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?

CHAPTER CONTINUED

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