The Hollister School for Girls

by Powerone

  He was right; she could not take any more of the flogger, her flesh so tender. She wasn't even sure how she would be able to stand him fucking her. “Fuck me."

  "I think you're going to have to get wet for me first, Justine. Can you be a good little girl? I'll masturbate you a bit but I need you to make your pussy cream for me. I know your pussy hurts, but try real hard.” He teased her, wanted her to force herself to accept it, get wet after being beaten, getting her pussy lubricated for his big cock.

  She could only nod her head, humiliated at the thought of having to get sexually aroused after he had beaten her so severely, get wet so that he could force himself on her and fuck her. Fuck her until he deposited his dirty semen inside her. She felt the bulbous head of his cock rub up and down her pussy slit, between her lips, push them ruthlessly aside. She felt the wetness; his cum drip out and rub up and down her slit. He pushed it against her vagina, so huge compared to her tiny opening. She was no longer a virgin, had been fucked before, but not very many times and that boy was small compared to Headmaster Michael.

  His hands slipped underneath her, his fingers found her bush and sought out her clit. He found it, his fingers pushed along the edges, pushed the clit hood out of the way, his two fingers squeezed it below the head. She jerked up when he touched it, pushed onto his hard cock, felt her vagina stretch open before she pushed back again, pushed her clit into his hand. “Yes, see you're starting to hump me already,” laughing at her discomfort. “You really want my hard cock to fuck your tight pussy. Maybe I should flog you anytime I want to fuck you to get you into the mood,” his voice cheerful as he continued to tease.

  "No, I hated it,” she blurted out. His other hand moved down to her vagina, one finger pushed in, the skin tender from the flogger. “Careful, that hurts."

  "I know, your pain makes my cock hard. What a nice, hot tight pussy, Justine. Yes, that's the way; your pussy is sucking my finger inside.” He felt her pussy clench on his finger, her pussy already wet. “Your pussy is already moist for me, Justine,” his other hand rubbed her clit back and forth, felt it swell. He pulled his finger from her pussy, too anxious to wait any longer, fisted his cock and placed it against the tiny opening of her vagina. It would take a lot of force to push it inside, but with her legs spread so wide, unable to move because of the tacks, she would willingly help to make it fit.

  "Oh God, it's too big, it'll never fit!” she began to cry as his cock head began to push in, feeling her vagina stretch. She planted her feet firmly, pushed back on her ass, not wanting to move her feet and feel the pain of the tacks. Not after all she suffered to avoid the painful puncture of her feet. It was so cruel of Headmaster Michael, he flogged her, and made her participate in her own debasement, now she had to help him by pushing back on his cock so he could drive his massive cock into her tiny vagina.

  "Oh that's so good, Justine, push that sweet little pussy onto my cock and then you can give me a good ride.” He grabbed her hips, rotated them, made his cock enlarge the opening as it slowly and painfully pushed into her pussy. “Just a little more and you will have the head, Justine, fuck back and let it inside you."

  She grit her teeth and pushed, the cock slid painfully inside her vagina, she gripped the large head as it twitched inside her. It was huge, and he would expect her to take the length now that she accepted the girth. “Hold still, please, let me get use to it,” she begged him.

  He rotated her hips again, moved them up and down, his head pulled out then pushed back in, it felt like it was caught in a giant vice. “That feels so good, Justine. Now take a little more inside your tight little pussy. I have over eight inches of steel cock to feed you.” He heard her moans of pain but her ass arched backward, her anus puckered out as she did, Michael pleased at how she was displayed. The tiny wrinkled opening of her anus would feel his finger soon, but first he wanted his cock sheathed inside her pussy. He couldn't believe how tight she was. Young girls always delighted him, their barely used pussies a waste, Headmaster Michael more than willing to take advantage of their lack of experience, always willing to teach them how to perform for him.

  Justine pushed back on the rigid cock pressed inside her pussy, felt the head rub hard along her pussy walls as it was forced in her. Back out again, his cock moved more easily, her pussy got wetter. Back in, deeper, his cock rubbed new spots inside her, filled her completely with his pulsating flesh. She felt him flex his cock, made it jump inside her, teased her. Out again, she clamped on the head as it pulled out, afraid it would slip out, make him mad or make it take longer. Her ass arched backward, drove her pussy on his cock as he patiently stood behind her, buried in her tight pussy while she rocked back and forth on it.

  Michael loved the way she performed for him, her hips pushed back and forth, pushed his cock in deeper and deeper as she moaned in pain as he filled her pussy. “You got half now, Justine. Such a good girl you are, fucking so nicely on my cock. I need you to take it deeper, I want it buried inside your cunt.” He used that word again, knowing that most women didn't like to have it called that, knowing that he degraded her further by referring to it as a cunt. He reached around her bent-over body, almost lying on her back, his cock half buried in the tightest pussy he had fucked in a while. His hand slid under her, cupped her sex with his hand, felt his rigid member stick out of her pussy. He traced his fingers around her pussy, felt her hole wrapped tightly around his cock, like a band that ran up and down his shaft as his cock moved in and out. “I'm going to play with your clit. I want my cock buried in your pussy in the next three strokes or I'm going to pinch it off. If you obey, I will rub it nice and make you cum with me."

  She knew that he would do it; the flogging convinced her of his desire to hurt her and sexually abuse her. “God!” She pushed back, buried almost all of his cock inside her, the massive weapon pushed aside all resistance, tore its way deep inside her. She felt his hand rub her pussy lips, felt his cock as she made it slip in and out. One final plunge, his cock banged against her cervix as she finally fully engulfed the hard cock. Thank goodness her legs were spread so wide, her pussy felt so full. She rested for a minute while it twitched inside her; her pussy clenching in spasms on it in return. She felt his fingers find her clit and gently rub as opposed to the pain he had only just caused her.

  "Now I want you to fuck back and forth, harder and faster each time. I want you to fuck me like a two-dollar whore and squeeze my cock with your tight pussy. And I want it hard, men love to fuck girls like you hard, make you squeal in pain. Please me or it's the flogger between your lovely thighs, again."

  She pushed back, grunted, wanting to please him to get it over with. His cock felt huge inside her, she was not used to anything that big. She felt it slowly push inside her, her pussy walls stretched to accept it, felt every bump and ridge on his cock as it pressed forward. It banged hard inside her, pulled back out, gripped it with her muscles as she did, the bulbous head pinched tightly. Back in again, harder, bruised as she was punched from the inside. She felt it twitch and jerk inside her.

  Headmaster Michael was pleased with the way she was fucking. He was almost ready to cum. But first he wanted to drag the maximum amount of pleasure from her inexperienced body. He had found through his years of experience that a pussy would tighten in response to pain, so he used this ploy as often as possible. She would not cum this time; this fucking was for his enjoyment only. He grabbed her hips tightly in one hand, pushed a button near him that controlled the tacks beneath her heels. “Rise up quickly on your toes, Justine, or the tacks will puncture your heels,” he ordered, enjoying the look of distress on her face as she stared back at him. But her hips raised instantly, her pussy clamped down on his cock. He knew that her thighs would tighten, exhausted from her previous stance, yet forced to tighten on his cock. “Continue fucking me back, Justine. Hard!” Her hips moved back and forth, his cock gripped as it pushed and pulled inside her hot, little pussy.

  She stretched up so high, her ass arched backw
ards, tired from the brutal fucking he forced upon her. Her pussy sandpapered by his cock, her muscles involuntarily gripped it tighter increasing her pain. She knew that he did this on purpose, forcing her to add to her discomfort to increase his pleasure.

  "Good girl, Justine, you're performing well for me. I'm ready to cum in that sweet little box of yours. One more thing first to make you tighten up even more,” his finger moved up to her asshole, the puckered opening danced from the obscene fucking he made her perform, opened and closed in time with her pussy muscles.

  "NO! NO!” She begged him, but she knew it would do no good, gritting her teeth, bracing her body for what she knew to be inevitable. She did not have to wait long, his finger found the spot, waited for it to open, plunged inside in one brutal thrust that knocked the air from her lungs. He had played with it before, but his finger had never moved so deep in her rectum, turned and twisted like a snake inside her as she bucked up and down. “Ah! That hurts! Too dry!” she screamed as her asshole burned from his finger.

  He didn't think he would be able to push his cock inside her pussy again, her muscles clenched so tight that he had to help her, shoved his hips forward in a brutal thrust that propelled aside all resistance until the head of his cock banged painfully into her cervix. That was all he needed, the first load of cum shot up from his balls, his cock swelled as her pussy clenched and unclenched, felt his finger along side the thin wall of her asshole.

  Her pussy was drenched with his hot juices, sprayed deep inside her filling her passage with his abundant semen. It stung, the salty fluid bathed her walls, already tender and sore from the fucking his cock inflicted on her. No, please not that!, His finger found her clit, twisted it, slapped it back and forth. No she couldn't, not when it hurt so much, she couldn't cum from the fucking he had forced her to perform. But it was too late; her body just too exhausted to stop the feelings, an orgasm hit her like none she had ever felt before. She fucked her hips back and forth with lightening speed, his stomach slapped painfully on her ass from behind, his balls swung up from below to hit her pussy.

  Headmaster Michael couldn't believe it, his finger rubbed her pussy just to force her to drive back on his cock, he had not expected her to cum from it. But that was what was happening, her hips blindly fucked back and forth, her asshole clenched onto his finger, her sphincter gripped it so tight he could hardly move it. And she came, her juices bathed his cock as their cum mixed inside her. They came together what seemed like long minutes, even though it was probably shorter than that. Each enjoyed the other's orgasm; the feeling of each other's organs brought each pleasure.

  Headmaster Michael finally pulled his cock from her pussy, a loud pop and a river of cum ran down her thighs as a testament to the pleasure they had both enjoyed. He made the tacks recede, released her from the pillory, Justine fell to the ground and curled up into a ball, her hand between her legs, her pussy still bringing her pleasure. “You seemed to like being fucked hard, Justine. Your pussy likes the pain,” she shuddered and turned red in humiliation at how her body betrayed her.

  The Board looked at Meredith.

  "I just love how he makes them give him so much pleasure. He made Justine rise up on her toes; I'm sure her pussy must have gripped his cock so hard. Then the finger in her asshole was priceless, the look on her face as she was pierced. But, I think Michael was actually surprised that she had cum with him, not expecting or even trying to make her cum. It just shows you how well he can train these girls to do degrading things and make them enjoy it.” Meredith smiled at the Board, pleased at the success of her having hired Michael.

  "We are very pleased at how good he is in training the girls. We are going to have to take advantage of that soon. We would like to see how well they will perform for complete strangers, mainly us."

  "Michael would be glad to, but I think he still has more planned for Justine. You did say severe punishment. I think he is going to being very meticulous about making sure she feels the pain, severe pain. I know he picked out some very nice torture tools to use on her lovely body. Let's sit back and enjoy."

  "Get up, Justine. Take a quick shower. Clean yourself for me.” He pulled her up by her arm, moved her over to the shower in the corner of the room. “Leave the curtain open, I like to look at your naked body,” enjoying seeing her humiliate herself in front of him.

  Justine begrudgingly got into the shower, her body already tired from the ordeal he had put her through, not sure what would happen next, afraid to ask. The shower refreshed her. She ignored Headmaster Michael, didn't want to see him watch her as she washed her pussy with the soap cleaning his cum from her body. She bowed her legs out, took the shower handle and shot it up her pussy, the spray too hard, it hurt as she did it, but she was eager to get rid of him from her body. She toweled herself off, wrapped the towel around her body. She moved toward Headmaster Michael, the towel just barely able to cover her sex.

  "Refreshed, I hope?"

  "May I go now Headmaster Michael?” she asked, hopeful; the smile on his face answered her.

  "Almost Justine, we just have one more task to accomplish."

  "Please, no more,” she cried, not sure she could take being abused again sexually.

  "Over here,” his cock already hard again, her crying made it jerk in pleasure. He pushed her over to a strange looking device he had found. Not sure what it was called, another antique, so he had named it himself. “This is a Maiden's Chair, Justine."

  "What's it for?” though she knew she shouldn't ask or have to, she knew whatever it was, it was for her body.

  "I think you'll be comfortable in it.” He pushed her to the chair, a large wood and iron structure. The back of the chair had rungs about every eight inches, evenly spaced to allow varying heights to secure the victim. There was no seat in the chair, just iron rings out to the side in a semi-circle pattern, one on each side. The rings had small round circles, big enough for chains or rope to be placed in them all along the length, again to secure the victims limbs in whatever position was desire. At the top of the back was a large contraption that he'd had trouble figuring out, finally determined that it would slide down to the shoulders of the victim, the rest fitting tightly around the head, securing it with various rings of iron with screws to make them tighter or looser.

  "Crouch down with your back to the rungs, Justine. Hurry now, I don't have time to waste with you.” She complied willingly, resigned with the control he had over her. Her knees bent her ass about two feet from the floor, as if she was sitting, but with no chair under her. “Put your arms up,” he ordered, did not wait for her, pulled them up, pushed them through one of the rungs in the ladder. He bent them at the elbow until her wrists met the clamps inside, her wrists almost fit inside the clamps perfectly. Obviously, the chair was built for females. Her arms were pulled up and bent back, secured in the back. With the way she was positioned, she wouldn't be able to rise up or she would risk breaking her elbows or wrists, a creative idea by the inventor. This left her butt and sex completely exposed, as well as her breasts thrust out for him. Her body would be so readily available to him.

  Fear returned, the position she was in-while not uncomfortable-did leave her unable to protect herself, as if it were possible to protect herself against Headmaster Michael. She didn't like the way her breasts were thrust out. While her knees were together protecting her sex, the strange iron bar that ran in a semi-circle to the sides of her legs scared her, the round circles looked like a way to secure ropes or chains. A large pile of rope was a short distance from where she was crouched did not dampen her fear.

  Headmaster Michael looked at her. She was already beginning to sweat in fear. She had reason to, he would enjoy the pain he inflicted on her, make sure that all of her body would be available to the instruments of torture he had found. He rose up and slid the head band down the ladder, Justine's eyes tried to catch a glimpse of it. He saw the panic in her eyes as it slid down her head, one heavy ring slipped down under her chin, th
e other banded around her forehead. Side pieces of heavy metal were only inches from her temples. All of them had iron screws, many rusted from years of inactivity.

  "Whhaat's that?” the panic rose in her voice.

  "It's only to keep your head in place. I wouldn't want you to get hurt,” he lied. He began to tighten the lower band, tighter and tighter until it fit snuggly around her neck, with more than enough room to breathe. It was not meant to asphyxiate her only to keep her head pointed straight ahead. He had plans for her. The head band was next, this one made tight, the metal band left an indent in her skin, her protests vocal. The side pieces were next, Michael tightened them; he wanted her to feel them.

  "It feels like you're squeezing my head,” she sobbed, the side pieces pushed in hard, her head pounded. She was scared, her head immobile, her arms bound. It had gone from bad to terrible.

  "It's nothing, Justine. I'll take your mind off of it in a minute,” laughing at her obvious discomfort. Her face framed by the black iron, her distressed look pleasing him. He looked down at her legs, barely made out her pussy between her tightly clenched legs, more than enough time to get them spread. “Such pretty hair, Justine,” he reached down and wrapped his hands around a large clump and yanked hard, feeling some of it rip from her head, the rest stretched painfully out. Her howl of pain pleased him. He released it, grabbed another chunk, repeated the process, her eyes wide opened in terror, tears in her eyes.

  She couldn't understand why he was doing this. The pain was excruciating, chunks of her hair pulled out, her scalp burned in pain. Her head forced still by the iron bands, “Why?” she screamed in pain. She felt him stop and grab another bunch, the pain quickly returned.

  Headmaster Michael moved to her ears, grabbed one in each hand, pulled them out, twisted them painfully, enjoying the way she suffered. He moved his hands to her face, one large hand completely engulfed her face, pushed in and moved about, fingers pushed painfully into her eyes, smashed her nose back and forth on her face, fingers searched out her lips, jammed into the corners and pulled them pulled wide, unable to scream as his fingers pinched her facial tissue. He put two fingers into her nose, his thick fingers jammed hard inside almost up to the knuckle, pulled upward, watched as her nose contorted, the holes pointed upward. “I love to play with your pretty face Justine,” her nose ran, saliva hung from her lips. He jammed two fingers into her mouth, her teeth clasped tight, banged into them until she opened, his fingers spread her jaw wide open. Three fingers inside her mouth now, pushed her tongue aside, went deeper, banged against her cheeks. “Such a nice mouth Justine.” He pushed four fingers in her mouth, her lips wrapped tightly around his hand as he twisted and turned them, rubbed the insides of her cheeks. “You can take more,” folded his thumb in and pushed all five fingers in her mouth. She began to choke, his long fingers reached to her throat, her gag made it easier to slide them down. He pulled them out only long enough to make them into a fist; her cheeks bulge out like a squirrel with a mouthful of nuts.