Assignment at Sherwood Academy
Bdsm Story

Assignment at Sherwood Academy

by Chris6160 17 min read 4.7 (12,300 views)
cunnilingus high school bdsm spaning anal toys humiliation student
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I don't think the usual caveats apply to this story per se; there's a lot of sex in it throughout. However, the actual BDSM content doesn't show up until later, so please don't be put off if the chains and such aren't around to start.

Also, hopefully this is clear from the text, but despite the high school setting, all sexually active characters are over 18.

========================================

The faint hint of chemical cleaner, stale water, and BO were not the most romantic bouquet to make love to.

Jennifer didn't care; they weren't making love anyway.

"Yes! Yes! Fuck me! Harder!" she cried out. The words echoed in the locker room, with all the surfaces being stone or metal. The slaps of her ass against his body as he plowed her doggy style also echoed.

"Shut up, for fucks sake," the man behind her growled, "It's already six, there could be people around."

"Just fuck me," Jennifer repeated.

Dick kept going. He was the academy "athletic advisor" because boujee places like Sherwood Academy didn't have anything so pedestrian as a gym teacher. They'd met in college, and immediately pissed each other off; he assumed she wanted in his pants because he played football, she retaliated by calling him Dick constantly, when he insisted everyone call him Rich. Of course they'd been fucking by Junior year, though they never made a relationship work.

She'd recommended him to the board of the school. An NFL prospect with the bad luck to blow his knee out senior year, he was a well-known enough name to gain the school some more clout. And the athletic director being a former NFL player cinched it.

School hadn't even officially started when Jennifer cornered him in the locker room the first time and they got "reacquainted". They were both married, but she didn't care.

"I wanna play with your tits," he said.

"No way," she grunted back as his cock continued to split her pussy open, "Like you said; people are coming. That's why I wear the fucking skirts."

She was proud of her tits. Full 34DDs with no artificial ingredients, she scandalized the older women of the school by wearing push-up bras that turned her chest into a spectacle. She barely had to work to get the attention of male students in her class. They weren't focused on the material so much, but anything to keep their minds from wandering, she could work with.

Dick reached around and pawed at her chest anyway. Despite the two layers of fabric the squeezing actually felt good; his usual clumsy, rough groping was muted into a nice massage of the breasts that helped her arousal.

"Ohhh fuck I'm close," he said.

"UP!" she cried, "Pick me up, finish me like that!"

This was one of the best features of fucking Dick. He used his physique to lift her legs by the knees and hold her against his chest. She came off the floor, wrapping a hand around his neck and feeling his hard pecs against her back. His thrusts into her were helped by gravity, and the angle meant the head of his cock rubbed right over her g-spot. She even got a little extra from her boobs bouncing around in her bra, her hard nipples rubbing against the fabric.

The effort stalled him long enough that he lasted an extra minute or so bouncing her on his cock. Jennifer heard him growl and felt the pulsing as he came. His arms gave a little and he dropped her farther, slamming his cock home deep in her pussy and actually touching her cervix. It felt a little like a punch in her pussy.

It made her cum.

It wasn't a huge orgasm, but it was enough to make her shudder and set her pussy quivering around his shaft. She felt a few drips of their combined fluids leak out of her.

"Put me down, put me down," she urged him.

He let her go and she scurried over to her bag, then ducked into one of the shower stalls to clean herself up. She pulled her skirt back down so it stopped somewhere above her knee again, rather than acting like an extra thick leather belt.

When she came out, Dick still sat there, his pants around his ankles and his shirt off, looking a bit despondent.

"Come on," he pleaded, "We've got some time. Come sit with me."

"Fuck's sake, Dick, we're pushing it as-is. Caught half-dressed in the locker room isn't any better than being caught fucking. If you want to snuggle, get in bed with your wife."

Dick sighed. "She isn't like that. She isn't even around half the time because of work."

"You signed up for that, remember?" Jennifer said as she found a mirror and re-did her ponytail. She had blonde hair long enough that she could make a "topknot ponytail" wrapped with her own hair and it still came down to her mid back. She finished and turned to him.

"I told you back then; I like teaching, and I need someone who can support that, practically and financially. You were going to be traveling everywhere for the NFL before. Now you're another teacher. I helped set you up with your hi-powered lawyer wife, remember?"

"You also said we'd keep each other company on the side," he said.

"What the fuck do you think we just did?" Jennifer retorted.

"That was a booty call," he said.

"Well unfortunately my husband is a little more demanding when it comes to my attention," Jennifer said, thinking in her head that was a vast understatement, "So I can't sneak off with you to a motel room for a sleepover. If you can't handle that, maybe you need to find another side piece."

Jennifer stormed out, the click of her heels on the floor partially drowning out his calls of "Jennifer!"

She wasn't angry with him, but she needed to set expectations. She was fine fucking him on the side, getting quickies in the morning or at lunch. Jennifer wasn't going to start a full-blown affair, though. She wouldn't be able to manage that with her husband.

She got to her classroom with plenty of time to spare before the bell went off. In the name of maintaining an "old-world feel," the school still used actual, ringing bells. All of the students filed in in their uniforms; jackets for everyone, pleated skirts and knee socks for the girls. Despite the dreams of porn fetishists everywhere, the skirts fell below the girls' knees and their blouses were always done up tight to the collar. Some of them might have been rebels and worn thongs or even gone commando, but that was as titillating as anything could get. The guys just looked like assembly-line suit models wearing the cheapest jackets and slacks that could be bought.

That meant her own jacketless, silk blouse and tight skirt combo with thigh-highs and three-inch heels may as well have been a bikini given the way most of the guys and some of the girls stared at her. She smiled at them.

"Bonjour classe," she said.

"Bonjour Madame Arlington."

=-=-=-=-=

"Are you taking me to lunch Mister Kalmus?" Jennifer asked as she fell into step beside the taller man.

"We seem to be going to lunch at the same time," he replied with a smile.

"And to the same place, I'll bet," Jennifer said.

"Unless you have somewhere else you have to eat," he said.

"Well I don't, but there are stories of young teachers sneaking off with other faculty during lunch you know," she said.

Mister Kalmus smiled and waggled his eyebrows. "Do they now?"

"I think they do," she said, "I've heard some strange sounds sometimes when I've needed to rush to make copies at lunch."

"Oh you mean that supply closet near the faculty bathrooms? Yes, rumors about that room for years. They say that's why it got one of the new coded locks; the old lock was too easy to pick," Mr. Kalmus said.

"Yes, and we teachers all have the code don't we? So if someone did want to fool around in one, it would have to be one of us. Or two of us," Jennifer suggested.

Kalmus chuckled, but sounded down. "Maybe twenty years ago, Madame Arlington. I'm too old to get anyone to play those games with anymore."

Jennifer personally disagreed. Peter Kalmus was older; he'd gone past 50 a few years ago. But he had the chiseled face and stocky frame of an old Hollywood star, with salt and pepper hair and a sensual voice he didn't even have to try to make sexy. He could read the phone book and get panties soaking. Rumor had it certain girls who didn't have anywhere near the required grades tried to get into his AP English classes just so they could hear him read Byron.

"You never know until you try," Jennifer suggested, "I bet you could put your arm around any two women in the school and they'd follow you right into your bedroom."

"And then have to carry me out when the heart attack kills me," Kalums replied.

Jennifer smiled along and chuckled as their banter steered away from the possible and into fantasyland. She'd established the game with him her first year after he'd asked her to stop into a class to comment on differences between meanings in original French literature and the English translations. Some of the content had been a little racy, and she'd used the opportunity to flirt with him after class. He came right back at her with the confidence of a tenured teacher with enough clout to survive a sexual harassment suit, or at least enough money to retire if it didn't go his way.

He had no idea Jennifer wasn't at all kidding, about any of it. She'd take him into the closet, take him home to his bed, even find another woman to join them if he'd only take her seriously. But she had to content herself with staring at him over lunch, then excusing herself to jill off in the bathroom just before class and wash her hands.

=-=-=-=-=

"[You wanted to see me, Madame Arlington]?"

Jennifer looked up at the thin boy standing in the doorway to her classroom. Micah Townsend was in the running for valedictorian of the senior class, basically neck and neck with Amy Hu, a stereotypical Asian girl down to the thin frame, chin-length black hair, aggressive "tiger" mother, and the violin.

He'd greeted her in French, which they were both practically fluent in; her actually, him from education.

Jennifer had cheated her way into education by having a fully French paternal grandmother who ended up raising her a lot of the time after her mother passed away from cancer. While her father tried to split his time between caring for her and working enough jobs to keep them fed, her grandmother inadvertently made her bilingual by speaking French around her as a toddler while her father spoke English. Even with mediocre grades from an unremarkable college, she'd been a shoo-in for the French teaching position; they could claim to all of their patrons that their French teacher was a "native speaker" but didn't have to sponsor her for a visa or pay extra because she was a scholar who'd come over from Europe; they could just pay her like any other second year teacher out of college. After all, they needed to keep the students' $85,000/year tuitions earmarked to maintain the varnish on all the wooden walls.

"[Why are you in my French four class, Micah]?" she asked.

He looked confused by her question and answered her in English. "I'm...it's the next class offered and-"

"You aced French three without even trying," she said, also switching to English "I know; I taught you. Your grade in that class was something like 120 because you did all the extra credit. Why am I teaching you French IV and not AP French?"

"I...I have a lot of other classes and activities and I had to prioritize," he stammered.

Jennifer smirked. He couldn't look her in the eyes, but his gaze hadn't traveled down to his shoes like a stereotypical nervous kid. No; they'd stopped a bit higher.

"Eyes, Micah," she said. She didn't snap, she gently reminded him. Despite that, he looked up, wide-eyed, then literally down at the floor while his face turned beet red.

"What other classes are you taking?" she asked, letting her voice get a little harder.

He listed off AP classes in Biology, Physics, Calculus, and Government, and two electives: Electrical design and a class related to a national business innovation competition. All classes that would look good to business or Ivy league schools, but the electives weren't rigorous. She knew the actual reason.

AP classes had a separate test, administered by a third party company that sponsored the curriculum. That test was difficult, and also given somewhat before the end of the school year. For that reason, the students usually didn't take finals in their AP classes, nor did they take midterms; their grade was only based on their quarter grades.

To prevent high-flying students from being "punished" for taking an AP class, the teachers tended to grade permissively; a student in AP getting less than a B required them to be actively delinquent. Their grades were also weighted higher due to the work being "college level." This generally preserved everyone's class rankings.

However, because of a quirk of the math, it was theoretically possible to take mostly AP classes and a conventional class, and because the conventional class had a midterm and final exam grade, if the student aced them, they would end up with a GPA higher than a student who took all AP classes.

Micah was trying to do that, and he was using her class as his loophole.

"Micah, I don't appreciate being played," she said, standing. He was shorter, for a guy; in her heels she had an inch or so on him in height, helped by his slouching or, at the moment, his cowering.

"I...I don't know-" he stammered.

"You picked my class as your safe bet. You plan to simply coast your way through on your talent, giving it only enough time and effort to ace the tests and extra credit work. Your focus won't be on me."

At "focus", she put her finger under his chin and lifted his head up. However, she stopped when his eyes were level with her chest.

She gave him fifteen seconds to stare at her chest, the outline of her bra slightly visible beneath the pearl-colored silk. Then she abruptly turned away, saying, "So I hope you're happy with salutatorian, because I'm not giving you perfect scores."

"What!?" he said after a moment.

"You're blatantly taking my class because you won't have to put in as much effort. I'm not rewarding laziness."

"You can't do that!" he insisted. Jennifer might have had more respect for him if his tone was authoritative and angry, but instead he sounded frustrated and pleading, almost whining his objection.

"Sure I can," Jennifer replied, "My tests involve essays. Their grading is subjective, and I am the authority on French at this academy."

"I'll switch into your AP class, then," he said.

"We're well into September, Micah; it's far too late. My class's enrollment is closed," Jennifer said.

Micah somehow seemed to slump even further, crushed and defeated.

"Is it really that big of a deal, Micah?" I asked, "Valedictorian? Salutatorian is just as prestigious."

"The really good colleges

reject

valedictorians. Forget anything less," Micah complained.

"So what are you planning to do with the extra time you don't have to try in my class?" Jennifer asked, "Go out with your girlfriend?"

Micah scoffed. "I don't have a girlfriend."

"Do you want one?" Jennifer asked.

"I mean...Sure, I guess. Not gonna happen though. Nobody thinks I'm hot. They just want me to do their homework for them," Micah grumbled.

"Did you?" Jennifer asked. She'd let her voice get more sympathetic, but she kept it low and sultry. She also slowly moved closer and lowered herself to Micah's level.

"Sometimes, at first," he said with a shrug.

"And what did you get for it?" Jennifer asked.

"Nothing."

"Well that's silly. They should have at least paid you. Or maybe offered you something more?" Jennifer suggested, running her finger up his thigh. He tensed at the contact and glanced back and forth between her face and her hand (and her tits; his eyes just couldn't help themselves, it seemed).

"Fuck no," he said, "Their boyfriends all threatened to beat me up."

"And they still ask you?" she asked.

"Y-yeah," Micah stammered. Jennifer's other hand had settled on his other thigh. She could also see his penis straining against his pants.

"Well that's not fair. Don't you think you should be compensated for helping all those students?" Jennifer asked.

"Um...yeah...it would be nice," Micah said.

"Well then."

Jennifer had his belt and pants undone lightning quick. She slid her hand around and goosed him enough that he flinched, which let her yank his pants down. His penis, rock hard and leaking, stood straight up in the air.

Jennifer's eyes briefly bulged in appreciation. Micah had a decent size cock on him. Probably eight inches and proportional in girth.

"Mad-Missus-what are you doing?" Micah said in near panic.

"Compensating you," she said, and then leaned forward and inhaled his cock.

She didn't go very far down, but she did engulf the whole head and part of the shaft. Her tongue swirled around his crown fast, and she gripped the shaft after a second. She could feel him trembling already. If her guess was right, she was giving him his first blowjob, and she predicted the results.

It took all of maybe fifteen seconds for his hormone-flooded brain and virgin cock to succumb to the new sensations of her mouth and tongue. His semen erupted out and hit her throat. She swallowed as fast as it emerged.

"Oh fuck. Shit. I-I didn't mean-"

"You're a young man," Jennifer said, pulling her mouth off of his cock but continuing to rub her hand up and down his shaft, "I expected that."

"Do you...um...you do this for a lot of guys?"

"Micah, how rude," Jennifer scolded, smiling at his extreme blush, "You never ask a woman for her body count."

"I...uhhh...fuck that feels good," he said. His eyes didn't seem to know where to settle.

"Do you want to feel good again Micah?" Jennfier asked. Micah just nodded. "Well then you have to be polite. Do you know how to be polite, Micah?"

Micah nodded again Jennifer stood and sat on top of the desk his chair was next to. She hiked up her skirt and spread her legs wide, resting her heels on the desks to either side of them. It was almost a full split.

Micah was briefly transfixed by the long, smooth, creamy white skin of her thighs, but then his libido caught up and locked his gaze on the triangle of red fabric between them. Her thong was barely underwear; it rode so low her pubic hair would have shown, but she had none. The fabric stopped just at the top of her slit, but it was pulled tight, giving her an obvious camel toe.

"Miss-...Mrs...What?"

"You said you'd be polite, Micah," she purred, running her fingers through his hair. "The polite thing to do," she continued as she settled her hand behind his head, "is return the favor."

She pulled his head forward. He didn't resist, but he seemed lost. She was able to move his head down to her pussy without any resistance, but he also didn't do anything; it was just his nose resting a little above her clit and his lips mashed against the gusset of the thong. Jennifer sighed inside; this was going to take some time.

"Use your mouth, Micah, and your tongue."

He didn't get it at first, trying to peck at and then suck on the panties. She finally gave him an encouraging moan when his tongue pressed against the fabric.

"Yes dear boy, keep doing that for a bit," Jennifer said.

It was little more than foreplay for her; the fabric kept him from giving her real stimulation, but it still felt good. After a few minutes she had him back off. She saw him rub his jaw.

"Was...was that enough?" he asked.

She couldn't help laughing. "Micah, when did I stop with you?"

"After...After I orgasmed," he replied.

"And did I orgasm?" Jennifer asked.

"Um...I don't know."

"So much to learn. Trust me, if a girl's having a really good orgasm, you can tell. And no, it isn't her screaming 'oh my God, I'm cumming so hard' like in porn, at least not always. But you'll be able to tell somehow. Now, why don't you try licking me directly?"

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