Pussy pain | School for Girls 2 | punishment bdsm stories

Mary Bridget, the Shy One

By Wednesday, Michael had toured the campus with Meredith as his guide and was surprised how well appointed it was. Not in the traditional, educational sense but in how well it was appointed to administer corporal punishment on the girls now entrusted to his care. His office was richly appointed with heavy furniture, desk, chairs and tables, all suitable for students to be placed on or bound to for punishment and the rest of the administration building was suitably equipped. There were special rooms for punishment, with one-way mirrors allowing members of the Board of Directors or parents to watch as punishments were administered to the girls. There was also a large room, with a giant conference table in its center, suitable for a young girl to be spread out on, the Board of Directors seated around her with an intimate view of her punishment.

Each of the rooms held a collection of bondage furniture, much of it specially made, showing an imagination and perversity by the Board of Directors that surprised him. He was astounded at the fine collection of whips, tawses, paddles, and canes at his disposal; a collection that numbered over one hundred implements for delightful torture. He would enjoy using them on a girl's flesh, able to use a new one each time, bringing about a variety of different levels of pain to the girl.

Today he would begin to meet his students, paying particular attention to the “charity” cases of the school. His first visitor was Mary Bridget. She had been sent to see the Headmaster for not paying attention in class. Her inattentiveness was reflected in her grades; while she was normally an “A” student, her last test had garnered her a “B". Michael had read her file, an orphan, picked by Meredith because of her high score indicating submissiveness on the test they administered to all prospective scholarship students. She normally had high grades, but her test results also indicated she lacked self confidence and self-esteem, a loner, not fitting in with the rest of the students, especially the rich and beautiful. Mary Bridget was plain. Most who saw her would probably not remember what she looked like five minutes later.

Michael studied her features and saw that she actually was a beautiful girl, a pair of dark rimmed glasses and lack of makeup hid rather than enhanced her beauty. She had a lovely pair of lips, her tongue continually pushing out her mouth to moisten them, Michael's cock hardened at the thought of how he could put her dainty tongue and full lips to good use. Her breasts were partially hidden by the school blazer, a glimpse of naked flesh between the buttons. Her breasts were probably small, tiny bumps on her chest but he enjoyed that. With small breasts, the nipples and areolas were usually large, filling the white flesh that surrounded it like large targets, targets his fingers would enjoy finding. He watched her crossing and uncrossing her legs, nervous at his leering glare. Her hips were broad, assuring Michael that she had a nice ass, an asset he planned to punish fully. The required short skirt gave him a good view of a lovely set of legs encased in white knee socks.

Mary Bridget sat in the large chair, uncomfortable on the hard wooden seat. She did not know that Michael had placed it there so he would have full views of a student's nubile bodies.

Headmaster Michael was standing over her with a long, wooden ruler in his hand.

"My first week and you are the lucky one to first test my abilities as the new Headmaster,” he spoke to her. “You will find that I am quite stern and use punishment as a deterrent to keep the bad behavior from repeating itself. You were sent to me for not paying attention in class. Your instructor felt that it was affecting your grades and I have to agree. What do you have to say for yourself, Mary Bridget?” He looked at her, hiding his grin, unable to contain the joy of the thought of his first student to punish. It had been a long time since he was deprived of such young flesh to abuse. Mary Bridget would have a long day in front of her in which to please him.

Mary Bridget was nervous. The previous Headmaster had left her alone, although the Chancellor had bothered her somewhat, with her leering glances but never anything physical. Now she was in the Headmaster's office. Though her head was bowed in shame, she saw the way he looked her body up and down as she trembled before him. “I'm sorry, Sir, it won't happen again,” finding apologies usually worked.

"Well, a sorry will not work with me young lady. You need to take pride in yourself, you are a very lovely girl, you just lack self-confidence. I am going to help you learn what you have to offer."

Mary Bridget looked up at Headmaster Michael, surprised that he said she was lovely. No one had ever told her that before. She raised her head to study him more closely. He was handsome in a rugged sort of way, probably about forty-five years old. She had heard some of the other girls talking about him, saying that he was single, wondering why some lucky lady had not snatched him up. He looked like he took care of his body, suddenly feeling herself blush as her eyes came to rest on the bulge in his pants.

Michael saw her looking at him, smiling as he saw her looking at his crotch. “Speak to me, Mary Bridget!"

She looked up, shocked at the tone of his voice. “Yes sir, I will do what you say."

"Sit up in the chair, don't slouch,” he ordered her, seeing her respond instantly. Yes, she will train well. He took the wooden ruler, a long one, over eighteen inches and began to lightly tap her knee, first one, and then the other. Each time he hit a bit harder until Mary Bridget slowly lets her legs part, smiling as she so willingly complied. He moved the ruler up higher, lightly tapping on her tender inner thighs.

Mary Bridget squirmed in the seat, her legs partly spread, the ruler beginning to hit harder. She brought her hands up to protest, but Headmaster Michael slapped them back down with the ruler, smashing her knuckles.

"Ow, that hurt!” she exclaimed, instantly realizing her mistake. “Sorry Sir,” she promptly stated and put her hands behind her back, her knuckles stinging from the blow of the ruler.

Michael smiled again and returned to slap at her inner thighs, each time the sickening sound of the wooden ruler against her flesh ringing out in the room. He slowly forced her to open her legs wider, her skirt riding up, her arms clenched behind her back, unable to prevent him from forcing her to spread for him.

"Yes, Mary Bridget, you will learn to obey. Now spread your legs a little wider so I can slap the tender flesh between them. You need to be punished.” Michael tapped the ruler harder on her thighs, the white flesh turning red from the constant barrage of slaps, her tender thighs exposed to the cruel instrument of pain. She looked directly into his eyes, pleading for him to stop, his smile his answer to her.

"Good girl,” as she allowed his continual punishment of her thighs, “now hang your legs over the armrests.” The ruler continued its relentless pursuit of untouched flesh, moving up and down her thighs, first her right leg, then her left. He slapped harder when she did not immediately obey, the ruler becoming progressively more painful with each tap of the hardwood on her skin.

Mary Bridget began to cry, her tender thighs unwillingly accepting the hot sting of the ruler, her hands sore from the ruler rapping on her knuckles, unable to stop him from making her slowly uncover her legs, her skirt riding higher and higher, her white panties barely hidden from his view.

"Ow, please that hurts,” she begged, but his eyes stared only on her near naked legs, focused on his punishment of her tender thighs and slowly uncovering her body to his gaze.

"I said put your legs up over the armrests. I won't tell you again.” He grew impatient with her lack of respect for his authority and slapped her right thigh hard, the ruler smacking her girlish flesh with a sickening sound that reverberated throughout in the room, accompanied by her cry of pain. The sobbing increasing but her legs reluctantly began to move. First the right one slipped over the thick wooden armrests, her leg dangled uselessly over the edge. She realized how obscene she looked, her legs spread wide. A tap of the ruler on her exposed inner thigh urged her to comply with the other leg, up and over the armrest, her already short skirt moving higher. She sat there humiliated. If he stood in front of her he would have an unobstructed view between her legs as she slid down in the chair, her legs spread wide over the armrests. “Much better, Mary Bridget. You are learning that it is much less painful to obey me."

His eyes stared down at her naked legs, making her feel ashamed as she saw his hard cock jutting out from his pants, knowing that she was the cause of his erection. “Yes Sir,” she whispered. Her legs trembled, wanting to close as he moved in front of her, knowing that he would now have an unobstructed view up her skirt, her simple white panties her only protection.

"Stay still,” he ordered her to stem her reluctance. He pulled his chair out from behind his desk, parking it in front of hers, sitting down, his gaze drawn to the darkness between her legs. She looked so good, her legs hanging over the arms of the chair, her thighs spread so wide. “You don't like me looking at your body this way do you, Mary Bridget?"

"No, Sir,” she managed, uncomfortable as he stared at her. She hoped he was finished, but her hopes were dampened as she watched him slowly move the ruler between her legs, the tip rubbing up and down her thighs, each time moving in closer.

"I find that humiliation teaches young girls like you to obey. See how responsive you already are? We have so much more to accomplish today, Mary Bridget. I will help you gain self confidence and using your body is one way to do it. You must feel comfortable with your own body and I can help teach you how, but you must cooperate. Can you do that, Mary Bridget?"

"What are you going to do?” she asked nervously, afraid of the answer she might get.

"You look so lovely in the chair, your legs hanging over the edge. I can almost see your pretty panties. I want you to pull up your skirt for me.” She was a beautiful sight, a young girl, her legs dangling over the arms of a wooden school chair, her skirt hiked up high on her thighs. He tapped her thighs with the rigid ruler, then let it slowly slide up the inside of her thigh, watching her eyes glued to the wooden ruler.

"I can't do that! No!” Mary Bridget exclaimed.

Michael leaned in closer, his hands on her knees, propped up high on the armrests. He let them slowly slide down her inner thighs, her legs still spread wide. “Hold still, Mary Bridget,” his hand grabbing her thigh flesh hard when she started to move, “I said hold still,” his voice firm. “I think you need to be punished more.” He stood up, towering over her. “Get up!” He ordered her in a stern tone, watching her jump at his loud voice, nervous now.

She got up, his large hand gripping her arm tightly, pulling her over to another chair, this one a little strange. It was a heavy wooden chair, just like the last one, but the back was very short, a little over a foot high and covered in padded leather. It was wide, over two feet, with heavy wooden legs; wooden dowels connecting the legs together, about six inches from the floor.

"Kneel on the chair, facing the back,” he ordered her, his hand pulling her over, not allowing her to protest. He watched as she reluctantly got up on the chair, kneeling on the seat, her ass already a tempting target. “That's a good girl,” his hands pushed her toward the back, “a little farther.”

He watched as her hands gripped the back of the chair and looked back, a puzzled look on her face as he manipulated her body for his pleasure.

She knew that her skirt was already riding high on her legs, realizing now that she might just as well have submitted to lifting her skirt before, his positioning of her body now doing what she had refused to do, resigned to the fact that her panties would soon be grossly exposed to his gaze.

She also feared now that she would have to endure a punishment for her refusal, afraid that her upraised posterior was what would suffer the punishment.

Michael looked down at her body, so tempting; her eyes wide open in fear as she watched him prepare her, letting him have his way with her young body. He was pleased with the way she had finally and fairly easily accepted his power over her. He would enjoy Mary Bridget so very much.

"You are being such a good girl. If you cooperate, I will not have to be so harsh with your punishment. But you must learn to obey without question.” His hands moved down to grip her hips, and felt her body tremble at his unfamiliar touch. “I want you to hang over the top of the chair, I will keep you from falling over, but I want your upper body draped over the top of the chair.” She began to move forward, his hands securely gripping her hips.

She let her head fall toward the floor, her body bending at the waist, now understanding why the back of the chair was so low. She was bent at the waist, her hair fanning out before her and felt a rush of dizziness as the blood rushed to her head. She panicked when her center of gravity shifted, her body leaning forward too far.

"I have you, Mary Bridget, trust me,” his voice soothed and her muscles relaxed, his hands tightened on her hips with a reassuring squeeze. “Now tightly grip the rung on the bottom of the chair with both of your hands. This will keep you from falling.” He watched her ass rise higher the lower her body went. He was pleased at the way she presented herself for her punishment.

Her face, partially hidden by her hanging hair, her face turned red as the blood rushed to it, her knuckles white as they gripped the chair rung tightly. He nodded to her, acknowledging the anguish in her eyes. “I'm going to let you go, hold tight, you won't fall,” he ordered, then waited until he felt her body begin to relax before he let her hips go, her body sliding forward, her grip tightening as she learned how to hold the position without falling. “Very good, Mary Bridget,” his hand lightly tapped her ass.

She was almost pleased with herself as she gripped the chair, his voice praising her. She could not see behind her but she knew that her skirt had already ridden high up over her butt, his hand gently patting bare skin. She felt his large calloused hands on her legs, running up between them before gripping each inner thigh; her body suddenly trembled with lust as his hands came dangerously close to her sex. God, how could this be making me sexually aroused! But it was, her body quivered as his hands pushed outward on her thighs, forcing her to spread her legs further apart, knowing how exposed she was making herself as she shifted to please his demanding hands.

"More, Mary Bridget, until you reach the arms of the chair. I want you spread wide open for me,” his hands urged her compliance, squeezing the tender thigh flesh tightly with his powerful hands when she hesitated, her body jumping instantly to his masterful touch.

How he loved young girls, their bodies and minds so pliant, so willing to be manipulated by a powerful authoritative figure. Her hips touched the edge of the chair, the gap between her legs over a foot and half, her inner thighs now open and exposed should he desire to punish the tender flesh. More important, her panty-covered crotch was so brazenly exposed, the tight white panties molding to every nook and cranny. He could almost make out a faint trace of wetness on the virginal white panties. Could she actually be enjoying her submission to him, already? She looked so inviting, her ass raised up high, offering young flesh for the painful spanking he would administer to her, her back curved downward, kneeling so submissively on the padded chair, her legs spread wide.

He chose a large leather paddle and moved in front of her so she could see the instrument that would soon inflict such pain on her body. He laid down two other paddles on the table near her, similar but one with holes in it to create a more powerful swing and the other with metal studs on it, a very formidable weapon. He noted the terror in her eyes and bent down very close to her. “If you were a good girl, I wouldn't have to do this to you,” he admonished her. “It's your own fault.

Maybe next time you will do what I tell you to do without question."

Resigned, she braced herself for the paddling, her butt raised up high in submission, knowing that she couldn't stop him. She would suffer her fate and take her punishment. She felt his hands on her hips, gripping tightly, knowing that her skirt had already pulled up high, her panties her only protection now.

"Now let's get this pesky skirt out of the way,” he chuckled, slowly pulling her skirt up until it lay high on her back. He admired the view, her taut buttocks stretching her white panties tightly, the slit down her backside visible. “So much better, Mary Bridget. You have such a nice ass,” his hands ran sensuously over her arched ass, feeling her clenching muscles as she suffered his fondling.

She gripped the rung tighter as his fingers took liberties with her upraised butt, unable to stop him. She was embarrassed as she imagined how she looked, knowing that her panties barely concealed her sex to him but unable to stop him from having his way with her. She feared what else he might do. She also feared what he was doing to her now. She noticed an unfamiliar tingling between her legs as his powerful hands gripped her cheeks, trembling as he moved closer to her sex but never quite touching her. It was as if she was being teased, yet here she was, waiting to be paddled, not something she would expect to get sexually aroused over. She was confused. When his hands left her, her breathing stopped, knowing what was going to happen, but not knowing how it would feel. She didn't have to wait long, the whooshing of the paddle swinging through the air made her body tense up in expectation, her ass cheeks tightening in anticipation.

It was worse than she had expected; her body unable to assimilate the pain as the paddle slapped hard against her upper thighs and catching the lower part of her buttocks. Her body pushed forward, her hands gripped the rung tighter. She yelled, biting her lip from the pain as it shot up her spine. It was terrible; her skin was on fire! She arched her ass back again, positioning her bottom for the next strike, afraid of further punishment if she did not obey.

Michael was pleased as she moved back into position, offering up her ass for the next hit. His hand roamed over her upper thighs, feeling the heat generated by the large leather paddle, feeling her body cringe as his touch ignited a fresh batch of pain. “Good girl, raise your ass up higher for me,” ordering her to expose herself more to the paddle, wanting her to get used to obeying all commands, no matter how painful they might be.

Mary Bridget obeyed, her ass arched higher, her legs still spread wide, braced for the next painful hit. She was not disappointed; Michael hit her squarely on her twin buttocks, the leather paddle sinking into the young flesh with a powerful jolt that rocked her body again. This time she didn't move, her body braced for the impact. She silently screamed in pain, her lips clenched tightly, not wanting to raise Michael's ire any more than it already was. She felt the hand again, casually rubbing over her clenched cheeks like a lover might do, rubbing the pain away, but Mary Bridget knew he was only preparing her for the next hit. She received a total of six strokes with the paddle, the last one with the studded paddle, the metal studs leaving deep gouges in her cheeks, a reminder of what Michael could inflict in the future. She was sobbing now, tears covering her face, her butt a mass of pain.

"Are you ready to obey me now, Mary Bridget?” Michael looked at her, pleased that she still stayed in the proper position.

"Yes, Headmaster Michael,” her eyes begged for the end of the punishment.

"You've been a good girl. You took your punishment well. Now I want you to stand in the corner, your back to the room and hold your skirt above your waist. You will do this for a half an hour.” He watched as she quickly got up from the chair and rushed over to the corner of the room. She lifted her skirt high above her waist, looking back at Michael for approval.

"That's good, now face the wall,” he ordered her, sitting down at his desk and began to work. He looked up at Mary Bridget every few minutes, his cock hard in his pants as he saw the delectable ass cheeks exposed to him. Finally thirty minutes were up; Michael rose from his chair and moved behind Mary Bridget. He felt her body tremble as his hands reached out and touched her buttocks, grasping the firm flesh in his large palms, squeezing the taut cheeks. His finger slid up and down her crack, making her feet fidget as she was rudely fondled.

"Turn around,” he ordered her, “but keep your skirt up."

Mary Bridget did as she was ordered, her skirt held high above her panties, the silky material having already crept between her pussy lips, embarrassed as how she looked, her pussy lips outlined in the white material. She looked in his eyes and then down to his hand as it moved to the front of her panties. She shivered when his fingers lightly touched her panty-covered pussy.

"Spread your legs for me. I'm going to make you feel good. You want that don't you, Mary Bridget?"

She hesitated only for a second before her legs began to shuffle outward, wider and wider until she saw acknowledgement in Michael's eyes, her legs now open over three feet wide. “Feel good, Sir?” She was confused at what he had meant but when she felt his fingers begin to move up and down her slit she understood.

"Have you ever masturbated, Mary Bridget?"

Her face turned crimson in shame; he was asking her the most intimate question. Should I lie or answer truthfully? If she lied and he found out, she knew she would be severely punished. Not wanting to take that chance she blurted out, “yes, Sir."

"I'm going to masturbate you, Mary Bridget. I want your eyes staring directly into mine. I want to see the look in your eyes as you cum for me. You want to cum for me, don't you, Mary Bridget?” His fingers moved between her pussy; powerful fingers pushing back the puffy lips, pushing her satin panties in the gap, sawing up and down her slit.

She shuddered as he touched her pussy, her eyes staring directly into his, seeing the lust as his strong fingers began to masturbate her. She shuffled her feet, allowing him to push in deeper, trembling as she felt the wetness between her legs. She turned red again, knowing that he could feel the same thing.

"You're getting wet for me, Mary Bridget. That pleases me.” His hand clutched her sex; his fingers still snuggled tightly between her pussy lips, in the heat of her body as she moved back and forth, his masturbating fingers sexually arousing her body.

No one had ever touched her like this before, especially as he was doing. Forced to stand there with her legs parted, allowing the Headmaster complete access to her sex, her hands clenching her skirt tightly as she endured the humiliation. But she also felt a deep arousal between her legs, a need that only his masturbating fingers could make go away.

His fingering of her pussy slit became more urgent, faster, soaking her silk panties in her own juices as she became more aroused. Her hips began a gentle motion, back and forth, pushing her sex onto his fingers. He looked into her eyes, seeing a glossy look in them as if she were hypnotized by him, staring almost blankly. “Are you enjoying my fingers, Mary Bridget?” His fingers moved higher, rubbing lightly over her clit, her eyes opening wide as he touched the sensitive button.

"Ooh,” she moaned softly, ashamed at how her body was reacting, gently fucking his fingers.

“Yes,” she whimpered, seeing the smile on his face as she humiliated herself for him.

"I want to feel your naked pussy, Mary Bridget.” His fingers slipped from her pussy, her eyes opened wide in disappointment, her hips trying to find the fingers that were giving her so much pleasure. He moved both hands up to the top of her panties, gripping the edge of the satin material, pulling it from her body. He slipped a hand into her panties, touching her naked abdomen for the first time.

"God,” she shuddered as his hand touched her naked flesh, her panties trapping his fingers inside them, embarrassed that things had gone this far. “Please, don't,” she begged, but her hips were already beginning to fuck back and forth again, searching for the touch of his hand on her pussy.

She didn't have to wait long; Headmaster Michael eagerly sought out the hot, wet pussy hidden by her panties, his fingers running through her sparsely covered bush before finding her slit again, this time his fingers touched her hot, wet pussy, without panties hindering the feel of her body. She shuddered, afraid that she would cum from the touch of his hand. No one had ever touched her like this. No one.

Headmaster Michael's finger slipped between her pussy lips, pushing apart the lips slick with her juices, his finger gliding up and down her slit. He felt her bow her legs out, spreading them wider, giving his finger access to her pussy. “I like that, Mary Bridget. I like when you open up yourself to me,” his eyes stared into hers, his finger circling the opening to her vagina, feeling the tightness of her body. “You're a virgin, aren't you?” he questioned her.

She pushed her hips forward, wanting his finger to find her opening, wanting him to explore her vagina. “Yes,” she replied, “no one has ever done what you are doing to me."

He pushed his finger into her vagina until he felt her hymen, a gasp from her lips at the sudden invasion. Her pussy clenched on his digit, her small opening struggled to receive him, her juices flowing freely. His thumb moved up to the top of her slit, searching out her clit, finding the swollen bud. He tapped it lightly with his thumb, her hips pulling back in shock at the feel of his finger.

"Oh God,” quickly pushing her hips forward again, her clit found his finger, her hips began a gentle rotation, her vagina received his finger fucking, her clit rubbed back and forth over his calloused finger, her legs shook as she was ready to cum.

"Do you want me to make you cum, Mary Bridget? Are you going to cum all over my fingers?”

He wanted to force her to say it.

"Yes,” she cried out, “make me cum,” her arousal at a fevered pitch, unable to control herself any longer. “Please!"

He shoved two fingers inside her tight pussy, his thumb rubbing her clit back and forth, his calloused finger rubbing the sensitive skin harshly. But, that was exactly what she needed. All that she needed to drive her over the edge. He looked into her eyes and could see it. The lust.

"Yes! Yes!” Her legs almost gave out, his fingers inside her pussy kept her upright, pushed upward, forcing her to rise up on her toes as he speared her virgin pussy. She shook her hips back and forth as she soaked his fingers with her juices, the wetness running down the inside of her thigh. She felt his powerful hand and fingers draw the orgasm from her body, unable to control her wanton response. She trembled and shook as a second, more powerful orgasm hit her, her pussy clenched tightly on his fingers. God, what would it feel like if it was his cock inside her? The thought prolonged her orgasm. Just when she thought she was finished his fingers twisted and turned inside her, reaching and touching unexplored territory in her virgin pussy sending one more, lesser orgasm through her body. She slumped against him; his other hand circled her body, holding her close to him. She could feel his hard cock against her thigh, wishing that it was deep inside her.

He liked the way she came for him, her body betraying her, his fingers soaked in her juices. He pulled one hand out of her panties, his other gripping her ass cheek, pulling her pussy against his rock hard cock, making it jerk. He moved his fingers up to her face, her eyes watched as they moved toward her mouth, her juices glistening on the tips. “Open your mouth. I want you to taste your juices,” his fingers demanding, forcing themselves into the corner of her mouth until her tongue hesitantly began to rub over the fingertips inside her mouth.

She liked the taste, slightly salty. She sucked his fingers in deep, her tongue bathing them, licking off her juices. His other hand still held her pushed against him; she could feel his hard cock twitching against her pussy, throbbing in desire. His hips began to rotate, his steel cock rubbed up and down her slit, feeling huge. He stared into her eyes.

Headmaster Michael pulled away from her, his cock needing satisfaction, but today would not be the day with Mary Bridget. He wanted to break her in gradually. “Be in my office tomorrow at three o'clock. We will have another session.” He pushed away from her, moved back to his desk, dismissed her, yet watched as she hurriedly rushed to fix her clothes, the look of the schoolgirl returning, except her flushed face that revealed her secret.

Mary Bridget rushed from the room, embarrassment taking over, humiliated at cumming in front of him, fearing another day tomorrow with him. What did he mean by “session?” Would he punish her again?

Mary Bridget was barely able to sleep, the thought of what Headmaster Michael had done to her flashing into her mind. She imagined how she looked when he masturbated her and came all over his hands. How could she have let him do that to her? But her hand slipped silently beneath the sheets and into her panties, turning over onto her stomach, her hand trapped between her legs, her face smothered into the pillow to silence her as her fingers began to rub. She imagined Headmaster Michael's hard cock. It felt so big when he pushed it into her pussy. Would he make her touch it? Would he put it inside her? The thoughts made her fingers work faster, moving up and down her slit, her ass rising up and down in the bed, fucking the fingers beneath them. She silently screamed into the pillow when she came, her body shuddered in ecstasy as she soaked the sheet beneath her with her cum.

She couldn't pay much attention in classes, her thoughts in the room with Headmaster Michael, taking liberties with her body. Doing things that no one had ever done to her before. The bell rang, the last class ended; time to go to the Headmaster's office again. She knocked on his door, his voice boomed.

"Come in."

Mary Bridget saw the Professor from her last class in the room with the Headmaster, who stopped talking as she entered, as if she had interrupted a private conversation.

"Thank you, Professor. I will take care of it.” The Professor left the room as Mary Bridget came to stand before him. She looked even lovelier than yesterday. Her orgasm seemed to have given her face a permanent flush.

"The Professor tells me you were very inattentive today, staring off into space. I thought our session yesterday would have taught you a lesson, but it seems that you need a stronger reminder,” he harshly lectured her.

It wasn't as she thought it would be. After the way he had masturbated her, his gentle touch, she thought he would be different, more lenient, more attentive. But he was yelling at her.

"I'm sorry, Headmaster Michael. I kept thinking about what you did to me yesterday,” she blurted out, almost immediately knowing that she shouldn't have said it.

"So it's my fault that you can't pay attention? I tried to be nice to you and now it's my fault!” his voice became louder. They always did this, he thought. Just because he made them cum, they thought that they could do anything; that things had changed, almost as if they thought of him as a lover. No, he was their disciplinarian and Mary Bridget would learn that the hard way today.

He enjoyed this part of the game. It made them so vulnerable when they found out the reality of their situation. It would make her so much more willing to accept the things he would do to her today.

"No! I'm sorry Sir,” she stammered, his angry voice expressed his disappointment in her. Just when she thought she was doing so well in pleasing him.

"You will be sorry when I'm finished with you. Stand over here.” pointing to his large, ornate desk. “Back straight, don't slouch. I can't tell whether you have any breasts or not.” He watched, as she stood up taller. “Take off your jacket. I can't see a damn thing with that on,” he ordered her, his impatience showing. She quickly removed it; Headmaster Michael threw it over into the corner. “That's better. Your breasts are a little small, you will have to arch you back and stick them out for me. Try to be a good girl for a change."

Mary Bridget arched her back, watching as her smallish breasts pushed out the front of her blouse. It looked obscene, the pose she was putting herself in, but he was already angry and she did not want to provoke him any further.

"Much better, now hold still. I want to feel them.” His hands reached out, her eyes watched as he slowly moved toward her breasts. He grabbed both of them in his large hands, able to encircle them in his wide palms. He tightened his grip, the pliable flesh underneath compressed in his grip. “Yes, small but very firm, I like that, Mary Bridget,” he complimented her, seeing her face grimace as he squeezed harder.

"Step out of your skirt, quickly,” he ordered her, watching as she reached around and pulled the zipper down on the plaid skirt, the blue garment falling into a puddle at her feet. Michael was pleased at how well she was responding. He looked at her as she trembled in her cute white panties and knee high socks. “Are you going to be a good girl for me, Mary Bridget,” his eyes looked into hers, seeing the fear in them.

"Yes, Headmaster Michael. I'm sorry,” she pleaded.

"First, you must be punished then I will show you how you can make it up to me. Now bend over the desk to receive your punishment like the naughty girl you are.” He turned her around, pushed her to his empty large wooden desk that seemed so big compared to her little body pressed against it. He pushed down on her back, watched as she slowly bent over, her ass pushing back as she did, her panties tightening on her firm butt. His hand moved down to her ass, capturing one cheek as she bent. “Yes, I'm going to have to punish your ass, Mary Bridget. It's the only way you will learn. Bend over farther, put your head on the desk and turn this way. I want you to see what I am going to do to you."

Mary Bridget shivered in fear as she sank down onto the desk, her breasts pushed into the hard, unyielding wood, her face flat on the cold top, facing Headmaster Michael as he'd ordered her.

Her cheeks relaxed as his hands continued to rub her butt, not wanting to inflame him anymore than he already was. He walked out of her line of vision then returned at the front of the desk.

“No!” she cried out when she saw the cane in his hand.

"You are lucky I'm only using the Preparatory School Cane. This is the smallest one with a diameter of” and a length of 30". You will receive four strokes of the cane. Two on your panties and the last two will be administered on your bare buttocks. If you move, the caning will begin all over. I expect you to count each stroke as I give them to you. Do you understand, Mary Bridget, what is expected of you?” He waited patiently, through her sobs. He stepped back to get a good swing with the cane that he knew would concentrate the pain in a tiny thin line. That what was so great about using a cane, the ability to continually hit new, untouched flesh, moving up and didn't require as many strokes to make an errant female willing to do anything to avoid any further punishment with it; though he did love to punish just for the sake of hearing the cries and the begging of him to stop.

"Yes, Sir,” Mary Bridget sobbed, her body already braced for the first stroke of the cane. The sound of the cane licking the air a precursor to the thud as it struck her flesh squarely on her panty-covered cheek. It didn't hurt as it struck, Mary Bridget was dumbfounded. She screamed as the burn suddenly shot out from the area she was struck, the intense pain rushing to her brain. It was nothing like the spanking he had administered to her yesterday with the paddle. The paddle had a broad dull aching pain; the cane felt like her body was torn open, a sharp eruption at the spot where the flexible rattan cane smacked her tender flesh. She didn't know how she would be able to stand three more, quickly adding “One, Sir!” not wanting to receive any more than the four.

Her scream almost made him cum, her body jerked in pain, her face covered in tears as she sobbed, trembled. Yes, she will be much more willing once he finished. And he would test her submissiveness to the fullest. She wouldn't be the only one to receive sexual gratification today; she would have to satisfy his lust, as well. He let her fully absorb the blow before he gave her another. He heard her suck in a deep breath as he swung the cane, the whoosh filling the room, the dull thud as it struck her flesh only inches from the last, then her loud shrill of pain, her feet dancing with the torment.

"Two, Sir!” she screamed, hopping on her feet, the pain driving her crazy. Her ass burned where the cane had struck her flesh, afraid she would not be able to sit for a week, constantly reminded of the sharp bite of the cane.

Michael enjoyed her dance of pain; with her panties off she would be so much more revealed. “It hurts doesn't it, Mary Bridget?” His hands ran down her ass cheeks, her body shuddered in pain when he traced over the welts he had inflicted on her body. He could feel the heat rise where the cane delivered its damage. “Let's slip those panties off you, Mary Bridget.” Mary Bridget shivered in fear, the second time that her panties were pulled down; embarrassed that Headmaster Michael had so much control over her body, stripping her at his whim, forcing her to suffer the humiliation of being naked before him. She was afraid of him and the punishment he could administer to her, he knew it and used it as leverage to make her submit to him. She trembled as his hands touched her naked ass cheeks, her panties slowly lowered, the feel of his eyes burning a hole in her as he watched from behind her. She clenched her cheeks and legs tightly together as the panties were slowly pulled down below the hill of her buttocks, his finger lightly tracing down the split in her cheeks, her muscles taut as she suffered the fondling of her naked body.

"I need to pull them down your legs, Mary Bridget. You are going to have to relax your thighs,”

his voice raised, impatient at her. “Now!” he shouted.

Mary Bridget quickly relaxed her legs, his voice frightening, afraid the last two strokes with the cane would be too painful to bear if she angered him any more. She felt her panties slipped down her legs, Headmaster Michael lifting her legs one at a time to pull her panties away, leaving her naked from the waist down. She felt him bow her legs out each time he lifted them, hold them open, his hands running up her naked inner thighs. Her sex was exposed and the cool air of the room coated her heated sex. She allowed him to manipulate her body, not willing to anger him any more.

His hands reached underneath her abdomen, “Raise up, Mary Bridgett. I want your ass up in the air.” He pulled her upward, watched when her muscles tightened as she had to raise up on her toes, enjoyed the way her slender legs looked, so lean and muscled. “That's much better, now stay in that position for your punishment!” he ordered, his hands returned to her butt, caressed the flesh, the twin red marks from the first strokes of the cane now visible.

"Ow,” she cried quietly as Headmaster Michael's hands ran over the area where the cane had inflicted its marks on her skin, cut and open, his fingers igniting the pain again. She strained on her toes, feeling so helpless, her butt arched up in the air, so exposed. If it hadn't been for her tightly clasped thighs she would have been more humiliated, at least her sex was hidden from his view. At least for now.

Michael picked up the cane again, admiring the way he had positioned her body for the final caning of her bare ass. Her legs were high and drawn on her toes, her muscles strained to keep the position. It pushed her ass up high, higher than her back, thrust out, her naked cheeks as an offering for the brutal stroke of the cane. He rubbed the cane over her flesh, Mary Bridgett looked over her shoulder at him, tears filled her eyes, fearful of the pain the cane would inflict on her naked flesh. Yes, she would be so much more submissive and willing to do whatever he ordered her when he finished. His cock was hard and she would satisfy his lust today, her caning brought so much pleasure to him. Next time he would whip or cane one of the other errant students, it would be enjoyable to have Mary Bridget on her knees in front of him, her mouth eagerly sucking his cock, the sound of the girl's screams as he whipped them always exciting him so much.

The cane whooshed through the air, Michael's arm reaching far back, wanting to get the maximum swing. It hit her white ass with a thump, the thin cane sinking into the delicate skin and flesh.

She was oblivious to the pain; her body trembled, but did not move, feeling the cane, but not the pain she expected. Then it hit the sharp, intense bite of the cane as it tore into her flesh. She screamed at the top of her lungs, her feet danced back and forth as the most intense pain she had ever felt rushed to her brain. God, how could he do this to her, how could he purposely inflict such terrible pain on her delicate body? Tears fell profusely from her eyes; her head on the desk, her bottom smarted from the caning. She almost forgot the, “three, Sir,” she managed to blurt out between sobs.

Michael's hands rushed back to her ass, the heat where the blow had struck, waited, pleased when the white flesh began to turn red then purple. She would remember this for a long time, especially when she sat down. He felt her flinch as he touched the wounds, re-igniting the pain.

“One more, Mary Bridgett, one more,” his cock so hard with the need to empty his cum into her mouth.

Oh God, one more. She couldn't stand one more, her bottom ablaze in pain, his hands made sure that she felt it. She arched up again on her toes, higher this time, willing to do anything to please him, not caring how obscene she looked from behind, only wanting to get the caning over with.

She bit her lip, clenched her mouth, held her breath as the cane rubbed across her abraded flesh, a precursor of the next blow her sobs began anew, her eyes closed to block out the sight of the cane, but her mind raced with fresh images of the cane moving through the air and striking her white, unblemished flesh. She held her breath at the sound of the cane breaking the still air behind her, her heart racing, feeling like she would pass out. She had little time for that, the cane made its mark on a new spot on her unblemished flesh, this time higher up her buttocks, striking across her tightly clenched cheeks, the cane ripped into her flesh with a powerful thud that shook her body and smashed it into the desk painfully. “God!!” she screamed again, hoarse, the caning taking a toll on her throat as the pain raced up her spine into her brain. Just when she thought it couldn't get any worse, Headmaster Michael seemed to muster up a newfound strength, delighting in inflicting yet more pain on her young body.

Michael watched as her body shook with the pain, her hips swayed from side to side to relieve some of the pain that radiated from her swollen bottom. Mary Bridget jumped up and down on her toes, oblivious to how sexy she looked from behind. His cock jerked in his pants, almost ready to cum.

"Four, Sir!” she cried, her face contoured in pain, her cheeks wet with her tears falling on the desk beneath her, her body convulsed by the pain the cane inflicted on her. Over at last, Mary Bridget would do whatever was required of her not to repeat the caning. Anything was better than this. Little did she know what kind of perversions Headmaster Michael planned on making Mary Bridgett submit to, the hope she would protest, the cane always ready to remind of her of the failure to obey.

Michael stroked her flanks as she continued to sob, her body still shaking from the pain of the cane. “You submitted well to your punishment, Mary Bridget. Hopefully you have learned a lesson."

"Yes, Headmaster Michael,” she immediately responded, hoping to get out of his office quickly.

When he released her, she stood; her butt hurting as the battered skin stretched. She was still half naked; her blouse barely covered her sex, her knee socks only highlighting her nakedness. She went to pick up her panties on the floor next to the desk.

"Not yet, Mary Bridget. I want to see how well you learned your lesson. Put your panties down and come over here."

Now what? She released the white cotton panties, walked over to the Headmaster, embarrassed by her nakedness, but feared any more punishment. “Yes, Sir."

"Sit on the desk.” Amused, he watched as she did; her legs tightly together, tugging on her blouse to hide her sex from his view. But he had other ideas for her. He was going to test her willingness to submit to him, test how far he could humiliate her. “Pull up your blouse above your waist; I don't want it hiding any of your beautiful assets.” Her hands moved quickly, pulling the material up, her hairy mound visible, her pussy lips tightly clenched between her legs. He put his hands on her knees, looked into her eyes and ordered, “Spread your legs for me Mary Bridget.” He so enjoyed the panic in her eyes at his command.

He was going to embarrass her, force her to expose her body to him or he would punish her again. Her butt hurt when she sat down, a grim reminder of the consequences of any denial of his commands. Would he masturbate her as he did yesterday? Make her cum while he watched? She was aroused while he was doing it, but once she climaxed, her shame spread quickly. She relaxed her legs, allowed his urgent hands to push her knees outward; her legs quickly spread wide, his hands already sliding up and down her sleek thighs. She looked down at his hands, saw how open she was. It had been only days ago that no male had ever seen her naked sex, now Headmaster Michael had forced her on two occasions to allow him access to that private place between her legs. She looked up; his eyes still stared at hers, her face red with shame at the way she was exposed.

His fingers dug harshly into her sensitive thighs, drawing a sharp intake of air from Mary Bridget as she endured the pain. “Good girl, Mary Bridget. Now I want you to reach down and spread your pussy lips apart for me. I want you to show me your pink pussy. Hold it open real wide for me,” he ordered her. He looked into her eyes and knew that he had won, her surrender showed in the blue eyes that stared back. He didn't even have to look down to see if she obeyed, her eyes reflected her acceptance.

"Please,” she murmured, her fingers were already between her legs, gently pulling apart the petals of her flower, opening up her pussy for his gaze, shamed into having to perform such a task, afraid of what else would be required of her. She saw the smile on his face and then his eyes move down below, following as she saw how exposed she had made herself for his pleasure. Her lips were pulled back far, without even realizing how stretched her puffy lips were, just wanting to please the Headmaster, not wanting a repeat of the caning, her buttocks still aflame in pain, the sharp pain now eroding to a deep dull ache.

Michael had to step back a bit to fully appreciate the show that Mary Bridget was performing for him, her legs now spread wide, Michael's knees having forced them wider and wider until he was pleased at the way she was exposed. Now as her fingers pulled back her only protection, her virgin pussy unveiled in the full light of the room, a light sheen of wetness coated the slick pink skin, the tiny hole that was her vagina still tightly clenched. “Now use your other hand and rub up and down your slit. I want you to get it wet for me, Mary Bridget, just as I did for you, yesterday. Can you be a good girl and do that, or should you turn over and give me your ass again to cane?” He taunted her, even though he knew he had won.

"Don't make me masturbate for you, Headmaster Michael.” Even as her eyes pleaded with him to spare her the humiliation of self-masturbation, her fingers began to move up and down her slit, still not wanting to offend him by her protest.

He would enjoy that when it was time, but not today. Today, she was going to take him in her mouth and he had a special trick for her with the cane that would drive her into an orgasm, an orgasm while she sucked his hard cock. “Just keep rubbing, higher up now, let me see your clit,”

he ordered her, ignoring her plea, wanting her to suffer the unknown.

She rubbed her clit just as she did when she was alone at night, her hands tucked tightly beneath her blankets, her face pressed into the pillow to keep her roommate from hearing her cum. It began to feel good, almost forgetting Headmaster Michael until she looked up, his eyes staring so intently at her fingers masturbating her wet pussy.

"Good girl, Mary Bridget, you may stop for now. Off the desk and on the floor now, on your hands and knees."

She went from one bad thing to another, exposed, crouched on the floor, her ass pushed out at him, her legs together, though she knew it would be useless, Headmaster Michael always made her spread her legs for him, but not willing to do it until the last possible moment.

Michael looked down, pleased at the way her small breasts hung down, her nipples hard and over an inch long; her own fingers seemed to have aroused her. Good, she would need that this time.

“Now off your knees, but keep your hands and feet on the floor. Yes, like that, but push your ass up higher, real high for me, Mary Bridget,” his hands slid under her naked hipbones and pulled her up until she was almost bent at the waist, her hands touching the floor, her feet supported only by her toes. Michael liked the way she looked. Now, for the finishing touches.

She knew it was coming, his no surprise.

"Spread your legs, Mary Bridget. Very wide this time. I want your cheeks pulled apart. I want to see that tiny, wrinkled hole between them. Can you show me your anus, Mary Bridget? Can you expose that puckered opening for me?” He almost laughed aloud at her anguish, her body red from the humiliation of his request to show her most intimate opening. But she did spread her legs, a loud huff by him showing his displeasure when she stopped, wider again until he was satisfied at the wide expanse, her pussy and asshole gaped open, Mary Bridget's body arched up high for him. He touched her ass, his hands roamed over the flesh; her body flinched as they touched the welts, deep red and purple lines adorning her white flesh like a badge.

He moved to the side to get a bottle of baby oil, pouring a small amount on her upraised ass.

“Relax now, Mary Bridget,” his hands slowly spread the oily substance over her cheeks, paying special attention to her exposed anus, felt her tremble as it touched her, the shock on her face priceless as his fingers sought out the tiny hole, running it around the opening.

"A dark brown little pucker Mary Bridget, that's all it is,” his finger teased the opening, touching the tiny nerve endings, sexually stimulating Mary Bridget in a place that she wouldn't think possible. “I'm going to finger your asshole, Mary Bridget, don't move now!” he ordered, his finger pressed harder against the hole, feeling her fighting the rude intrusion into her body.

She felt his other hand raise her up higher, her ass now conveniently located for the fingering, a place that no boy had ever touched, a place she never knew one would want to touch. Ahhh!”

Her anus pierced suddenly by his finger, slipping on the baby oil in a swift insertion into her rectum, her sphincter clamped down on the foreign object so ruthlessly thrust into a hole that was used to having things pushed out, not in. She balanced precariously on her hands and feet, the finger giving her an uncomfortable and full feeling as it moved around inside her, massaging the muscle of her sphincter as it began to spasm, afraid she might have an accident, tightening up, trying to force it out.

"You have a very tight asshole Mary Bridget, almost too tight. I bet you don't like my finger in there do you?” He was pleased with her tightness. He would enjoy loosening her up, he had such a nice selection of anal probes in varying sizes from the very small to butt busters, all with attachments to secure them to a chair, the female forced to impale herself on the long probes. He even had one that was electrified, used to train a girl's sphincter to massage a large cock inside her. He continued to finger her, heard her groan and moan as she suffered his crude penetration.

He pulled his finger out, her puckered opening now shiny with the oil, pink from the constant agitation of his finger.

She was relieved when he pulled his finger from her butt, her anus closing up tightly.

"Over to the desk Mary Bridget. Lie down on it, on your back, head at the edge.” He picked up the cane, the look on Mary Bridget's face making his cock hard, a look of fear; fear that she would be caned again. He waited, wanting her to ponder on all the bad things that might happen to her before he told her what it might be. He picked up five small items that looked like fat rubber bands, but thicker. They were about one-inch wide and a quarter-inch thick. He slipped them on the cane toward the bottom; Mary Bridget's eyes followed every step as she got into position on the desk, not even bothering to close her legs, her mind too concerned with concentrating on the cane.

"Please, Headmaster Michael, I've been a good girl. I'll do anything, just not the cane again,” she begged, Michael pleased with her response. It would make it so much easier now.

"This time it will bring you pleasure, Mary Bridget, not pain. I am going to slip the cane through your legs and between your pussy lips. Then I'm going to bind your thighs tight, trapping the cane. While you take care of me, I will let the cane slide up and down your slit, the rubber bands on the cane will work magic on your pretty little pussy."

She didn't like the sound of “while you take care of me.” What was he going to force her to do?

She didn't have time to dwell on it. Headmaster Michael moved between her legs, the ridged cane sliding between her pussy lips as he sawed it back and forth, before finally drawing it down until the ridges slid harshly through her lips.

"Hold your legs together tight, Mary Bridget,” he ordered her, securing a thick leather strap around her thighs, tightening it until it pushed deep into her flesh, a knot securing it in place.

“Relax your legs now; the leather will keep them tight."

She did, her thighs tightly clenched together, almost too tight, the skin around the band turned white as the blood was pushed from the constraining leather. She saw the cane sticking obscenely out from between her legs, almost as if she had a penis, the hard rigid cane erect. Her attention turned back to the Headmaster as he moved toward her head. He grabbed her hair in his hand, pulled her to the edge, turned her head sideways, forcing Mary Bridget to flip on her side, the cane protruding from between her legs, only inches from the Headmaster. One of his large hands held her face away from him, his other hand disappearing from sight. “No!” she cried as she heard the sound of a zipper sliding down, his hand holding her face tightly. “No, please I can't do that,” she cried in fear. She had heard other girls who dated a lot of boys talk about how they had made them use their mouths on their penis. Some even said they forced them, opening their mouths and forcing their rigid members inside the hot confines, their hands controlling their head, forcing them to service their penis with their mouth. And finally, cumming inside their mouth. It was so dirty! She could never do such a thing.

Michael noted the panic in her eyes as he pulled his hard cock from his pants, fisted it, eager to feel her lips around it. First he had to get her to settle down, his hand reaching for the cane protruding from between her legs, gripped it tightly. He began to pull on it, her tightly clenched thighs trapping it. Harder, until he felt it begin to move, Mary Bridget looked down to see what he was doing.

"Oh, No!” she cried out as the ribs on the cane began to pass through her pussy lips, sliding harshly along the silky flesh, rubbing hard as first one, then the next ridge slid through. Her body reacted, wet, easing the passage of the cane. It took such a long time before all five rings passed, Headmaster Michael stopped, the cane almost pulled out. “No, not again,” she begged, but Headmaster Michael pushed the cane back in, this time forcing it through her legs, Mary Bridget's body bracing for the inevitable pain as the thick rings rubbed unevenly between her pussy lips. She groaned as Headmaster Michael kept up the attack on her pussy, the cane sliding almost effortlessly on her juices, the pain of the ridges now turned to a pleasurable experience, the uneven bumps sent shivers through her body as they caressed her silky pussy.

Now that he had her attention on the pleasure between her legs, it was his turn to be serviced, his hard cock in one hand, his other hand still held her face tightly, tucked underneath her chin, tilting her head up until his hard shaft touched her forehead.

It felt like his hot cock was branding her flesh; eyes opened wide, a shocked look on her face as she was face to face with a real live penis. It was huge, not like the tiny penis she saw on the little boys she babysat as a teenager. This had to be at least eight inches long. And, the head, a dark red, a crown, with a single hole in the center like a giant eye, glistened with cum. A large vein bulged on the side, dark blue and pulsating. The head had to be at least two inches across; her mouth would barely be able to contain it. She had heard that a penis got bigger when ready to cum. Would it tear her lips when it did that? He pulled on the cane again, this time faster, up and down two quick times, the ridges painful again. She looked down at his hand.

Her attention drawn to the cane again, he quickly stuck a finger in her mouth, prying it open before she had a chance to react, the head of his cock quickly forced between her lips. He thought he would cum when he felt her hot breath on his cock, her wet lips allowing his cock to slide along until the head was inside her mouth. Her tongue accidentally touched his cock and then rushed back as if it had struck a hot iron.

"How does it feel to have a cock inside your mouth, Mary Bridget? You look so lovely, your big blue eyes, your red lips wrapped so tightly around my cock.” He let the cane slide back and forth between her legs again, gentle this time, her pleasure returned. “I can make it feel good or make it hurt. Which would you rather the cane do to your pussy?"

She looked up at him, “guud” she mumbled, the word almost unintelligible, his thick cock on her tongue, her lips wrapped around it.

He made it jerk inside her mouth, the surprise in her eyes pleasing him. He loved teaching girls to suck cock for the first time. Everything is so new and they are usually so eager to please and get it over with. With time she would readily attempt to please him, learn what he liked and duplicate it, each time with a little more enthusiasm. He began to gently saw the cane back and forth between her legs, this time higher, seeking out her clit. She jumped, knowing that he was successful in his quest, making the cane bend with each thrust to rub the ridges over her clit.

"Time to suck, Mary Bridget. Time to suck my cock. Run your tongue over it,” two hands now held her head tightly, moved her face up and down, making her take more of his cock inside her mouth as he began to face fuck her.

It seemed to swell, her tongue tentatively touched the head of his cock, the taste of cum quickly mixed with the abundance of saliva in her mouth, permeating every corner. She almost gagged; the thick salty fluid had an unmistakable taste, the texture thick, failing to blend with her saliva, feeling like lumps in mash potatoes. What would it be like when he came in her mouth? How much cum would there be? Did he expect her to swallow it? She had little time to ponder these thoughts, his hands more urgent, one hand rocked the cane back and forth, the ridges doing a good job of sexually arousing her, her pussy stained the rattan with her juices. His other hand gripped her hair in a ball on top of her head using it like the reins on a horse to urge her head up and down, masturbating his cock with her mouth.

Her hands moved up when he pushed in deeper and hit the back of her throat, forcing a gag from her; her eyes teared up. He slapped them back down, “Don't you dare,” he threatened her. “Keep your hands down while I face fuck you, Mary Bridget.” He yanked her hair hard, almost tearing strands from her head as she felt the pain of her resistance. “Take a deep breath now, Mary Bridget,” He forced her mouth down on his cock, over three inches, feeling her gag on the head of his cock, getting her used to a hard, long cock inside. She continued to gag, Michael liked that. Some girls learned quickly how to stop their gag reflex, swallowing a hard cock with ease.

Others, like Mary Bridget, would never learn, destined to always choke on a cock, something Michael always loved. It was as if they were sucking cock for the first time, inexperienced, surprised when it made them gag. Not like some whore that swallowed a cock as if she were a sword swallower.

She thought he would push it through her head to come out the other side, his forceful hand drove her head farther and farther down the shaft of his pulsating cock. Mary Bridget choked as it filled her throat, her breathing ragged, learning quickly that she could only breathe through her nose. She felt the cane between her legs, up and back, the protruding ridges made her clit swell up as it was abused, almost like a machine, a masturbating machine. She sucked in a deep breath as his cock pulled from her throat; the sharp intake rang out in the room. It was short lived, his hand pushed her head back down on his cock, her tongue lapped at it as it slid inside her mouth, hoping to make him cum quickly, choking and gagging again, her stomach lurched from the harsh face fucking he was giving her.

"I'm going to enjoy punishing you this year, Mary Bridget. I'm going to enjoy making your body mine. Now make me cum and yourself at the same time, or I'll take the cane to your pussy instead of your ass.” He punched his cock down her throat, her eyes wide open as the thick meat stretched her throat wide, the spasms inside her throat massaged his cock like magic fingers. She gagged, as she opened up her throat, his bulbous head sitting and pulsating inside her once virgin mouth. He moved the cane more quickly; her juices made it so slippery as it moved almost effortlessly up and down, her bound thighs trapped it between them.

"Mmm,” she gurgled, the cane finally brought the orgasm she desperately needed. Her tongue lapped up and down the shaft, sucking in a deep breath as it pulled from her throat, thankful for the reprieve, not knowing that Michael was ready to cum and he wanted to make sure she tasted his cock. In her mouth.

He would teach her to be a cum lover. He planned to use her mouth often, and others would also do the same. Cum rushed up from his balls, he held back as her tongue danced over the tip, already lapping at the cum leaking out. Mary Bridget was now too far along to protest the taste, her orgasm ripped through her body.

She knew how she looked, her thighs bound, the cane that inflicted so much pain on her ass now bringing her so much pleasure. How she must look with his cock in her mouth, eagerly sucking, eagerly trying to make him cum! A sight she could not even imagine two days ago, now a reality. She felt the cock in her mouth grow, the hot flesh pulsating, braced for a load of cum to fill her mouth. Her mouth went from empty to full of cum, the thick salty cream bulged out her cheeks as she coughed and sputtered from the massive amount of liquid. She tried to gulp, choked as it passed. She was surprised when it began to shoot again, thinking it would be only once, her mouth, still partly filled, bulged out again as his fluids filled her oral cavity. She coughed and gagged as she tried to swallow, his cock shot into the back of her mouth, going down the wrong path, making her choke.

Her face contoured in pain as she choked on his cum, her eyes watered, cum shot out of her nose, her lips wrapped around his cock, cum leaked from the corner of her mouth. He laughed at her obvious discomfort, his cock still spewing in her mouth, her body rocked in orgasm as she came on the cane between her legs. He continued to push the cane back and forth, knowing that it would be more of an irritant than a help to her orgasm, but he would teach her who the master was. He finally finished in her mouth, his softening cock pulled slowly from her mouth. “Lick it clean, Mary Bridget. Lick the cum from my cock,” he watched as she eagerly complied, his cock pulled from her lips glistened with her saliva.

He dismissed her matter of factly. “You may go now, Mary Bridget and remember to be good or you will be back here for more punishment"

But he knew that no matter how good she was, he would punish her again. Not because she was bad, but because she was so good, punishing her sexually pleased him. She quickly dressed, pulled the cane from between her legs, rushed out of the room but not before saying, “Thank you, Headmaster Michael.” Michael was not sure how she meant it, but was eager to find out.

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