paper grading. What an absolutely cute mare. You can see little smiles come across her lips as she reads the fillies' papers. Although she doesn't notice you, you do your best to stay sneaky. Don't wanna get caught looking at her.

Looking at the sheet of paper is so boring. Your glances become more and more frequent. It's as if something is forcing you to look at this benevolent mare behind the desk. As you look at her, you begin to wonder what she's like in private. You never really got to know her. What music does she like? What books does she read? What positions -

You are suddenly brought back to reality as you realize Cheerilee is staring right at you. Sweat forms on your forehead and spaghetti fills your pockets. You can't look back at the paper. You're fucked, and you know it.

"Anon, what are you doing?"

"N-nothing..." Slowly, you lower your gaze back to the paper. You can still feel Cheerilee's piercing gaze upon you. It is pricking into you like needles. It's exhilarating. You finally grab the pencil and put it to the paper. Instead of actually answering the quiz, you instead find yourself drawing pictures of Cheerilee. Not that you were very good at drawing, but it's not like you don't have an imagination. At first it's just doodles of her as you get into the whole drawing thing. But after a few sketches, you quickly start drawing her more and more questionably. With whips, gags, rulers. Spread out on the desk with sultry eyes. As you look at the images, you feel slight attention from your buddy down below the desk. This is all quickly forgotten as you hear a noise from your left.

"Psst!"

You look over at Sweetie Belle. She's got a ball of paper in her hoof, motioning a throw towards you with a smile.

You look back and forth from Sweetie to Cheerilee. You have to make sure she doesn't see this. W.hen you feel the coast is clear you nod to Sweetie Belle. She quietly tosses you the ball of paper. You catch it and quickly stow it under your desk. Cheerilee hasn't noticed a thing. From the looks of it she's deeply concentrated on her work. Slowly, you unfold the piece of paper in your lap. Adrenaline is rushing through your body. It's just like being in 4th grade again. You realize it's kind of silly, but screw that, this is genuine fun. On the paper is simply words.

"Why did you come back? Do you LIKE Cheerilee? ;)"

You quickly look up at Sweetie Belle. She's just focusing on her test. There is a huge, shit-eating grin on her face though. You glare at her for but a moment until you hear Cheerilee clearing her throat. panic.jpg

"Anon, is there something you'd like to share with the rest of the class?"

Now she's even being sarcastic. You can barely sit still from all of this. Once again you find yourself in a contest of endurance. It is a battle of the eyes, of the minds. Cheerilee is trained in this. She does this every day. Resistance is futile. Her gaze is piercing your very being. As a result you lose all concentration.

"My dick."

Although the classroom had been silent up until that point, it seemed as if a groundbreaking one had taken its place. You feel stares even from Sweetie Belle now. But the reaction from Cheerilee isn't quite what you would have expected.

"Your what now?"

She seems genuinely confused. From the corner of your eye it seems Sweetie Belle has the same expression on her face. This is your chance to save this shitty situation.

"Sweetie is passing notes!" you blurt out.

Cheerilee is quite obviously taken by surprise.

"WHAT?!" Sweetie Belle creaks in disbelief. It seems to have worked. Cheerilee is no longer looking at you, but Sweetie. Just like in fifth grade when you blamed that annoying girl for spilling milk everywhere.

"Sweetie Belle, I thought you knew better than this."

"B-but, I-"

"You will be silent and do the rest of the quiz."

Sweetie just grumbles and stares daggers at you. For some reason you want to rub it in even further.

"Here's what she gave me."

You feel the daggers intensifying, and you hand Cheerilee the piece of paper. You sly fucker you. You really outdid yourself this- uh oh. Is that a drawing of a pony on the paper? Realizing what you've just done, spaghetti once again starts spilling from every orifice. However, it's too late to stop it. It's happening. Cheerilee unfolds the paper. Her face is a mixture of horror, surprise, and... no, she couldn't be blushing.

"Sweetie Belle! What is this?!"

Sweetie takes one glance at the paper.

"I DIDN'T EVEN DO THAT! THAT WAS HIM!"

"Proper schoolponies do not lie, Sweetie!"

"You KNOW how badly I draw! I can't even make macaroni pictures! Besides, that is DISGUSTING!"

Cheerilee's head slowly turns towards you. That sly smirk is long gone. It's hopped on over to Sweetie.

"Sweetie Belle, you may leave."

Cheerilee doesn't even look away from you while saying that. Sweetie leaves with a smirk. You simply gulp. For what feels like the millionth time today, you have locked eyes with the teacher. But this time, something's different. You revel in her mental domination of you. Her overpowering glare and authority radiating a strange form of desire. As you stare into her deep, green eyes your throat and lips dry out. You slowly lick your lips. You tell yourself it's to moisten them. Both of you know that's bullshit.

"Stop."

Cheerilee doesn't look one bit pleased. You thought for sure this was it. Instead of succumbing to your manliness, she seems infuriated. With calm and calculated movements she gets off her chair. With the grace of a million women she moves towards your desk. Still locking you in place with those eyes. You swear she must have had lessons from Fluttershy. Both of her hooves are suddenly on your desk. She's mere inches from your face. This beautiful mare smells magnificent. Unlike anything you've ever smelled before. And her breath on your face is like an intoxicating drug, lulling you into a false sense of security.

"You will not move a muscle unless I tell you to, understood?" she whispers.

You can do nothing but obey her. Except for the slight twitches coming from your lower body. It's not like you could control it anyway. After a good 20 seconds have passed she is convinced you are obeying her. Shee tilts her head slightly to the side and moves her lips just close enough to touch yours. It is the purest of agony you have ever felt in your life. Confined by nothing more than your word you are unable to give in to your desires and take what you want. Cheerilee feels this and smirks.

"My, aren't you a good student."

With every word her lips graze yours. The stimulation that could be is driving you mad. It takes all of your willpower not to throw yourself at this mare right then and there. But there is no way you would fuck this up. Her gentle hoof strokes your cheek.

"Oh yes, you are indeed a perfect student."

She finally gives you what you need for but a brief second. Her lips press against yours. It is the most passionate, one-sided kiss you have ever experienced. Not kissing back is almost unbearable. After breaking the kiss, Cheerilee simply looks at and studies you.

"Bend over my desk, Anon. You did, after all, not perform very well during detention. Punishment is in order for such behavior."

After scurrying over to the desk like the good student you are, you practically throw yourself onto it stomach first
an audible "pomf" is heard. But it's a wooden desk. How is this possible?

"W-What are we going to do on the desk, Cheerilee?"

Before you can even think of what she might answer, you feel a sharp pain in your back. Pain you haven't felt in a long time. You actually have to hold back tears. The teacher has her front hooves firmly planted on your back after having stomped them onto you.

"I did not give you permission to speak!" she hisses at you.

Although you cannot turn to face her, you know exactly what her face looks like. She twists her hooves into your back, eliciting further pain. You bite your lower lip to the point of bleeding to avoid making any noise.

"That's better."

She gets off of you, pain immediately leaving your body. The mare is rummaging through the drawers in the desk.

"Now, unfortunately we are not at my home, in which I have more... adequate tools for punishing misbehaving students. This ruler will have to suffice, I guess."

You get a quick glance at it. It's long, it's solid, it looks like pain. Before fully registering the situation, Cheerilee has forcefully pulled your pants down to your ankles, leaving you in just your boxers.

"Get ready", she says through her mouth holding the ruler.

The first hit comes faster than you expected. And the pain which it causes to your buttocks in indescribable. The fights you've been in are nothing compared to this. Pain of this magnitude should not befall you. Before even fully accepting the pain you have received, another blow is struck. This time harder and faster. Your body is tensed up and tears are now freely flowing from your eyes. This is not what you expected it to be.

"Good! Students! Do not! Resist!"

She hits you with every word, emphasizing your position and the pain. You want to sob, yet you somehow manage to hold back. Despite the tears, you grow accustomed to the pain. You welcome it. She is your teacher, and you her student. Slowly, your body relaxes and absorbs the pain not as something negative, but as something wonderful and joyous. When the fourteenth hit lands on you, a small moan escapes your lips. Cheerilee temporarily stops.

"Did you not learn you lesson before?!"

She quickly resumes her strikes. But all you can do is moan.

"You're a terrible student! Dirty, villainous, bastard!"

At this point you have let go and your moans fill the classroom and possibly the entire school ground. Cheerilee stops all of a sudden.

"You obviously need harsher punishment."

You hear a spit. You feel your boxers drop. Before comprehending what she is doing you feel it. The ruler is slowly drilling its way into your rectum. You scream out in half pain, half pleasure.

"What's the matter, poor Anon can't handle a little fun?"

With the ruler lodged firmly in your anus, Cheerilee's teasing sounds like the singing of angels. You're still not convinced of this whole ass thing. Anything to take your mind away from it is welcomed.

"How do you like it? Answer me!" S. he gives a slight twist of the ruler. Your insides are stretching in ways you didn't think possible.

"I-I don't t-think I want m-more", you manage to stutter.

"What's that? You want MORE?" Cheerilee sounds like a madman at this point.

"N-no! That's n-no!"

She pulls out the ruler in one fluid motion. The mixture of relief, pleasure and pain is a strange sensation, but you are happy to have it out of there. Behind you the sound of a bottle being opened and a liquid being drunk is heard. You don't care, you simply rest after the ordeal.

"Uh... Ugh, OHHH!" Cheerilee's grunts of seeming pain catches your attention.

"A-are you okay back there? What's going on?"

Two fuchsia hooves slam onto the table beside you. The teacher's face appears mere inches beside your own.

"PERMISSION TO SPEAK: NOT GRANTED!"

With those words you feel something horrible. Meat. On your back. A long rod of lovemaking throbbing against your ass cheeks and lower back.

"W-what"

"SHUT UP!"

She bites your neck. A far more tolerable pain and far more pleasurable. But as she does, you feel her shifting, and voila, her head is aligned with your anus.

"You're going to enjoy this", she smirks.

Never in your life has fear gripped you quite like in this moment. This unknown event is about to change everything. And everything started out so well.

"Here. We. Go."

You bite your lip as you prepare for entry. Instead of a fat horsecock in your anus, the front door opens. Probably should have locked that.

"Look, I'm really sorry about w-"

With absolute horror you realize the words were spoken by Sweetie Belle. You slowly turn your head towards the door and see not only the white unicorn, but also Apple Bloom and Scootaloo. This is it, your life is over.

"W-whut's goin' on?" Apple Bloom squeaks.

Gotta think fast. Think man, think! You put on your best calm voice.

"Well, t-this is my extra punishment for passing notes during detention."

Cheerilee picks up on it and nods eagerly.

"What kind of punishment is this?" Scootaloo asks

Fucking kids and all their questions.

"This is adult punishment, Scootaloo." Cheerilee is amazingly calm for the situation. "Adults and foals are different, so we punish adults differently, of course. This is very natural."

You nod and give a weak smile.

"Why do you have a penis?" Sweetie Belle asks. Silence. You didn't think the fillies were old enough to understand any of this.

"Mares aren't supposed to have this, only stallions!" Cheerilee is mumbling. Shit, shit, shit.

"Girls, come in and sit down". Cheerilee's voice is back to her usual, motherly voice she sports during teaching. The fillies are nervous but listen to their teacher and sit down each at a desk.

"Well, girls, normally we don't have sexual education for another year, but since we're here, we might as well get into it."

The girls look unnerved. You feel weirded out by the whole thing. Her head is still throbbing against your anus, and they are watching.

"While you are right, Sweetie, only stallions have penises, it's actually not always the case."

Oh boy, here we go.

"You see, some ponies are born with BOTH genders for instance! Me, on the other hand, I drank a potion made by Zecora. It's very powerful magic, but it only lasts for about a day with no side effects. It's like playing pretend, just for real."

The girls are opening up to the idea a bit more, but they have begun to blush.

"So, why do ya need tah have a.. penis to punsh Anon?" Apple Bloom asks.

Uh oh.

"Good question! You see, stallions put their penis inside of mares to make them feel good, but if a mare puts something into the stallion, it doesn't feel all that good for him. For most stallions, at least. So I'm doing this to punish Anon for his bad behavior!"

Her eager voice and natural teaching element is sickening to your ears in this situation. "Here, let me show you!"

You completely forgot about the fact that this could still happen. And it did. She plunges into you and moans loudly. Strangely, the feeling of a cock inside you isn't as bad as you imagined. It's actually quite pleasurable. You just have to get used to the feeling. As a result, you can't help letting out a moan after the initial thrust. All of the fillies blush, but you no longer care. You are at Cheerilee's mercy. She seems to have dropped the dominatrix act for now and lets you voice your pleasure. She pumps your ass with her lovestick in a slow, rhythmic fashion.

"Now girls, as you can see, this punishment seems to be ineffective on Anon."

The girls probably aren't even listening to their teacher any more.

"Anon seems to be enjoying this quite a bit, in fact", she smirks. You can only moan in reply. Although she is a mare, and you an ass-virgin, she moves with skill you thought impossible. You have never had more fulfilling sex in your life. And you're playing the part of woman.

"Hey! Ah know what could help!" Apple Bloom suddenly chides.

Wat.

She jumps off her chair and moves towards you.

"Apple.. Bloom, what are you... doing?" Cheerilee manages between thrusts.

"Ah'm givin' Anon ah BJ!"

You have no time to react to this. All you know is there is now a filly sitting underneath your legs, licking your rock hard member. You want to stop her; make Cheerilee stop her. But the pleasure is too much. Words cannot be formed in your state. Resistance is futile. Apple Bloom may not be an expert, but at this point, anything is bliss. Never in your life have you experienced such sweet salvation. Feeling Cheerilee fill you up to the brim with her sweet, magical cock. Massaging your insides and vigorously slamming your prostate. You are at her complete mercy, and it feels liberating. At the same time, Apple Bloom is doing all she can just to pleasure you. She is your little bitch. This mix of being used and abusing the filly is creating indescribable feelings. You think you spot the two remaining fillies with their hooves at their nether regions. But you don't care, it's all about you. As Cheerilee thrusts and grunts, you feel her throbbing member spasm inside you. With one final, hard thrust she shoots her seed inside you and groans in feminine pleasure. The force from the thrust forces your own cock deep into Apple Bloom's throat. She was clearly not prepared.

As Cheerilee moans, Apple Bloom gags as you reach your own climax and grace her with your manly sperm. She clearly didn't know about this part. You can feel her trying to get off, but you reach down and hold her in place. She's gotta learn to swallow. Might as well learn early. She is frantically hitting your legs. Gurgling and heaving for air. You think she pukes, but it could just be more of your love-juice. As she swallows more and more, her frantic wailing stops and she accepts her fate. After enjoying the afterglow for a full minute, the three of you release yourselves. Apple Bloom slumps to the ground.

You only have eyes for one mare. Or should you say, your mistress. After this ordeal you have fully accepted your place as her tool for pleasure. As Scootaloo and Sweetie Belle frantically run to their friend, you simply embrace Cheerilee and engage in a deep kiss. Kissing ponies was a bit odd, but in the end, so was kissing humans. You register the voice of fillies, but hear not what they say. After a good minute, you reluctantly break the kiss and stare longingly into Cheerilee's eyes. She gives you a sultry smile.

"I'll see you after class tomorrow."

"Yes, ma'am."