The Hollister School for Girls

by Powerone

  She had not expected that, his hand grabbed her ass instead of her pussy. His hands gripped her cheeks; she tightened her buttocks together when he went too far and tried to touch the crack in her ass, afraid of where his fingers would go next. She felt his hands move down again, then slip under her panties, pulled outward by the rope that held her leg open as he grasped her naked cheeks. Fingers moved over her cheek, felt her crack.

  "You don't like that, do you, Justine?” He pushed his finger in harder; her muscles tightened more, as he teased her. He would wait until she was naked. Then he would spread her out on a different piece of equipment, spread out with no way to stop him from enjoying the tiny asshole between her cheeks. He pulled his hands out, but not out of her panties, he tore them from her, the blue panties easily ripping by his powerful hands.

  Her panties dug into her flesh, especially her crotch, before they were ripped free; Headmaster Michael pulled them from her body. Naked now, her skirt still on but pulled back, not covering anything. She saw his stare; his eyes burning a hole between her legs.

  He touched her bound leg and pushed it out, bowed it, opened up her pussy to his gaze. It was the sweetest thing he had seen, a small patch of hair at the top, closely cropped into a V, the rest of her pubes naked, a pair of puffy lips unable to contain her pink pussy from his gaze, the bondage did an effective job of leaving her vulnerable and exposed. He let his hands touch her inner thighs just shy of her pussy, grabbed her roughly, knowing that she was probably creaming herself.

  "You have the prettiest cunt I've seen in a long time,” he used the coarse word to describe her pussy, seeing her turn red in embarrassment. His fingers moved up to her pussy lips, spread each out to the side, ready to peel back her lips, eager to see her pink pussy, her tight vagina. He saw the lust in her face. She wanted to cum. He touched her lips, pulled them back as he dug his fingers in, watched them part, her pink inside opened. He gripped the puffy flesh, her wet, silky pussy lips exposed, glistened in the light. “You're so wet. Ask me to masturbate you, Justine.” He looked at her face; so young, but the unmistakable look of a girl on the edge of cumming. If she hadn't been bound she would have had her fingers in her pussy, finger fucking herself until she came. But for now, she would have to beg him to do her.

  God, please let me go. Please let me do it myself. I need to cum so bad, my pussy is so hot. Headmaster Michael watched her, waiting for her response, wanting her to say it, to humiliate her. She hesitated before she finally whispered, “Please."

  "Please what, Justine? What do you want me to do to you?"

  She hesitated again. “Please masturbate me,” she murmured.

  "And what, Justine?"

  "Make me cum,” humiliated at having to admit it, to ask him to make her cum.

  She jumped as if touched by a bolt of lightening, his finger slowly ran up and down her slit, her juices immediately soaked it while he inspected her inner lips; his fingers touched every bit of wet flesh, up and down, all over her vagina, feeling how tight she was.

  He was like a doctor as he examined her. Justine allowed him access to the most intimate places on her body. He held her body open as he ran his fingers up and down her slit, bowed her leg back, her pussy gaped wide, embarrassed at how she must look, the pillory not allowing her to see.

  Michael ran his finger around her vagina, a tiny little hole. She hadn't been fucked much. The thought pleased him. Once he tenderized her skin with a whip, made her more willing to fuck him he was going to test that little hole. He pushed with his finger; felt her slowly open for him, “Such a nice tight pussy, Justine,” pushed harder, her body tightened on his finger. His finger slid in easily on her juices, a tiny gasp escaped her when he pushed in to the knuckle, twisted his finger, massaged the soft sides. Her hips began to move, “Let me feel how tight you are, Justine. Tighten your pussy on my finger, show me what a good girl you can be."

  She heard his voice urge her to perform for him. It was embarrassing, making her tighten her pussy on his finger like a trained dog, but she needed to cum and it wasn't as if his finger didn't feel good. He seemed to discover new places inside her that sent shivers through her body, places that even she hadn't known about. Maybe it was just because she had no choice, the bondage prevented her from protesting what he was doing. “Mmmm,” squeezing tight, “Mmmm” again, feeling as he twisted his finger when she tightened on it.

  "Yes, like that, Justine. I like that."

  She felt proud of herself that she pleased him. She couldn't understand why she felt she had to, but she continued to squeeze, his finger so big inside her.

  Michael slipped his finger out, back in, this time two fingers slid inside, felt her stretch to take the digits. She would be so tight around his big cock. “Squeeze again, feel how full you are with my fingers, Justine."

  She wished she could bow her other leg out, give him more room, his fingers twisted and turned inside her, his knuckles rubbed hard on the sides of her pussy. She could almost cum just from his fingers, if only he would touch her clit. Soft moans as she tightened on the fingers, held her muscles tight as he moved within her. God, it felt so good. She released, his finger plunged deep inside her until his knuckles painfully banged against her opening. She felt him start finger fucking her, each time in deep, then out and back in again. She just had to cum! “Please!” she begged him.

  Michael looked at her, “What do you want?” He would make her beg for it.

  "My clit, please, touch it,” the lust reflected in her voice.

  "Of course my dear, I'd love to do that. I want you to cum for me.” He pulled his fingers from her pussy, felt her tighten on them as he did, not wanting them to leave. One hand went around to her ass, slid along her flanks before finding the crease in her buttocks; let it slide sensuously up and down, teasing the tiny anus, not touching it but stopping just short. His other hand moved up, fingers pushed aside her pussy lips, two fat fingers slid on her juices until it hit her clit, suddenly he pinched the erect bud in their powerful grip. He thought she would jump out of the pillory, her body jerked up and down. “Yes, Justine, ride up and down on my fingers, fuck back.” He let his finger slide down to her anus and pushed on the tiny opening. She jumped again, her body sought to get away from the finger, push her swollen clit into the fingers that gripped it so tight.

  The touch was electric, the hard, brutal touch of his fingers on her clit. She expected a gentle touch, surprised when the pain mixed with the pleasure, her body shook in ecstasy as the highly-aroused organ was so harshly handled, bucking up and down, not sure whether she tried to avoid it or make him pinch harder. She didn't have time to even think about it, his other hand slipped around to her ass, slid close to her anus, the forbidden spot between her cheeks. She cried out as the finger pushed against her defenseless anus, the thick, calloused finger slowly ground on the opening, his other fingers twisted her clit painfully. “God, no! Not there!” She threw her head back in protest as she felt his fingers on her most intimate opening, a place that shouldn't be touched.

  It was so tight; her sphincter fought the intrusion of his finger in her asshole. He ground the tip on the tiny opening, her struggles made it more difficult. He pinched her clit hard between his fingertips, her piercing scream, the pain forcing her asshole to relax and gave him the chance he needed. His finger plunged inside her rectum, his dry finger dragged painfully inside. Her hot, tight asshole clenched on his finger.

  She thought he was going to tear her clit off, his fingers dug harshly into it. As she screamed in pain she jerked, his finger plunged into her anus. She'd never felt anything like it, a strange burning sensation followed by the thick finger rubbing her clenching muscle. His finger returned to her clit, snapped the aroused bud back and forth until she exploded, her hips ground back and forth to feel the pleasure of his finger but at the same time escape the ruthless finger in her backside.

  She came harder than she had ever before, her body covered in sweat, her nipples swollen with
lust, the juices ran down her thighs as his fingers continued to manipulate her body against her will. “God, yes!” His finger pulled from her asshole to plunge inside her pussy, two fat fingers fucking her without regard to the pain or pleasure it inflicted.

  Her body jerked in pain when he “accidentally” banged a fingernail into her soft inner walls only to return as his fingers plucked such pleasure from her clit. Her asshole still burned, as if it was still full of his finger, spasms of her anus gave her a strange tingling between her legs. He pulled on her clit, another orgasm hit; his fingers played her young body. She began to cry, sobbed as she came, humiliated at being forced to cum by Headmaster Michael, his fingers still kept her sexually aroused, a third and final orgasm shattered her body. She slumped down exhausted from the ordeal.

  "Ssshhh, Justine. You're such a good girl to cum like that for me. If you're good, I will make you cum so much more,” stroking her head as he cradled her body, his hand still played across her bush, rubbing her lips, his fingers wet with her cum. He so enjoyed the way she cried.

  They watched her cum, her naked body hung beneath the pillory as Headmaster Michael continued to manipulate her body, keeping her legs splayed open so they could see her pussy gush.

  "See how he fingered her asshole and still made her cum,” Meredith commented to the others. “He kept her sexually aroused and made her suffer the pain in order to get to the pleasure.

  "The next part you will enjoy. He told me that he's going to whip her and I'm sure that her various sexual parts will receive the brunt of the punishment. I understand he loves to whip a nice pussy, forcing her to spread her legs for the whip. And those lovely tits will dance under it as well. I don't think he'll be able to hold out after that, taking his sexual gratification with her body."

  Michael pulled the pillory open, removing Justine from it, holding her to keep her from falling, her body exhausted from the extended orgasm he had just induced in her.

  Justine was so thankful to finally be released from the constraining pillory around her neck. While he had done some painful things to her body, it hadn't been as bad as she thought it would be, the pleasure overcoming her pain. Hopefully he would now let her go, the humiliation of being forcefully masturbated her punishment. “Thank you, Headmaster Michael,” his arms still cradled her. He let her slump to the floor, and moved away from her.

  Michael pulled the canvas cover from the next piece of furniture. She wasn't even paying attention, still too exhausted, slumped on the floor. He liked this one, another heavy wooden pillory, but this one was a bit different. It had a large base on the floor with interconnecting pieces, each having various mechanisms to make the pieces go up, down, left or right. The top piece was similar to the other, but it was at a right angle, Justin would have to bend over to stick her head and hands in the holes. He went over to where she was, bent down and lifted her up under her arms, not missing a chance to touch her breasts. “Over here now, Justine. It's time again."

  She looked up, caught a glimpse of the wooden structure out of the corner of her eye, turned her head to stare at the massive, wooden structure. “No! Not again!” It was almost like the last one, a place for her head and hands, but on the floor it was built for two legs to be placed into. She struggled, but Headmaster Michael was too powerful.

  "Shhh, Justine, settle down,” pushing her over to the pillory. This one was easier, already open; he forced Justine down by pushing down on her head until her neck fit so nicely into the hole. “Put your arms up and in them, I won't tell you twice."

  She complied, not sure why, her body too exhausted, the fight taken out of her. She saw the wood under the neck hole stained dark, victims’ saliva having soaked it. She put her hands up, her legs pressed tightly together, her thighs sticky with her cum. He released her head, the shadow of the pillory fell down until she it touched the back of her neck and wrists, Headmaster Michael banged the padlock noisily. She tried to move but it was as before, the thick solid wood secured her tightly. This time the neck fit tightly, she hoped that there wouldn't be a rubber collar. She didn't like when her breathing was so constrained, it had made her panic.

  He looked down at her, her skirt still around her, but naked from the waist up. She was bent over, not quite to the waist, but it did allow her breasts to hang freely beneath her. Her naked back, still damp from sweat, angled downward, her butt pushed out, her skirt clung to it, Headmaster Michael knew that beneath it she was naked. He smiled as he saw her legs tight together, he laughed at her foolish attempt to stop him from getting between her legs. Soon she would willingly comply, spread her legs for him, and let him visit the whip up between her thighs to slap harshly on her naked pubes. “You look very lovely like this, bent over, your nice plump ass sticking out."

  "What are you going to do now?” He had moved out of her range, his hands on her back the only way she knew where he was.

  "I'm going to tenderize your lovely body, Justine, with a whip, paying special attention to your ass, your tits and between your legs. Yes, your tender pussy is going to feel the sting of the leather. I'm going to enjoy making you scream in pain. It's going to make my cock very hard. And you're going to help me, Justine. You're going to spread those tanned thighs for me. Real wide so the leather can slap your inner pussy lips. You won't believe just how much that will hurt."

  "This is what I like,” one of the Board members stated and reached down to make his hard cock comfortable in his pants.

  "Maybe Headmaster Michael can get a girl for you to whip. How would you like her?” Meredith asked certain the headmaster would be pleased to help him.

  "Can you string her up into the air by her ankles, upside down, legs spread wide? I have a razor strap that I would love to use in the area between her legs. Maybe even take it to her tits, make them dance for me."

  "That would be perfect. You could then pull her up when you finish until her mouth is level with your cock. I'm sure that she would be more than willing to let your fuck her face. Either that or you could whip her pussy more, her choice.” They both laughed.

  In the meantime, Headmaster Michael had moved a mirror in front of Justine. “I want you to be able to see in back of you, to see what I am doing to you. And also to see my special toy. I want to make sure you have every chance to avoid the pain it could inflict on you if you cooperate. But first, let's get rid of that skirt. It's covering a nice naked ass.” He let his hands roam freely over her ass, felt her tight butt beneath it. He took out his knife again, sliced the skirt down the seam; the rag fell to the floor. He admired her ass, thrust out for him. “Yes, I like that,” his hands returned to touch her flesh.

  Justine hadn't even moved when he stripped the last of the clothes from her body, his hands returned to caress her naked skin. She clenched her thighs together, determined to keep him from the treasures nestled between them. She looked into the mirror, a double reflection off a mirror behind her, shined back the image of her backside. She looked so obscene, her butt pushed up in the air, naked, the crack in her butt so crudely exposed, her clenched thighs her only relief.

  Michael moved to the side of her where she could see him. He reached over and grabbed one of her breasts, milking it with his hand like a cock, the tit hung down, the nipples not yet hard. He picked up a flogger he had just bought. While it was not what he was used to, he thought it appropriate for his new position. He let his hand run through the fall. “This is an American Classic Flogger, Justine. It is built to sting, with 40 falls, that vary in length at 12 inches, 18 inches or 24 inches. It is an excellent flogger to go into hard to reach places, the alternating lengths of the falls make sure that every part of the body, even the darkest recesses, will feel the sting of this suede flogger."

  "You can't use that on me!” she proclaimed, the pillory shook as she tried to pull free. She was getting her strength back, but it was too late, the pillory held her secure.

  "I'll let you feel it a couple of times on your back, just so you will know what
to expect.” He drew the flogger up into the air, let it fly, then landed it on the center of Justine's back with the signature “thud” as all 40 falls tore into her skin.

  Justine screamed in pain. He had been right, the sharp sting concentrated on her back. It hadn't been just one spot, but the whole area; she was sure that her skin was torn. She did not have time to protest before a second and more powerful “thud” disturbed her scream of pain, her agony doubled, her back a mass of conflicted pain.

  Michael rubbed his hand over her inflamed back, the skin already warm, turned a light pink. “Now that you know what to expect, let's try a more intimate part, Justine. How about if I flog your hanging breasts?” His hands reached down to one, grabbed it in his palm, squeezed it harshly before he moved on to her nipple, pulled and yanked until it began to harden, not sure if it was pleasure or pain that brought it about, Michael had not really cared, just wanted to give himself a bigger target to abuse.

  "You can't hit a girl there!” she exclaimed, but knew better. Headmaster Michael enjoyed inflicting pain and she knew that her breasts wouldn't be the only place. He had already threatened to whip her between her legs.

  He let the flogger fly, swung side-arm, got enough force behind it to slap against her breast flesh, numerous falls tearing at her areola and nipples. He was pleased with the scream that he tore from her lungs. He imagined how it felt, 40 suede falls attacking her breast. He let her feel the pain for a minute, faded to a dull ache before he slashed at it again, aimed lower, put the full force of the blow on the tip of her breast, her nipple.

  She thought he had ripped her nipple from her breast; the fall hit the hard flesh with a powerful force, the second one even more painful than the first. She began to cry, even as he switched sides, Justine turned her head just in time to see the flogger sail through the air and strike her untouched breast. Two more blows, each time harder and faster, her breast bounced around as it suffered the terrible flogging. She couldn't stop screaming; Headmaster Michael moved from one side of her to the other, each time extracted fresh screams from her, each time her breast suffered the terrible sting of the flogger. She panted, her voice hoarse from her screams, sure that her breasts bled.