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.
