Chapter Text
You had gone too far. That's what Leighton said. You didn't really see how. Yes, you picked fights, you struggled to show up on time, yes you would wear the occasional item that wasn't school uniform. But you don't remember doing anything so bad that this was happening... This? What was happening?
You were called to the Headmaster's office during your History lesson. Winter was less than happy about it, but he waved you off with a frown. Of course, people tried to trip you but their attempts at this point was laughable. You got to the headmaster’s office in good time just to avoid pissing Leighton off further from whatever you did in the first place.
His voice wasn’t angry when you knocked, which was new. He was calm, almost as if he was actually pleased to see you. Leighton takes a moment to admire the look of slight confusion on your face before chuckling.
“Don’t worry. You are in deep trouble.” Leighton points at the chair opposite of his desk.
Stomach lurching, you promptly sit down, wondering what the hell you’ve done, skimming through your memory. Too busy skimming, to notice Leighton’s hungry eyes. They were always hungry, as they prowled the corridors, but this wasn’t the look of a wolf on the hunt. This was the look of a wolf with a deer’s neck in its jaws, savouring the moment before it ripped it apart. You always failed to notice him fussing with his desk drawer and retrieving a pink phial from its depths.
“You’ll be here for a while.” His smooth voice broke your worried thinking, and you blinked owlishly at him as he passed over an opened water bottle. “I suggest you have a drink before we start.”
Leighton held eye contact with you as you held the water bottle. He already opened it, not a good sign. Nor was the fact that you could smell something faintly... Familiar. You awkwardly set it down on the desk.
“I already drank something at lun-”
“Drink.” The carefree tone was gone. “Or I get your little orphan friend in here as well.”
Your breath hitched and your hands shook. With that sentiment hanging in the air, you took the water bottle and sipped at it. Leighton watched, drumming his fingers. He remained silent. He refused to speak until you had downed the whole thing, but by then, you really weren’t in a state to talk.
Mason hurried into the staff room, almost colliding into Doren as he stood reading an answer on his exam, chortling to himself.
“Shi- Hell, sorry.”
“Don’t worry about it.” Doren had a kind smile behind that scruffy beard.
Mason went to his coat hanger and tugged it free, trying to shrug it on as quick as possible. He noticed River out the corner of his eye also trying to make a speedy escape while Winter took his time. Sirris ducked in shortly after, rubbing their eyes as they leisurely made their way to one of the chairs by the table.
“Take it easy, Mason, you’re going to rip that coat one of these days if you put it on any faster.” Sirris took off their glasses and smiled at him.
“Yeah, I guess.” Mason paused a moment. He did like Sirris. “It’s raining out, so I want to squeeze in a few laps before it gets dark.”
Winter perked up slightly with interest.
“Remember to-”
“Show you anything I pick up that looks interesting, I kno-” Mason noticed Winter narrowed his eyes at him with scrutiny. “Sorry Mister Winter.”
Winter nodded and went back to slipping on his gloves. River remained silent while looking out the window and shrugging his coat on. Probably thinking about what needs to be done at the soup kitchen. Mason was always surprised that he picked up so much about his colleagues. Well, everyone except-
Slam!
Speak of the devil.
Leighton walked in. River froze up a slight bit before continuing with his task, winding his scarf around his neck. Sirris and Winter seemed oblivious to the slightly uncomfortable atmosphere now permeating in the staff room. Doren tucked away the exam into his folder for marking and made his way to his own coat, winding one of his fingers into his beard.
Leighton didn’t mind the lack of talking. In fact, he smirked.
“Where are you all off to?” His tone was light, airy... Not good.
River and Doren shared a glance, too quick for Mason to decipher. Sirris glanced at the rest of them before shifting in his seat.
“I was going to wait until Sydney left-”
“Not you, Sirris.” Leighton interrupted. “Them.”
“... I was going to go swimming.” Mason finally spoke.
There was that look. Leighton didn’t give it to anyone else on the staff. Leering. If he was into muscles, he would have been all over Doren, so Mason had been slow to embrace the idea it was his youth that drew such a look.
“Soup kitchen will be open in a few.” River spoke but Leighton continued to look at Mason. Took him a few moments to acknowledge the Math teacher.
“I was just going to head home for a bit.” Doren grumbled.
“It’s Friday so I was going to head into the museum for the evening to make sure all the artifacts are in good condition before it opens tomorrow.” Winter finished putting on their gloves before a thought stilled him. “Headmaster, the student you called from my class...”
Leighton fixed him with a relaxed look, but his smile got wider.
“They never came back. May I have a copy of the locker keys to put their bag into their locke-”
“Never came back?” Doren spoke up, Sirris also swivelling around with a worried look. “Which student? If it’s Whitney then it’s honestly on you if you thought he’d come back.”
“No, not Whitney.” Winter sniffed, almost insulted at the comment. Like he would ever have faith in Whitney when it came to history. “One of the orphans. Friends with the shy one... Robin. Robin’s friend-”
“Come now.” Leighton murmured and Winter froze up slightly. “You knew their name perfectly well.”
They all knew your name perfectly. Mason fiddled with the cuff of his coat.
“I could ask Sydney if he saw them? He practically has their schedule memorized. Imagine that!” Sirris gave a nervous chuckle.
“I can.” Doren muttered darkly, obviously thinking of another student.
“No need.” Leighton spoke over him. “In fact, I wanted to talk to you all about them.”
Mason felt a bit ill. For himself or for them, he didn’t know. On one hand, they were already orphaned, he doubted that any other news could really destroy them. On the other hand-
“I know you’ve been letting them off easy.”
No one spoke. Leighton basked in the atmosphere.
“We have a way when it comes to disciplining delinquents. But it seems you all know so much better than a tried-and-true method, hm?”
Leighton let the statement hang.
Mason remembered the booklet he got when he first became a teacher here. Little book, Leighton had given it to him to serve as an easy reminder. When a student acts out, picks fights, arrives late or has an issue with their uniform, send them to the Headmaster’s office. Very simple. Mason had looked through, wondering if there were any times he would have to be the one sitting in for detention, but Leighton always was the one doing it. He also heard that students hated detention. Always emerged teary eyed and humiliated and... Mason wanted to do that for you. You were a good swimmer, you paid attention. You joined him for swims but didn’t bug him or try to get a better look at his... Yes. Anyway. It was a onetime occurrence. Your innocent looks at him, asking to swim naked. He... He refused to think about the fact he blushed, but it wasn’t because one of his students was naked. No, it was because you were the one naked. But for god’s sake, he wasn’t going to report you for it.
Mason felt like the other teachers were thinking the same. You were just... Charming enough that they would overlook small things. Maybe you were wearing sunglasses, or late to class. You knew each teacher in and out of school and they did show favouritism because of it.
“Well. Think of this as a disciplinary hearing for all of you. Blatant disregard for the school rules.”
“Headmaster!” Sirris protested. “I doubt letting students get away with small-”
“It’s not just any student, is it, Sirris?” Leighton leaned down, his hand on the table, to glare straight at Sirris. “It’s the same student that keeps being let off for disregarding what are clear school rules. It’s unacceptable.”
Leighton regained his composure, his wide smile returning.
While the others waited with bated breath to hear what Leighton had in mind, Mason’s mind was running. You never returned to your lesson. Your bag was left behind. Leighton pulled you from your lesson. You didn’t go back. There was no need to ask one of your friends where you were. He had a terrible feeling that something had happened... Or was going to happen.
“You must all stay behind. No soup kitchen, no museum, no swimming. I shall perform each disciplinary hearing individually and then you must return and sit here till everyone else has finished. I won’t tolerate anyone leaving before or after.”
Disciplinary hearing... That sounded okay. If Leighton was only chewing him out, he could survive that.
“Come along Mason, you’re first.” Leighton cast an appreciative look over Mason before watching the other teachers slowly take off their coats and sit down at the table.
Satisfied, he turned on his heel and left the room, Mason walking after him.
No.
Mason thought this many times. A whole symphony of No. No, No, No.
“No.” He finally whispered.
“What’s that?” Leighton looked up from where he was setting up his camera.
“No. I won’t.” Mason wanted to take his eyes off of you. He did. He respected you, he... He liked you.
He didn’t want to see you like this, stripped of all your clothes, your dignity. Yes, he saw you naked but this... Ass red and raw from a ruthless spanking, spread out on the table with your legs dangling off, aroused pussy inviting him in- What the fuck, no!
“Well. Off you trot then. I’m sure the board will be interested to know that you happily let one of your students swim naked. In front of the whole class. The same student that spends evenings with you at a secluded area from what I’ve heard.” Leighton walked over, draping an arm over his shoulders. He was smiling as he leaned in, whispering into his ear. “You would never work in a school again. Work full stop. Hell, you would go on some sort of permanent file.”
Mason exhaled shakily, eyes flicking from your pussy to your face. You were awake... Kind of? Flushed and sweaty, your eyes slowly blink as you panted. You looked...
“All I’m asking you to do,” Leighton continued, eyes drifting over to you as well. “Is to make up for all those transgressions you let go. Punish them and then you can go, and swim, and bend them over in a few hours anyway.”
“I’m not-!” Mason cut himself off, feeling his hands shake.
Leighton smirked.
“And look at that.” He murmured. “You’re already good to go.”
No.
Why was he hard? He shouldn’t be. For fuck’s sake, you were like his... His little sibling! His friend! No, a student he happened to be fond of!
No.
You were someone who let him pretend he wasn’t staring at you while you sat half naked in the pond with him. Flirted and chatted and smiled and the reason he practically leapt up to tell you about the spring underneath your orphanage wasn’t because he really saw you as a really, really good friend. Shit.
“What’s the camera for?” Mason asked with a dry mouth.
“Well, I was thinking up this little punishment, when I wondered how would I make sure my staff wouldn’t repeat their little slip up... When it occurred to me! Why don’t we film it? Have a little reminder that ignoring punishments won’t be tolerated... For both staff and students.”
Mason felt himself begin to sweat.
“You would have-”
“Yes, my own copy. I do enjoy my films, Mason. Now.” Leighton brushed against his erection with the back of his hand. “Work for my forgiveness.”
Mason’s internal No’s continued, as you unbuckled his trousers, revealing his swimming shorts underneath, much to Leighton’s delight. His denying chant continued on, up until the head of his cock was pressed into your entrance. Then the only thing he could think was “Fuck.” Didn’t even realize he whispered it.
“I know.” Leighton checked his camera but hungrily looked on.
Mason shivered, looking down at you... Your pussy. He didn’t even know if his hefty cock could fit all the way inside of you. Attempting to zone out your soft whines and keens, Mason concentrated on pushing into you as slow as he could, fighting back his own groans as he did. Fuck, you felt good. There were always whispers about you, and try as he might, he couldn’t just zone it out. But he had no idea if he should even believe them now, tight, and soft and warm. Didn’t fit into his image of a... A sex worker.
“C’mon Mason.” Leighton murmured. “You’re punishing them. Now punish them with your cock.”
Mason felt gross, hearing Leighton talk about his body like that, but his erection twitched in interest. He continued to stare at your pussy, swallowing his cock inch by inch until he was snug inside of you. Couldn’t put it off anymore.
The swim teacher finally made eye contact with you. Fuck. You were drooling, eyes cloudy with a strange pink haze. Handcuffs secured your wrists to the drawers behind your head, so your chest was naturally sticking up slightly to stay comfortable in this position. Speaking off... Mason was dying to fondle your chest. Soft and pert and- Shit, not this was...Punishment... For...
For all those times you strutted around his swimming pool, naked and baring all to the world. Your eyes seeking out his to see how he was reacting. The way you touched him while at the pond.
Mason’s hips gave a slow thrust.
“Fuuuck.” You whined and wrapped your legs around his waist.
“Good boy.” He could feel Leighton’s eyes on where he was joined with you.
Oh fuck. Fuck it.
Mason will later try to drown the memory of what happened in his laps, swimming way past his usual time. Later, he will furiously jerk off to the memory. Gripping your hips as he slammed into you, moaning into your mouth. He was no virgin, but he felt like one, hungrily humping his cock into you, enjoying the feeling of your chest against his. He completely tuned Leighton out, too busy enjoying the feeling of your tongue in his mouth, your moans, the way you urged him deeper into you with your legs.
Much to Leighton’s chagrin, it took only one orgasm for Mason to return to his senses. Hurriedly pulling out, trying not to look at your cunt, his cum tucked safe inside.
“Thank you Mason.” Leighton hummed.
Mason said nothing and just wrenched up his trousers and leave the office, staring at the floor. He walked back into the staff room, ignoring the enquiring looks his colleagues shot him.
“Don’t tell him.” Sirris whispered into your ear, hands shaking where they lay upon your hips. “Please don’t tell Sydney about this.”
Leighton was enjoying his pleas a bit too much. He wasn’t even begging the headmaster. Sirris was whining in your ear as his other hand reaches down to unzip his trousers. He wasn’t begging for your forgiveness, he was begging for his son not to find out. Really, Leighton thought to himself, for a teacher so beloved for being so patient and nice, he wasn’t living up to his reputation very well.
You didn’t seem to care. At all. Instead, you were trying to tug Sirris into you, manoeuvring him by his hips with your feet.
Sirris meanwhile was biting back so many comments. You’re awful, you’re not fit to be a headmaster, you’re evil, all aimed at Leighton, palming his own cock as he watched through the lens of the camera. Loosen up a bit, I want to go deeper. Let me kiss you. You feel so good around me. You made these comments run through his head. Sirris wanted to close his eyes and kiss you and just thrust until you’re both cumming, but he can’t. This was so close to being a fantasy come true, if only Leighton was gone, preferably somewhere surrounded by quicksand.
The camera’s soft hum made his cock throb inside of you, making him slow down his thrusts. If this was anything else other than this situation, Sirris would have stammered and asked for a copy of the tape, just the moment between the both of you. You were so soft and cute and felt so warm and so, so good and it’s... It’s been a while since Sirris had someone like this, had someone with him to make one of his tapes.
Worst of all, his imagination kept running away from him. If this had been... Not what it was, he’d have taken you around his shop first, encouraged you to pick out some toys before getting his camera and... Jesus. Blood rushed to his throbbing cock. Don’t cum in them, don’t cum, not in this clenching, warm, wet hole-
Shit.
…It felt good.
“There’s plenty of tape left, Sirris. Go on.”
“I should kill you.”
“Threatening the principle? You’re already in my bad books, Doren.”
“Well, I should.”
C’mon. Not this. Not to you.
“Maybe you shouldn’t have given your student the keys to your flat and let them visit you directly after school every day.”
Who the fuck told him?
“Hurry up Doren. The other two also need a good amount of tape.”
Doren’s stomach clenched. He should have known. Mason stayed silent but the glance he managed to see of Sirris...
“Fuck your student.”
He should punch his teeth out. He wanted to take care of them. Not this. Not-
“The best way to help your student right now is to stuff them full of cock and cum and then have your two other colleagues have their turn. They must be gagging for it by now.”
Did this fucker read minds? Doren scowled and looked at your puffy cunt. You must be sensitive, it shouldn’t look that sore after two goes. Unless someone went again- If he goes down that train of thought, he will punch out a member of staff. Probably the wrong member.
He undid his belt and gripped your knees, pushing them so you were lying on your side, handcuffed hands at an awkward angle. He proceeded to loop his strong arm underneath your knees, putting his own knee on the desk, pulling his cock out. Maybe he could get away with giving you a thigh job, he thought, tugging you closer carefully, as you rested on your side.
“For all that complaining, you’re awfully hard.”
Jesus Christ does this guy ever stop talking. Likes the sound of his own voice, doesn’t he? He refused to even acknowledge his words. Doren carefully slipped his cock between your soft thighs and Leighton sighed but made no objection. He was going to let him cum over your thighs, good. Now you just had to sit still and let him get this over with- Your high pitch whine cut through his thoughts. What the-
Leighton let out a surprised chuckle as you shifted against him, trying to slide his cock up from between your sweaty thighs to your cunt.
“Think they’re in pain. Look at that, Doren, they’re craving a cock.”
Doren stared down at you, and gripped your thighs, firmly tucking his erection below your cunt. You hiccupped and let a few tears fall as you realized that he wasn’t going to press that deliciously big cock into you.
“No-” He attempted to lecture you, but you leaned forward and pressed your salty lips against his, tongue weakly pressing against his.
Not a single peep left Leighton as Doren froze, the feeling of your smaller tongue hungrily swiping around his making his brain short circuit. He never thought of himself as someone who was weak, or who enjoyed being stronger than most people, but your pathetic little kisses against his mouth, your thighs shivering with anticipation around his cock... He wanted to cover your smaller body with his and press into you and let you try and hump his cock as it completely obliterated you. After all you were... Someone in need of his help. Someone who needed him.
You hungrily took advantage of his state and shimmied down a bit, so his meaty cock pressed against your pussy. You faintly remember that one patron of yours had asked to rut his cock between your pussy lips and came almost immediately. You learned from Briar that yes, Pussy jobs were a thing. Your clit was humped at enough for you to feel good, but you felt like Doren had the ability to use your pussy like his own personal jerk off toy and still make you see stars.
Leighton leaned back in his chair as you pathetically humped at your English teacher’s huge cock, squealing with every brush of his cockhead against your clit. It wasn’t long before Doren slowly clamped your knees together and began to earnestly fuck against your pussy, grunting into your mouth all the while. There would be a mess of cum over his desk, your thighs and all over your pussy before Doren jerked out of his reverie and he slowly left the office, ears as red as his hair.
Winter already knew his way around your pussy. He pretends it was to punish you, but he often thinks back to the first afternoon he saw you. Pathetically humping at your fingers. You couldn’t take your hands off of yourself. He loathed when his charges were promiscuous but after so many weekends of you coming in and eagerly pushing an artifact over to him, he couldn’t bring himself to hate you. Just teach you a lesson on what happened to naughty nymphs who couldn’t go an hour without stuffing their hole.
Winter never got angry at the fact that you still masturbated with fervour after that, nor was he irritated you somehow managed to get the chastity belt off. No doubt your admirers helped you in yanking it off. He never had a taste for sex, seeing it as unnecessarily filthy, awkward, and simply primitive. Everyone knew this.
So, it was a surprise that the history teacher ignored your cummy pussy and grimly pressed himself against your ass, hands slowly cupping your ass. What was more surprising was that he didn’t respond to any of the headmaster’s taunt at him, or you. Simply pressed a thumb into your hole, testing it to see how much lube you’d need for him to press his cock into you.
What no one knew but Winter, is that he was imagining you and him elsewhere. You were a naughty run away, or a servant that acted out, or maybe a prisoner that had information. You could just imagine you, pretty little you, tied down and he’s called in, a respected man, a general, the master of the house. You’d whine for him to take mercy and he’d take his pleasure.
Letting you whine and moan and gasp as he pressed into your ass, staying still so you would hump at him pathetically before he took over. After all, Leighton was right. You had been bad, and he had been weak, and he had to teach you the error of your ways.
If only you were in his room. He had many instruments to teach someone the error of their ways and you were whore enough to stiffen and stifle a moan when he had bent down to whisper in your ear. Or maybe you lusted after older men who you couldn’t proposition without getting into trouble.
To your merit, you did remind him of the tales of sweet demure trophies, who would reward the conqueror, the hero, the general with their body. His thoughts were getting hard to maintain. Your ass was tight, and your whines and moans of pleasure kept making him wonder if he should just keep you on his cock until you were all out of orgasms.
He came deep in your ass without any fuss, maybe just a bit sweaty, with his hair dangling in his eyes until he swept it back.
Leighton struggled to taunt him as he left, still thinking about how sweet you would look if you wore one of those old simplistic white gowns to welcome him home and let him subject you to his many husbandly duties.
If Leighton liked River, he would have had him gone first. He was a squeamish prude who struggled with even the thought of sex.
But he wasn’t all that fond, so River went last. Your body was stuffed with cum, in your ass, your pussy, even between your thighs. He would have to share in one of his colleagues’ cum if he was going to walk out without consequences.
“I don’t think-”
“So don’t think.”
“Leighton-”
“Do it, River.”
“This-”
“River.”
The math teacher finally went silent, looking down at you with a look of mortification. He was already unsteady on his feet.
“If you can’t, I’ll help.” Leighton said, irritated.
“I- What?”
“You heard me. Or was this your plan all along?”
River stared at him as Leighton got to his feet, letting the camera whirr on. His cock was sore from how long he spent tugging on it, watching you get ruined on his staff’s cocks but he had energy for one more... Maybe two more, he might need a go on you too.
“Face them.” Leighton instructed, coming up behind River.
He felt sluggish when forced into position by his superior, the head master already fumbling at River’s belt to take his cock out.
“Now, because I still owe you for making the maths competion a thing, and I gotta to see this one’s pretty little body, which hole?”
“W-Wha-”
“Christ man, pick the hole you want.”
“I... Front.”
Leighton wondered if River ever even had sex. For one so squeamish, his cock was already hard and throbbing in his hand. The headmaster gripped your knee and yanked you closer till your legs were dangling off the desk again. With a low exhale, he slowly presses the other man’s cock into your ruined little pussy, enjoying the way River flinched at the feeling of the mixture of hot and cooling cum inside of you.
You sighed happily, as River was fully sheathed into you. He shook in Leighton’s grasp, his cock already throbbing.
Leighton smirked and gripped his waist, his other hand grabbing River’s hand to force him to cup your knee to properly thrust into your now lazy and limp form. River didn’t move an inch while inside of you, bright red and struggling to look at the student in front of him. The headmaster sighed and bucked his own hips, forcing River to thrust into you, the maths teacher half squeaking, half moaning with the movement.
River didn’t want to enjoy it. The two of you grew close over the soup kitchen, the maths competition, even throwing Whitney out of his class. To be fair, you two were extremely close now... Including Leighton. Balls deep inside of you, Leighton pressuring him to keep thrusting until instinct took over and he stepped back so River can thrust into your freely, head too foggy to even think about pulling out. You did appreciate it, cooing for your teacher and pulling him closer until he messily jerked his cock out of you and orgasmed over your tummy.
River trailed back into the staff room and took a seat, Leighton bringing up the rear.
None of the teachers looked at each other.
“Now. Those were very good disciplinary meetings, well done all.” Leighton smiled, internally noting to himself that you deserved a gold star after all that help. “Just remember the rules. No matter you personal feelings about a student, if they’re a delinquent, they deserve the punishments they get. No more helping a bad student under any circumstances.”
The teachers nodded, either staring at the floor or fighting back another erection.
“Anyway.” Leighton shrugged. “You’re all have to stay distant during school now. They won’t remember this at all.”
He would turn his back on the staff, staring at him, and go back to his office, ringing Bailey up to come and collect his charge from his office while he oversaw the extended detention for other troublemakers.
Bailey, to his credit, did come. Very pissed his orphan wasn’t even paid for their time after all that hassle. He did take out a £50 from Leighton’s wallet as he draped his coat over you, all cock dumb. Only because it saved the looks shot at a naked person. Bailey wrote himself a reminder to add an extra £150 for his pea coat. Had nasty cum stains on it now.