by Powerone
"I love how you fight my fingers. Are you trying to stop me from touching your tiny anus snuggled deep in the cleft of your ass? All of your body is mine for the taking, Carleigh, and that includes your asshole. You will soon learn what it feels like to pleasure a hard cock with your asshole. You will be taught to tighten your silky insides on it, to draw my semen from my balls, to have your colon filled with hot cum.” Michael's hands ran up to the top of her panties, felt her jump when he pulled the elastic waistband out, his large hand barely able to slide inside the form-fitting panties. He relished the luxurious feel of her silken skin as he grasped her naked cheeks for the first time, loved how she clenched tight, pushed her pussy into his hard cock, rubbed up and down the throbbing member, not realizing how much pleasure her attempts to escape his probing fingers brought to his cock, masturbated it with her panty-covered pussy.
His fingers drove her hips forward, realization dawned when she felt the dampness between her legs, her pussy lips speared apart by the hard cock she thrust up against, rubbed as sensuously back and forth just as she would do with her fingers when she masturbated. It was so thick, the size of bottle, it throbbed each time she moved against it, her hips danced for his pleasure. She acted like a cheap whore, grinding her pussy on the nearest cock. She tried to stop, relax her cheeks, fight the urge not to shoot her hips forward, but his fingers sensed her surrender and found their way deeper into the cleft of her ass, up and down the slit, ever closer to the virgin anus nested deep inside her cheeks.
"You are so good, Carleigh. Do you want more of that delicious feeling between your legs?"
She shivered in fear when she heard the sound of a zipper pulled down; his body temporarily pulled away from hers, her pussy felt almost empty. She shuddered when he pressed his body up against her again. But this time it was different. There was no longer a barrier of clothes between him and her pussy. Only the briefest of panties separated her wet pussy from the hot, hard cock pressed up against her. She shuddered as he slid it up to her slit, used his hand to guide the large head up and down her lips, pushed them apart, her silky panties slid in the gap, his throbbing head followed. Once he settled it deep inside her lips his other hand slid to grab her panty-clad rear end, one thick middle finger snuggled up along her crease.
"Now masturbate my cock with your pussy again,” his finger pushed hard against her clenched cheeks, not taking no for an answer, a shudder and muffled gasp came from her gagged mouth as his finger touched her panty-covered anus for the first time, something she had never even fathomed that would happen to her. Her hips shot forward to escape the fat finger, slid her pussy up and down the naked cock pushed against her. He tapped her anus with his finger, each time her hips shot forward then back, as if she was willingly fucking him. “Faster,” he urged her, his finger tapped harder, made sure she felt it.
His cock seemed to get bigger, jerking back and forth up her slit. His finger touched her anus, her cheeks unable to prevent him, her hips shot up so high that his cock rubbed against her clit, a shudder of pleasure ran through her body, her damp panties stuck to her flesh. The strong finger pushed against her tiny opening, her panties the only thing that saved her anus from being fully pierced by the digit. Even then, his finger pushed her panties into the tiny hole, her hips rocking back and forth each time to escape the painful prodding of his fingers. How could anyone want to do a thing like this, his finger seeking entrance into a hole that was not meant for sex? She fucked her hips back and forth, no other choice to escape the cruel ravishment of her bottom. His other hand kept her cheeks spread open, his fingers forcing them wide, his other hand free to ravage her anus. She began to sweat, tired from the simulated fucking. She felt him shudder, his finger on her anus pushed harder than before, her panties shoved deep into her anus, the panty-covered finger pushed into her rectum, the dry material rubbed harshly as she was slowly impaled for the first time.
Michael could last no longer, his finger pushed into her anus drove her hips forward, her pussy lips wrapped so tenderly around his aroused cock. He felt her sphincter fight the panty-covered finger pressing inside her rectum. That was all he needed, rubbing his cock up and down her slit, finally shot out onto her panties, his thick cum quickly soaking the flimsy material.
It was disgusting, one minute he rubbed up and down, the next he pierced her anus with his finger and shot his cum onto her panties, drenched the already damp material with his copious fluids. She thought he would never stop, the hard cock jerked and shot, surprised as more fluids bathed her virgin pussy. She finally felt it get soft, her hips still pressed forward, to escape the finger that moved around inside her rectum, forced her to move back and forth over the spewing cock. He finally moved back, Carleigh looked, his cock now shrinking in size, but still much larger than she had expected it to be, gleaming with the cum that drenched her panties. She looked up, her face red in shame as his eyes caught her looking at his cock.
"Yes, look at what your sweet pussy did, Carleigh. It made my cock cum. But don't worry, with a body as lovely as yours, I will have no trouble getting hard again,” his hand reached down to lightly stroke up and down his cock. “But, I seem to have gotten your panties wet. I guess I should take them off, wouldn't want you to get a rash from wearing wet panties,” he laughed at her discomfort, his cock already hard again at the thought of her body naked.
"Such a lovely pussy, Carleigh,” his eyes feasted on the drenched panties that pushed deep between her lips, her vulva clearly outlined. She had a flawless camel toe, the perfection of a woman's crotch area with the look of a camel's halved toes that allows labial creases to be visible through her pants-one of Michael's weaknesses. His hands reached out to touch her, his fingers played along the outer lips, rubbed his cum up and down her panties as she shuddered from being so rudely handled. He pinched her lips between two fingers, was rewarded with a jerk of her hips, another pinch, a gasp from her widely stretched lips. His hands hand grabbed the elastic waistband of her panties and knelt as he began to slowly lower them, his eyes only inches from her pussy.
"I love a red bush, Carleigh. I'm glad you only trim it; I would have hated it if you shaved your pubes bald. Yours looks like a tiny heart. Do you have a secret boy that you show your pussy to, Carleigh? Is that why you are so neatly trimmed down there?” He laughed at her shame, his hands continued to strip her panties off. Lower her panties slid until he stopped just below the vee of her legs, her pussy now completely exposed to him, her panties fell to the spreader bar. Michael quickly cut them off, balled the wet panties and brought the cum soaked panties in front of Carleigh's face.
No, he couldn't be thinking of doing that Nooo! Carleigh cried silently as his hand move forward toward her widely spaced lips, the ring gag efficiently leaving her mouth open for whatever he desired to place inside. She did not want to even think about his remark of “using her mouth,” instead tried to ignore it. But she could not ignore his intentions as his hand slipped under her chin, lifted her head, her mouth a gaping hole, his other hand moved the drenched panties closer. She inhaled the unmistakable smell of sex as the panties touched her lips; her senses shocked by the cold, wet feel of silk lingered on her lips as his fingers slowly began to insert the balled panties into her mouth. Her tongue was the first to be invaded by the foul tasting cum, the thick, salty fluids drenched in her panties rubbed over her taste buds, the fluids from the garment mixed with her saliva and filled her mouth. Her face reflected her distaste of his cum. His fingers pushed the panties completely, her cheeks bulged, a leather cover placed over the opening trapped her soiled panties in her mouth, her tongue tried to push it aside, succeeded only in releasing more of the awful tasting semen.
"That should give you a taste of things to cum, literally,” Headmaster Michael laughed at his own joke as she shook her head in disgust. He slipped down to her legs again, adjusted the spreader bar over two-feet wide; he wanted her legs wider for his examination. “Time to examine your pussy, Carleigh. Just want
to make sure you're a virgin.” His hands slid up her thighs again, pleased at the spread of her legs. He guessed she was still a virgin, her pussy lips were tight together even with her legs spread. He let his fingers rub over her near bald vulva, her tiny bush accented the smooth flesh, felt her shudder again. He inhaled her scent, the musty smell of sexual arousal. While he was satisfied with her masturbation of his cock, he was sure that she had been aroused by it, left hanging by his orgasm. He wanted her to stay that way, sexually aroused. It would make it much easier to make her beg him to fuck her. He would enjoy taking her virginity from her forever.
He engulfed her pussy with his large palm, gripped her tightly, squeezed, his fingers dug into the flesh, felt her push her ass out, trying to escape his groping hand. He released, then grabbed her again, enjoyed the way it made her hump his hand. He bent down in front of her, felt her shiver as he blew on her pussy, knew it sent tremors through her body. His fingers lightly touched the lips of her pussy. “You seem to be awfully wet, Carleigh. Could you be enjoying this?” He laughed, pulled her lips apart, rewarded with the sight of the pink flesh inside, wet with her juices reflecting the lights in the room. He blew again, her vagina seemed to flutter open and closed. He gripped just one side, pulled it out wide, one finger from his other hand slowly ran up and down the tender slit, intimately feeling every bit of her silky skin. He blew again, was aware of her shiver, her pussy seemed to be wetter. The other side was given the same treatment, her pussy now glistened. “How do you like being examined so intimately, Carleigh?” He moved his fingers to her vagina, a tight little hole, his fingers pushed apart her lips. “Such a tiny hole, Carleigh. How are you ever going to take my big cock in that little hole?” Headmaster Michael leaned in close to her ear and whispered harshly, “It's going to hurt when I fuck you, Carleigh. I will make sure of that. I will love the screams that you will make when I fuck you, the feel as a hard cock busts your hymen. It makes my cock that much harder; makes it want to fuck you, to make you scream some more.” He moved his fingers to the entrance of her womanhood. He pushed outward with his fingers, her muscles struggled against his powerful digits as she fought to stop their entrance. He blew on her super-heated pussy, the shock of the air on her insides made her jump, gave him just the opportunity he needed to pull her open wider. He kept his fingers spread, the tiny hole struggled to stretch an inch. She would soon learn how much she would have to open to receive the girth of his cock.
She screamed into the ring gag, only a muffled sound escaped. She couldn't believe he had done that. She was so humiliated, his head only inches from her sex as his fingers manipulated her flesh, pulled apart her labia, ran his fingers up and down her slit, unable to stop her sex from being lubricated, embarrassed that he saw her arousal. It hurt when his finger pulled apart her vagina, her tiny sex never received more than her pinky finger when she got too excited masturbating. Her hips began a gentle roll, she couldn't even stop when his fingers pushed down on the sides of her clit, exposed the swollen nodule to his gaze, his finger tapped it, her body shuddered. Her clit was always very sensitive, needing only a first touch of her fingers to bring herself to orgasm. But it was the touch of his tongue that almost drove her over the edge. No one had ever done that to her. She felt the hot, wet tongue lap close to her clit like it was sending a bolt of electricity up her spine. And, he didn't stop there. His tongue pushed apart her pussy lips as it lapped like a dog, her body jumped as it ran over her vagina. She shook her head back and forth in protest. He had to stop! It was so humiliating, to be bound and licked. The worse part was that it felt good. Better than anything she had ever felt and she wasn't sure how much longer she could hold out. If he didn't stop soon, she would cum, cum all over his tongue. Not something that he would not notice. He would see what a slut she was, cumming from his tongue.
He inhaled her scent, tasted the sweet juices that soaked her pussy, his cock jerked in pleasure. He felt her virgin body shudder in pleasure as he licked her pussy. “You like that, Carleigh. Ever had a boy eat your pussy before, did anyone ever make you cum that way?” He teased her with his tongue some more, moved close to her clit but never quite touched it again. “Your not going to cum yet, Carleigh, there is so much more for you to experience."
She watched as he stood, his hard cock bobbed up and down. He moved behind her, the sound of scraping as something heavy was dragged across the floor, unable to turn and see what it was, almost afraid to know. He returned in front of her, his hands moved down to take the spreader bar from between her legs. She moved her legs closer together. She felt her arms lowered until they hung loosely from the rope, still secured but giving her more freedom of movement. What was he going to do? She was afraid of the answer.
"You're just going for a ride,” but the evil tone of his voice told her that it wasn't what she thought it would be. She knew that whatever it was, it would be painful; she remembered his promise to make her beg him to fuck her and take her virginity.
Something wooden banged against the back of her legs seeking entrance between her thighs.
"Let it go between your legs. You can make it easy or hard. Either way it is going between your legs.” He nudged the back of her thighs with the wooden device until he she let her thighs part.
She looked down as a massive wooden structure slid between her legs, moved out at least three feet in front of her. It stood about three feet high; the center of the structure was a wooden plank. It wasn't parallel to the floor, but perpendicular, the edge of the plank standing straight up. She saw the edge, stained and pointed. Not into a sharp point, but a thin round edge that seemed to have been worn down over time. The plank was supported by a thick wooden frame that firmly anchored it, unable to tip or fall. There were side boards that ran at an angle from the upright board, each one tilted outward. There seemed to be some sort of mechanism, with many handles and levers throughout the device. Her fear instantly increased. She was not sure what the device was meant to do, but she knew that somehow it would be inflicted on her. What would it do to her?
"It is called the “wooden pony". This one is from Europe and over 500 years old. It is similar to what the Japanese call the “wooden horse” used as a sado-sexual device. The horse is a more triangle shaped plank, this one has a thin plank. Do you know where the plank will be placed, Carleigh?"
She was afraid to answer, did not want to acknowledge what he was going to do to her. But she knew that with the placement of the plank between her legs, her sex was going to be abused by the evil device. It was low now, but she knew that the mechanisms on the wooden pony would be raised higher. How could he do such a thing to a girl, her sex too delicate to stand such an evil device? She began to cry, tears ran down her cheeks.
He loved this device. The wooden horse was more severe, the wooden pony a gentler, kinder horse. Carleigh would have to straddle the narrow plank, her labia parted on either side. They had used it often on some of the more reluctant girls, forced to perch high on their tiptoes until exhaustion or cramps set in, then their crotch would be forced down onto the narrow plank, which pressed hard against the pelvis. A flood of sensations would sweep through their sex as the delicate flesh received the first of many small bruises. The girl would rise up again on her toes until she no longer could keep the position, forced down on the plank again, seeking a new, unmarked place. Eventually the girl's sex would swell, unable to find a comfortable spot, constantly squirming to escape the pain. For the more reluctant ones, a nice, slender willow rod used on their breasts, butt, thighs and abdomen, would keep them in constant motion. Their cries of pain from the rod mixed with the harsh rubbing of her swollen sex on the plank made it possible to make her ride the wooden pony for long periods of time.
It was important that the plank not be placed too high, otherwise the rider would feel only pain. The narrower distance provided more pleasure than pain. If situated perfectly, the rider would learn how to move her crotch just slightly back and forth along the plank to maximiz
e the pleasure and minimize the pain. He knew that Carleigh would become exhausted from continual pleasure and would be more able to take his large cock up her virgin hole, even willingly beg him to fuck her. She would do anything to escape the pain and pleasure that the wooden pony would inflict on her. “It is time, Carleigh.” Michael moved the controls, pumped up the plank as it rose in sudden shifts, the antique mechanism clumsy in comparison to the more modern mechanical devices he more frequently used. But his cock hardened at the thought of the hundreds of pussies that were split painfully by the pony, their juices stained the plank. The plank moved higher, pressed between her tight thighs, her legs forced outward as the unrelenting device had its way with her body.
Carleigh watched the plank move higher, felt the vibrations as it jerked in fits and starts, the creaky mechanism made the device shudder beneath her. She trembled when it touched her tender inner thighs, pushed outward with her legs as the wood plank rubbed harshly along her flesh. But it was never far enough; the continual rise of the plank each time forced her to spread wider. She screamed through her panty-filled mouth, the ring gag allowed only muffled sounds as she felt the wood hit the vee of her legs, pressed lightly against her sex. She knew that it would not stop, the lust in Headmaster Michael's eyes provided proof, as he worked the mechanism, the slow, gradual rise of the evil plank continued.
"I think it best to rise on your toes now, Carleigh. The plank is going to move a little higher and unless you rise up, it will painfully split your labia apart and bruise your tender inner pussy.” Michael watched as she first resisted, defiant in not relenting. But the plank was ruthless, not caring about her, moved higher up, Michael pleased at the way it dug between her labia, splitting her up the middle, the wooden plank nestled neatly between them. “Yes, I knew you would agree that it was less painful to rise on your toes,” her face cringed in pain as it moved up, split her painfully apart, her toes finally relented to the power the machine had over her body, higher and higher as the machine kept up its gradual ascent. Michael let the plank rise, his fingers pulled apart her labia, made sure that the plank would rub painfully against her tender inner flesh, the pink flesh that would soon be raw from the harsh wood. He finally stopped it, Carleigh perched up high on her toes, the muscles in her legs drawn taut. He liked the look of her body as she struggled to keep her sex away from the wooden plank that dug so painfully between her labia.