Just sending an ask to let you know that Headmaster’s Lesson like… awakened something in me. 🥵💦 That fic is unreasonably hot. Just. Hoo boy. Thank you for the delicious meal. Something about the ‘I absolutely shouldn’t but I am ROCK HARD and since I have no choice’ just hits different.
Question: does it make it harder for Doren to be alone with you in their apartment, having been with you like that? What about Mason at the lake? Winter when he catches you touching yourself in class? (I have not successfully fucked Winter but I WANT TO)
You don’t have to write a sequel or anything I just CANNOT stop thinking about this fic. So I wanted to ask about the aftermath.
saioiojdsajsio im SO GLAD YOU LIKED IT! Legit, its one of my favorites that I've written so I love that so many of yall love it! also shhhhh, but there shall be some kinda writings based off of headmaster's lesson in the future, someone asked for Leighton/PC/River, so that's something to keep an eye out for~!
content warning. Uh, yes, is a aftermath of Headmaster's lesson, so shall be references to a filmed encounter of the teachers running a train on you, with Leighton watching. Made sense at the time. Guilty feelings, not-so-guilty-feelings. Masturbation, emotional manipulation, blackmail, anal play, mason in a mood, sex toys, pretend incest, pretend marriage, bondage. 8.1K words.
Okay, so! Headmaster's lesson here, if you want context! Also more River x PC x Leighton here
Leighton has a strange new look in his eye when you come back into school. Cannot stop looking at you. The groping's increase and it seems you're called into the office far more for doing absolutely nothing!
But, this was always gonna happen. No, what Leighton does later on is worse. If he notices that you're still quite close to one of the teachers, he will want to ruin that. He would get hard just thinking of it. If you're getting close again to one of his staff, he'll call you back into his office and seat you down, making idle chat, snide smile on his face. He'll ask you to sit in his chair and have a look at something for him.
Said teacher will be called into the office a bit later, under the pretense that Leighton wanted to ask something about class scheduling and they'll come face to face to you sitting in Leighton's chair, watching something on his computer as the headmaster idly massages your shoulders. The teacher will have no doubt what is is. He can hear himself grunting softly after the soft jeers and will know you've finally found out about that day.
Leighton loves the look on both of yours faces, whether you are ashen and horrified or flushed and aroused. Sirris, River and Mason will be beyond horrified that you've seen it while Winter's face remains stoic. Doren... Doren will absolutely try to punch Leighton.
He does have you on his cock far more after that day, either under blackmail of releasing the video or, if you're into it, because he didn't get his turn that day and you have to thank him somehow for revealing the "true face" of your beloved teachers.
Its his favorite video. The evenings he has spent, sitting back and watching your body being fucked into, whiskey glass in one hand as his slowly tugs at his cock, will always be his favorite part of the day. Loves when his cock throbs as his staff fumble and fuck into you. The moment they break, become breathless and obviously ache to continue, are his favorite. Not even the Friday night shows, where you pretend to be gangbanged in your uniform can compare.
Especially when it comes to the end of the video, and River shuffles off, horrified. The door is heard shutting and Leighton walks over, cock tenting against his trousers, and fishes his erection out. You try to paw at him, still so cock hungry, and he lets you for a few moments try to pull him to your hole. Hushes you and you whine and he leans over to press his lips against yours, replacing your hand with his as he jerks off over you, cockhead nudging against your belly. Sips his drink as he sees his own tongue pressing into your mouth and how hungrily you suck on it. How he messily cums all over you and you scoop some of the fluid up just to press it into your hole before Leighton stops the recording.
Evening like that as his cum cooling against his fingers, glass empty, and your stolen underwear from that day pressed against his face.
Won't be long until he has you over at his house on the weekends. What can he say, you're stunning on camera. His house is obviously meant for a family, from the double bed he fucks you on, camera whirring, to the kitchen, where you pad to go get a drink and he kneels down behind you to messily rim you as you clutch the sink. It doesn't matter if you're there willingly, or under threat of the video releasing of you fucking all your teachers. Leighton wants you there on weekends, so he can indulge properly. He also makes plans to go out of town properly, go to hotels and either play one of two games. One is to tell the hotel staff you're married, young thing hanging off his arm and being fucked on the bed loudly. Having your knee stroked underneath the table and making you eat off his fork and being overly handsy with you where you two go. Or, the other, which is tell them that you're his child. Fine when you two check in, but not as the stay goes on. Wants you in the same room as him, wants to ruin you every night, on every surface, wants to record you two while you call him Daddy. Make it loud too. Still just as handsy with you if you two were pretending to be spouses. Loves the look on hotel staff face when you two check out, hickies all over your neck and collarbones, your "father's" hand cupping and kneading your ass.
At home, with his cum cooling inside of you as you snooze beside him, Leighton reflects that he should get all of his staff a fruit basket or something. After all, its their fault that you have to bounce on Leighton's cock, both in and out of school.
Sirris is going to have a hard time. Sydney is fond of you, he's fond of you and he always treated you like his kid until that day. Will try to distance himself from you but its hard, you're helping out at their shop, you're always with little Syd and you're still their favorite student in their class.
All it takes is one day that Sydney can't come to the shop. One day. You're handling the delivery for the day and unpacking and Sirris can't focus on painting the backroom because of it. He knows you'll be handling the toys and usually he'd be fine with that, the youth have to know eventually, right? But after that afternoon? Hazy thoughts appear like after images, his cock warm and snug and so good inside of you, he can't continue but to think. Would you whine if he prepped you to take The Kraken, the biggest tentacle toy they had for sale? Would you wriggle and ask for another toy to be pressed into you, one silicone cock not enough? Sirris can so vividly imagine your lips, flecked with spit and drooling around a gag.
"Mister Sirris?" You called and he shakily set down his paint roller. He'll just pop his head around the door, check you're alright. No need to get too close.
You smile as he appears and he notices a lady stood directly behind you, eyes trained on the back of your neck.
"This lady said she's one of your... Preorder customers? Has to pick up the product today to demonstrate it to her... her..."
"My Toy Parties, darling. The ladies of the neighborhood must know what's good instore!" The customer gives you a sly smile and you cough a bit.
When he picks up the preorder package, of course she won't head off without wanting to examine the toy. Sirris practically hops from foot to foot to get her out of here as her perfectly manicured nails pries apart the package and a couple of sets of nipple clamps come tumbling out.
"Darling, mind putting these on?" Her gaze turns to you, playful and you stutter a bit before nodding, tugging up your shirt, Sirris' ill-fated reminder that customer is always king echoing in your head.
Sirris stares hard at the counter as you reveal your chest, pretending to be fascinated by the wood until the aforementioned customer snaps her fingers in his face.
"Mind putting them onto the cute thing?" She waves her nails at him. "Bit fiddly."
He stares a moment before clearing his through and picking up the nipple clamps, sweat beading at the back of his neck as he gently turns you by your hip to face him.
Deeply shameful, but Sirris will never forget the soft hisses of breath you sounded as he clipped the damned thing to you, nipples hardening under the cool metal. Nor will he forget the feeling of your flesh skimming his fingers as he worked those damnable fiddly things. The lady admired you for a few seconds and gave her approval, and Sirris couldn't help but notice that your nipples had become soft and swollen from how long the metal bit into your skin. It was a punishment to look away.
There wasn't much to do afterwards, and Sirris tried facing away from you at all times up until quietly locking the front doors of the shop. You softly bade him a good night and he didn't mean for the following words to tumble so clumsily from his lips.
"Let me drive you home." The sentence was rushed, said in one breath.
And you let him. Because he's your teacher, and would never hurt you.
Except he parks where Avery usually does, just a little way away from the orphanage, somewhat blocked by trees so no one can see the car except if they're coming straight from the front doors. Sirris' hands don't leave the wheel, knuckles white as his thumbs rub against the rubber.
Too caught up in his own feelings, his own half chub, his own breath, he didn't realize how you would be feeling.
Sirris wouldn't know of course. Wouldn't know that every time he comes close, your legs become shaky. His cologne, somehow warm and homely has swooning, shifting in your seat to hide the arousal. You could just imagine his chest against yours, your nose in his neck as he pants and tells you not to tell Sydney, cock pummeling into you, with his scent flooding you. As if it actually happened. Your toes curl at the thought and your stomach tightens.
So when your science teacher shivers next to you in the dark, you take a leap.
"They're still sore."
Sirris snaps his head up to see your shirt back up, one hand tenderly brushing against your nipples, slowly hardening in the cool air of the car. They do look sore, as they usually do with nipple clamps. In the past whenever Sirris used the clamps on a partner, he'd tongue their nipples as they whined, tugging on the puffy flesh so they popped into his mouth.
He struggles to take all of you, from your lazily spread legs, the soft of your stomach, the perky nipples, and Sirris can't take it anymore. One hand on your thigh, sliding dangerously close to your crotch, he ducks his head and presses open mouth kisses against your nipples, turning into urgent sucks quickly.
You two press closer and one of your hands drags through his hair as he basically sprawls over you, your other hand sliding down to cup his throbbing cock through his trousers. His own hands find your hips and yanks you back over to his side, practically whimpering against your chest, wanting, no, needing, you back against him,
Luckily no one glanced out their windows to the car below, fogged up windows just a hint to the science teacher whispering for you to bounce on their cock, as you press closer, murmuring that you wanted nothing more than to do that, and more. Wanted to get fucked by him, wanted to suck him off under the desk, wanting to be nothing to fuck him and never stop.
Sirris should feel more guilty, and he does, but its not enough for him to shakily pull his own camera out of his bag and set it on the hand rest, recording as you sink yourself down onto his cock.
If you had a quid for every time there was a recording of you bouncing on your science teacher's cock that a member of staff spent too much time jerking off two, you'd have two pound. Isn't a lot, but there's about to be way more made anyway.
River. Someone check up on him. Has to pull out a paper bag and breath into it about three times a day because he keeps remembers what he did. What he did and that he really liked it.
Ever now and then, he thinks back, and feels back in the moment. The principle gripping the base of his cock, just as it meets your dripping hole, the soft squish as he sunk in, stopping just as the head popped in. River shouldn't grow hard from the memory, he shouldn't. The hands of his hips, making him roll his hips to inch slowly deeper, forcing him to feel it all fully. Your soft hums and breaths as he throbbed alarmingly inside of you. Barely even down to the base of his cock and his balls were about to burst.
He refuses to think further, or his heart would stop. Simply due to the fact that your legs wound slowly around his hips and you yourself practically used him as a breathing sex toy, doing most of the work for him. River could only brace his hands either side of you and try to quiet his loud, erratic breaths as you closed your eyes in bliss. Leighton's snide, soft comments didn't fly over his head either, murmurs of between a drugged fuck toy and a teacher, he didn't expect the teacher to be the more submissive one. Reworded in River's head so he doesn't faint.
Something that River would rather die than to have anyone find out, was it didn't stop after one orgasm. No, Leighton took the camera off the tripod and placed it on the cabinets nearer to the desk. Pulled you up and told River to lie down on the desk. Humiliated, he shuffled over, awkwardly sitting on the desk before Leighton sank you back onto his cock, hands splayed against your ass to help your drugged induced state to balance.
River didn't want to remember the sounds he made. The sounds you made. Even though he had to, having both lived through it and re-watched it, Leighton's arm slung over his shoulder all chummy as he re-winded the video afterwards. The camera's new angle showed your back, arching and sweaty as you rode the teacher, River's own hands gripping your hips, digging into the skin with such strength that it obviously left bruises, Leighton standing by with one hand on your ass, giving an appreciative squeeze every now and then.
Not only did he cum in you a second time, but changed positions, and let you... Let you fuck him.
His awkwardness around you was obvious. Whitney loved it, almost stripping you in every lesson just to enjoy the pale look on his face as he broke out in cold sweat. Worth all the shouting and being sent out.
You had privately hoped that it was just in school he'd keep up this strange behavior. You REALLY hoped so. You didn't know when but there was something attractive about River. From his lean hips, that seemed perfect to straddle, the tips of his ears going red or the fact his stoic, cool demeanor would just crumble when he laid eyes on you.
So, you still went to help out at the Soup Kitchen. Where it was apparent that his behavior somehow worsened. River wouldn't even look at you, would spill so much that one of the nuns actually told him off. You couldn't even hand him something without him snapping at you to put it down, he can get it himself.
Towards the end of the night, he was struggling to clean up an oil spill that he caused and sighed. This was ridiculous. He was going to have to ban you from the Soup Kitchen, tell the Temple you were stealing or something. River straightened up to grab more paper towels, just for you to walk past, unaware of the spill. Before he could warn you, you yelped and slipped, landing on your back.
River quickly bent down to help you, but froze. He could imagine the scene perfectly, your hand, instead of reaching out to take his to help you up, winding into his hair as you pressed his face into your crotch, legs lazily splayed open. Rub his face against the fabric as he eagerly tried to get to the prize underneath. Make him flip onto his back and sit on his face. Call him a good boy and feel him cum untouched. The next second, the scene was gone and his face was red, as you blinked up at him, still on your back, legs gently apart.
He spluttered and yanked you up by your forearm before scuttling off, ears burning red.
You sighed and rubbed your bruised tailbone. One of the nuns trotted over, offering to take over for you for the day and you agreed. You had been planning on heading to the brothel afterwards anyway and you could use the extra half an hour. Though, now your back felt so stiff, you doubted dancing was in the question. Basement it was.
The basement wasn't so bad, really. The others always advised you to grab a pillow for your knees, and would quietly leave water bottles by you to keep hydrated. Briar even gave in to requests and got every cubicle a box of tissues to wipe off afterwards.
So, despite Briar's disappointment and sigh, you trotted down the stairs awkwardly, pillow under your arm as you crammed a snack into your mouth, just for the energy.
"£15 today, sweetheart." The man by the door yawned, engrossed in what seemed to be a cooking magazine. "Slow night."
You nodded and ducked into your usual one, tucking the pillow under your knees as you faced the cum stained hole, eying your bag and wondering if you could read a bit more of Raul and Janet to make the time fly by. However, within moments of you reaching for your bag, a shadow moved past the gloryhole. Paused at you before there was a zipping sound and an already hard cock poked through.
Somewhat surprised, you abandoned your back and pressed a kiss to the head, making whoever was on the other side shiver. You dragged your tongue under the underside of the cockhead before popping it in your mouth and made sure to moan.
He wasn't proud. He didn't mean to follow you... Here. River just wanted to get a hold of himself and apologize and tell you to to please keep away from the Soup Kitchen. Felt like a pervert trailing after you, repeating the thought that it was just to catch up to you. It became less and less plausible the deeper into town he went.
But now? He felt more like a pervert. When he realized what building you went into, he blushed but didn't turn away. Just yanked his collar up and dug around in his briefcase for a hat. He knew he looked ridiculous, the owner of the brothel fighting back a smirk as he rushed past, downstairs.
River knew he was never going to be able to justify any of this to himself. Why did he ask the man by the stairs after the cubicle with the one wearing the student uniform, the man accurately believing he was a creep with a fixation. Couldn't justify dropping a £10 and a £5 note through the hole before looking around, face ablaze before practically stuffing his hard cock into the hole, not wanting anyone else to see his dick. Except you apparently.
Now, he was ruined. Your lips around his cock, sucking it into your mouth, tongue dipping into his slit. The soft moans vibrating his cock in such a nice way. River rested his forearms against the stall, and buried his face in them, ashamed as his cock throbbed in your mouth, the gentle sucks making him shiver. Oh, he was fucked, so so fucked. Too soon, he was cumming in your mouth and he felt you swallow. Fuck.
Even as his cock was softening again, River dug his wallet out and began digging through before pulling away from the hole enough to slip more money through. You make a soft sound of surprise before slipping your fingers through the hole enough to push into the stranger's trousers, cupping his warm, full balls, as you mouthed the underside. River buried his face back into his forearms, wanting everything else to fall away as you gagged on his cock, quietly hoping that you were also touching yourself. Really wanted you to be fingering yourself as you sucked him off, this mystery stranger making you as horny as you made him. River couldn't take it if you were bored, or turned off, or worse, disgusted with his cock in your mouth. Wanted you pressing your nose into his happy trail to get more, wanted to be good for you.
Too quickly, he was cumming again and his face was getting redder. He shakily slipped a £20 out and shoved it through, but this time whispered a soft request.
"F-Fuck my cock." He gritted out, already shoving his face back into the safety of his hands.
He was going to burst into flames if you told him no but there was silence. River slowly started to pull his face away from his hands but froze up when he felt something wet, warm, and familiar press against his cockhead.
You, meanwhile, tossed the lube back to your bag, as you sunk onto the saliva streaked cock, pleasantly surprised by how eager this customer was. The stretch felt good, long but not too thick that it was hard to sink down. You moaned softly, biting your bottom lip as you started to hump against it, a bit awkwardly inside the small cubicle.
River couldn't believe it. That he was here, that he was paying for you, his poor student he was forced to take advantage of, was massaging his cock so deliciously, he was already gripping the next wad of notes. He was not this person, not someone who'd even go into this part of town, wasn't a person that looked at a student like that. But he was. He followed you into a brothel, he couldn't stop paying you more and more for your lips and now you against his cock. Hell, he was delusional about this before he trotted after you, looking a bit too long whenever Whitney yanked his shirt off and made you do the same.
Hypocrite. Yet, the words faded away with every sweaty slap of skin against skin, growing louder. Even the guy at the stairs glanced up from the Crème Brûlée recipe to watch, eyes dark with interest.
"Feeling pent up today, eh, professor?"
River could have died on the spot as you paused on his cock. Caught by a former student balls deep in a current studen-
The way you tightened considerably had him gasping as you sped you, properly punishing his cock and he braced himself against the wood.
He was so fucked.
Doren definitely feels the most guilt. Not just because you were his student, someone he was supposed to protect. But you were... You.
He had sworn to look out for you when Whitney attacked you in the playground, had stripped you down, and when you smelled of... Well, and he took you outside to talk.
How Leighton knew his gave you his apartment key was beyond him.
Doren went home that night and sat down on his couch, prying the cap off an ancient beer bottle in his fridge. He needed to decide on what to do. It was obvious that the police were out. If he himself confronted Leighton, he could spin the tale easily that it was just Doren recording himself after drugging a student, and he'd end up in circumstances that would leave him unable to help you at all. Worst of all, he couldn't close his flat door to you. He considered it, since the headmaster knew so much about it, but couldn't. This was your safe space. So, Doren thought as he emptied the last dregs of his beer, he was going to go above and beyond to help you. Anything you needed.
Except that was harder than expected.
In school was easy, he'd just chase other off you, like Kylar or Whitney, or any other of those little creeps but... When you quietly entered the flat?
Being so close was dizzying. Doren loathed the fact that he was a sheepish schoolboy again, sitting by someone attractive while he was meant to be focusing.
But he knew what is was like to be inside of you now. How you made little noises when he pushed inside, the breathless whines of So big and love big, fat cock already had him feeling slightly dizzy as he remembered. Doren was glad that your first trip back to the apartment didn't have you crying or horrified at the state you had been in when you were left in the office, somewhat thankful for the fact you couldn't remember, but... He knew. He knew and he was forever tainted by that night.
From the little happy sighs you made when he gave you a hug, the way your eyes glinted when you looked at him, even... Even when you got out of his shower, water running down your legs, it all... Made him think back to your moans, your hazy, fucked dumb eyes, the cum rolling down your legs.
He shouldn't be seeing you like that, but he couldn't stop. Worst of all, he knew that you really loved his cock.
You didn't even know what a struggle it was to pull out of you, not only because he didn't want to, but the way you whimpered and tried to slide back down on his cock when he tried to slip out of you. Leighton was chuckling as he tried to be gentle, cock hardening as you humped at him relentlessly. You'd twist out of his firm grip and push back on him, practically fighting him to keep on the cock that stretched you out beautifully. Doren's heart thumped when he finally pulled out of you, cum flooding out of you, as you made such a pitiful sound.
Doren couldn't stop the nasty, filthy thoughts that filled his head whenever he thought back. You were so distressed when he pulled out, it felt like it hurt you. Not to mention to drunken babbling when he pushed in, filled with moans and gasps. You don't remember that you were so cock drunk on him, Doren thinks as he lets you in, shaking the thought loose as you stepped into his space. No memory of the lust filled babbling, the fucked out expression, when he finally did sink into you, as you smiled at him, making yourself comfortable on the couch. Doren offered you a snack and hide away in his kitchen for a few moment, staring at the shopping bag with biscuits and fruit he got just for you. At this point, the whispering thought hissed at him, its unbearably cruel to withhold them from such pleasure. You're the one who fucked them and remembering it or not, they know. They know and they need more. You're not a monster are you? Not letting them feel so good after such a horrible night? You know they'll crave your cock for the rest of their life, so why not sink into them and allow them to become the pretty little nymphomaniac they are supposed to become, just for you?
Doren's hands shook as he slowly peeled a clementine, squeezing too tight. The juice soaked his fingers and the feeling of the sticky liquid dripping down his wrist was too much. He crushed the fruit in his hand before letting it fall, somewhat stunned by his own actions.
"Doren?" You spoke up behind him and the teacher nearly jumped out of his skin, spinning around to stare down at you, noses practically skimming each other from how close you were.
You blinked up at him. He seemed flustered, cheeks red under his vibrant beard. Your gaze feel to his wet hand and you dragged a finger against his palm. Doren followed the motion with his eyes, breathing getting slower. Gaze fixed on the tip of your finger as you popped it in your mouth, tasting the clementine juice and your eyes met.
"Fuck."
You smiled at the expletive and let your saliva covered finger drop from your mouth, instead raising it to his own lips.
"Tastes good."
One soft nudge from your moist finger had his mind going blank. He couldn't control himself, pushing you down to the floor with a thud, and towering over you, on all fours with his big hands either side of your head. You didn't panic, and still looked at him with all the trust in the world. Doren gripped your wrist and pressed clumsy kisses to all your fingers, lingering on the one that you sucked on before looking down at you.
"Yer going to kill me."
Right now, he felt like a beast above you, one that should have you running away, but you used your other hand, the one not clasping in his, to run your fingers through his beard. You widened your legs and sighed softly, seeing his monstrous erection strain against his trousers.
"Please, Doren?" You hummed, using the hand trapped in his to press against your clothed crotch, warmth from your arousal hitting the back of his hand through the fabric.
"Fuck." He repeated, and took a moment to shut his eyes tight. You were asking him... To help you. He opened his eyes again.
"Only if it's what you need."
You nodded with a smile and he desperately pressed his lips against yours, freeing your hand to rip your trousers off with his own.
Doren will keep whispering the words "Only to help you" as he presses into you, cock throbbing painfully as your heat welcomed him back.
He fucked you like a beast against his kitchen floor that night, hammering into you as you moaned and begged for more, cumming numerous times before he did. Little by little, the guilt faded, with every arched back and messy kiss exchanged.
After all, the thought hummed as he pulled out of you, creamy white ring around the base of his cock before he pressed into your mouth, its best to give them what they really need. And what this cute thing wants, is to be split open on a fat cock.
If you didn't want this, Doren wouldn't make you, but the thought was proven right every time you skipped through his door and immediately knelt down, digging into his trousers. Doren ended up agreeing, watching you worship his cock while sitting on his couch, beer in hand.
Winter was a tough customer to understand, even for some of his oldest friends. The inscrutable look in those pale eyes to the perfectly calm look on his face was enough for people to struggle to read him.
Leighton wasn't exempt from this. There was one occasion he told Winter that all the teachers were getting a raise, thanks to Quinn and the man just nodded. Solemn, like he was told that the cream machine at Sam's Café was broken and the deluxe bun wasn't available anymore. Even then people usually sigh in disappointment.
So, the headmaster didn't know what to expect the next day. He could expect hostility from Doren, blushing and stammering from Mason and Sirris, maybe River in a crumpled heap of shame in his stock room, but he couldn't even begin to guess for Winter. Leighton was somewhat let down when the man came in, same as usual, calm and collected with not even a grimace when meeting Leighton's eyes.
You were just a disappointed as Leighton. You could barely remember yesterday, only remembering Bailey's grip at the back of your neck as he shoved you to the floor of the orphanage, striding away with the comment of owing him a new coat.
But you did want... Something from Winter. You didn't know what but when Robin mentioned going to find a seat for history, you felt butterflies fluttering in your stomach. You knew Winter was stronger than what most people expected from him, from all the demonstrations at the museum where he helped you, but there was a strange feeling that you clung to this morning. It didn't feel like your imagination came up with it, more like a hazy glance into a dream. Cold hands manhandling your legs, tugging you into the right position. That's it. It was something you kept on repeat, dream-like as it was, and by the time history rolled around, you were excited to see the teacher. Didn't truly know why, he wasn't about to fuck you in the class but you still sat up straight when he walked in, glancing over some test papers before tucking those away as he swept his eyes over the classroom. They paused on you and you shivered. You swear you could feel a flick of a smile on his lips before he cleared his throat to quieten down the classroom.
Your hand twitched.
You had been in trouble with the history teacher before, masturbating in his lesson when Whitney had cornered you, waving a parasite in your face. You couldn't help it, nor could you help the way you had arched your back when Winter had leaned down to whisper into your ear about what happens to students who couldn't stop touching themselves in his lesson.
Yes, you admit, you didn't expect the chastity belt.
You also didn't expect the soft but strict coaching of Winter when he got you into it, the way he swiveled your hips to check it wasn't unnecessarily tight but still taut against your body, and the way he locked you in, before slipping the key into his waistcoat pocket and ushering you out.
Just the memory, along with the distant dream had your breath quickening, and, blind to Robin's worried look, had you squirming in your seat.
Worth it. It's worth it.
Winter had made up his mind to pay a tad more attention to the other students over you that day. But at this point, it felt like they were attuned to you, attention snapping over the moment you sighed slowly. He rustled his papers, pretending to be frowning at the worksheets the class turned in while watching your hand rustle beneath your clothes, moving, playing with yourself. Winter never considered anyone being so depraved to touch themselves like that as playing, yet here it was the perfect word for you. More like a nymph from an old Grecian inspired portrait, brimming with sexual energy, yet playful, who couldn't help but indulge in their own body.
Before yesterday, Winter had never considered you such. Yet here they were, thinking you more like a sweet being of pleasure, more likely to be draped over a rock by a lake, enraptured by the beauty and sensitivity of their own body than a flustered student, bunching up their uniform to rub at their genitals.
Winter's favorite story for the longest time was a fae, captured by knights, and hung up uncomfortably until they told them what they needed to know. He always liked it because it was the earliest known occurrence of the Shame Pillory, used by the temple to humiliate people, unlike the pillory they used later on, which was more like the stocks. But when he got home last night, instead of prepping the museum, he went back to his books and found the illustration of the pretty young thing, chained to the standing post by an iron collar around their neck. Winter finished a bottle of wine while looking at it before putting it back in his shelf.
Yes, mankind always liked to put their hands over nature's children, and Winter was not ashamed to be looking forward to repeating that.
So, he watched your body shiver and convulse gently in your seat, rocking like the smallest ripples in a pond before slowly standing. You watched him. Like you knew what he had done the night before. Like you wanted him to do it again.
This time, he just crooked his finger at you and you followed, Robin making a small noise of distress as you followed the teacher to the back and into the stock room for the history class. Winter shut the door after you before turning slowly to look at you, and those doe eyes, not an ounce of shame in them.
Now that Winter had a taste of you too, he couldn't blame you.
"Undress yourself." Winter's voice was quiet yet you shuddered, as if he had shouted at you.
Eager little thing, he thought, as you stripped down, before he himself turned to the back of the room, the collection of his artifacts calling him.
He found the Shame Post he was looking at last night, and weighed the collar in his hand. Heavy. He exhaled and turned to root around in a metal box, stored some of the older things that Quinn deemed too perverted for the museum. Winter's hand brushed against the smooth, cool wood of what he was looking for and he smiled to himself.
"Come here." He looked over his shoulder at you, eyes calm but heart not as you stood bare and shivering.
You padded forward, feeling the long forgotten urge to cover yourself but didn't, eyes fixed on Winter's frame. He turned back to you, holding the chastity belt you were so familiar with in one hand and the collar connecting to the rickety post behind him in the other.
"Bare your throat." You felt like a dog but tilted your chin back, eyes on the top most shelf as he hooked the collar behind your neck before snapping it shut. It was snug, like a hand enclosing on your throat.
Winter carefully tugged the chain forward and you stumbled towards him, missing his secret smirk completely.
"Now stand still." He knelt down and your stomach flipped as his hand slid down your leg.
He placed one cool hand on your hip and turned you to the side, admiring the curve of your ass as he did. Your gaze was fixed right in front of you so Winter took his time, sliding the wooden dildo from his pocket, retrieved from the metal box. It wasn't actually an artifact, but a mock up of one he found. He always thought it was a shame that Quinn rejected its entry into the museum, but not anymore.
Winter snagged a bottle of oil from another shelf and doused the dildo in a fine layer, holding the end between two fingers to not get any of himself. He then cupped your ass, noting the excited shiver that ran through you, before spreading your cheeks, admiring your hole. It had felt good, when he pressed in. Warm and welcoming. Winter hoped for your sake that you were just as relaxed as you were then. Holding up the dildo, he nudged it against your hole, feeling you freeze up and looking back at him, strange hope in your eyes.
Ah. You wanted him to be the one in you. Silly thing.
As soon as he met your gaze, he slide the entire length of the phallic piece of wood inside you, enjoying the way your eyes widened and your body stiffened up. Not in pain, thankfully, as your back arched and a low sigh echoed around the room. Seems you were still loose from yesterday. Winter patted the base of the dildo, snug against your hole before gripping your ankles and maneuvering you into the chastity belt, your body pliable and limp to his ministrations. The long, thick dildo inside of you meant that with every movement, a shiver of pleasure ran through you. It was also feeling warmer. As if someone was actually pushing their cock deeper inside of you. You didn't realize what he was doing until the belt snapped shut and he turned the key in the lock, locking you in.
You blinked up at him, pouting like you had been somehow betrayed. Winter smiled at you, ignoring the way his cock had grown heavy and hot.
"I shall be back at the end of the day for the end of your punishment."
With that he left the stockroom, locking the door behind himself, ignoring Robin's staring and sat back down.
He disliked lying but your punishment was just starting by the end of the day, not ending.
Mason needed his swimming time more now than ever. Except, it seemed that even swimming was failing him. While the cool water flowing over his body helped still his mind from all the hassle of the week past, it seemed their hypnotic ways had deserted him, perhaps for good. The familiar drag of the water did nothing, and he could only think of that day as he swam. He gave up an hour earlier into his swim and trudged from the lake, uncharacteristically grumpy.
He snatched his towel and began to towel dry his hair with annoyance, movements jerky and harsh. Mason gritted his teeth before hissing a swear, having yanked on his hair too hard.
At least he was close to you in age! He wasn't some old fossil that fucked into you!
Mason scowled to himself and abandoned drying his hair for wiping down his legs.
And you actually liked hanging out with him! Not that it matters, but... Yes it does. You're flirty with Mason for a reason! You two liked hanging out after his swim.
Mason huffed and grabbed his trunks, lying by the side and shimmied them back on, angrily ignoring the half chub his cock had gotten to.
So, you can't be angry at him. If anything, he should be angry at you! Swimming nude in his lessons, swimming out to him and making it obvious you knew he wasn't wearing anything, finding him at the pond. He should never have made friends with you, o-or even more! Look where that got him! Anyway, he wouldn't have been hard during it if you... If you! If it hadn't been you, the one trying to fuck him with your eyes!
Mason packed his things together hastily, before stopping and sighing in defeat. He sat down hard on a a fallen log by the water, rubbing his eyes.
That was unfair of him. He would never have thought that of anyone, especially you, but...
That afternoon had shook something up inside of himself. He never wanted to start off his career with something like... This. Fucking a student against both of their wills and having it filmed. Mason pretended like that was it, that and the fact that it was an innocent student it was forced on.
Not the fact that he knew, on the recording, it would show him enjoying it completely. Despite putting up quite a fight in the beginning, by the end, his thighs are shaking as he fucks into you, sloppy noises growing louder and louder as you moan, his tongue in your fucking mouth as you both moan.
Mason liked you. That was obvious to himself and you, the moment he practically flailed in excitement when he remembered the spring underneath your home. He wanted you to be happy.
And you were beyond happy being pumped full of his cock.
Mason abruptly stood up and slung the bag over his shoulder. He should go straight home. Maybe type of his resignation, maybe close all the blinds and hide underneath his covers as he guiltily jerked off to the memory for the fifth time. Yet he didn't go home. He could pretend he was going to the pond to unwind and relax, but even as he closed his eyes and leaned his head back, enjoying his private seclusion, Mason knew he was waiting for you to slink in, to sit on the edge and chat away.
As per usual, you didn't disappoint.
You were dripping, but this time with water, fresh out the lake. Your grin at the sight of him was bright and charming and Mason thanked the whatever above that you didn't remember what happened. Though... Maybe you'd greet him the exact same way, if you remembered, and would slide in next to him, fingers pawing at his cock. Mason coughed into his hand and straightened up at the sight of you, small smile gracing his features.
"I thought you were gonna still be swimming." You mused as you tugged off your drenched shirt and shorts, revealing the swim costume underneath before sinking into the pond, opposite him.
"Didn't want to overdo it." Mason replies a bit too quickly.
There was a loud rippling noise as you suddenly moved closer to him, water shivering as it bounced off the edges of the pool. Mason's stomach tightened but he didn't move away, coolly watching you come closer until you were basically leaning against his shoulder. A few days ago, he'd have backed up, chuckling awkwardly, and he should, he should put space between the two of you, make a joke, anything but he struggled to find a reason not to. Which is also a liar, he knew plenty, but he ignored all of them.
Why should he stop this anymore?
He always thought of him as a good one, an understanding teacher, who didn't get mad at you for fucking around, who didn't demand you to back off when you found him swimming or at the pond, but it was all for nothing when it came to you. If one of his other students had come along, he'd encourage them to kindly piss off, but out there, saved on Leighton's computer and who knows where else, was a video of him cumming into you as he plays with your chest, biting down on a nipple. What reason was there to stay away from you now?
Mason had no reason not to admit, now, that you were his type. That you made his stomach flip and fill with butterflies. That if you weren't his student, he would have awkwardly asked you out ages ago. His parents would refer to you as Mason's Little Sweetheart when he talked about you to them. His childhood friends would tease him for falling for a townie and the two of you would drop by Sam's Café to share a milkshake after visiting his folks.
Then he'd take you to the beach and slide your swimming suit aside and watch how you'd shiver with pleasure with his cock ruining your insides. Then again back at home. Again in the morning. If you were Mason's, he doubted he could ever take his hands off you.
So, as you smile up at Mason, and he looks back down at you, the restriction of student, student, they're your student, faded away. Who was going to stop the two of you? Leighton, who had him fuck you in the first place? The other teachers? He at least gets away with dating you, being nearly the same age, while those fossils look like cradle robbers. The line of student and teacher had already been crossed, straight up encourage by the one man in charge, so why not.
Why not?
Why not? and with that thought Mason dipped his head, feeling your soft inhale of surprise before pressing his lips against yours, enjoying the excited shivers between the two of you.
A few perfect moments of kissing passed, his tongue eagerly tasting your bottom lip, before you pressed your hand against his thigh, fingertips skimming his rousing cock, once more rising to half chub. Mason grinned gently against your lips and pulled your hand to his cock, enjoying your experiences touches.
You two parted for air and he tucked his head into your neck, sucking hickies into the skin.
"Mason?" You whispered, as your hand dips into his swimming trunks, beginning to jerk him off, water rippling steadily around the two of you.
"Don't tell anyone at school." He mumbled, abandoning the crook of your neck for just below your jaw. "Pretend at school, please. For me."
Didn't want other students think he was going to fuck any of them. No, he thought as he lay you down properly over the side of the pool, and hooked your knee over his shoulder, you were the one that the rules had already been shattered for. You're the only one he was going to have like this.
Mason wanted to feel the twinge of guilt, of anything, as you pulled your swim suit down, of seeing your body again, but the he could only think "Finally."
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