Loopholes Ch. 02

Feeling her anus meekly capitulating to his invading shaft, well aware of the incessant trickles of sweet nectar overflowing her virgin pussy and drenching his nub-frigging fingers, Nick estimated that Sharon was ready to take a few more inches of his throbbing schlong into her asshole. Not wanting to rush things but rather choosing to err on the side of caution, Nick was about to ask her if she was okay enough to let him push his dick a little bit deeper up her butt, when Sharon preceded him by brokenly voicing her wanton anal lust through sexy, panting moans.

"Mm-mmh-more, Nick... Go slow but uhh fuck... Uuugnh fuck my ass, Nick, I need more!"

Blinking in glad surprise as he took in the cock-hardening expression of mind-numbing pleasure painted on Sharon's sculpted features, Nick didn't actually move yet but instead shared a silent glance with Sally. Getting a rapid nod and a complicit smile in reply from the keeling blonde, certain that Sally of all people would be a perfect judge of her own twin's readiness, Nick inhaled deeply, grabbed onto Sharon's round heart-shaped rump with one hand as he kept diddling her clit with the other, and then gently pushed his hips forward.

A long, breathless gasp from Sharon punctuated the slow but firm motion that forced another good couple of inches of Nick's enormous boner to slide into her butthole, increasing the strange yet satisfying sense of stuffing fullness in her ass that was making her hairless pussy drool and her whole svelte body shake in unprecedented delight. Pausing his penetration and savoring the intense suckling squeezes that Sharon's amazingly tight anus was treating him to as it molded around his shaft, Nick only had to glance at Sally to signify that he wanted her to apply more lube on her sister's cock-gobbling, overdilated butt-ring.

Giggling and nodding before focusing her bright blue eyes on the amazing sight of her twin's dick-stuffed asshole, Sally poured a big dribble of lubricant right where the pink elastic ring of Sharon's tautly stretched sphincter was gripping Nick's shaft in an obscenely sexy chokehold. With his cock and her butthole greased up to perfection, sure that the pastor's daughter was as ready as she was going to be, Nick took a deep breath and focused on the glorious task of opening up Sharon's virginally tight ass while her twin sister watched, helpfully holding the bottle of lube for him.

While his fingers kept methodically rubbing her nectar-squishy clit, Nick started humping Sharon's round little bubble-butt with exaggeratedly slow and intentionally shallow back and forth motions, stirring his enormous truncheon inside Sharon's super snug chute while barely moving in and out of her dick-clenching anus. Still, even if it was only by minimal increments, Nick's huge precum-oozing glans was in fact advancing, drilling a tiny bit deeper into the slim blonde's untouched rectum every second. Inexorably, Nick's enormous pole kept sliding further up Sharon's ass a millimeter at a time through micro thrusts so gentle that she barely felt any additional discomfort at all, a naughty buzz of delight instead growing inside her as more and more of his thick dickmeat was crammed into her exquisite little butthole.

The sedated rhythm of that anal penetration was crucial for Sharon, who was getting her anal cherry popped by a monstercock as impressive as Nick's, but he too was profiting from it. Sharon's asshole was so virginally tight and sinfully warm, so alive with the incessant shaft-tugging pulsations of her capitulating anal muscles and so incredibly soft and hugging as its velvety walls enveloped more and more of his meaty length that Nick didn't really have any choice but to ease his way up her ass at the slowest pace possible, otherwise the pastor's blonde daughter's narrow forbidden orifice would have sucked the cum right out of him in a matter of seconds.

Still, other factors were in place as well, making it extremely difficult for Nick not to blow his load too soon, namely Sally.

Lewdly keen on helping her twin sister take Nick's enormous dick up her ass, Sally quickly got very involved in providing additional lube for that steamy anal coupling. Instead of squeezing dribbles of the slippery fluid onto Sharon's dilated sphincter to reduce the friction of Nick's truncheon gently easing its way into her snug anal passage, Sally decided to take a more direct approach. While Sharon mewled constantly in dazed lust-addled delight and Nick kept patiently stuffing her virgin little asshole full his swollen dickmeat, Sally began squirting lube directly on the palm of her own tiny hand and then applying it on Nick's butt-humping schlong by stroking and rubbing the significant portion of his shaft that was still outside of her twin's cock-gobbling anus. Massaging the oily gel onto his pole with slow tugging caresses, Sally was soon jacking Nick off as he jammed his veiny horsecock into Sharon's sweet ass.

Groaning and grunting and doing his best not to cum just yet, Nick had half a mind to tell Sally not to stroke the lube onto the exposed part of his boner by giving him what was in fact a deliciously devoted handjob, but he simply couldn't bring himself to stop that unexpected masturbatory treat. So, gritting his teeth even as his breathing got more and more labored by the second, Nick focused stoically on his primary goal: to properly deflower Sharon's adorable pink rosebud and bury his whole raging hardness deep inside her cock-hugging rectum before he pumped her bowels full of cum.

As Nick's huge, incessantly delving schlong filled her ass up and stretched her butt-ring out more and more, sinking slowly but surely deeper into the smooth warmth of her super tight chute, Sharon started to feel something new and intense and mind-crushingly pleasurable happening to her.

It was something that overrode even the sweet, soothing flow of clit-centered wavelets that Nick's talented fingers were gifting her. It felt like a deep pulsing vibration that radiated outward from her dick-jammed anus and electrified her whole body with unprecedented jolts of anal bliss that were much more delightful and heady than the naughty buzz she had previously received from masturbating her asshole with Tessa's buttplugs. The weirdly good sensation of having a real cock sliding deep into her ass, which at first had been mixed with a hint of discomfort, was now solely pleasurable for Sharon, and it was actually becoming better and more intense the deeper Nick pushed himself into her narrow, rippling anal passage.

Having her tiniest and most sensitive hole filled by a big hard dick wasn't affecting Sharon just physically, but also mentally. Beside the fact that the forbidden thrill of getting fucked in the ass was driving her crazy with delicious excitement, Sharon was loving the indescribable sensation of finally having sex and having a man inside her body for the very first time. On top of it all, the emotional safety of being near her twin and the calming awareness that Nick was totally nice and trustworthy, meaning that he would never hurt her even though his cock was so huge and her asshole so tiny, allowed Sharon to really give up control and thus let herself freely savor the whirling storm of new, powerful pleasure coalescing deep inside her.

As Nick's meaty truncheon sank deeper and deeper into Sharon's snug anal depths, her cock-packed rectum rippled with constant shocks of ecstasy, which unavoidably merged with the pulses of clitoral delight that his talented fingers were causing. To experience such an amazing clash of pleasurable stimuli during her first assfuck caught Sharon by surprise, especially because that delicious combination rapidly grew into a bubble of pre-orgasmic build up so mind-shatteringly big that she could barely even find the breath to moan out her awestruck joy.

By the time Nick managed to slowly stuff half of his humongous horsecock inside her insanely tight asshole, Sharon was on the verge of such a gigantic climax that she was almost scared to feel it burst. The massive orgasmic wave looming over her surrendered body roared even more fiercely when Nick seamlessly shifted his rump-skewering pace and started gently pumping half of his massive boner in and out of her slippery little asshole with steady back and forth butt-stretching thrusts.

On the out-strokes, when he pulled out of her snug anal sheath until just his huge glans remained locked within the clingy suctioning vise of her butt-ring, Sharon felt her eyes roll back in her head as she gloried in the slick friction that Nick's veiny pole caused along her buttery anal walls while sliding out, stimulating nerve endings and pleasure centers that she didn't even know she had. Similarly, the slim blonde couldn't help but gasp and pant and melt inside in toe-curling delight when Nick pushed his ass-jamming shaft back into her quivering rectum, making her see stars just by wedging half of his thick dickmeat up her ass before gliding back all over again to repeat the delicious cycle of his measured yet breathtaking sodomizing routine.

It took barely a couple of minutes of having her sensitive anal passage gently fucked by half of Nick's fat schlong before Sharon succumbed to the colossal build up that had been accumulating inside her since her virgin little orifice had opened up to accept his incredible monstercock into her ass. Nick had just finished cramming his meaty length halfway inside her dick-squeezing chute when Sharon's velvety anal walls started spasming erratically around the embedded part of his truncheon, trapping him within the warm, slippery tightness of her anus. At the same time, a gushing overflow of girlcum bathed Nick's clit-frigging digits while Sharon, gasping for air and trembling like a stranded fish, brokenly yelled out her breathtaking orgasm in a trembling, almost disbelieving voice.

"Oowwhh! Uuhnghh... I'm c-c-uhh... Uuhh fuuuck! Oohh shiiit yeahh! I'm uuhnghh... C-c-cuhhm-mmiiiing!"

As she heard her own climax-shrill words dissolve into squealing gasps of release, Sharon felt her whole body sizzle and shake under the impact of the devastating orgasm that suddenly smashed full force into her, exploding outward from her cock-stuffed asshole to wrack her very being. Rivulets of liquid pleasure gushed from her virgin pussy while the steamy walls of her snug rectum tightened their already desperate grip around Nick's half-buried boner even more, tugging so intensely on his fat shaft that they milked glob upon spurting glob of precum from his spongy glans, making him growl with pleasure as he strained not to cum just yet.

Still holding the exposed half of Nick's fleshy truncheon in her dainty, lube-rubbing hand, Sally couldn't help but feel her own pussy get wetter and her tiny asshole get even itchier to get fucked as she witness her twin cumming spectacularly from anal sex right before her eyes. Despite her having merely half of Nick's raging erection stuffed up her ass, Sharon's brain-melting orgasm seemed so obviously intense and all-encompassing to Sally that she was barely able to contain her need to trade places with her screaming sister and have her own pristine anus deeply sodomized by Nick's ass-stretching monstercock.

Twitching and shivering uncontrollably all through her glorious climax, while her convulsing rectum sucked avidly on the massive slab of dickmeat plugging her narrow tunnel and her pussy wept joyous dribbles of girlcum all over Nick's clit-pinching digits, Sharon inadvertently shifted from her position on her side. Through erratic movements and orgasm-induces spasms, she somehow managed to twitch and roll until she ended up lying flat on her tummy, with her trembling legs sliding messily off the edge of the bed. Even though that unexpected repositioning forced Sally to let go of his well-greased schlong, Nick went along with Sharon's movements, maneuvering with care to make sure that the swollen half of his fat cock that was jammed inside her shaft-tugging asshole remained always firmly buried there, much to her mewling delight.

Once the most devastating part of Sharon's climax was finally over, Nick removed his nectar-drenched fingers from her sweet virgin pussy and placed both hands on her round little bubble-butt. Caressing and kneading her cock-impaled booty as he held possessively onto it, Nick guided a panting and still shivering Sharon into a proper doggy position with her knees planted firmly on the floor and her upper body pressed into the crumpled sheets, her flustered face resting sideways as her slack mouth still let out long, sexy moans of anal bliss.

"Wow! Sharon, that was awesome!" Sally exclaimed as her twin's panting mewls gradually diminished in volume and the constricting spasms of her overstretched butt-ring became less desperate around Nick's half-embedded pole. "You have no idea how hot it was to watch you cum like that, sis! That giant dick sliding into your asshole was totally epic, better than any porn!"

"Mmh, Sal... Oowhh my god, this feels sooo fucking good!" Sharon mumbled groggily as she turned her head to look over her shoulder at Sally, a dopey grin dancing on her lips. "Uuuhh shit, Nick's cock is so big and hard... He's sooo deep in my ass, it's so amazing! Oowhh fuck, I never came like that, I'm still all tingly... You're gonna love it, Sal, I promise."

"Oh, I'm gonna love it alright!" Sally giggled in reply, blushing adorably even as she winked at Nick, who couldn't help but grin broadly at her. "And by the way, Sharon, just so you know..." Sally pointed out, taking a dramatic pause before concluding: "Nick is only halfway up your ass right now!"

"What?! Seriously?" Sharon gasped, craning her neck in an attempt to see over the protruding mounds of her curvy tushy to get a visual confirmation of that shocking revelation. "Oh my god, it feels like I have a baseball bat up my ass and he's only halfway in?! Unbelievable..."

"Yep, unbelievable but true!" Sally nodded, smiling as she anticipated the moment when she would be the one screaming in climax with Nick's incredible horsecock jammed up her ass. "But that's good news, isn't it? I mean, you already came like crazy with only half of it inside you, so..."

"So I want it all! Not just half, all of it!" Sharon brusquely interrupted her sister, her lust-thick words ringing as needy as they were determined. Tucking her chin-length locks behind her ears, Sharon turned to look Nick right in the eyes and continued speaking, trying to steady her trembling voice even as she kept incessantly cooing from the pleasure of having his thick veiny dickmeat wedged halfway into her overdilated butthole. "Nick, I want you to ram all of that fat cock of yours up my ass! Come on, I can take it! You opened me up real nice and I need to feel you balls-deep inside me. Can you just do it, please?"

"Yeah, if you're sure... Your asshole should have loosened up enough now, plus that big orgasm seems to have relaxed you a lot. I'll try to go all the way in, if you really want me to," Nick concluded with a shrug, getting a vigorous nod of assent from Sharon.

Filling his palms with her toned round buttcheeks and splaying them wide apart to clearly reveal the thick half of his shaft sticking out from her pink cock-stretched orifice, Nick frowned as he added: "Sharon, I've got to warn you... If I go balls-deep and I start fucking you, I won't last long. It's a miracle I haven't cum yet, really. Your little asshole is so fucking tight, it's crazy how hot it is and how hard you're squeezing me."

Cooing in anticipation as she rested her head on her forearm while reaching to her drooling pussy with the other hand, Sharon just closed her eyes and smiled languidly as she replied. "Mmh, I don't care, Nick. Just do it. I want you balls-deep in my ass, and I want your cum too. That sounds so nasty and hot... Fuck me, Nick, fuck my tight little asshole and fill it with cum!"

"Whoa, sis, that's so hot... I'm gonna want that too, Nick," Sally mumbled, her voice weirdly shaky.

Turning away from the mesmerizing vision of Sharon's clingy dick-crammed sphincter, Nick glanced at Sally to find that she had repositioned and was now sitting back against the headboard with her legs drawn up to her chest and her virgin holes lewdly exposed to him. The most enticing detail, upon which Nick's bespectacled eyes instantly zeroed in, was that Sally had retrieved Tessa's silver buttplug and was now sliding the tapered toy in and out of her adorable pink butthole. Smiling with slutty joy as she noticed how intently Nick was watching her dainty hand pumping the buttplug into her own tiny anus, loving to see that her little masturbatory sideshow was making his half-buried cock flex and swell against the tautly stretched ring of her sister's gummy orifice, Sally mumbled in a soft sexy tone: "Fuck Sharon's ass, Nick. Fuck her fast, so you can stretch my tight virgin asshole too!"

Groaning with arousal as a huge dollop of precum spurted from his butt-jamming glans to further lube up Sharon's smooth slick anal walls, Nick took a deep steadying breath and temporarily put aside the mind-blowingly hot thought that he had another pristine ass to deflower, willing himself to concentrate on the task at hand instead. A big grin was painted on Nick's thin face as his hands grabbed possessively onto Sharon's perfect little bubble-butt and his hips pumped forward, driving his overswollen boner deeper into her warm, dick-hugging rectum.

"Uuhh! Uuhhnghh yeess!" Sharon squealed as she felt the meaty thickness of Nick's massively hard cock push further up her ass and widen her deepest and previously unplumbed anal depths, making her sensitive chute light up with sinfully pleasurable stimuli. "Oowwhh yeees, Nick! Keep pushing into my ass, go deep in meee... D-d-don't stop, pleeease! Sooo fucking good... Uuhhh fuuuck!"

Gritting his teeth and straining to delay his ejaculation as he plunged deeper and deeper into Sharon's freshly deflowered anus, Nick took advantage of the insane amounts of lube that Sally had rubbed onto his shaft by jacking him off, while at the same time he also capitalized on Sharon's moment of complete post-orgasmic relaxation. Pleasure-loosened and adapted to his invading girth, Sharon's asshole resisted his penetration only with the delicious natural snugness of her narrow chute, which barely slowed the advance of Nick's huge yet perfectly greased schlong while actually making it even more satisfying thanks to the warm dick-hugging caresses that her rippling rectum was imparting on his rock-hard pole. To the sound of her squealing moans of anal bliss, Nick determinedly wedged inch after veiny inch of his throbbing truncheon into the soft, scorching hot sheath of Sharon's buttery bowels, packing her ass full of his thick boner in one long, uninterrupted butt-cramming push.

Gleefully lust-crazed, hooked on the super intense thrill of feeling her ass get stuffed increasingly fuller the deeper Nick's massive dick slid into her tight rectum, Sharon all of a sudden found herself gasping then panting then yelling and cumming all at the same time when she finally felt his huge seed-laden balls bump into her hairless labia, signaling his complete penetration into her sweet little asshole. Nick's hefty scrotum was brushing against Sharon's clit-flicking fingers as her pussy overflowed with girlcum, her tautly stretched butt-ring meanwhile twitching erratically around the very base of his enormous shaft, trapping his entire length within her quivering, steamy anal sheath.

Up to that moment, the process of having her clingy anus gradually filled with more and more of Nick's boner had already been pleasurable beyond Sharon's expectations, but having his whole monstercock jammed balls-deep inside her tiny forbidden hole instantly pushed her to a whole new level of naughty exhilaration. Getting her ass packed full of cock was such a magnificently brain-melting feeling that Sharon knew right there and then that she would crave it again and again in the future, it was just too insanely good, so much so that she couldn't help but scream out her slutty joy.