The Hollister School for Girls

by Powerone

  The plank hurt, hurt terribly, Carleigh had no choice but to rise up on her toes, each time higher as the plank moved. She hated having to submit to him. Would he ever stop or was she just postponing the inevitable pain? She was relieved when Headmaster Michael stopped the evil machine, but she was balanced precariously on her toes, her legs stretched tight, the plank only millimeters from her pussy, the ache in her muscles already beginning. If she tired, her sex would be forced down on the plank, a painful idea that she tried to block from her mind as she strained.

  Michael watched as she struggled to maintain the position. Soon she would feel the plank, her legs already weakened from balancing on her toes as he had made her dance on the rope for him. He moved behind her head, unloosened the leather strap of the ring gag; he wanted to hear her cries of pain, her begging as she rode the pony for his enjoyment. He stretched her mouth open wider to remove the gag out of her mouth, listened indulgently to her muffled cry as he pulled it harshly out. His fingers returned to her mouth, her lips parted, eager to have him take the foul tasting panties stuffed so tightly inside.

  She coughed, spit ran down her chin as she was finally relieved of the harsh device that kept her mouth open and available to him. She tried to reason with him. “Please Headmaster Michael, I won't tell anyone if you let me go,” anything to stop the inevitable pain she knew she would receive as soon as her legs tired.

  "Shh, Carleigh, begging will get you nowhere. I intend to abuse your lovely body until you consent to giving me your virginity. I just want to hear your cries of pain. It excites me. You excite me very much.” He moved along the side of her, his hands returned to her naked waist. He felt her cringe from his touch. “Such a lovely body. You don't mind if I explore while I wait for your legs to tire, do you, Carleigh?” His hands moved over her flesh, up to her cup her naked breasts, his large palm cupped one, his other hand moved toward the nipple, gripped it tightly, twisted and turned it as Carleigh moved in pain, to escape the fingers that bit into her tender nipple.

  The first cramp hit her right foot, her toes tightened, with no choice but to lower down, slowly, she fought the pain as the plank moved tighter between her lips, moved her hips slightly, tried to find a place that was not painful, settled on finding the place where her sex was bruised the least, grit her teeth as the unyielding wood smashed her tender sex into her pubic bone.

  "Slowly, Carleigh. Find a nice place to settle onto the plank. I know it hurts, but you bring such delight to me,” his hand moved to the top of her pubes, held her tightly, guided her onto the plank. “Yes, can you feel the pain now?” Her labia parted on each side of the plank, his fingers stroked the outer flesh as her body shuddered in pain. He moved his finger up to the top of her slit, found her clit, felt her tremble as he stroked the swollen flesh, gave her the feel of pleasure mixed with pain.

  "No, don't touch me there,” she begged, she not wanted to give into the pleasure, defiant in her resistance even as the plank dug painfully into her sex. It felt like a knife was between her legs, she attempted to stay perfectly still, the pain acute each time she moved. His finger on her clit forced her legs to shift, a sharp stabbing pain came from her sex as she moved too quickly. “Ow! You're splitting me up the middle!” she screamed. “Don't touch me!"

  Michael ignored her, his hands rubbed over her sex, fingers slid up and down her slit until he felt the harsh wood that smashed into her sex, the wood already damp with her juices. He wouldn't let her cum on the plank, he wanted her to cum when he took her virginity-forced to cum when she lost her maidenhood forever, to be turned into a sexual plaything for her stepdaddy. He watched her rise back up on her toes, shivered with his own pleasure at her moans as her pussy was relieved of the terrible wood. His hands moved down to the vee of her legs, fingers pushed into where the plank had been, along the smooth, inner lips, felt her jerk in pain as his fingers touched the spots that were already bruised and swollen. He rubbed until he felt her juices begin to flow again. “Yes, give me some of your cream, Carleigh. Get your pussy wet. Your legs won't last much longer; soon you will have to sink down on the plank again. It will be easier if you are wet."

  "Please take me off of this!” she cried, tears poured down her face as her legs already began to cramp again, aware of what the plank would inflict on her body, afraid as her legs began to tire. She felt his hands on her pussy, between her lips, unaccustomed to the feel of male fingers where only her own masturbating fingers had been. He played along her inner lips, rubbed up and down the flesh. At first it was the pain, his fingers re-visited the spots the wooden plank had already been. But then the fingers became more insistent, the pain replaced by the pleasure as his fingers massaged her flesh. She could only stand there, perched high on her toes as she let him have his way with her pussy, the wetness between her legs, ashamed at how easily he was able to make her juices flow. She cried out again, this time her left leg seized by a cramp in her calve. She slowly let herself down onto her feet again, felt his fingers part her labia, holding them apart as she lowered down onto the wooden plank, made sure that the plank visited the tenderest parts of her body. “Oooww!” the pain between her legs began, but at least the cramp in her leg began to subside, not sure which pain was worse.

  Michael's hand moved to her ass, over her tight cheeks, skimmed the light coat of sweat on her body as she endured the pony. His hand slid down her crease, passed over her anus, stopped when he reached the point where her pussy met the plank, his finger played over lips pressed tightly around the wood. Her body jerked in pain, her hips moved forward to escape his probing fingers, almost forgetting the immense pain that even the tiniest movements provoked. He lightly slapped her ass, rewarded with a sharp cry of pain as her pussy slid harshly over the wood in response to his spank.

  She could wait no longer, rose up on her toes again; anything to escape his fingers that so freely played over her body. She settled back down on the plank, carefully pressed her sex onto the harsh plank, cringed as she tried to find a spot that was not already bruised, the process more painful each time.

  "It's getting more difficult to stay on your toes, your moans of pain as you slide along the plank makes my cock harder. Soon your pussy will grip it tightly like a little whore.” He stressed the last word, let Carleigh know what she was to become. He played over her ass again, this time his fingers pushed between her crease, her tightened cheeks were rewarded with a sharp pain in her pussy as her sex rubbed on the plank. He felt her relax her cheeks, to avoid inflicting any more pain on her sex than was necessary. His fingers continued the exploration of her crease, slid along the moist crease, her sweat lubricated his finger as it moved down until it felt the ridge of her anus.

  "God, that hurts!” she screamed as she shoved her hips forward to escape the probing finger, the rough wood rasped along her tender pussy, rubbed her raw.

  "Stay still, it won't hurt as much,” he rubbed her wrinkled opening, felt her strain to fight the power of his finger. He ran the calloused fingertip around the tiny hole, felt it clenched as she endured the rude fondling of her most intimate hole. She finally let him do as he wished, the least painful way, his finger slowly ran into the hole, slid along the inner edge as he pushed inward, the tiny hole gave way. He pushed in deeper, a throaty moan her only protest, his fingertip massaged the muscle that protected the tiny opening. Around and around, his finger slowly stretched the hole open as it moved into her rectum, her sphincter clenched on the invading finger.

  It felt strange, the finger that played with her ass. He slid inside, she was unable to stop him from doing this unspeakable thing to her, the finger moved around inside her like a small animal. She tried to remain still, suffered as the finger massaged the muscle that protected her tiny hole, forced herself to keep her hips still, her pussy sat painfully on the plank, crushed by her own weight. She felt it leave, Headmaster Michael moved from behind her to his desk, sat down, feet up, his hand grabbed his crotch as he stared at her. The minutes slowly ticked
by, her crotch more painful as she held the position. She whimpered as she moved her hips, rose up for a brief second on her toes, her muscles exhausted, placed her pussy back down on the plank. She gasped as her flesh rested on the plank, the wood dug into the tender flesh, bruised a new spot, the pain instantaneous. “Please, Headmaster, it hurts.” Headmaster Michael just watched her, rubbed his cock beneath his pants, and she knew he enjoyed her plight. Each time she rose up, the relief in her crotch was temporary; cringed as she settled back down on the plank, the sensations shot up her spine as the unyielding wood made contact with her tender flesh.

  Michael stroked his cock as he watched. She made tiny panting noises, a gasp of pain as she placed her pussy back down on the wood, the plank turned dark as her juices dampened it. It was a combination of pain and pleasure that swept over her body. She found her rhythm, no longer taking her pussy off of the plank, but moving it slightly back and forth over the wooden plank, minimized the pain and maximized the pleasure. It was no longer a fight to get off the plank, but the urge to cum that drove her.

  The pain was secondary to the pleasure she felt. She fucked the plank, slid along the old wood, her juices made the trip back and forth easier as her pussy slid along. She felt a familiar tingling between her legs, but this time it was different. It wasn't her fingers aroused her but a torture device, her pussy forced to rub harshly up and down the edge of the plank, raw, but still brought powerful bursts of pleasure. Headmaster Michael had taken his cock out, his hand wrapped around it, stroked it up and down. It was huge, much thicker than any pictures she had ever seen. It wasn't a penis, but a cock. And he intended to fuck her with it. The thick head was almost purple, his semen on the tip glistened in the light. It was long, longer than his hand. How would she ever take such a huge thing inside her body without screaming in pain? But that is what he wanted, to feel her suffer under him as he thrust inside her virgin pussy. The pleasure spread through her body, her nipples felt like they would explode, the tips hard. She looked down, her labia swollen, now fat puffy lips that clung to the plank as she jerked back and forth slowly on the plank.

  "I think you are having a little too much pleasure, Carleigh. I don't want you cumming, only begging to be fucked.” He reached for a small whip, a modern one made of fiberglass, similar to a fishing rod, flexible, able to bend almost in half and snap back into shape with a sharp bite. “First, I think you should be a little bit more comfortable.” He pressed the remote, the tension in the rope on her arms taken out, her arms rose up towards the ceiling again. “Your legs must be tired; I think they need to relax.” He grabbed two pieces of rawhide, tied each around her tiny ankles, let the leather dig painfully into her flesh. She moaned as he jerked her legs, forced her pussy back and forth abruptly on the plank.

  "What are you doing?” as she cried out in pain. He lifted her legs up towards the back of the plank, forced her body to bend forward, drove her spread pussy to slide along the plank, her labia pulled back, the plank touched almost her whole slit, from the bottom all the way up as it crushed her clit. She screamed in excruciating pain as her own weight smashed her clit into the hardwood. Hands fumbled with her ankles, pulled out on her legs, bound her ankles together behind her, the rope on top of the plank, her legs up and back.

  "Hurts, doesn't it?” Michael stroked his cock as he saw the pained look on her face. He looked down at her pussy, the plank riding up her slit. He pushed a few levers and the side panels began to push outward at an angle. The top piece stayed stationary but the bottom of the side panel began to fan out like a wing. “Just to get your legs spread a bit,” pumped the handle, the panel slid out farther and farther, pushed out on her thighs, her legs forced out.

  The plank dug into her slit, her legs apart as if she was being split up the middle, all the pain centered in her sex. The panels finally stopped, her legs spread out obscenely, her weight focused all on her crushed sex. She trembled in pain, unable to move to even attempt to relieve any of it, not even sure it would do any good if she could. She saw the whip in his hand. “What are you going to do?"

  "I want you to dance for me again, Carleigh. You can stop me any time. Just beg me to fuck you and take your virginity. Then, I expect you to get on the desk and spread your legs for me and peel back your pussy so I can see what I am going to fuck. All you have to do is beg me.” He laughed, let her hear the swish of the whip as it cut through the air.

  "Never, I'll never beg you, no matter what you do!” Defiant in her answer, but she wasn't sure she could stand the pain that he intended to inflict on her, especially if she was forced to ride the pony, the plank rubbed harshly over her crush clit.

  Michael was pleased with the scream he tore from her lips as the whip slapped hard across her buttocks, a red line appeared instantly. He touched it, felt her cringe in pain, felt the heat from the mark. “It really bites hard, doesn't it, Carleigh? All you have to do is beg me to fuck you.” He let the whip slap her flesh again, this time on her abdomen, just above her beautiful red bush; a new line matched the bright-colored hair. She jerked, another scream torn from her lips as her clit was crushed back and forth on the board.

  She whimpered in pain, her eyes flooded with tears. Her crotch was on fire, blazing from the rapid movement as her hips were driven forward from the cruel whip. She saw the whip move towards her breasts, the tip slapped lightly at her nipples, drew them out, made them hard as he lightly tapped each one. She wasn't ready for this pain. The whip moved back, then forward, Headmaster Michael's hand made it fly across the enlarged nipple of her right breast. The pain was instantaneous, one minute nothing, the next a hot pain shot through her nipple. She squealed with the pain, her hips jerked back and forth as she danced to the pain, the plank sent hot sensations through her body as her slit rubbed up and down the wood, her clit dragged along. It was not so much pain in her crotch as a tingling of pleasure, her clit sensitized by the harsh plank, a need for any stimulation, pleasure or pain.

  He waited until she looked up at him, the whip lightly tapped her other nipple, waited for her to fully understand what he was going to do next. He smiled when it dawned on her, her mouth clenched, braced for the pain, the whip shot over her other nipple, not disappointing her as it snapped over the youthful tip. He played the whip all over her body, paid particular attention to her nipples, swollen and red, the whip ignited unbelievable pain as her body danced on the plank between her legs.

  It didn't take much longer, her hoarse, whimpering voice mumbled “please fuck me."

  He let the whip dance over her body a few more times before he said, “what did you say, Carleigh?"

  "Please fuck me, Headmaster Michael. Take my virginity,” the pain too much and the unsatisfied tingling between her legs finally took its toll on her young body.

  He put the whip aside, moved along her body, his hand lightly stroked her face. “Why I would love to fuck you, Carleigh? Are you going to go over to the desk and spread yourself open for me?"

  "Yes, Headmaster Michael,” she sobbed as she his hand roamed over her breasts, touched her pained nipples, the slightest touch brought such pain to her body.

  "You're going to dance on my cock so nicely, Carleigh. With your nipples and your pussy so tender, my hard cock and hands are going to make you dance on my cock.” He moved to release her ankles, to shift the side panels back in before he did, her feet touched the floor again as the plank lowered down, her groans of pain as her swollen pussy moved along the harsh wood. He let her hands come down, untied them, watched her painfully lift her leg over the edge of the plank, unconcerned by how exposed she left herself. She moved towards the desk, her legs taking cautious steps, her thighs spread apart as she walked bowlegged. He removed the rest of his clothes until he was naked. He saw her look at him, his cock jutted out in front, his heavy laden balls hung down below, filled with his cum.

  She didn't believe that it would get bigger as he stroked it, but it did. He was naked, his body in good shape for someone his age, es
pecially his cock. It was what she feared the most. With her body so battered, her labia swollen, her nipples tender, the hard cock would not only be her first fuck, but it would be a painful one. She lay obediently down on the desk, slid back until her ass sat on the edge, knew Headmaster Michael watched her. She leaned back, her body burned from the whip as it hit the desk. She moved her butt a little until she felt the edge of the desk. She spread her legs, her swollen pussy exposed, the lips puffy, the pink insides red.

  "Open your pussy up for me, Carleigh."

  She began to cry as her fingers touched her labia, the pain began anew as she touched the inflamed flesh. She began to pull them apart, felt Headmaster Michael move over to her, watched him stroke his cock between her legs as he stared down at her pussy. She felt the whip tap against her nipple again, the pain shot into the abused tip as a warning. Her fingers dug in deeper, pulled her vaginal entrance open, Headmaster Michael's eyes pinned to the bright red and moist opening.

  "Wider,” the whip lightly tapped her other nipple, her fingers moved quickly to open her vagina wider, ignored the pain of the stretch, anything to please the Headmaster.