Jim's Best Man by NYAcademic Jim's spent but still distended, proudly oversized prick swung heavily between his powerful legs as he walked, still slick with his own discharged semen and low slung from its prior triumphant occupations, taking his wife again and again on their wedding night, and waking her with his prick this morning, but the thoughts of his promise to his best friend which he had made solemnly again and again kept his spent prick semihard and trembling with anticipation. At the same time he was afraid that his young wife might not survive the promised sacrifice of her tight ass to his friend's eager cock and yet he knew that her ass had to be broken in to ready service. His prick swelling at the idea, Jim drew his naked wife behind him, walking clumsily like the freshly and vigorously, already repeatedly fucked young bride that she was. She had been crying from the quick spanking he had administered as much to persuade her to obey him or to prepare her, and he had fucked her quickly with a morning stiffness that had intensified as he spanked her at the sight of her trembling round ass as she bucked across his lap and the feel of her agony as he repeatedly raised his open hand and then brought it down hard on her upraised ass, again and again, until he turned her over and fucked his stiff cock quickly to a fast explosion inside her. She had not come as he pumped her full of his own hot sperm, gasping his release and kissing her cries away. She was still whimpering softly from the recent rough experience, her breasts heaving with trepidation, her high, rounded ass streaked with the traces of Jim's semen and thoroughly reddened from the beating and morning rearentry fucking he had so enjoyed enforcing in his eager need to prepare her for this moment, he had come within moments of entering her, pumping her full of his thick jets of semen. They entered into the spacious playroom where his oldest friend David had let himself in after arriving early. David's horse-sized cock had already been quite hard for a long while, David realized to his astonishment, groping its raging contours when he walked in, finding his hard erection prominent under his trousers, throbbbing in anticipation of the assfucking fest he had been promised by his newly married friend, so proud of his formerly virgin young wife's tight, little, still-virgin asshole. Greeted by the sight of the whips on the walls, the leather covered discipline horse in the corner of the room and a leather cuffed strap hanging down from a ceiling beam, David had quickly stripped off his shirt and trousers to release his erect, massively oversized prick and began to rub its flaring tip and stroke the shaft slowly. Rubbing and kneading his monstrous tool, he stood heavily muscled and magnificently naked as the beautiful young couple entered the room to meet him, his hard throbbbing prick pulsing with anticipation, its purple, broadly flaring cap intruding, the thick shaft threateningly long and hard in his big hand, pistoning langourously, pistoning grip. David smiled broadly at Amy, who did not greet him as Jim did. She was sobbing and wonderfully naked, her ass ready for his fucking, just as promised. He stared purposefully at her reddened, round soft already tender beaten ass fully exposed to his inspecting gaze. She was new to assfucking or, he noted, drily, so he had been promised, given the dried streaks of Jim's come he could not help but register with rising jelousy, traces of which had dried to his annoyed notice right between her ass cheeks and all over her deliciously beaten, nicely reddened, pertly swelling ass, he felt cheated, but his prick lurched all the same. He grinned at her, slightly embarrassed at what he was doing and thinking yet he kept his lubricious grip hard on his giant prick and continued slowly fisting the monstrous cock pointing upward like a satyr's tool between his legs. Thrusting himself slightly towards her - as if to let Amy know what she was in for - he pointed his monster prick at her, rampant and angry. His big prick throbbed with special anticipation. He was very, very oversized and usually could only fuck men when he wanted to fuck ass as he loved to do, because the women he knew never let him try to insert his massive member in their bottoms once they had seen or felt it driven into their distended cunts despite their screams - and they always screamed until he finished fucking. Amy was horrified at the sight of such a monstrous penis and even disgusted by his vulgar display of lust and David could not believe his luck, joyful, his cock throbbed almost painfully as he contined to stroke himself in slow anticipation of his promised opportunity. He looked at her curving ass and then deliberately down at his throbbing erection so that her eyes would be led down to see the size of his huge cock. He really wanted to enjoy the moment of their first nude encounter and he wanted to emphasize the plans he had for her ass. He delightedly saw her awed eyes fixed on his big prick, and he slowly frigged his jutting weapon in earnest, showing off its thick length, slicking back his tight foreskin, revealing the flared dusky cap, already smooth with his own lubricating precum. He grinned more broadly as Amy groaned and tried to retreat in justified horror. Jim kept her from fleeing by kissing her on the mouth, his own prick jerking to growing attention as he roughly kneaded and stroked the stripes on her ass betraying the harsh discipline he had had to administer when he told her about his promise while fucking her earlier and indeed the night before. Later he knew that would spank her hard again and then finish by reaming her ass once again with his own huge prick so that dear Amy would get very, very used to having a huge cock constantly ripping into her tight little ass before too long. David waved Jim away from Amy, and as Jim withdrew with his own prick now fully distendended and rehardened, David instructed Amy, in a husky voice, his tense hand still hard on his own throbbing monster cock, to stand up straight in the middle of the room and hold onto a length of leather that was hanging with looped cuffs from the exposed beam of the ceiling and warned her not to let go. Amy did so awkwardly and was thrilled to see Jim's eyes glued to her breasts which were thrust forward. Releasing his massive erection, David strapped her hands into the leather cuffs, making sure he jabbed his huge tool hard against her protruding ass, drinking in the sensations as he fastened her wrists, and the posture lifted her ass delightfully, his oversize prick slipping into her tight crack, immediately lodging itself as if it belonged there. Amy felt afraid and embarrassed as the stranger deliberately jabbed forward, driving his hugely swollen tool into her tight cleft against her tensed asshole, while sliding his hands down along her naked body, and shuddered at the thought that she would soon feel that threateningly thick penis poking at her tight asshole completely penetrate her almost virgin ass - but Jim told her that David was to fuck her as long as he pleased without mentioning that he was to be the first to pump her ass full of his semen - just as her husband had promised his oldest friend at their wedding several weeks ago. Jim massaged and kissed her breasts and David's big hands glided urgently over her back and paying especial attention to the buttocks that had been promised to his engorged cock deliciously and tightly emdedded between her full globes. It was incredibly sensual for Amy to be slowly stroked by the two men and she moaned, waving her tight ass back and forth despite the thick prick inserted deep in her ass cheeks. David began to slide his giant prick in the tight cleft of the pertly rounded ass that had been promised to him as he stroked her back and thighs roughly and whispered to her that before he fucked her lovely little ass with his big cock she wasn't to speak and absolutely wasnt allowed to have an orgasm:, if she did either, there would be punishment for it. She could come as much as she wished when he had rammed his giant, punishing cock deep into her and she was free to come as much as she wished while her little ass was being thoroughly reamed by his big, hard prick as it soon would be. She immediately said "Yes David" not taking him literally and smiled at Jim holding his gaze for a long moment as they continued to massage her body from feet to the top of her head. Shivers of pleasure went thru her at the fingers caressing her scalp and shoulders. Jim's mouth on her breasts felt heavenly. David knelt behind her his incongruously huge club of a throbbing, hard prick pointing rampantly up between his thighs at the ass of his conscious desire and began to run his tongue over the sensitive skin where the backs of her thighs joined her ass, tasting Jim's cum and soothing the lingering marks left by the paddle and strap where Jim had disciplined her in between fucking her throughout the morning (in the ass, amy remembered, shuddering with pain) and the night before. As David's tongue parted the tiny rosette of her asshol, Amy groaned in pleasure and the remembered pain of her once deflowered ass and the present pleasure, and let her head fall back, closing her eyes and lost herself to the sensations of her skin, never had she enjoyed her body more. Jim dropped to his knees before her and buried his face between her legs increasing her pleasure. Amy held on with all her might to the ropes above her and leaned her ass into David who now stood behind her, his excited prick again poking threateningly into the crack of her excitingly inviting little bottom. His hands came around and caressed her breasts, pinching and pulling on them. Jim's tongue was working her viciously and she tried to pull her hips away before she exploded all over him. He kept after her and now began to work his fingers inside her. Three fingers moved in and out of her vagina in rythym with his tongue, the pace increasing and Amy had to bite her lower lip to keep silent as they had asked. The fight to hold back was making her sweat, her mind was centered on the feeling of his hands and mouth, as well as David's hands that worked her nipples cruelly without mercy, his big prick rammed hard but sensuously into the tight crack of her swaying ass, throbbing erotically between her ass cheeks, his violent kneading promising her more violence from the urgent cockhead now pressing more insistently and almost penetrating her trembling, partly virgin asshole. She finally began to plead with them. " oh Jim..please..I cant hold it...please...... AH! Jim....PLEASE...." "No" David said, jabbing his huge cock forward and groaning in pleasure as the swollen tip suddenly entered her soft ass exquisitely beginning her second defloration and in the excitement of feeling himself ever so slightly fucking the flared head of his cock into her ass, David pinched her fiercely, but the excruiciating pain of the intruding flaring cockhead in her ass and the torment to her nipples added to the pleasure and it became too much for her, throwing her head back she screamed out her release, thrusting her hips harder onto the probing fingers, freeing herself from the fat tip of the thick intruder rammed into her ass and actually lifting herself off of the ground by the ropes she held onto. David whimpered his disappointment as he felt his prick head pop out of its promised home, waving uselessly in the air as the girl began to come. The two men let her finish until she hung limply, panting for air. They walked away from her then and Amy saw them again bring out David's large bag. She felt ashamed of herself for not holding back, she should have tried harder! Now it was too late.Curse Jim and his fingers!! Jim lay down on the floor between Amys legs, his new erection standing vertically before her and David released her and pushed her down to kneel over Jim's face, then stretched her out, keeping her ass bucked high until her face was even with Jim's hard throbbing prick. She had never seen anything so delicious as his long white vermilion tipped throbbing column in her life and couldn't wait to taste it, but waited for them to tell her to. She was already occupied in trying to figure out what they wanted from her, she knew she had disobeyed but this didnt seem like punishment to her! "Begin, Amy" David said from somewhere behind her. "Keep your ass raised up. That's right: keep it real high for me. Take his cock deep into your mouth. Now your ass will get the first part of what you have coming to you." She didn't understand but she quickly took the head of Jim's erect phallus into her mouth, drawing the broad glans in deeply, then became inspired. She drew back and gathered her longhair in her hands, then slowly wrapped it around his swollen prick from the base to the tip. She then unwrapped it slowly, like a gift, and covered his thick cockshaft with eager strokes of her tongue as it reappeared. She threw herself into the task and was gratified to feel his tongue probing her again. Then she was startled by the sudden painful sting of something hitting her fully upraised ass. She cried out and turned to see David, his stiff monster of a prick dripping with desire for the uplifted bottom swaying with pain and shock before him, his hand holding what looked to be a riding crop "Keep your ass raised up for your punishment" he said as he raised his arm bringing the cruel leather tool down hard across her rounded ass again and she yelped in pain and hurriedly went back to work on Jim's excited cock. "That's right, Keep your mouth on his cock and keep your ass high for me, or there'll be more" he said. Trembling, Amy lifted her ass high again, David's grunt of pleasure told her the position was right, as the crop again lashed across her upraised bottom, tried to hold still for David's hard cuts across her ass lifted high for David's visual delight and convenience, and took more of Jim's long thick prick deep into her mouth, sucking his rigidly swollen throbbing penis as hard as she could and trying to take his whole thick cock into her mouth but she was distracted by the slashing blows repeatedly falling on her upraised ass and by Jim's face burrowing deeped between her legs. What an incredibly sensual picture she made for David, still holding his jutting erection pointed towards her ass, kneeling over her husband's face, with his eager tongue thrust into her cunt as the whip's blows echoed across her ass and her bruised ass sticking up towards David, seemingly poised to receive his prick as well as the preliminary lashes from the crop. With each pleasurable stroke from Jim's tongue came a joltingly painful one on her uplifted reddening ass from the crop. She became wild, she moved faster up and down on Jim's prick, grinding her hips down onto his waiting tongue, then up to meet the stinging strike of the crop's blows. Jim gave a deep moan and his throbbing cock began to explode, gushing cum deep into her mouth and Amy eagerly swallowed it all, drawing it out and increasing his pleasure and was then pushed aside as Jim sat up and took the crop from David. David laid her on her back, knelt behind her head, pinning her arms up over with one hand and forced her legs wide apart at the knees with the other, Jim then knelt between her upraised knees, holding the crop and stroked her clitoris again. Amy, pinned down and unable to move immediately started to come again but Jim saw what was happening and stopped, bringing the crop sharply down onto her spread open lips. Amy howled, the pain catching her offguard. Jim continued to spank the tender skin of her wide open labia and the tight ring of her ass with lighter but still stinging strikes of the crop. She looked at him thru tear filled eyes but said nothing as she sobbed with pain. He paused and said "This belongs to me now, you will never have another man here without my permission" Again the crop fell between her legs. " Never do it again!" She saw that hitting her had begun to bring his cock back to its former swollen erection. The crop whistled thru the air and struck her again, he continued to punish her in this manner, moving up and down between her legs he left no part alone, David spread her wider for the crop and it struck her clitoris again and again. Amy cried out loud at the blows but deep down she knew she deserved it.She gave herself up to the punishment, pushing her hips up further, wanting it now, loving every strike, the crop began to get wet and the noise changed as it now fell on dampened flesh. When every inch of her was a bright red Jim stopped, his massive prick again fully engorged by beating her even after ejaculating thickly in her mouth and now pointing upward, still dripping with his last cum, staring at her tender, beaten cunt and let her catch her breath as he panted, his cock continued to swell, her eyes were glazed over and she was dazed. Jim helped her up and hugged her to him, kissing her and darting his tongue deep into her mouth while nudging her arms up to again grasp the ropes, he cuffed her quickly and then lifted her up, still kissing her deeply and wrapped her legs around his waist and suddenly drove his thick stiff cock inside her, thrusting it violently to its base with a powerful single thrust. Amy sighed and held him tight with her legs, drawing him deeper inside her. "Oh Jim, I love you..please forgive me." He said nothing, staring at David's swollen cock and held her closer, and kissed her again, fucking his excitement into her, to atrrange the tableau they had discussed together for weeks, his eyes on his friends swollen tool as he drove his own big cock brutally again and again into her with deep dominating violent strokes. David moved up behind Amy just as arranged, holding his massive prick in both hands, purple with unrelieved excitement, and angrily erect, pointing at her tight ass, he motioned to Jim to hold still and then he slowly began to insert his mantool roughly into her asshole as he spread her cheeks wide to allow the violation. 'Now I'm going to take you up the ass," he said, "I'm going to fuck my cock up your ass," and as he said this, smiling and licking his lips sensually at Jim, as he cruelly rammed the bulbous head crudely against her exposed asshole, meaning at last to violate her small, tight asshole. "Spread your legs wide" he said. Jim arched his cock to force her toward David. Overtaken with lust, David spread her cheeks wider, grippping her ass hard to spread it with his strong fingers as the flaring head of his turgid giant cock roughly probed into the tight entrance to her ass. "Open up for my cock, I said." Amy tensed up already stretched by Jim's huge member slowly jerking in Jim's excitement, thrusting with shallow motions deep inside her and prepared for another painful violation. Jim tried to see the moment of violation of his wife's ass on the mirrored wall and was excited at the long awaited sight of his friend's long thick bulging purple penis beginning to penetrate her widely streched asshole. Her nails dug deep into her palms as she felt the tight muscles begin to give way to the violent intrusion of David's massive cockhead. She cried out in agony as her ass began to stretch to acomodate David's powerfully invading member. He grunted in pleasure, ignoring her cries as he kept his tight grip on her stretched out ass and pushed his thick tool relentlessly into her vulnerable ass and as soon as he had inserted a good part of the shaft of his thick cock in her ass, he began to buck it slowly back and forth to drive it to the hilt: "Take my big cock in your ass," he said. "Yeah, spread your legs wide: take the cock" he gasped, shoving his thick prick remorsely into her trembling asshole, inching it past her resisting sphincter muscles, "Take my big cock deep in your ass," he grunted, "take it all," he said, ramming his giant broad prick deeper into the girl's painfully distended bottom, efficiently fucking the massive meatshaft into her with shifting, twisting motions. "Take my cock deep in your tight little ass!" he repeatedly gasped as he began to fuck his shaft deeper and deeper into her now violated, widely stretched asshole. "Take it, lift your ass for my cock, take it all, take it deep, raise that ass high for me." Amy had fought the pain till finally the thick prick was buried to the hilt and David held it there in his triumph bwefore withdrawing slightly to ram it home again, as she screamed, and he leant forward to thrust his excited tongue into Jim's sucking mouth as he fucked his prick into her ass, thrilling to the rapturous feel of Jim's big encunted cock bucking against his prick in his wife's ass. She had now taken both cocks inside her and was held up by the ropes at her wrist and by Jim holding tight to her legs. Never had she felt so full and the men were considerate, giving her a moment to adjust to the double penetration, then they each began to fuck their cocks slowly into her and then began to fuck her with violent thrusts and she groaned with pain inmixed with pleasure. It was like nothing else, they moved their cocks together, she saw that they were kissing one another deeply, tonging one another's mouths, with passionate urgent kisses, their tongues were now thrust deep into each others mouths, kissing each other as they fucked her hard, simultaneously ramming their giant engines of pain deep into her, fucking cock against pistoning cock, feeling each other's big throbbing thick pounding pricks through her and tonguing one another sensuously, in deep kisses of ecstatic joy, both cocks fucking into her repeatedly till she thought she would faint, the men withdrawing their long hard cocks for a moment only for both to plunge back in to the hilt, fucking prick against prick through the thin membrane. Never before had she experienced a taking that was so utterly complete, so thourough. Every movement she felt exquisitely,the borderline pain/pleasure of David's cock raping her in her ass and the wonderful oddness of Jim eagerly thrusting his tongue into David's mouth sucking David's tongue hungrily as he rammed his throbbing prick deep up inside her vagina at the same time molded into one earth shattering feeling and she grunted and moaned like an animal, unable to do anything else. She hung limply between them as they thrust their swollen pricks up into her again and again, embracing, fucking each other through her, not slowly now but violently, fast and now they alternated. When Jim would withdraw his massive member, he would kiss David deeply and groping David's muscular, powerful fucking ass, as he fucked his prick back into Amy's cunt, David would flex his tight hips in response to Jim's sensuous caress as he thrust his hard cock firmly upward into the no longervirgin asshole of his doubly violated wife. The two men taking turns enjoying the sensation of cock against cock and giving her no respite from the feelings. On and on the two men went, driving her body to new lengths of pleasure-pain. " ohhh Jim....ohh I.... AHHH...... o oh" They worked her roughly, ramming her cunt and ass equally hard with their giant, wildly bucking cocks, taking her thouroughly as they found themselves now wildly kissing each another, each tonguing the other deeply, mouth on mouth as cock stroked on cock, lost in ecstasy, giving her all the giant cock she could take and then more till she screamed out, her passion rising to an unbearable degree. David added to it by sharply slapping the side of her buttocks between powerful strokes of his throbbing male machine as he pistoned his prick violently into her vulnerable ass and Jim began to rub her clitoris with one hand in time with kneading of David's hard muscled, wildly pistoning ass with the other, delighting in the sensation of the cock thrusting against his own thrusting prick. Amy began to orgasm in a powerful wave that brought an amimal cry from deep in her throat and a matching one from each of the men. Jim thought he would die from the pleasure of feeling his cock being buried deep in his wife and watching her writhe, her ass painfully impaled on David's thick hard shaft which stroked his prick with each quick ass-fucking thrust. He had never seen her so wild and wanton. As his tongue probed David's mouth, he was amazed at the male excitement he felt marveled at the sounds she made as he felt his own cock against David's big thrusting cock, and the double violation went on and on. He was afraid for her but didn't want to stop, bucking his own prick faster and faster caught up in the strangest experience of his life. Jim heard David give a hard moan and then felt David drive his thick tongue deep into his throat as his exquisitely jerking giant prick finally began to explode, violently pulsing his jetting cum deep within her ass, gasping with agonized pleasure, his ecstatic jerks caressing Jim's rigid pillar, Jim wanted to feel every second of David's orgasm and he treasured this shared moment with his wife as he had no other. Jim's own overstimulated prick answered with his own tribute, pumping his last gift of sperm deep into his wife's cunt and as he felt himself come, he thrust his own tongue deep into David's gasping mouth and repeatedly fucked his spurting cock into his wife, driving hard and deep still feeling the throbbing aftershocks of David's still-hard, still deeply embedded prick. They kissed each other for some time after both had spent, then they looked at Amy crushed between them, silent and stunned by the entire experience. In a gentle contrast to the rough fucking she had just endured from the two of them, they carefully withdrew their softening pricks from her ass and her cunt and Jim led her to lay face up on the coffee table and smoothed her hair back from her forehead, calming her and himself, before leaving her alone again to reflect on it all. Amy watched both men leave and her eyes lingered on her husband. She had never loved him more and tears began to run down her cheeks as she dealt with her torrent of emotions.Her body ached and throbbed but she could bear it, and she would, for Jim. She lay there where he had left her and began to doze off, her last thought was of Jim's new dominance over her and she smiled, drifting off into sleep.
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