The Hollister School for Girls

by Powerone

  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.

  CHAPTER 3

  The Chastisement of Justine for the Pleasure of the Board of Directors

  "Come in,” Michael commanded.

  He looked up as the door opened, pleasantly surprised to see Meredith. “Good morning, Chancellor."

  "It's Meredith, Michael. No need to be so formal when we aren't in front of the students.” She smiled at him.

  He watched as she walked over to the chair in front of his desk, his eyes gazed down at her legs as she crossed them, her short skirt rode higher on those gorgeous thighs, a quick glimpse between her legs making his cock hard. “So good to see you, Meredith. What I can do for you, today?"

  "Not for me, for the Board of Directors."

  "Anything in particular? Not that I don't already suspect what they would like."

  "I have told the Board of the good things I have heard about you around campus the last couple of days."

  "And what have you heard, Meredith? Only the truth, I hope."

  "I heard that you have already punished one of the students. A Mary Bridget, to be specific. From what I hear, she has had trouble sitting since. Rumor has it that she was caned. Care to confirm or deny?” She smiled, uncrossed her legs and then crossed them again, slowly so that his eyes followed her every movement.

  His cock throbbed in his pants. “Mary Bridget, yes a very errant young woman. I brought her into my office the first day for her poor grades. I gave her a sound spanking. It seems it didn't do much good, as the next day I had her back after learning that she had been inattentive in class. I thought that she needed a more severe punishment. The caning apparently worked wonders on her disposition; it only took four strokes to convince her of the error of her ways."

  "Over her panties,” Meredith shot back.

  Michael smiled, “The first two. The last two were with her panties off, her naked ass cheeks bearing the brunt. She did a very enjoyable dance for my benefit."

  "I imagine she did,” her mind pictured Mary Bridget bent over, naked, her legs dancing, giving Michael a very intimate glimpse of her naked sex. “Was she grateful when you were finished?"

  "Actually, it was rather funny. The first day I even helped her out, masturbating her until she came in front of me. The girl turned beat red when she came, but she soaked my hand as she shook with her release. The next day, I made her perform for me, showing me her naked body in a variety of very compromising and revealing positions. Even had a chance to feel how tight her asshole was. She was very cooperative,” he explained.

  "And you? Did she do anything to help you out? I'm sure your cock must have been very hard after punishing such a delightful little body for two days."

 
"Now that you mention it, I thought I might have to call you,” laughed as he said it. “But I decided that Mary Bridget should do it since she was the cause of my hard cock. So I took her mouth while I masturbated her pussy with my cane. It had special little rubber bands around it, raised bands. I tied her legs together and let the cane saw up and down that sensitive little slit while I face fucked her. We both had such an enjoyable climax; Mary Bridget swallowed all of my cum while she came again for me. She has a very lovely body and could be trained very easily to please anyone. She will do anything to avoid punishment, though that does take some of the joy out of it."

  "You know you made my panties soaked with that story, don't you Michael? I think you enjoy doing that."

  "I love to make any girl wet, Meredith. Now, what would the Board like?"

  "Once I told them about Mary Bridget they were as excited as I was. As I told you when I hired you, the Board is very interested in corporal punishment. They would like to observe you putting one of the girls through her paces. In the special punishment room, so they can observe through the two-way mirror.” She knew the grin on his face was proof he would love to display his prowess to the Board; almost as much as he would enjoy punishing the girl.

  "I'm sure that I can find someone that would provide suitable enjoyment for the Board. Anything special they might like?"

  "They want a very severe punishment. They prefer to start on Thursday. With it being a holiday weekend, should it be necessary for the unfortunate girl to spend a few days in the infirmary she would be in better shape by Monday.” Meredith could more than imagine how his cock jerked in his pants at the thought.

  "How severe?"

  "We have such lovely antique bondage equipment, many dating back to when corporal punishment was legal. The Board would like to see her bound in some, slowly stripped naked, and you using some of the more painful devices and equipment on the more delicate and sensitive parts of her body. They enjoy the screams of the girls."