Loopholes Ch. 01

Witnessing the perfect synchronicity that their older sister and her ex boyfriend shared in their anal coupling was just as astounding to Sharon and Sally as the gush-inducing sight of Nick's enormous cock gradually disappearing inside Tessa's pink little asshole. Craning their necks and leaning closer from their respective corners of the bed, the twins kept frigging their pussies as if through a trance while they stared transfixed at Tessa's lube-glazed rubbery sphincter stretching out to the limit around Nick's massive hardness. Much to the twins' disbelieving awe, as inch after veiny inch of Nick's dickmeat disappeared into her docile ass, Tessa's slick rosy butt-ring kept steadily gobbling that obscenely huge boner with relative ease, like a greedy, overdilated little mouth.

"Wow! It's really... She's actually... Oh my god she's taking him in her ass for real!" Sally exhaled, both her hands buried in her crotch to rub her clit and finger her dripping slit at the same time.

"I know, it's sooo hot..." Sharon replied in a daze, rolling her pulsating nub lazily between the thumb and forefinger of one hand while with the other she teased her thick nipples in turn, pulling and pinching them under her top. "And look at Tessie, she's loving it! She's, like, cumming non-stop!"

Not even registering her little sisters' amazed voices, her world reduced only to her dripping pussy, her well-rubbed clit and her thoroughly dick-stuffed asshole, Tessa was already too far gone at that point to do anything more than reciprocate Nick's smoldering kisses and try to keep her twitching slit-frigging fingers working on her juice-soaked love button. As always, anal sex with Nick was getting Tessa so high on lust that she was in the throes of a constant orgasmic state from the very moment he jammed himself inside her hineyhole and started moving his big fat cock deeper and deeper into her ass. Now, with most of his enormous boner tucked within her silky smooth rectum and his butt-stretching penetration almost completed, the pastor's eldest daughter felt dangerously close to one of those mind-melting climaxes that she had gotten so fond of experiencing every time she got assfucked by Nick.

As it had often been the case during their many previous buttfucks, Tessa's immense build-up reached its breaking point when Nick's beefy cum-laden balls finally bumped into her sopping labia and her oily sphincter wrapped itself tightly around the very base of his massive dickmeat, engulfing him from tip to root within her snug buttery bowels. The full realization that she was once again being filled to bursting with Nick's incredible monstercock was all it took to finally push Tessa over the edge, detonating her climax in a specular, toe-curling explosion of ass-centered bliss.

"Mmmh!! Mmpphh!" Tessa mutedly yelled into Nick's smooching mouth as her dick-packed anal chute started convulsing erratically around his veiny length and the first roaring waves of her orgasm crashed into her with a force that she both feared and craved in equal measure.

Buried balls-deep inside Tessa's perfect ass, suddenly feeling the heavenly tightness of her steamy anal walls become impossibly snugger as her slick, narrow tunnel clenched and unclenched crazily all around his swollen boner in a sequence of intense yet velvety soft squeezes, Nick trembled and grunted, rooted in place. Overwhelmed by the sheer awesomeness of Tessa's climaxing little butthole and by the shaft-hugging warmth of her rippling, powerfully climaxing rectum, already hyper aroused by the twins' double blowjob and by the fact that he was once again buried balls-deep inside the first ass he had ever fucked in his life, Nick suddenly unglued his mouth from Tessa's succulent lips and brokenly announced his incoming ejaculation.

"Tess, oooh, Tess! I'm gonna cum! I can't hold it... Your ass... Soo tight, so fucking hot and tight! You're squeezing me so good, babe, you're incredible! I'm gonna... Aahh fuuck!"

"Uuhh yeees Niiick! Cum in me, pleeease! Fill meee! Fill my ass, I need iiit!" Tessa squealed between gasps, her mouth slack and O-shaped as her anal walls contracted crazily around her lover's massive truncheon, her body shaking like a leaf as her earth-shattering orgasm kept roaring through her like a thunderstorm of deep anal ecstasy. "Uuhhh Niiick... Cum in my ass, babyyy!"

Moments later, his lips were once again pressed into hers in a devouring soulkiss as Tessa felt Nick's enormous boner flex crazily and swell even harder and bigger inside her convulsing chute, only to then explode in a torrential ejaculation that blasted rope upon thick rope of warm cum deep into her orgasming rectum. The indescribable sensation of once again having Nick's throbbing rock-hard dickmeat spraying her receptive anal depths with a deluge of his creamy seed undid Tessa completely, empowering her climax and making it re-detonate even harder. As her vision faded to white and her girlcum gushed incessantly from her virgin pussy while her cock-packed asshole got filled to the brink with her lover's pearly semen, Tessa soundlessly screamed her immense pleasure into Nick's kissing mouth, glorying in the best orgasm she'd had since their last anal coupling.

Intoxicated by her kiss-muffled sounds of appreciation, blown away by the exquisite sensation of having his fully embedded pole sucked and massaged and milked to perfection within the tight, slippery warmth of her climaxing anal walls as his geyser-like ejaculation inundated her ass, Nick kept his arms wrapped possessively around Tessa's bent-over frame, holding her soft curvy body glued to his chest while he pumped her snuggest, deepest depths full of cum. Even after the explosive part of his orgasm was over and the initial barrage of long white ribbons petered out to dense gooey dollops oozing from his fat glans to plaster Tessa's cozy chute, Nick 's overswollen shaft still bucked and throbbed with horniness within the velvety soft embrace of his ex girlfriend's tight, dick-squeezing rectum.

The idea that he could somehow feel Tessa's heartbeat in each of the cock-suctioning pulsations of her exquisite asshole hit Nick very hard, reviving the deep, intimate connection that he and the pastor's eldest daughter had always shared and that unfailingly got renewed and celebrated every time they had anal sex. Failing to find any word apt to properly describe the sense of pure visceral closeness he felt for Tessa, Nick chose to lovingly kiss her gorgeous trembling lips instead, meanwhile leaving his imposing schlong immersed to the hilt inside her epic ass, allowing them both to savor in full the lascivious, satisfying perfection of their anal joining.

Moaning and smooching sounds filled the room along with the heady smell of passionate sex while Sharon and Sally stared at the lovers' deeply conjoined bodies, their eyes mesmerized by the image of Tessa's pink dilated sphincter wrapped tightly around the thick base of Nick's massive dickmeat.

The pearly, frothy crown of overflowing cum slowly seeping past the tautly stretched rim of their big sister's cock-plugged butthole gave the twins a clear idea of just how humongous a load of sperm Nick had just pumped inside Tessa's ass. On top of that, the sight of her gushing pussy dripping so much girlcum that her thighs were visibly streaked with her nectar further testified to the immense pleasure that their sister had just received through anal sex. That tangible, undeniable proof that they too could experience orgasms as amazing as the ones that Tessa had just enjoyed, while still preserving their virginity in the process, made both Sharon and Sally's already raspy breathing accelerate even more, thrilling them to the core and filling their lust-high brains with naughty prospects, their nectar-slick fingers meanwhile still busy frigging away on their drooling little slits.

Finally, when Sally gathered herself enough to speak, her voice was trembling with amazement, husky from cumming repeatedly on her own clit-circling digits while avidly watching Nick and Tessa's awesome anal coupling. All she managed to gasp was a heartfelt: "Fuck!"

Whimpering throatily as she dipped her forefinger into her own sopping pussy and then rubbed it all around the gummy rim of her tiny, twitching hineyhole, Sharon could only reply to her twin's astounded exclamation with a long mewling sigh, followed by a dreamy: "I know, right!"

All the while, as the twins kept watching and masturbating in awestruck silence, Nick and Tessa never stopped languidly making out, his chest glued to her arched back and his huge boner crammed to the hilt inside her tight, cum-flooded little asshole. Still hard as a rock in spite of the ungodly ejaculation he had just sprayed into the warm, silky snugness of her rectum, Nick began slowly rocking his butt-jamming truncheon inside Tessa's buttery anal passage while they savored their afterglow together, silently celebrating their newfound closeness.

When he finally unglued his lips from her soft welcoming mouth so that they could both take a long steadying breath, Nick unlocked his arms from around Tessa's voluptuous frame and reached a hand to her face, gently caressing her flushed cheek and tucking a long strand of chocolate brown hair behind her ear before he spoke.

"Sorry, Tess, I didn't mean to cum so soon. The thing is, well, your ass is even more incredible than I remembered!" Nick chuckled while peppering the pastor's eldest daughter's neck with butterfly kisses. "I really, really love your ass, Tess. I mean it."

"Mmh thanks, baby, I've always loved hearing you say that!" Tessa cooed, glowing with post-orgasmic bliss and wiggling the curvy plumpness of her dick-skewered bubble-butt against Nick's slowly grinding groin. "And there's no need to be sorry either. You know how much I love to feel you cumming in my ass! Besides," she added with an impish grin, biting her gorgeous lips in anticipation as she expertly started working her anal muscles around Nick's unyielding hardness, expertly sucking on his massive dickmeat with her seed-slick rectum, "now that we've got the first one out of the way, you can buttfuck me for real! Long and hard and deep... You know, the way I like it..."

"Yeah, I like that too!" Nick replied with a smile, his boner flexing deep inside Tessa's cozy cum-lubed anus as he gloried in the suctioning feel of having her cock-massaging anal walls and clingy little butthole nursing lewdly on his raging pole. After trading a few more smooches, sighing with pleasure as Tessa redoubled the tender, dick-engulfing rhythm of her masterful anal squeezes, Nick spoke again, a smile in his deep, calm voice.

"So, what shall it be then, my anal princess? How do you want me to make sweet love to your ass?"

Laughing brightly as she savored the naughty thrill of being once again called his anal princess and being asked how she wanted him to sodomize her, Tessa gave Nick one final passionate kiss before murmuring her sultry, unequivocal reply: "Ride me hard, baby! Ride my ass and make it yours."

Those words and the deep, delicious squeeze that her creamy rectum gave to his fat butt-stretching pole were all the encouragement Nick needed. He merely took the time to suck on Tessa's soft lips one last time and push his glasses back on his nose before he straightened up and swiftly repositioned, squatting over her majestic booty with his feet firmly planted on the bed right outside of her knees.

Crouched over her round juicy rump, holding his cock tucked snugly inside her greedy forbidden hole all the while, Nick grabbed firmly onto Tessa's bouncy buttcheeks and looked at her. Tessa's beaming face was pressed sideways into the bedspread and her hazel eyes were shiny with emotion as they met Nick's bespectacled gaze. Not needing words, he just raised his eyebrows questioningly and she instantly nodded her assent, grinning and biting her succulent lower lip in wanton anticipation.

As Nick slowly withdrew his girthy cum-lubed shaft from the cling warmth of her anus until he was halfway out, Tessa whimpered and panted, enjoying the sweet butt-stretching friction of his massive schlong sliding out of her narrow chute. A long cooing sigh tumbled out of Tessa's mouth as soon as Nick stopped pulling out and pushed himself back into her ass instead, slotting his boner balls-deep into her rectum again with a deliberate gliding in-stroke. After pausing for a moment to savor the thrill of full anal penetration, Nick repeated that whole process again. Once, twice, three times he slid his thick truncheon halfway out of Tessa's butt and then jammed it back in to the hilt, going slow and steady, making sure that her exquisite asshole was relaxed and ready for him to truly plow.

By small but unstoppable increments, Nick started putting more force into his motions, picking up a little bit of speed at each butt-cramming push while retreating a fraction of an inch more at each out-stroke, gradually adding length and depth to his thrusts. The welcoming yet deliciously tight grip of Tessa's anal walls around his throbbing pole felt heavenly as Nick got into an increasingly firmer and faster assfucking pace, the buttery heat and rippling softness of her rectum egging him on along with her sexy, blissful mewls of delight. Without causing her any pain, helped by the slippery sheen of cum and lube and spittle coating both her smooth dick-hugging bowels and his veiny schlong, Nick was soon pumping his huge boner at full speed in and out of Tessa's plump booty, sodomizing her with all the passionate intensity of his feelings for her.

As Nick rode her rump at a powerful ass-plowing rhythm, Tessa couldn't help but get deliciously faint with pleasure, overwhelmed as she was by climax after rolling mini-climax. Her sensitive anal tunnel sizzled with orgasmic joy as Nick's meaty shaft pistoned steadily in and out of her greedy little sphincter, stuffing her rectum so totally full of his stiff cockmeat that she could barely hang on to rationality at all, she was so mindblown by the sheer potency of the pleasure radiating throughout her surrender body. As Nick's beefy pole kept plunging relentlessly into her gummy pink asshole, triggering a new surge of climactic wavelets every time he slammed balls-deep into her tightest and hottest anal depths,Tessa simply closed her eyes and mewled like a satisfied sexy kitten, letting the sounds of her languid delight tumble freely from her parted, broadly smiling lips.

For the most part, the pastor's eldest daughter only gasped and sighed and moaned non-stop in unintelligible ecstasy, but from time to time some semblance of meaning did manage to seep into her vocalization. Invariably, Tessa's trembling words were a mix of exhortation and appreciation of her devoted buttfucker's well-honed booty-plundering skills.

"Uuungh... Ooohh my god, Niiiick! Oohh yesss like thaaat... Uuuuhh yeaahh fuck my ass! Ooohh baby, yeeess!"

As was always the case when she had anal sex with Nick, Tessa tried to participate in the coupling either by pushing her fabulous bubble-butt back to meet her lover's rump-skewering thrusts, or by squeezing and releasing her anal muscles around his pole to match his sodomizing rhythm, in an attempt to suck him off within her soft rectum in the same way that she did when he was buried to the hilt in her ass, enormous yet motionless inside her cozy rectal passage. Tessa wanted to do all that, she wished she could focus enough to do it, but she simply couldn't pull it off, not while she was getting royally assfucked by Nick's awesome horsecock.

Ever since she had gifted him with her anal virginity, once his fat rock-hard dick started seriously slamming into her receptive little rosebud and that indescribable mixture of extreme pressure, slippery friction and meaty fullness inside her anus built up past a certain level, Tessa simply lost control. Overwhelmed by the combination of scorching pleasure, thrilling sinfulness and ultimate intimacy that anal sex meant to her, the pastor's eldest daughter had never been able to conjure up neither the lucidity nor the energy to act in any way while Nick fucked her ass, and this time was no different. All she managed to do was moan and pant and languidly enjoy the deep thrusting rhythm of Nick's butt-pounding cock wedging itself over and over into her snug rectum, making her cum and cum and cum in the process.

Underlined by Tessa's purring, ego-boosting vocalizations and by the fleshy clapping impacts of his thighs slamming over and over into the jiggly fullness of her magnificent round buttcheeks, Nick's rump-riding rampage kept getting more savage by the minute. His slick, furiously intense ass-stuffing thrusts were causing a breathtaking sequence of back-to-back orgasms to surge from the very core of Tessa's being, blowing her away to the point that she couldn't even find the mental clarity and physical strength to work her fingers on her clit anymore. Not that it really mattered to her: at that point, with Nick's big cum-laden balls swinging into her drooling pussy at each in-stroke and his sperm-glazed shaft plunging fluidly into the deepest depths of her steamy rectum, Tessa had reached that unique, blissful place where she could climax merely from anal stimulation and thus experience orgasm after rolling orgasm just as long as she had Nick's perfect cock sawing in and out of her eager little asshole.

Just as her slack mouth was drooling on the crumpled bedspread while her body was assaulted by wave after thundering wave of butt-centered pleasure, Tessa's virgin pussy was incessantly overflowing with rivulets of sweet, shiny girlcum. Her shapely thighs were drenched in her gushing juices and a puddle of dripping nectar was forming right between her knees, and yet her lust-hazy brain desperately egged her on to speak and beg for more whenever her O-shaped lips weren't busy letting out bursts of broken, husky moans of delight.

"Uuhh fuck... Oowwhh Nick... Yes, yes, stretch my ass like thaaat! Oohh yeaaah, go deep in me, deeper yeaahhh... Uuhngh sooo biiig! Sooo haaard uuhhh! Oowhh you fill me so much, baby... I love your cock in my aaaass!"

Docile and hyper horny, blatantly radiant with anal pleasure, with her beautiful cock-jammed ass stuck up in the air, her face pressed down on the bedspread and her fabulously big tits bulging out from underneath her curvy bent-over frame, Tessa looked like the very picture of perfect sexual ecstasy in the eyes of her awestruck younger sisters. The obscenely beautiful image of Nick crouching dominantly over Tessa's sumptuous bubble-butt with his massive dickmeat pistoning full force in and out of her oily stretched-out sphincter etched itself indelibly in Sharon and Sally's lust-high minds, along with the jealousy-inducing sight of their big sis's shaved virgin pussy constantly dribbling her liquid pleasure as she was shaken by one delicious orgasm after the other.

Mesmerized by that scene of indisputable anal bliss, Sharon and Sally kept caressing their dripping slits as they seamlessly shifted from their sitting positions on opposite corners of Tessa's bed to lying on their sides. With their taut round asses pushed out and hanging off each side of the bed, both twins had begun fingering their twitching buttholes as soon as Nick started pounding away at Tessa's booty, the temptation to somehow emulate the lovers' passionate anal coupling having grown simply too big for the girls to resist.

While each twin kept one hand always busy diddling her own juice-slippery pussy to maintain a steady ebb and flow of clit-centered pleasure, the way Sharon and Sally masturbated their rosebuds was very different. While Sharon held two digits buried knuckle-deep and motionless inside her anus as she flicked her engorged nub, Sally was recklessly pumping her slim middle finger in and out of her own virginally tight sphincter, trying to match the ass-pummeling cadence that Nick imposed on Tessa's bouncy, fabulous booty. Despite their different approaches to anal masturbation though, the twins were both convinced by Tessa and Nick's demonstration about the merits of buttsex: no matter if what happened in anal porn was just acting, neither Sharon nor Sally was going to doubt that Tessa's orgasms were absolutely real and amazingly powerful.