School's Head Mistress Tamed by Student
by MagisterJohn
Copyright© 2025 by MagisterJohn
Fantasy Sex Story: The Head Mistress of an exclusive Private school for Rich Brats is kidnapped and forced to go from Cock Teaser to Cock Pleaser by one of her students
Caution: This Fantasy Sex Story contains strong sexual content, including NonConsensual Rape Heterosexual School Humiliation Light Bond Rough Anal Sex Facial Oral Sex Pregnancy Teacher/Student .
Theresa was the vision of the stern Head Mistress of an exclusive private school for the country’s rich and elite (which worked well since that’s what she was).
At the age of 32, Theresa Collins was the youngest Head Mistress in the 120-year History of Princewood Academy. She was proud of her achievements and the power it had brought her. The students at Princewood fell silent when she walked thru the hallways on her daily patrol. Teachers and staff feared her as well. She had a well-earned reputation for being harsh, even cruel and a temper that made anyone take a step back.
On top of her cold reputation, she had a body that would stun at any Beauty Pageant, even standing next to the perky teens that normally fill those contests. She was just a shade under Six foot tall, 150 pounds with a lean, muscular frame that made her surprising 38 DD breasts stand out above her tapered waist and wide rounded hips. Breeder’s hips they used to call them. Her long dark auburn hair was kept pulled back and in a tight bun on the back of her head during school hours; but draped down her back almost to her butt when she let it down at night. Her skin was flawless white with just the faintest hint of freckles that she hid on her face with makeup; but that still showed on her massive tits when she left an extra button open on her blouse, not that she often did.
Her dress style was impeccable. Formal, businesslike, yet those tight-fitting skits and jackets only served to accentuate her figure. The dark stockings hugging her long legs, the pencil skirt split just a bit up one side, the form fitting jacket that cupped her breasts, and the high heeled shoes that looked as much like weapons as footwear, Theresa was the full package.
In addition to her duties as Head Mistress, Theresa also taught one unit of World History each semester. Normally the students that were assigned to her class where ones she considered... ‘problems’. Problems that she planned to break each and every one of them.
Chief among those problems had been Benjamin Powers. Like many Seniors Ben had developed an attitude problem this year. Senioritis Teachers liked to call it. He already had early admission locked in at a prestigious University, and his father’s wealth guaranteed he didn’t need to worry about paying tuition. Theresa had spoken to his father John Powers about it. Mr. Powers was a formidable man, even wealthier than most of the other parents at the Academy; but with dark rumors about where some of that wealth had come from.
When Theresa called him into her office she spent 20 minutes telling Mr. Powers what a problem Ben had become. He was failing to turn in assignments, not participating in class, even mocking her. Powers sat quietly for a moment, and then checked his watch. Rising to his feet he said simply, “I’ll take care of it”, turned and left the room without another word. Theresa stood flabbergasted; apparently arrogance ran in the Powers family.
In the weeks that followed Theresa noticed a change in Ben’s work. The arrogance was gone, or at least controlled, home work was on time and spot perfect. Ben even chimed in on classroom debates. Theresa was amazed, wondering what Ben’s father had done. If she only knew she would have understood the sly glances and leering smile she occasionally caught on Ben’s face. She just assumed Ben’s father had bribed him with some expensive indulgence to motivate him.
Soon she would find out just exactly how right she was.
It was Friday night at the end of a very long week. Monday was a Holiday and Theresa was looking forward to a long weekend at home. Her cottage sat alone in the country, just a few miles from the Academy. Close enough to be convenient, far enough away to allow her some privacy. Theresa had stripped off the suit she had worn all day, let down her long hair, showered and slipped into a long emerald green silk nightgown. Pouring herself a glass of chardonnay Theresa picked up a book she had been reading and began turning off the lights in the house in preparation to go to bed. She had just turned off the last light in the hallway leading to her bedroom when she heard a footstep behind her. She spun around just in time to see two large men dressed head to toe in black and wearing balaclavas covering their faces grab her arms. Instinctively she tried throwing the glass of chardonnay into the face of one of her attackers only to realize he was wearing goggles that protected his eyes. Her other hand tried to strike at the second assailant with the book she was carrying, but the dull thud told her he was wearing soft body armor. Clearly, these men were professionals, not some cheap burglars.
“She’s got some fight Bravo”, the first attacker called out.
“That she does Alpha”, the second attacker chimed in as he pulled a rag from a plastic bag on his belt and forced it over Theresa’s mouth and nose.
The rag was damp and smelled, Theresa tried to twist her face away but her attackers were skilled. This was obviously not their first time.
“Stop it ... let me go ... what are you do...” Theresa suddenly began to feel dizzy and light headed. Her arms became heavy as the room began to spin around her and her mind sank into darkness.
“Delta, bring the van around to the back” were the last words she heard as Alpha spoke into his radio before he and Bravo lifted the unconscious Head Mistress up and carried her to the van waiting outside her back door.
A dim light penetrated Theresa’s mind, slowly pushing her back towards consciousness. Her groggy mind began to claw back to reality, “What a dream, no that was a full-blown Nightmare” she thought to herself. As her eyes slowly opened and begin to focus, she realized it was no dream ... and her nightmare was only beginning.
This was definitely NOT her bedroom. At least twice the size of her comfortable bedroom, this room was covered with fine mahogany paneling at least a century old, far beyond even her generous salary and the occasional ‘gift’ from satisfied parents. The bed was enormous, bigger than any she had ever seen and covered in luxurious deep red satin sheets. As her mind cleared further, she tried to roll over and get a better look at the room only to discover cuffs locked on her wrists secured to chains securely bolted to the thick headboard of the bed holding her there. Adrenaline rush finished clearing her mind as the next horror came into focus.
Theresa was nude.
Her nightgown gone, she lay chained to the bed, exposed. Her mind scrambled to come to grips with the situation and her muscular body began to struggle against the chains that held her captive.
“How did this happen? How long was I out? Where the Hell am I?” Theresa’s mind raced as her eyes darted around the room.
“Well hello Teach” a calm, familiar voice said to her. “I was wondering if you were ever going to wake up.”
Ben Powers, her reformed problem student stood in a robe at the foot of the bed. Casually sitting down on the edge of the bed Ben placed a hand on Theresa’s bare right ankle and slowly began stroking the inside of her calf with his fingertips as he spoke. “Did you have a good nap? Get lot of rest?” he smiled as he spoke to her tauntingly. “Hope you did. You’re going to need your strength.”
Theresa turned red head to toe as much from anger as embarrassment. Few men had been afforded the privilege of seeing her naked body, never a teenager and never under circumstances like these.
“What the Hell do you think you are doing young man?” Theresa snapped in her best angry teacher voice. The fire now burning in her sharpened her mind as she pulled her leg away from Ben’s touch and kicked at him, “Get these damn chains off me ... NOW!” she fairly screamed.
Ben quickly recovered from the surprise of her attempt to break free and kick him. Laughing, he grabbed her right ankle again, this time locking it under his arm and holding her in place while she continued to kick about with her left leg. “Save some of that energy Teach, you’re going to need it later on.”
Attack hadn’t worked so Theresa quickly decided to change tactics. “Having defined a problem, the first step in reaching a solution is the acquisition of data” she reasoned. “Ben, what’s going on here? Why was I kidnapped? Why am I like this?” now seemed a good time for a logical appeal. “This is wrong, you’ll go to jail for this. You’ll ruin your entire life. Let me go and we’ll keep this our little secret, no one will ever know.” Theresa could tell by the look in his eyes that logic wasn’t working, so she tried an emotional appeal, “Ben please you’re scaring me. These chains are too tight, they hurt. You’re a great guy, one of my favorite students; but you’re frightening me’. Theresa made her eyes as wide and childlike as she could, she even managed some tears.
“Aww” Ben said teasingly, “Nothing to be frightened of Teach. In fact, eventually, you’ll learn to love this. Oh, it may take a few months, but you’ll accept your new life; and eventually you’ll even learn to just love every minute of it.”
“MONTHS!?” Theresa’s temper got the better of her. “Alright Ben, what the Hell are you up to? What is this all about?”
Ben began stroking the inside of her calf again and started slowly working his way up to her thigh. “Have you noticed how much better my grades have been lately?”
Theresa slowed her struggling, “Yes, you’ve been doing very well since your father and I spoke. The change has been very impressive. Now again, what the hell is this all about?!” Theresa snapped.
“Well, after your little talk, Dad came to me and made me an offer. If I got my grades up,” the pause hung in the air for minutes, “I could have anything I wanted for my Birthday.” Ben’s smile was ear to ear.
“Fine, Daddy bribed you, what the Hell does that have to do with this?” Theresa demanded.
“Patience Teach,” Ben chuckled. “I’m getting to that.” Ben’s arrogance was palatable, “You see, today’s my Birthday,” Ben’s hand began sliding up Theresa’s thigh and his fingertips began to gently tickle her pussy lips, “It’s time for me to start playing with my present.”
Theresa began twisting and bucking as well as she could; but with her leg trapped in Ben’s arm lock she could do little.
“Stop it!” she snarled as Ben’s fingers began probing just inside her labia. “I SAID STOP IT! Take your hands off me; I’m nobody’s damn Birthday present!” Theresa was as angry as she had ever been in her lifetime.
“Poor baby,” Ben said teasingly, “but don’t worry. You’re not just a Birthday present. You’re my Sex Slave!” Ben’s eyes opened wide and fairly glowed in pure Victory. His lust rose with each word. “Dad thought I wanted one of those silly little Asian girls. You should have seen the look on his face when I told him I wanted you!” With that Ben forced his index finger into her unprepared pussy and began working it deeper inside her unwilling body. His thumb slipped onto her clitoris and started massaging it.
“Uuuugh!” Theresa grunted at the combination of her dry pussy being penetrated and her clit being stimulated. The sound was as much anger as pain.
Ben leaned close to kiss her twitching clit and slide his tongue onto her pussy lips. The drool from his mouth lubricated his fingers as he slipped his second finger inside her pussy. The moisture made slipping the second finger inside easier than the first, but Theresa’s 32-year-old pussy was still far tighter than Ben had ever dreamed. She was no virgin, her maidenhead having been surrendered to a lusty Professor in college, but her cunt remained tight thru years of Kegel exercises. She tried in vain to squeeze his invading fingers out of her pussy; but he was too strong ... and too well-motivated. Each thrust took his fingers deeper inside her. Worse than that, her body had begun to automatically respond to the invasion and the attention Ben’s tongue continued to lavish on her twat. Slowly her own natural lubrication began to flow easing Ben’s forced probing of her sweet interior.
“Stop it!” Theresa shouted. “I’m no one’s Sex slave, you’re not going to do this to me. I won’t let you.”
“You can’t stop me slave.” Ben didn’t know what he enjoyed more, probing his teacher’s private parts, or listening to her try and resist while he did it.
The fight for her freedom caused Theresa to breathe hard, and the deep breaths she drew caused her chest to rise and draw Ben’s attention.
“Every guy in the Academy has been dreaming about those tits,” he drooled as he spoke, “Some of the girls to. Starting tonight, they’re all mine.” Ben release Theresa leg and for a moment she thought she might push him away; but Ben crawled on top of her pinning down leaving his face at mouth level to begin the mauling of her tits. “Just look at these beauties,” Ben said as his hands started groping her tits, squeezing them, pressing them together, slapping them, pinching and twisting her sensitive nipples.
“Owww, stop that! Don’t you dare touch me like that. I am a Lady and I will not be treated like this!” Theresa’s voice was filled with indignity. “I am your teacher and you will show me some respect young man, now get off me!”
Ben’s face filled with anger as he grabbed her nipples between the thumb and forefingers of each hand and pinched hard.
“Arrrrgh”
“Now listen to me. You’re a slut, you’re my slut. I own you and I’ll do anything I want with you. You’re going to learn to obey me, to serve me, to satisfy me. You’re going to do it for the rest of your life, and you’re going to start ... RIGHT NOW!”
Theresa had never heard anyone speak to her like that before, and she did NOT like it. As Ben started to suck on her tits, she let loose with a spray of curse words that would have done any sailor proud.
“Cuss all you like slut, I’ve been waiting a long time to see these tits, and now they are mine!” Ben greedily sucked on one tit while his hand played with the other. Theresa wasn’t enjoying the attention, but her body’s natural responses took over once again as her nipples began to harden and stand erect. “You like teasing us all with these big tits don’t you slut? I’m going to teach you what these tits are really made for” Ben yelled as his teeth gently but firmly began to nibble on her rock-hard nipples.
Theresa scream was as much surprise and humiliation as it was pain. She had never been treated like this and by the look in Ben’s eyes she suspected worse was yet to come.
She was right...
Ben sat up and straddled Theresa’s twisting body. Slowly he untied the belt on his robe and pulled the plush garment off to reveal his naked body. Theresa had seen Ben and the other students in the gym on occasions and knew he was in good shape already; but as her eyes scanned down from his lust filled face, she got quite a surprise. Even only semi-erect Ben’s cock was enormous. She couldn’t stop herself from staring wide eyed at the rapidly hardening monster that now lay pulsing on her smooth belly.
“Like what you see slut?” Ben laughed.
Theresa was near panic at the size of the member that now held her transfixed. The reality sunk in. She was going to be forced to satisfy that monster, and despite her brave protests, she knew deep down, there was nothing she could do to physically stop it from happening.
“Ever had those big titties fucked Teach?” Ben stared down at her with open lust.
The truth was Theresa had been titty fucked ... several times. She hated it, found it degrading, but a useful tool when she wanted something from one of her college instructors and didn’t want to give up her pussy.
“You have, haven’t you?” Ben teased. “How long has it been slut?”
“It’s been a long time,” Theresa decided to switch tactics again. “I’ll let you fuck my tits; but then you have to let me go home. I promise I’ll make it really good for you, just take these chains off so I can use my hands to squeeze these big tits around that big cock of yours. I’ll play with them for you while you fuck ‘em. You can get off all over them ... cover your teacher’s tits with your cum. That’s what you want, isn’t it? To shoot your big creamy load all over your teacher’s big tits.”
Ben smiled as he mounted her chest and dropped his now hard cock between her breasts and placing his hands on them squeezed those D Cup mams around his cock as Theresa’s magnificent breasts formed a perfect titty tunnel for Ben’s cock to begin sliding back and forth in as the young man moaned lightly with growing satisfaction.
Theresa was almost in a panic as she realized another of her escape plans was failing. “Come on baby, unchain me, and let me play with my tits for you. You want to see me play with them, don’t you? They’re so big ... I can lick my nipples while you fuck my tits. Don’t you want that?”
Ben laughed as he squeezed Theresa’s tits roughly and increased the speed of his strokes between them. “You stupid slut, you actually think I’d dumb enough to take your chains off? Besides, you’re already home, this is your home now. I own you, and I can do whatever I want to with you whenever I want to for the rest of your fucking life!”
Theresa pulled on the chains that held her arms in frustration. Trapped, a captive in a strange house, prisoner in a strange bedroom, helpless on a massive bed, being molested by a teen who only hours before had been one of her meek, subservient students. The normally strong dominating woman found herself crying as she was used for a teenager’s wicked carnal pleasure.
She found herself wishing Ben would cum. Maybe then she’d have a respite from this humiliation.
Ben’s treatment of her tits was becoming rougher the longer he went on, and he seemed to go on forever. Theresa knew it could only be a few minutes; but she felt like Ben’s cock had been sliding between her prized breasts for an hour with no sign of him shooting his load. She closed her eyes to try and pretend this wasn’t happening to her, but tears still spilled down her cheek no matter how tightly she closed her eyelids.
Unexpectedly, Ben took one hand from her breasts and slipped it under her head, lifting it and forcing her to look down at the thick cock sliding between her tits.
“Look at that big cock fucking your tits slut ... LOOK AT IT!” Ben yelled.
Slowly Theresa forced her eyes open just a crack. The sight that greeted her started her tears falling in earnest. Ben’s long hard cock was thrust out from between her tits and forcing closer to her chin and face with each thrust. The thought of that hard teen cock approaching her face filled her with dread as she realized what was going to happen next.
“Look at it, slut ... look at how thick it is, how fat it is. See how it reaches almost to your lips while I fuck your tits.” Ben’s tongue licked his lips in anticipation. “Want to suck it slut. Want to see what it tastes like? Want to feel your Master in your mouth? Want to feel him sliding down your throat?”
All her education, all her training, all the experience of her life never prepared Theresa for this moment. She opened her mouth to speak; but nothing came out. Silence. She lay there, chained to the bed, her head held up by a teen boy, her lips slightly parted, unable to say a thing. After long moments, Theresa managed to whisper “no” in a soft, teary voice. “Please, no” every word quiet, pleading and painfully. “Please, don’t make me do this...” her faint voice trailed off to nothingness.
Quietly enjoying his victory and what was yet to come, Ben softly laid her head back on the pillow and stroked her hair. Effortlessly he took hold of the headboard and lifted himself till his cock hovered over her tear-covered face.
“Kiss it slut” Ben said as he lowered himself onto her lips. “Kiss your owner’s cock.”
Meekly terrified Theresa puckered her lips and kissed the tip of the think throbbing member in front of her. Slowly, she kissed it again, then again working her way around the head with her soft lips.
“That’s it, slut. Show your owner what a good little slut you can be.” Ben’s voice was a low growl. “Now, take that pretty little tongue out and lick it. Lick your owner’s cock.”
Obediently, Theresa slowly slid her tongue out and began gently licking Ben’s cock, being careful to stop every few licks and gently kiss it over and over again before returning to her increasing forceful licking. Ben tasted clean, fresh, not at all like Theresa had feared he might. Apparently, he had freshly showered just before she woke up.
Fresh and clean or not, Theresa still hated giving blow jobs, and the few times she had agreed to it was with partner’s who were nowhere near as well-endowed as Ben. The thought of what was about to happen sicken her; but she had no choice.
Every time she had sucked cock before the man was anxious to get his dick into her mouth and enjoy himself at her expense. Ben was busy enjoying the treat Theresa’s skilled tongue was delivering to his stiff shaft. Soon to her surprise Theresa was running her tongue from the tip of Ben’s cock all the way to the base, slowly, stopping only to rapidly flick the tip of her tongue on Ben’s cum hole. Each time she slid her tongue down the shaft at Ben’s large, hairy ball sack with dread. She had never licked a man’s balls; but girlfriends in college described it as one of the worst things they had ever been tricked into doing.
Ben had other plans for her ... for now.
As Theresa licking reached back to the tip of Ben’s cock he grabbed hold of the hair at the back of her head. This was the moment Theresa had feared. Pushing his cockhead inside her parted lips Ben gave the order she had been dreading.
“Time to suck your owner’s cock slut.”
Theresa slowly opened her mouth as far as it would stretch in order to take Ben inside her mouth. Instantly her jaw was sore from the effort, she had never imagined a man’s penis could have such a girth and especially not on a man so young.
Passively she began to suck on the cock filling mouth. A thought flashed in her mind for a moment to bite down on the hard yet sensitive flesh in her mouth; but she quickly reasoned that to be a bad choice. She would still be chained to the bed, and the punishment for such an act would very likely be worse than death, if not death itself.
“Come on slut; show your owner what you can do ... earn your keep.” Ben now held her head with both hands and had begun fucking her mouth with an increasing ferocity. “Come on slut, you can do better than that!” Ben raged.
Theresa started sucking on Ben’s cock faster and harder, taking over the action by thrusting her head forward and pushing the fat dick deeper inside her mouth and down toward her throat. She hated what she was doing, but damn she was good at it. Her sucking became almost violent as she tried to force the long cock down her throat, deep, deep down, pushing hard till she felt the warmth of Ben’s testicles lying on her chin. With one final push, she took his entire length in her throat and then shook her hear viciously trying to take it down further, trying to swallow it whole. Theresa had been a champion swimmer in school and today her breath-holding skills served her well. For a long minute Theresa held Ben there, the muscles of her throat massaging his cock as she gagged on the massive invading organ now deeply lodged in her.
Slowly, seemingly a millimeter at a time, Theresa pulled back as Ben’s cock enjoyed the passage out of her throat as much as it had the trip down. Suddenly, as Ben’s cock reached the more open space of Theresa’s mouth, she greedily gasped and swallowed a lung full of air before forcing her throat deep around Ben’s cock for a second time. In a moments time she was once again shaking her head to try and take the long cock in even further. Her gagging sound, so soon again after he heard it before was intoxicating to Ben as he held his cock in place while Theresa mind began to swirl and fade to black from the lack of oxygen.
When the light finally returned to Theresa’s mind she was still chained to the bed and Ben was hovering over her face. It was like he was doing pushups over her face; but in this form of the traditional exercise Ben’s hard cock was in Theresa’s mouth, mouth fucking the unconscious woman while she lay helpless. Theresa had hoped that her active attention to his cock would cause him to cum and end his molestation of her. The hardness of the cock plunging in and out of her mouth told her she had once again failed. She cried as she returned to passively sucking Ben’s cock and wondered what she would be forced to do next.
She wouldn’t have to wait long to find out.
The feeling of her lips closing around his cock told Ben that Theresa had regained consciousness. “Welcome back slut. Glad you’re awake, wouldn’t want you to miss what comes next” Ben smirked as he slowly pulled his cock from Theresa’s sore mouth. Lifting his cock straight up moved his balls over Theresa’s mouth. Lowering himself slightly as he straddled her face Ben’s nut sack covered her panting mouth as she gasped for breath.
“Mmmmph” Theresa’s words of protest were smothered before she could speak them. A short slap to the side of her head refocused Theresa.
“Clean those balls slut. Lick ‘em clean!” Ben yelled. “Show your owner what a good job you can do. You’re going to be licking those balls clean every day from now on.”
The tears now flowed from her eyes in streams. Theresa felt angry and disgusted ... with herself. How could she have let herself get into this situation? Forced to degrade herself and submit to the depraved wishes of a teenage boy. Still, submitting seemed the best choice open to her. Play along. Lure him off guard and wait for her opportunity for escape. Forcing down her anger, she began doing something she had sworn she would never do ... lick a man’s balls.
“That’s a good little slut. Show your owner how much you love him.” Ben taunted her. “Smart Lady like you, bet you know what those balls are full of, don’t you.”
Her mouth otherwise occupied, Theresa could only manage another “Mmmmmph” is response.
“Don’t worry slut, your owner will teach you everything you need to know,” Ben seems to almost purr the words. “I’m going to take good, good care of you.”
Busy as she was licking, Theresa was also confused. Ben’s words seemed almost tender ... gentle even. Almost as if he really cared about her. The thought caused her tense body to relax ever so slightly. Unconsciously her licking even became a little more passionate and Ben moaned in appreciation.
“ ... take good, good care of my slut...” Ben sounded almost dreamy as he reached down and stroked her hair softly.
Theresa found herself almost cooing at the tender touch on her long Auburn hair. With out even realizing what she was doing, show opened her mouth and sucked one of Ben’s balls inside to be massaged by her tongue.
Ben moaned low and deep. He hadn’t even ordered her to suck his balls, and obediently she had done it. Realization flashed into Theresa eyes as she sucked on Ben’s cum filled ball. She had done this on her own. It was instinctive, she had never done it before, and yet somehow, she just knew what to do, what was expected on her. Quietly she released the testicle from her mouth and repeated the act on the other sending Ben into a rush of passion.
If Theresa thought her actions would earn her a reprieve from Ben’s rough treatment of her, she was about to be surprised.
Ben roared with an animal lust he had never felt before.
“That’s it slut, it’s time!”
Ben slide down Theresa’s nude body and roughly forced her legs apart and slipped his hands under them, lifting them in the air, grabbing her ankles and spreading her long muscular legs wide apart.
The move was so fast and well-practiced that Theresa didn’t even have a moment to resist. Suddenly she found herself, flat on her back with her legs over the arms of a young man who only hours a go she thought of as nothing but a groveling little man-child. As reality set in she tried to push her legs down and deny Ben the prize he sought, but he had her. Theresa squirmed and struggled; but she was trapped. Pinned and helpless against the hormone fueled lust of a teen aged boy.
Ben almost was growling as he laid the head of his throbbing cock on Theresa’s wet pussy lips; but instead of sliding it in, he began to slowly slide the cock head up and down on those tender lips. Theresa gritted her teeth and growled back in fury as she expected Ben to begin forcing his way inside her; but the forced entry didn’t come.
Instead, Ben taunted her.
“You know what’s going to happen to you know, slut?” Ben thundered as he looked down on his struggling former teacher. “Do you know what your owner is going to do to you now, slut?”
Theresa summoned up her angriest look and stared hard into Ben’s eyes, hoping her defiance would defeat him where her struggles had failed.
“I imagine you’re going to fuck me.” Theresa said, before managing a defiant spit at Ben’s face.
Whatever reaction she expected, it wasn’t the one Theresa got.
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