The Hollister School for Girls

by Powerone

  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 delica
te 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 looke
d 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.