Violet lay panting as Jared's dick slowly softened inside her hole, amazed at the brutal scene involving her friend that she'd just watched. It had been a serious turn on.
That evening after dinner they watched the movie of Violet at the club while she gave Jared another blowjob. It disgusted her to watch as the fat security guard fucked her from behind, especially when he shoved that nightstick in her pussy, but Jared kept pulling her hair back from her brown eyes to make sure she was watching. Drinking the cum that spilled down her throat she marveled at the many sexual experiences that she'd been opened up to by this contest.
It was a relief when they went to bed without visiting the basement, although she did ask him about it rather curiously.
"Tomorrow," his grin was a shining beacon in that black face, "I wanted to make sure that you were well rested for it, you're going to need it."
The morning was spent with Jared doing work again, which really just made it all the more worse for Violet because she was left alone to reflect on his words the night before. The fact that he wanted her well-rested for whatever was going to happen told her that she was in for another rough session... surprisingly she desired it as much as it made her anxious and frightened. That morning she actually spent some time masturbating as she thought about the whipping he'd given her, and the way he'd fucked her without mercy, still abusing her sore body. Yesterday had been much gentler, and for obvious reasons... he wanted to have the very rough days with her without breaking her.
Thinking over the apparatus's in the basement she shivered a little as her imagination ran away with her... retreating to the library she curled up with a book and tried not to think about it.
Violet was strapped over the strange I-shaped horse, her hips resting securely on one wide end and her cheek resting on the other with her tits hanging down on either side of the narrow part. Her hands and legs were tied to the posts on the horse and a strap around her middle secured her as well. Considering the ordeal he'd put her through the other day when she'd been bound just as securely, this was not comforting. She groaned as he fastened clothespins to her nipples, squeezing them so that they burned painfully. Panting a little, she felt his finger invading her pussy hole... she was wet. No clamp was placed on her clit which made her feel a little worried.
He walked around her and pushed his finger into her mouth, and she sucked it clean, the taste of her own pussy on her tongue as big hazel eyes looked up at his smiling face.
"Good girl," he smiled, pulling his finger from her mouth and replacing it with his dick, "Do not bite me."
Wide-eyed she looked up at him, unable to answer as her face was pressed against his groin, thick cock stretching her throat. Grinning at her, he pulled out slightly and picked up an even longer multi-strand leather whip than the one before, this one was knotted at the ends. As his dick thrust in and out of her wet mouth, gliding over her pink tongue, he slapped her ass with the whip and the knots hit her tender pussy. Fucking her face, he continued to beat her ass and pussy, although always on the edges of her pussy. She was squealing a little, taking care not to bite down as she reacted to the pain. Tears were in her eyes as her cheeks turned pink, little marks wherever the knotted ends had hit her cheeks or thighs... her pussy was burning a little. One hard slap that hit her open pussy squarely, the ends slapping painfully against her inner lips and clit, made her mouth involuntarily close a bit and the ends of her teeth just barely grazed the dick in her mouth.
Shaking his head, Jared pulled out and grabbed the penis gag again, "I'm very disappointed in you Violet." She hung her head, knowing protests would be useless - he'd set her up for failure. Opening her mouth for the gag she looked up at his impassive face, "Now you'll have to be punished." And he grinned.
Pulling the clothespins from her tender nipples, she winced as he placed them on the table and picked up rubber tipped clamps. Rubbing her breasts, he pinched her nipples and rolled them between his fingers, making sure the blood was running through them again before applying the clamps. Violet moaned in pain as her nipples were harshly pinched, sharp pain making her pant. At her other end Jared toyed with her pussy, sucking her clit into her mouth and she whimpered, knowing very well what was coming at the end of this pleasure. Jared tightened the clamp cruelly on her sensitive bud as she shrieked with pain and thrashed, sobbing as he flicked it.
Greasing her asshole with lube, he began pressing something very large into her. She couldn't see it, but it was a long probe with 4 balls on it that got bigger as it went down till the biggest one had a 3" circumference. The first one was only half an inch, and there was a short space between each of the balls so that her asshole would close over it. Jared grinned as he pressed the first one in, and she moaned a little as it felt pleasurable, her ass closing over the small ball. Her back arched a little as her ass stretched over the second one and he worked her ass with the small space between the balls. The next one, a 2" circumference made her gasp and pant, especially as the probe was now pressing much deeper into her ass as the tight hole close over the third ball. Giving her a few minutes to adjust, he twisted the probe in her ass, even pulled it out once so that only the first ball was in her before pushing it back in. Violet shuddered as he began to push in the third ball, crying out in agony behind her gag as her ass stretched its widest ever around the ball, the probe digging deep into her ass. Tears trickled down her cheeks and onto the horse when it finally popped in and Jared twisted it in her ass, the four balls massaging her insides and giving her slight cramps in her stomach. It hurt terribly as he pressed it further into her ass, just leaving the handle out.
Taking a leather paddle he began spanking her ass, watching her cheeks dance and her small hole clench around the probe that was sticking out of it. Every time her ass clenched down around the big balls it hurt but she couldn't help it, that was her instinctive reaction to the spanking. On and on it went, her ass turning pinker and pinker and her insides churning as he occasionally twisted the probe or pulled and pushed it a little. A few times he knocked the handle with the probe and she groaned with the pain of it.
Finally he set the paddle down, stepping behind her and pressing his dick into her pussy. She was still a little sore from two days before, but the main reason for her discomfort was the balls in her ass... it felt very nice for Jared as it made interesting ridges in her pussy, but Violet felt overly full. It especially hurt when his dick had completely slid into her and his body was pressing against the handle sticking out of her ass, balls slapping against her clamped clit. Reaching over, dick still buried in her pussy, he picked up a long braided single strand whip from the table.
Violet shrieked in surprise and pain when it hit her breast flesh, making her clamped nipple ache and spreading pain through her entire tit; it didn't help that her back automatically arched which placed the balls at an odd position in her ass as well as pressing the handle against Jared's body which meant that the probe dug even deeper. Starting to pull out of her pussy and then push back in, Jared began whipping her breasts steadily as he fucked her... really he was being quite gentle and careful of her body although it didn't feel like it to her. But he was fucking her slowly, and was careful not to put too much of his body weight against the probe in her ass, and was very careful not to hit her breasts too hard as they were pressed up against the horse and so could easily be very badly hurt. Still, Violet was sobbing as he fucked her, discomfort everywhere as he whipped her tits, the probe pressing into her ass, thick cock in her sore pussy, and his balls hitting the clamp on her clit every time he thrust. None of that stopped her pussy from leaking more and more fluid as he fucked her, she was turning into quite the painslut as the pleasure mixed with the pain, filling her body in a confusion blend.
Finally Jared seemed to take pity on her and he dropped the whip and pulled the probe from her ass - making her cry out as the balls stretched her ass open while they left. Bending over her shuddering body he began pumping her pussy hard, balls slapping against her clit as his hands gripped her slender waist. Crying out behind her gag, Violet came hard, and then screamed as the swelling of her clit made the clamp pinch into her even more cruelly... as her pussy convulsed around his dick Jared reached forward and pulled the clamps from her nipples. They stretched downwards until the clamps popped off, making the girl yelp and squeal as they pulled and then blood started rushing into them again. Her orgasm was incredibly intense with the agony and ecstasy coursing through her, her clit swelling in the confines of the clamp, tender flesh bulging around its tight grip.
As her body thrashed in the throes of her orgasm Jared pulled his dick from her sore cunt and speared her rather stretched asshole, unloading spurts of creaminess into her body. When he'd finished cumming he immediately pulled out of her and released her clit from its clamp, making her moan again as the blood finally pooled in the sensitive bud. Kissing it, he tickled the little nub with his tongue, soothing it after all the abuse it had taken.
Again, after he'd untied her he carried her up to his room and placed her in his bed. She was so exhausted that she was falling asleep in his arms, and didn't even wake up for dinner that night. Jared slid in beside her, gently stroking her back and pulling her close to him before falling asleep himself.
Violet woke moaning as Jared's body heaved on top of her, cock deep in her pussy as his lips pressed against the soft skin of her neck. Panting and heaving together, his body rubbed against her extremely sore clit, bringing her to a passionate morning orgasm.
Things were very informal during the day, he let her stay in bed and sleep in (after their morning sex anyway) while he went and did some work. Waking her for lunch, he helped her down the stairs as the area between her legs was very sensitive. After lunch they relaxed in his Jacuzzi on the back porch, just talking and kissing, he occasionally fondled her body and she winced and bore it - although she did feel aroused as he handled her sore breasts, pussy, and ass.
After dinner he spoiled her a little, and they watched the tape of Danielle losing her anal virginity to a very long cock. Sitting on the couch, Violet's legs were spread wide as Jared's mouth covered her pussy while she watched a long black cock spear her friend's last virgin hole. Moaning as his tongue soothed the soreness in her pussy, her hands ran over his head and shoulders... he'd said that she'd been so good yesterday that he wanted to reward her. He'd already seen the tape, it was time for her to really enjoy herself while watching - besides she wasn't really up to anything other than the gentle licking of her pussy. In bed, before sleeping, she crawled beneath the sheets and to his delighted surprise proceeded to give him a first class blowjob. Afterwards he pulled her into his arms and cradled her as they fell asleep.
Violet was more than a little apprehensive as Jared gave her a second day to rest up. Yes, he woke her up with morning sex again, and didn't hold back as he fucked her hard, her legs up in the air over his broad shoulders. Although her pussy had been a little sore it had felt fantastic, and the discomfort had rapidly disappeared as she came hard, moaning his name. Her body was almost completely recovered anyway... and yet he had told her (after cumming in her pussy) that she was going to have another day of rest.
The morning he spent working as usual, and she watched the tape of herself taking the anal train from the guys, playing with herself all the while. Lunch was pleasant, she cooked for him and he surprised her by coming up behind her as she washed the dishes afterwards, pressing his dick into her pussy to wet it and then fucking her hard in the ass while she bent over the sink. It had been spontaneous and exciting, but certainly not painful as his fingers rolled her clit, making her cum while his dick shot yet another load of cum into her ass.
In the afternoon they did go down into the basement, but the activity down there consisted of him filling her bowels with warm water. He gave her three enemas, making her hold them for a long while as she cramped and pleaded to be allowed to void herself. After each one he had her release over the drain and then poured water down from the shower head to clean her and the floor. During the last one he had her stand facing the wall, hands up against it with her legs spread while he spanked her, and she whimpered and pleaded as little trickles fell from her full ass. Again, nothing to cause pain even though it filled her with humiliation.
Dinner passed quickly as they talked, and then they went into the other room for TV time again. This time he gave her a large dildo, just slightly smaller than himself and jerked his dick while watching her play with herself as they both watched Danielle with Christine for the first time. She jerked and moaned as her cream covered the big dildo, and he stood in front of her, sliding his hand up and down his long shaft until white ropes of cum spurted and covered her tits and face. Opening her lips she caught some of it in her mouth, pink tongue sliding out to lick the whiteness from her lips. Jared watched, eyes glowing as she rubbed his cum into her breasts, bringing cum-coated fingers to her mouth to suck clean. Violet was turning into a very dirty girl.
That night they fucked decadently and passionately, Violet clasping him to her as he pummeled her cunt ferociously. Moaning and gasping they came together, backs arched and bodies spasming with pleasure. They fell asleep with Jared still inside her pussy, his heavy weight comforting on top of her.
~Day Six - the Final Day~
In the morning Violet awakened to a dick thrusting in and out of her pussy again, and she moaned excitedly, squirming beneath his heaving body. It wasn't very long until they were both cumming again... waking up horny meant that neither of them had much control as they fucked hard.
"I hope you enjoyed that," Jared kissed her, dark eyes excited, "It's going to be a long afternoon for you so I suggest you get as much rest as possible."
"Oh..." said Violet, flirtatiously teasing, "I hadn't realized that I'd been such a bad girl."
"You've been a very naughty little girl," the husky heat in his voice made her shiver with delight, even as she was very anxious for what he would have planned for their last day together, "For teasing me for so long without letting me have you... so today you're going to be punished for that."
Violet's hazel eyes were wide, "Sounds like it's going to be rough."
"Stay in bed for awhile and get some rest," he advised, kissing her lips before pulling his dick out of her pussy and going downstairs to get some work done.
Of course, with that warning as his final words there was no way that Violet could rest. There was only one apparatus left in his basement, that odd triangular horse... and her active imagination couldn't think up a single way that it could possibly work. Instead she tossed and turned, eventually getting up to eat and go to the library where she tried to concentrate on a book. Finally it was lunchtime, and then time to go to the basement.
Jared lifted one of her legs over the strange horse, and cuffed her wrists together with wide leather cuffs. She grimaced a little, and shifted weight as he did this, the center blunt edge of the triangle split her pussy and ass cheeks very uncomfortably. Violet groaned when Jared secured her hands above her head to the hook hanging down... the positioning of the hook and her body on the horse meant that she was leaning forward with all her weight pressing the wedge tightly into her pussy, and worst of all her clit was crushed.
"Oh please Jared... this hurts," she begged, wriggling a little to try and find a more comfortable, less painful position - there wasn't one, "Please don't leave me up here for too long." Her toes were barely grazing the floor.
"Don't worry," he chuckled, picking up a very very long braided whip, "You won't be up there for too long."
The whip swished and cracked, landing on her right breast and leaving a very angry red mark.
SWISH CRACK! Scream. SWISH CRACK! Scream.
Violet's agonized voice echoed off the walls as he beat her tits, the whip sometimes also wrapping around her to strike her back. The worst hits were when just the end of it snapped against her flesh... it was the first time that he hadn't gagged her, and now her screams and cries echoed. Rocking on the triangle made her entire body ache with agonizing pain, it shot from her spread cunt up to her breasts, nipples shrieking with sharp jabbing pain as he flicked them with the very end of the whip. It hurt so much that she didn't even have the voice to beg, just scream and scream as her tender breasts were covered with red welts, her rocking body crushing her poor pussy lips and clit... but she couldn't help herself from moving as he punished her.
Finally it stopped... it felt like she'd been up there for hours, but in reality it was less than five minutes. Her breasts were bright pink and glowing, welts cropping up all over the tender flesh, nipples purplish and raw. When Jared released her hands she practically fell onto him, moaning as her pussy was finally off the wood. There was a large wet spot where her body had rested on the horse.
Jared laid her on her back, spreading her thighs with his hand, and without further ado began to push himself into her bruised cunt.
Violet screamed again, sobbing as tears ran down her face and his dick spread her aching body open, "OH GOD JARED!!!! PLEASE STOP... IT HURTS, IT HURTS SO BAD... PLEASE..."
His eyes glowed with emotion as he answered her, "Did you think I've been immune all these years to your teasing? To all your comments about how much you'd like to have me under you? What did you think I was little girl?" Sliding all the way in as she sobbed, he began a brutal quick thrusting, "I'm not your toy. I'm not some wimpy man that you can push around. Now you're my little slut... how does it feel slut? How does it feel to have a real man in you, on top of you?"
She sobbed all the harder as he grabbed her wrists, holding them over her head so that her body was stretched out on the ground beneath him, breasts rubbing painfully against his chest as her pussy was impaled on him. It was true... it was all true. Constantly she had teased him, saying how much she'd love to see him tied up and serving her... now she couldn't imagine him in that position at all. More frightening, she did want to be his slut, his toy, even as he punished her more brutally than she'd ever treated any man in her bed.
Body arching, pain screeching through her, "OH FUCK! OH GOD JARED... I'M CUMMING! OH GOD IT HURTS... I'M CUMMING SO HARD!!!!! OH PLEASE STOP!!!!!! PLEASE STOP I CAN'T TAKE IT!!!!!!!!" her voice went higher and higher, turning into a despairing wail as he continued to pound her hard as she thrashed beneath him. The sensitive crushed bud that was her clit was completely overwhelmed by the pain and ecstasy that he'd aroused in her, it was the most painful and intense orgasm she'd ever had in her life.