Fresh out of college, Colleen took a teaching position at a prestigious all-girls’ school. She checked out the school for any hint of a scandal regarding the inappropriate treatment of the students by the teachers. That was her first mistake. She should have checked out how they treated the teachers!
Colleen always knew there was something hidden deep
inside her, a taste of it only beginning to surface just before she took the
Headmaster Michael called his newest Professor into his
office, finally getting his wish.
She had made a grave mistake, confronting one of the students in a
manner that was unacceptable at
His philosophy regarding Professors was the complete opposite of the manner he treated the students. He believed that a good Professor is a disciplined Professor, Headmaster Michael using corrective punishment as a deterrent to future misdeeds. And corporal punishment was his number one method. He looked at Professor Colleen standing in front of his desk. She knew she would have to submit to him, dressing for the occasion, hoping to sway him to give her a more lenient treatment. Her legs were barely covered by the short, blue skirt, making Michael’s cock erect. A lovely white cashmere sweater could barely contain her conical breasts that pushed out the front, her nipples obviously aroused, almost pointed. He couldn’t wait to see that lovely ass.
Colleen stood in front of his large, mahogany desk, afraid but also excited. She had secretly seen what Professor Samuel had done to Professor Rebecca, the whip lashing at her naked ass cheeks as she submissively bent over the spanking bench. And Colleen had cum as she had never before when Rebecca had bound her. As well as when Joe had handcuffed her and forced her to masturbate him until he spewed his cum all over her hands. Have I always had these deep desires to be overpowered? To be bound and taken by force? She knew that it would be only a matter of time before Headmaster Michael had her stripped naked for his pleasure and her pain. It made her pussy damp with desire.
“Step into the other room, Professor Colleen.” He opened the door to the punishment room, a large display of furniture filling the room, all meant to secure a female in the most provocative and defenseless positions. He saw her stop when she saw them, sure that she didn’t realize the full extent of the punishment she would have to endure. “Don’t hesitate. It will only make it worse for you.”
She didn’t think it would be like this, the room filled with large, wood and metal frames, benches, stools and various other devices, all having leather cuffs that were meant to secure the victim in the most obscene positions. And then what would happen to the victim? She could only tremble in fear. She started walking again, no chance to change her mind.
“I think I need to get you out of some of those clothes first.” He stood in front of her, his hard cock pushed out so far that it almost rubbed against her, no doubt in her mind of his arousal and what she would have to do in the end to satisfy his lust.
She watched as if it were happening to someone else, her boss, Headmaster Michael, looking at her with lust in his eyes, and from the bulge in his pants, something much more. She shivered when his hands touched her naked skin, grabbing the edge of her sweater as he slowly raised it up her body. She did the only thing she could, raising her arms as he pulled it over her head. She pulled her arms out of it, Headmaster Michael putting it down on a table. His hands returned to her naked skin, turning her around until her back was to him, Colleen knowing that it would be her bra that would go next. She felt his body push up against her, his hands on her hips, guiding her ass back and forth leaving no doubt of his intentions. The swish of her skirt along his pants only highlighted the obvious, that he was openly masturbating against her ass cheeks, feeling his cock throbbing in excitement. She pushed back her ass harder against his cock, hoping that he would make it easier on her.
Michael enjoyed the way she pushed against him, his cock throbbing for release. Even when he let go of her hips, they continued to move back and forth over his cock. He made short work of her bra, looking over her shoulders as he slowly slipped the bra straps off her shoulders and the flimsy bra slipped to the floor. “Hands laced behind your head, Professor Colleen,” his voice demanding obedience from her. He looked in the mirror in front of her, strategically placed so he could enjoy her nakedness, and it tended to make her a little more humiliated to be stripped so systematically. Her reflection shone back at her, her skirt hanging low on her hips, a wide expanse of naked flesh all the way up her body. Her firm, full breasts were almost pointed, hard, sharp nipples begging to be touched. Or worse. With her arms laced behind her, she looked so submissive, her naked body revealed.
She felt a flush run over her body as he pulled her bra off, feeling the bra slip over her nipples, igniting a lust in them as they were bared to the mirror in front of her. She got into the position he required of her, standing like a slave waiting for her Master to have his way with her. She watched as if in slow motion as his large hands slid under her arms and cupped her breasts almost gently. She stared, mesmerized as his thumbs curled up and slowly ran over her rigid nipples, gasping loudly from the first touch. “OOOOHHH,” she moaned, biting her lip as she tried to suppress her lust.
It looked as if her nipples were stretching to touch his fingers, Michael holding them just out of reach, feeling Colleen arching her back until he felt the sharp tips touching his thumbs. His thumbs ran over the rubbery tips, teasing them into stiffening, feeling the blood pounding in the dark flesh. His hands engulfed the firm flesh of her young breasts, squeezing them, her ass shoving back against his cock in response to the harsh treatment, but her hips continued their gentle masturbation.
His hands were hot and powerful, gripping her breasts and squeezing them until she thought her nipples would pop. He released them, only to feel his fingertips grip her nipples as though they were in a vise, pinching the flesh, pushing the blood out of them. She rose up on her toes as he pulled her breasts up by her nipples, the brown flesh yanked grotesquely out of shape.
He released her nipples, the resilient flesh bouncing back, his hands cradling them again, the nipples now twice their normal size, slightly red from the abuse. His hands slid down over her hips, finding the button on the side of her skirt, opening it, the swish of the zipper going down filling the silence of the room. He released her skirt, falling to a puddle at her feet. His hands slid over her abdomen, pushing her naked cheeks against his cock. The thong she wore clearly outlined her mound, Michael able to make out a wetness where the thong had pushed between her puffy pussy lips.
She felt her pussy flood her thong when his hand slid over her abdomen pushing down lower until she felt his fingers trace across her bush, the follicles tingling in excitement. She spread her legs in anticipation for when his fingers gripped her twin lips and squeezed them tightly together. Her body jerked back and forth as he pinched and released her pussy lips in his powerful fingers. His hand engulfed her mound, one fat finger slicing between her pussy lips, pushing her thong between her lips to soak up the abundant juices. “MMMMmmmm,” trying hard not to cry out in ecstasy.
His finger was already wet as he moved in up and down her slit, her ass rhythmically humping back onto his cock. She was enjoying this too much, Michael pulling his hand away, seeing the disappointed look on her face. “Slip those off,” he instructed her, hating to move away from the lovely naked ass cheeks that were rubbing his cock so expertly, but he needed to get to the punishment part before the pleasure part for her.
Headmaster Michael moved in front of her as she bent over, her naked breasts hanging down as she slowly pulled her thong off. The material pulled from between her pussy lips, seeing the material wet with her arousal. She pushed them off of her feet, standing back up, naked in front of Headmaster Michael, his eyes glued to her mound. She knew what she had to do, spreading her legs provocatively until she could feel her pussy lips pull apart, knowing she was opening for his inspection.
She looked so intoxicating, naked except for her heels, her legs spread just enough to give him a glimpse between those puffy, wet lips. “Turn around,” his voice breaking the silence of the room, Colleen jumping at the unexpected noise. She did as he said, turning her back to him, his cock throbbing at the sight of her twin buttocks, split deliciously by the sharp crack, her muscles clenched tight as if she was trying to hide her charms from his eyes. “Bend over.” Her ass rose up when she bent over, the muscles growing taut as she did. “Your legs, spread them to the edge of the chair.”
At least he wouldn’t see her shame as she bent over thrusting her naked ass up submissively into the air. To make matters worse, she had to spread her legs, trying to keep her cheeks tightly clenched, but she could feel her cheeks parting, unable to stop the display of her most intimate body to his piercing eyes.
He could make out the dark split between her cheeks, her pussy peeking out from behind, glistening with her juices. “Reach behind and spread your cheeks open, Professor Colleen.”
Her hands were shaking as she did as he said, her fingers gripping her cheeks, fighting her own body’s reflexes as she pulled her cheeks apart until she felt the cool air of the room blowing across her exposed anus. She knew he could see everything. Including her anus, ashamed at spreading herself so obscenely for him. He didn’t say a word for long minutes, the blood rushing to Colleen’s head as she stayed bent over submissively.
Such a tiny asshole, the little star between her cheeks barely visible. Lower down, her pussy lips pulled apart to reveal the pink, wet flesh of her inner lips and the dark tight hole. He would have loved to sodomize her the way she was, her hands spreading her cheeks while he placed the head of his thick cock against the throbbing hole, but it was time for the punishment. He moved closer to her. “Put your hands in front of you.” She turned, crossing her wrists, she held them out in front of her, Michael ready with the rough, hemp rope, tying them tight. He pulled her close, pressing his cock against her bound hands.
It was just as Joe had done to her, binding her wrists, and then pushing his cock between them, forcing her to masturbate him until he was satisfied. Instead, Headmaster Michael pushed her away, even when her fingers had curled around the thick shaft that lay beneath his pants.
Her fingers were eager, but he had the punishment to mete out first before he would give her the opportunity to satisfy his lust. “Over here,” leading her over to his favorite. It was a kinder, gentler version of the wooden horse. Instead of a triangle shaped board, sharp end up, this one was called a wooden pony. It was a thin board on end instead of the sharp triangle. And it was situated closer to the ground, allowing the victim to put her feet on the ground, though she would have to stand on her toes. Still it would be painful when her feet tire and she had to lower herself down on the board, her most delicate flesh pressed against the hard, unyielding wood, bruising her sex.
She panicked as soon as she saw it. Though she didn’t understand it fully, she knew enough from seeing it that it was her pussy that would be crushed down onto the thin board, cutting painfully between her legs. He led her over to it, raising her arms up by the cuffs until he could run the cuffs through the hook that hung down from the ceiling. There was a gentle hum, Colleen looking up to see a small pulley over her head slowly drawing the hook and her wrists up toward the ceiling. She tried to struggle, but the machine was unforgiving, steadily pulling her arms up until her naked body was drawn taut.
She was quite a sight to see, his cock throbbing at her naked body drawn taut, her naked breasts almost sticking up into the air, her abdomen drawn tight. He took the pony, sliding it down almost to the floor and then pushing it between her legs. He looked up at her pussy. In spite of everything, it was still wet, glistening with her juices. Michael slid the thin board up, sliding up between her legs until it began to push against her clenched thighs. By sheer force he pushed it higher, pinching her delicate thighs until she reluctantly spread her legs and allowed him to move it up. He pushed the button on the chain just as he got the top edge of the board almost too her crotch. “On your toes now, Colleen.” The motor hummed as it pulled her body up higher, Colleen having no choice as her bound arms pulled her body up.
She did the only thing she could do. It was either hang by her wrists or stretch onto her toes. She took the latter; her body perched precariously on her toes, her calf muscles drawn taut. She could feel the board between her thighs, Headmaster Michael moving it up higher until she felt it touching her crotch so delicately. She managed to get just a bit higher on her toes, Headmaster Michael moving back away from her, Colleen looking down to see the thin board protruding from between her legs in front of her.
Michael looked at her, the board a centimeter from her pussy. She was an erotic sight to behold, her body drawn tight, her muscles extended, a light sheen of sweat already beginning to glisten on her naked body. In spite of it all, her nipples stood out like hard rocks. Michael couldn’t wait any longer, slowly taking off his clothes, wanting to free his cock of the tight pants. Her eyes were drawn to the front of his pants, his zipper going down slowly until his cock bulged the tight shorts beneath. He took them off, laying them on the chair, his hands sliding the shorts down, his cock springing free of its bondage, bobbing up and down. His hand stroked it as he looked her straight into her eyes.
He was undressing, his cock slowly revealed. She subconsciously licked her lips when it popped free, the large cock bouncing up and down until his fingers wrapped around the thick shaft. She almost forgot the wooden board between her legs until the cramp hit her calf muscle. “EEEEhhh,” she cried out when she felt the spasm of the muscle. Luckily it stopped as quickly as it started, but she knew it was only a matter of time.
Michael slid up along side her, his cock bouncing along her naked hip. His hands slid up her naked side to gently cup one of her breasts, teasing the hard nipple with his hard nail, snapping it back and forth with a loud thud each time. Her body jerked each time, his cock appreciating the bounce of her skin along the head of his cock dragging along her hip.
Her nipple felt like it was on fire, the sharp snap of his fingernail hitting it with a resounding thud that sent pain lacing through her breast. His fingers suddenly became gentle, lightly touching around her areola, sending goose bumps over the brown circle, her nipple feeling like it was pulsating. Her body began to sweat profusely, Headmaster Michael’s hands running indiscriminately over her naked breasts, igniting a lust in her that she felt between her legs. Her legs were already tiring, her toes trembling as she tried to keep in the position. Her arms were held up just high enough to keep her body taut, but if she went off her toes, she would find her pussy split by the evil board that loomed between her legs.
His hands continued to explore her naked body. Starting with her breasts, his hands moved down over her naked hips and onto her firm ass cheeks. His hands ran over the taut flesh, feeling her muscles tighten, her cheeks clenching when he neared the delicious crack that split her buttocks. He loved to tease her, knowing she was exerting more energy to try to keep him from an indefensible hole. He would have his way with her asshole soon enough, but he let her feel that she had won, his finger sliding up and down the sweat-drenched crack, her muscles keeping her cheeks clenched tight.
His fingers explored her ass, Colleen feeling uncomfortable when they ran over her crack, her cheeks clenching unconsciously as his finger dragged along her crack. No one had ever touched her there. His fingers slid down lower, down her ass and between her legs, tickling at her pussy from behind. They felt good, too good as they slid along her pussy lips, pushing them back to explore the wet inner flesh.
“Such a nice wet pussy, Colleen.” One of Michael’s hands went in front, the other behind her, both of them beginning to rub over her pussy. Her hips began to move instantaneously, unable to stop the pleasure he was extracting from her bound, naked body.
She began to hump the two hands that were masturbating her, forgetting all about the wooden board that was only a centimeter away from her pussy. It was hard balancing on her toes while the pleasure raced through her crotch, fingers plucking away at her pussy as her hips humped back and forth like a dog in heat. “Please, I can’t stay this way much longer,” the muscles of her calves beginning to revolt, ready to cramp.
“Yes, you are riding my hands quite hard. Maybe you should lower your feet.”
“NO! I can’t do that.” She knew the board was below her, sinking down on the balls of her feet would drive her pussy onto the harsh, unyielding wood of the plank.
Michael continued to play with her pussy, his fat fingers sliding up and down her increasingly drenched pussy lips, exploring her inner lips intimately with his fingertips. “Just for a moment. It will give you a chance to rest. And you can lower yourself gently. If your feet cramp, you’ll fall hard onto the board. I wouldn’t want that sweet pussy to get bruised too badly.” Michael smiled as he teased her. His fingers never stopped playing with her pussy, but he wouldn’t touch her clit yet.
He was right, feeling her muscles tighten, knowing it was just a matter of time before her toes or calves would cramp. And Headmaster Michael was not going to let her off the board until she did. She slowly began to move down, feeling the first touch of the board between her legs as soon as she moved lower. The hard wood pushed between her lips, Michael’s fingers deserting her to the harshness of the wood. His hand in front stayed, moving higher up her slit, but still not touching her clit, though she hoped that he would soon. “OOOHH,” she moaned softly when her crotch pushed harder onto the wood, trying to find a comfortable way to push her pussy onto the hard wood without bruising her flesh. She could feel her pussy lips curl around the wood almost lovingly, sure that her wetness was staining it. It hurt, feeling like a knife was slicing up her pussy. She lowered down more, feeling her flesh pinned between her pelvic bone and the harsh wood, trapping it, crushing it. Her feet finally hit the ground, but her relief was short lived, the pain only transferred from her legs to her crotch.
Michael’s cock jerked up and down as he watched her labia splitting by the wood, the light-colored wood stained with her wetness. Even though the wood was smooth, it wouldn’t feel that way. His finger traced up her ass crack when he saw her cheeks unclench, his finger running up the moist crack and over her raised anal bud before she knew what was happening. She jerked forward unexpectedly, a sharp gasp from her lips as she felt her pussy slide along the unforgiving sharpness of the board.
It felt like she was cut up the middle, her hips jerking uncontrollably when his fingers touched her anus, tightening her cheeks to keep it out, but sliding her pussy along the board. The board didn’t feel smooth, her slick pussy lips feeling every minute bump and crack in the wood as if it were serrated. She couldn’t believe the pain that shot through her pussy, straining with every muscle to raise herself up again, feeling the instantaneous relief when her pussy pulled from the board. “Please,” she begged. “Take it out.”
Michael’s hands returned to her pussy, front and back, teasing at the flesh until her hips began the movement again, moving back and forth on his masturbating fingers. “Feels good, doesn’t it, Colleen.”
Time went by quickly, her toes losing their ability to stay up so high. Headmaster Michael seemed to know before she did, his fingers deserting her, staring into her face as she was resigned to the fact, slowly lowering down, just in time before the cramps hit. She moved quicker, her crotch split harder, the wood slicing between her lips and crushing the delicate flesh. She had to move forward a bit, trying to find a spot that wasn’t already bruised. “EEEEGGG,” unable to contain her cry of pain. It was so cruel of Headmaster Michael, forcing her to crush her delicate flesh in such a harsh manner. She felt his fingers returning to her ass, two fingers pushing apart her ass crack to open her up obscenely. She could only imagine how she looked, but she struggled not to clench her cheeks, only making her pussy clench on the wooden plank harder if she did. She felt the fingers tickling along her crack, slowly running over her anus, sending it into spasms when it lingered too long on her defenseless hole. She froze, unable to move, afraid of his finger, but just as afraid of the wood that split her sex so painfully.
Michael could feel the heat in her asshole, his finger playing around the tiny hole, teasing it as the muscles began to spasm. He pushed harder with his finger, feeling the hole begin to give, but he pulled his finger away just before he breached the tight knot of her asshole. He wanted to tease her longer. His fingers went in front, sliding up her slit until he found her clit, hard and swollen. He pinched it.
“EEEWWW,” Michael suddenly pinching her clit, sending her hips backward, tearing her pussy along the sharp board. Another pinch, her hips jerking again. Her body was torn, finally getting her clit the attention it wanted, even though it was a bit rough. But the board cut her pussy, slicing along her inner lips, sure that she was bleeding. She went from pain to pleasure in a split second. Her muscles strained one last time, rising up, this time barely able to get off the wooden board. She knew she wouldn’t last much longer. Her legs were giving out on her. She would be resigned to split her pussy on the board.
He loved the look of anguish on her face, knowing that she couldn’t sustain keeping her pussy from the board. Michael’s fingers went between her legs, testing the swollen lips of her pussy, already suffering from being bruised by the board. Her body jerked each time he touched her, but she didn’t cry out. In spite of the pain, her pussy was drenched as well as the board. “Very good, Colleen.” Two fingers entered her, finding her pussy tight and wet, her body jerking up in unexpected shock. He fingered her for a moment, then pulled his fingers out.
It felt good, too good when his fingers slid up her pussy. But just as fast as they invaded her, they deserted her. She knew that she had to settle back down on the wooden plank, not sure she would be able to get off of it again, the muscles in her toes and calves just feeling like mush. He watched her as she slowly settled down, sliding forward, the wood cutting up her pussy as she tried to find a spot where she wasn’t already bruised. “OOOHHH,” she cried out in pain, finally staying perfectly still.
“Try to stay still if you can, Colleen.” Michael would test her now. His hand slid over her ass cheeks, Colleen looking at him, knowing where it was going. His finger traced down her sweat-drenched crack until he got to her anus, stopping, the tip of his finger wet with her sweat, poised in the center of the tight knot of her asshole. He began to apply pressure, moving his finger in a gentle circle when her muscles began to give way to be penetrated.
She couldn’t stop him, his finger poised on her anus. She felt the pressure building, the finger not still, moving around, opening up her tight hole, pressing deeper. She couldn’t keep still, the slightest movement sending her pussy sliding over the harsh wooden plank, slicing her delicate flesh. She was surprised, her anal ring suddenly popped open, the tip of his finger sliding easily inside her pressing hard against the muscles in her rectum. It didn’t really hurt, more uncomfortable and embarrassing to be touch so intimately in such a place. His finger didn’t stop moving, pressing this way and that, fighting her muscles as it twisted and turned inside her asshole.
He couldn’t believe how incredibly tight and hot her asshole was, sucking his finger into a blast furnace. Her muscles fought to keep his finger out, but was no match for the power of his finger. Her hips jerked and shuddered as his finger dug deeper into her asshole, searching the mysterious depths of her hot hole. She was crying out as her hips jerked back and forth on the wooden plank, slicing up her pussy, but his attention was deep in her asshole, his finger probing deeper into her guts.
It felt like a giant snake moving in her ass, slinking back and forth, always going deeper. Her pussy was being torn up, but she couldn’t stay still as his finger probed deep into her asshole. For long minutes he fingered her ass, one finger becoming two, her anal ring stretched too far, the fingers digging too deep. All while her pussy was being rasped along the wooden plank.
He had two fingers deep in her asshole, Colleen groaning when he separated them deep inside her, opening her up from within, her body jerking painfully along the wooden plank, the board slick with her juices.
“Please, take me off the board before you tear my pussy to ribbons,” Colleen begged. “I’ll do anything.” She regretted saying it as soon as the words were out of her mouth, but she had to stop it before her pussy was rendered useless.
“I think I can accommodate you. That is if you will accommodate me.” Michael pulled his fingers reluctantly from her asshole, the tiny hole staying open for long seconds before it closed up tight.
“Whatever you want,” her voice resigned to her fate. She’d fuck him, suck him, anything to end it.
Michael helped her pull up from the board so as to not damage her pussy anymore, long enough for him to lower it to the ground, pulling it out from between her legs and out of the way. He hit the button until her arms were lowered so she could stand flat on her feet. “Spread your legs.”
His hands turned her, Colleen spreading her legs too willingly, her torn pussy lips pulling apart almost painfully. He pushed down on her back until her ass arched up. So he was going to take her from behind. Anything, wanting a cock in her as bad as he wanted to fuck her. She wanted to erase the pain in her pussy, and she knew that Headmaster Michael’s cock would do it. He didn’t let her cum yet, and she needed that.
Michael fisted his cock, pushing down on her back until her ass arched up, her legs spread open, all of her treasures open for him to plunder. He rubbed his cock up and down her slit from behind. In spite of the pain he had inflicted on it, his cockhead was covered with her juices when he finished. He pushed his cock up her backside until he got to her asshole. He stopped, his hands gripping her hips, his own hips driving forward with a powerful thrust that sent the head of his massive cock into the tight asshole with a pop and a piercing scream from Colleen. It felt like a vise had a hold of his cock, her velvet insides gripping him possessively as her muscles rippled up and down the plum-like head of his cock.
She couldn’t believe that she was so naïve. One moment she was waiting for his cock to enter her pussy, the next she cried out in pain when a thick cock split open her asshole and sank into the depths of her intestines. It felt like her anal ring was torn, stretching so far until it gripped the head of his cock in a warm embrace. She should have seen it coming; instead she was impaled on his cock, waiting for him to enter her deeper, waiting for him to sodomize her. And she couldn’t do anything but feel the thick cock sink deeper and deeper into her guts, gasping with each shove of his hips, gulping as if he were shoving it down her throat instead of her asshole.
This was an outtake of my newest novel, Subjected Teacher.