Loopholes Ch. 02

"Uuuhh fuuuuckk! Oohhh Niiiiick! Ooowwwhh my god, yeeeeeesss!"

Gladly surprised to see Sharon suddenly succumb to a sneaky yet obviously powerful climax, Nick exhaled in pleasure as he gloried in the slick, shaft-engulfing warmth of her narrow rectum constricting his boner from tip to root in a series of smooth, potent orgasmic spasms. The delicious cock-tugging squeezes that Sharon's virginally tight anal passage was imparting on his fully buried length were just incredible, they made Nick grunt with pleasure just as much as the sight of her pink gummy orifice stretching out to obscenely beautiful limits around the thick root of his embedded pole. Ironically though, the very awesomeness of that heady combination of visual and physical bliss forced Nick to quickly find some kind of distraction, so that he could avoid spraying Sharon's dick-milking anal depths full of cum before he even got a chance to properly sodomize her.

Unfortunately, Nick's idea to shift his gaze away from Sharon's dick-impaled asshole turned out not to be so useful in terms of diminishing his arousal and fighting back his simmering ejaculation. As soon as he looked to the side, Nick's bespectacled eyes were met by the super sexy sight of a panting, softly mewling Sally lying back with her shapely legs spread wide apart as she determinedly fucked her own virgin little asshole with Tessa's silver buttplug. The image of Sally's smooth untouched pussy glinting with juices and glazed with the trickles of sweet nectar that drooled down her taint to lube her adorable pink butt-ring would have been cock-stiffening enough in and of itself in any other situation, but it became even more enticing right there and then as it enhanced the vision of her adorable rosebud clinging slickly to the tapered toy that Sally's dainty hand was driving relentlessly in and out of her tiny sphincter. That hyper erotic spectacle immediately sent a further jolt of arousal to Nick's already flexing truncheon, making his meaty length swell even bigger and harder inside Sharon's rippling, extra tight rectum.

Aware that he was only going to last another minute or two at the very best, horny beyond description and past the ability to contain his buttlust, Nick growled deep in his throat as he pulled almost all the way out of Sharon's quivering anal sheath and then swiftly rammed his massive pole balls-deep into her ass again, only to withdraw and thrust in all the way immediately after, then again, and again, and again, quickly setting a strong butt-pounding rhythm.

Dizzy from the climax that her first full anal penetration had just gifted her, Sharon felt her whole body ignite with incapacitating pleasure all over again as Nick began hammering away at her twitching forbidden hole with unbridled fury. Sliding out until only his huge precum-oozing glans remained trapped in the rubbery grip of her butt-ring and then slamming his entire pulsating horsecock into her rectum again until his beefy balls slapped against her girlcum-drooling slit, Nick took Sharon's breath away with his lustful assault on her freshly deflowered asshole, making her cum like crazy in the process.

Glad to have taken his time earlier when he had gently lubed and prepped her anus and gradually stuffed her virgin rosebud so that her narrow anal tunnel submitted willingly to his massive schlong, Nick made good use of Sharon's orgasmic mellowness to complete his conquest of her snug slippery butthole. Booty-plundering and relentless, each of his powerful balls-deep thrusts into her receptive ass made Sharon scream out with lewd ecstasy as her buttery bowels got stuffed to the limit over and over again, making her afterglow light up into a new fiery, blinding anal climax each time Nick's rampaging boner plowed full force into her tiniest, most sensitive hole.

"Fuuuckk! Uuhhh fuck y-y-yeaahhh Niiiick! Ooowhhh f-f-uuh-uuuhh-uuhck!"

Yelping out brokenly, gasping for air as her vision faded to white and her pussy gushed away all over her own trembling clit-flicking fingers, Sharon could barely believe how violent her back-to-back climaxes were and how incredibly awesome it was that she was managing to cum non-stop like that while getting lustfully assfucked by Nick's raging horsecock. Still wedged in the soft clef of her labia, Sharon's digits were twitching out of control as her velvety soft rectum sucked and spasmed around Nick's enormous dickmeat, her fingertips automatically flicking and pinching her clit even though her ability to focus on frigging herself properly was pretty much gone thanks to the savage orgasm-triggering assault that Nick's throbbing truncheon was imparting on her oily little butthole.

Fast and deep and wild as his sodomizing thrusts were, Nick's final rump-impaling barrage was super intense but unavoidably short-lived. Egged on by Sharon's pleasure screams and by the incessant squirts of girlcum cascading on his huge scrotum when he plunged balls-deep into her ass, Nick pounded the slim blonde's cock-clenching rectum with all he had, recklessly rushing to his climax. Lust-high as he was, Nick couldn't have stopped slamming his achingly swollen schlong into Sharon's tight anal sheath even if he had wanted to, and he didn't.

Snug and clingy like only an anal virgin's tiny forbidden orifice could be, Sharon's asshole was engulfing Nick's massive shaft divinely, suckling deeply on his length and treating him to an incessant sequence of dick-massaging squeezes brought on by the ripples of delight that his relentless rump-riding rhythm was triggering non stop in Sharon's narrow, sensitive rectum. In truth, each of Nick's ass-pummeling in-strokes ignited a new orgasmic burst deep inside Sharon's bent-over body, and each gliding out-stroke overcharged her anal nerve endings once more, rigging them to explode in climax moments later when he crammed his flexing boner all the way into her warm, well-greased anus all over again.

As Sharon was wracked by orgasm after earth-shattering orgasm, Nick's only wish was to enjoy the smooth heat of her snug anal walls clutching slickly around his pistoning boner for as long as possible. Still, as much as he strove to continue fueling the delicious cycle of their shared sodomizing bliss by keeping up his furious butt-drilling tempo, he soon had to capitulate before the warmth and softness and tightness of Sharon's slippery little asshole.

"Ahh fuck! Fuck, Sharon... I'm gonna cum!" Nick grunted over the mixed sounds of his groin clapping against her taut round buttcheeks and her breathless, mindless yells of pleasure. "Ohh fuck, here it cums! Aahh fuuuck yeaahh!"

With a final butt-jamming thrust, Nick let out a bestial growl while he buried his whole enormous boner to the hilt inside Sharon's exquisite ass and let his long-denied first ejaculation of the day explode deep within her rectum in a torrential spray of dense cum. As rope after huge rope of warm seed blasted out of Nick's pulsating cockhead to paint her bowels white, Sharon threw her head back and opened her pleasure-glazed eyes in delighted shock, a new overwhelming orgasm meanwhile crashing into her with the tidal force of the deluge of jetting cum that was quickly flooding the deepest anal depths. On top of every other new forbidden pleasure she had experienced that day, the unique feeling of having her tight little asshole forcefully pumped full of spurting semen by a huge throbbing cock undid Sharon completely, overdosing her with more physical ecstasy than she had ever experienced or was ready to endure.

Gasps, moans and increasingly weaker and less intelligible sounds tumbled out of Sharon's O-shaped mouth, her heavy-lidded eyes meanwhile slowly closing again as a big dopey grin illuminated her flustered face. Noticing all of that even as his overswollen schlong kept hosing her cock-tugging rectum with an ungodly flood of surging cum, Nick grinned with satisfaction, his hips still rocking and grinding into Sharon's thoroughly dick-impaled rump as if trying to push his veiny hardness impossibly deeper inside her heavenly ass.

As her immense climax burned through Sharon's slim body, Nick gleefully basked in the sperm-slick warmth and unbelievable tightness of the pastor's daughter's quivering anal tunnel lewdly suckling on his shaft and massaging his thick length from tip to root, milking him beatifically dry. Exhaling as his final gooey spurts plastered her buttery bowels with his potent seed, Nick felt his goofy smile grow even broader as he realized that Sharon was close to passing out from the sheer brain-shattering pleasure of her very first anal coupling. As if in response to that super erotic thought, a soft trembling voice resounded beside Nick, calling him back to reality.

"Oohh my god, look at her... She's cumming so much that she's, like, fainting or something! Wow, Nick... I want that too, I want it sooo badly!"

Turning to the side, Nick felt his butt-stuffing pole flex with renewed arousal inside Sharon's constricting anal chute as he took in the sight of Sally reclining back against the headboard with her shapely legs held together and raised straight up to reveal her pristine juicy slit and her tiny, adorably pink rosebud twitching with need around her ass-probing fingers. The bottle of lube and the silver buttplug lay discarded on the sheets right beside Sally's rounded little booty, but Nick could tell that the girl had made good use of both. Although there was definitely a component of trickling girlcum, Nick was certain that most of the glinting sheen of wetness coating Sally's puckered sphincter was in fact lube, and, based on the the ease with which the pastor's usually timid daughter managed to slide two and even three digits into her clingy hineyhole, it was safe to assume that she had prepped her anus intensely while he was busy sodomizing her twin sister.

As Nick's bespectacled gaze met Sally's pleasure-hooded blue eyes, the slender blonde spoke with a sexy languidness in her voice that made his fully hilted shaft flex with renewed horniness inside Sharon's seed-flooded rectum.

"Please, Nick, tell me that you're still hard for me... I need your big cock, I'm dying to feel you inside me... Can you fuck my ass now?" Sally pleadingly cooed, sliding both her forefingers into her rosy butthole and gently pulling its gummy rim apart, gaping her miniature anal opening for him. "Mmh... My asshole is so horny for your cock, Nick..." Sally murmured while biting her lips and stretching out her delicious little sphincter with her dainty digits, maddeningly excited. "Come here and fuck my ass, Nick, pleeease! It's yours, my tight virgin asshole is all yours!"

If under any other circumstances an invitation like that would have made Nick's cock instantly rock-hard, right there and then it just made him even harder than he already was. Moreover, some of the words Sally chose and the position she was in, on her back looking up at him with an expression of pure lustful need painted on her flushed face, reminded Nick of the circumstances of his very first time doing anal with Tessa, which only added to his excitement about popping Sally's willingly offered butt cherry. After taking one final look at Sharon's barely conscious and weakly moaning form, Nick simply nodded at Sally, who reacted with a huge beaming smile that was made even more beautiful by the further reddening of her sculpted cheeks and by the twitch of anticipation that made her finger-stretched little butt-ring visibly wink at him.

Letting go of Sharon's heart-shaped rump, Nick extracted his ass-cramming boner from the passed out blonde's overdilated orifice with deliberate slowness, thus letting Sally appreciate just how much of his massively thick length was tucked deep inside her sister's no-longer-virgin rectum. Once his huge bulbous glans finally slipped out of Sharon's distended sphincter with a slurping, obscenely beautiful popping sound, Nick couldn't help but take a moment to feast his eyes on the delightful spectacle of the unconscious track star's stretched out pink butthole instantly starting to twitch and pulsate hungrily in response to that unnerving emptiness, while at the same time thick dribbles of his creamy seed bubbled out of her suddenly unplugged orifice.

Moments later, as Sharon's tender sperm-leaking rosebud already started to shrink shut on itself, Nick stepped closer to the head of the bed and held his mighty erection at the base, pointing it right at Sally's round, meekly offered ass. As his bespectacled gaze met Sally's lust-glazed blue eyes, Nick looked intently at the horny, softly cooing girl and spoke in his deep calm voice.

"See, Sally? I'm still plenty hard for you," Nick simply said, smiling at her even as his enormous, juice-shiny truncheon flexed with unyielding buttlust and his fat purple glans began oozing precum, as if salivating at the idea of plunging deep into another virgin asshole right away.

Much to his glad surprise, Sally didn't show any sign of intimidation at the sight of the veiny, sperm-lathered slab of dickmeat that was about to deflower her miniature asshole, but instead she pushed her butt-plugging forefingers deeper into her slippery rosebud and pulled them a little further apart, dilating her pink anal opening a bit more. Her breathing was ragged as she ran her tongue over her gorgeous lips and spoke in a sensuous purring tone, her eyes never leaving Nick's overswollen schlong.

"Oooh fuck yeah! Mmmh look at that monster, all covered in cum... Oohh, Nick! I'd suck you off right now, but my asshole is just dying to get fucked! Come on, stick it in me, Nick. I'm ready, I'm sooo ready..."

Panting with anticipation himself, Nick placed his hands on the taut, perfectly round buns of Sally's bubble-butt and gently dragged her reclining form toward him until her delicious little booty was hanging off the edge of the bed. Tittering while Nick positioned her to better plunder her hineyhole, Sally let out a cooing gasp as she felt his bloated cockhead pushing up against the soft nectar-drenched cleft of her labia, soon followed by his meaty shaft sliding slowly back and forth between her slippery pussy lips for a couple of girlcum-gathering strokes that teased her engorged clit and made her shiver with anticipation even more. Once Sally's sweet juices had been added to the sheen of lube and cum already coating his boner, Nick finally aimed his meaty schlong lower, wedging the very tip of his fat purple knob into the little opening of Sally's anus, which the purring blonde was still trying to gape with her forefingers.

"I'll take it from here, Sally," Nick said with a smile as looked into Sally's lust-glazed eyes. "You just worry about keeping your legs up like this and rubbing your clit, okay? I'll handle the rest."

Chuckling and nodding urgently, Sally removed her fingers from her well-greased asshole, bringing one hand to her pussy while she hooked her other arm around the back of her knees, pulling her long legs back toward her pert tits while still holding them tightly together, enhancing their shapeliness while increasing the enticing roundness of her flawless little bubble-butt. Offered and accessible like that, Sally's curvy ass was as irresistible as a fresh crunchy apple, which made it impossible for Nick to wait another moment before he savored it.

Sally's dainty fingers had barely started circling her engorged clit and the tiny gape she had imposed on her elastic butt-ring was trying to seal itself shut around the tip of Nick's spongy knob, thus nibbling and squeezing lewdly on it, when he gave a firm forward push and swiftly eased his whole huge glans into the slick, warm grip of the pastor's daughter's docile sphincter.

"Ooohh yeees! Oh my god, Nick, yeaahh!" Sally exhaled in lascivious joy as her well-prepped asshole stretched out around his bloated cockhead. Much to her delight, the gummy rim of her forbidden orifice widened with surprising ease around Nick's fat glans, accepting him so eagerly in fact that he managed to also slip a couple of thick inches of his shaft inside her anus with that initial deflowering thrust alone.

"Everything okay, Sally?" Nick asked as he enjoyed the steamy squeezes that the gasping blonde's tight butthole was treating him to as it molded tenderly around his invading dickmeat.

Even before she answered though, Nick could tell that Sally's anal muscles were quite relaxed and far from cramping. In a way, it felt like her virginally tight sphincter was intent on sucking his bulbous cockhead into her asshole, actually drawing him in instead of resisting his penetration. Reminded once again of the spontaneous docility of Tessa's sweet little rosebud and of how deliciously willing she had been when he had taken her anal cherry, Nick felt his boner throb with excitement as Sally dreamily smiled and nodded in response between squealing moans.

"Mmhh yeah, Nick, I'm okay. Oowwh it's weird... It doesn't really hurt, it's just sooo intense... Uuhh god, you feel so big in my ass but... Uunggh it's super fucking good!"

Grinning back at an ecstatic Sally, Nick gave a couple of shallow back and forth strokes, testing the receptiveness of her miniature backdoor. Despite feeling her anus respond with as much relaxation as could be expected from an anal virgin taking a huge pole like his as the first cock ever to delve into her hineyhole, Nick chose to play it safe and pulled all the way out, causing a sexy slurping sound as his ass-stretching glans popped out of Sally's eager butt-ring.

The expression of dopey, pouty surprise painted on the slim blonde's face was comical enough to make Nick chuckle, but not enough to distract him from his pleasurable task. Before Sally's groans could actually coalesce into words of protest, he had already grabbed the bottle of lube, pressed it against the dilated pink opening of her anus and started squeezing a liberal dose of the slippery gel straight into her warm anal tunnel. The cold feel of the lubricant squirting into her butthole made Sally wince for a second, but her lips curled up into a beaming smile moments later when she felt Nick's huge cockhead wedge itself into her pink winking orifice again and then gently slide inside her steamy chute. Helped by the added lube and by Sally's joyous acceptance of her anal deflowering, Nick's shaft pushed deeper than before into her narrow rectum with minimal effort, plunging fluidly up her ass until a good third of his massive truncheon was embedded within her buttery bowels.

Again, Nick decided not to force his penetration of Sally's virginally tight albeit clearly willing asshole, so, after a few short and careful in and out butt-stirring strokes, he withdrew all the way again, exiting her gummy orifice with another loud squishy pop. Much to Nick's delight, Sally giggled instead of protesting as she heard the obscenely exciting sound of his bloated glans escaping the clingy, suckling grip of her little anus. Purring mewls of anticipation replaced Sally's laughter moments later, as Nick squirted another generous amount of lube right into her velvety soft anal passage and smoothly slipped his massive dick inside her oily asshole again, making her exhale with bliss while her clit-rubbing fingers trembled and frigged her engorged nub with increased zeal.

To the sound of Sally's naughty giggles, lustful moans and rapturous sighs, Nick methodically repeated that pattern of pushing then withdrawing then lubing up before an even longer push, so that at each pass he was jamming his meaty truncheon deeper and deeper inside the slim blonde's untouched anal depths. While he drilled his fat boner further up Sally's ass with those increasingly longer yet always gentle butt-cramming thrusts, Nick never failed to reverently cup her round little booty in his hands and pay homage to her soft curvy buns with his kneading and caressing touch.