CYOA - Cheerilee (Clop)

>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."
>sigh and look down at the paper

>no fuck this
>you are anon and you are not doing this stupid shit
>stand up and turn around
>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 embarassment course through your body
>start shaking and feel like an idiot
"O-of course, ma'am"
>only thing you can utter as you scamper back to your seat
>Sweetie Belle stares at you in disbelief the entire way
>blushing at full force as you hit the seat
>Cheerliee eyeing 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 realise 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 sneakey
>don't wanna get caught looking at her
>but 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 realise Cheerilee is staring right at you
>sweat forming on your forehead and spaghetti filling 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 lower your gaze back to the paper
>you can still feel Cheerilee's piercing gaze upon you
>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, getting 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
>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
>insinuating throwing it to you and nodding


>look back and forth from Sweetie to Cheerilee
>have to make sure she doesn't see this
>when 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 unfold the piece of paper in your lap
>adrenaline rush going strong
>it's just like being in 4th grade again
>realise 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? ;)"
>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
>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?
>realising what you've just done, spaghetti once again starts spilling from every orifice
>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
>not like you could control it anyway
>after a good 20 seconds have passed she is convinced you are obeying her
>she 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 you
>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 audiable "pomf" is heard
>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 teahcer 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 hoves 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 ancles, 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 nothin 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, emphazising your position and the pain
>you want to sob
>but 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, villanous, 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!"
>she 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 fuschia 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 realise 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 pleasuable
>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, rythmic 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 moan, 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 lovejuice
>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."
End