Loopholes Ch. 02

Slowly twirling the embedded toys and working their tapered lengths gently back and forth inside Sharon and Sally's snug anal chutes, Nick couldn't help but smile while he watched the girls' untouched pussies getting rapidly wet, a shiny glint of nectar almost instantly coating their puffy, smooth pink labia. At first Nick just teased the twins' receptive sphincters by shallowly sawing the buttplugs in and out of their anuses, which made their bent-over bodies shiver with delight at the prospect of soon having a much bigger and meatier intruder sliding into their hineyholes. Then, as the girls kept moaning sexily, Nick continued pumping Sharon's anal toy with one hand while with the other he slotted Sally's buttplug firmly back into place up her receptive ass and then reached down across her soaked pussy lips with his thumb, so that he could rub her engorged clit. Sally's gasps got immediately louder and her juices flowed ever more profusely, egging Nick on to continue his manipulations on her for a little longer before imparting them on Sharon too.

Mewling and panting, both Sharon and Sally were on the verge of climax by the time Nick reverted once again to simply masturbating their assholes with gentle in and out motions of the buttplugs. The slow but steady butt-stretching tempo that he set was drawing such languid and sexy squeals from the twins' O-shaped mouths that Nick felt his already rock-hard boner flex almost painfully while dollop upon dollop of precum formed on his bloated purple knob and trickled down his veiny shaft. Anxious to move to the next step almost as much as Sharon and Sally were, Nick tried not to betray his anal lust too much as he asked: "Are you doing okay, girls? Feeling good and relaxed?"

"Fuck, yeah... This feels good!" Sharon mumbled as she looked at Nick over her shoulders, her pleasure-hooded eyes instantly zeroing in on his massively erect dickmeat. "My asshole is all tingly and my pussy is sooo wet... Oohh this is gonna be so much fun!"

"Uhh Nick... Will you lick us like you did with Tessie, please?" Sally requested as she panted and wiggled her heart-shaped ass, rocking back and forth to match the maddeningly exciting rhythm at which Nick was driving the buttplug in and out of her clingy anus. "I guess we're good to go already, but it looked so hot when you rimmed Tessie's asshole! I've been thinking about it, like, all the time since the other day... Can you do it to us, pleeease?"

Smiling broadly Nick nodded at Sally, making her smile with wanton joy even as he turned to Sharon and instructed her in his calm, deep tone: "Keep prepping your ass with the buttplug like I was doing, Sharon, and feel free to rub your clit too. Your sister asked first, so I'll start with her, but I'll be right back to do it to you too, okay?"

Choosing to consider Sharon's playful grin as a good enough answer, Nick chuckled and leaned down until his face was wedged in the cleft of Sally's butt, his palms meanwhile cupping her round, flawless asscheeks. Pausing for a moment to inhale the intoxicating scent of Sally's arousal, Nick avidly drank in the sight of her soon-to-be-deflowered hineyhole clinging tautly around the silver base of the buttplug while glinting drops of her sweet juices dribbled from her little virgin pussy. Egged on by that awesome vision, without wasting another second Nick dove in tongue first into Sally's slit and started lapping away as he slowly and deliberately pulled the buttplug out of her anus.

A stream of sexy moans erupted from Sally's slack mouth as the ass-stretching toy was extracted from her sensitive rosebud, her vocalizations reaching a squealing peak when Nick stopped his withdrawing of the tapered dildo right while its largest part was about to slide out of Sally's distended anal ring. Holding the buttplug in place as her pink twitching orifice remained dilated to the max, Nick eagerly attacked Sally's engorged clit with a devastating flurry of tongue swipes that made the slender girl tremble all over as a stabbing climax snuck up on her, making her pussy gush her liquid pleasure all over his slurping mouth.

As Sally enjoyed the throes of her blinding orgasm, Nick resumed the removal of the buttplug, making the pastor's daughter cum even harder on his clit-sucking lips, her climax flaring brighter thanks to the delightful mixture of stretching and friction radiating from her clingy sphincter. As soon as the plastic toy popped completely out of her elastic asshole, Sally couldn't help but bemoan the unnerving sense of emptiness suddenly pervading her winking butt-ring. Her languid sigh of displeasure was cut short almost immediately though, replaced by the sharp trembling gasp of delight caused by the feel of Nick's wet warm tongue leaving her pussy and diving straight into the slightly gaping yet rapidly shrinking entrance of her pink, rubbery hineyhole.

The unprecedented, incredibly pleasurable sensation of having a wet wriggling tongue push its slobbering way into her pulsating little butthole and starting to lap away at her ass hit Sally like a thunderbolt, making her scream out in ecstasy. Her rolling orgasm exploded yet again and grew even stronger while Nick began voraciously licking and devotedly tongue-fucking her pristine anus, blowing her mind completely and forcing her to yell out in naughty bliss.

"Oohh shiiiit! Ooowww yesss, Nick, lick my aaass! Uuhh yeeaah, like thaat!"

Smiling between Sally's smooth round buttcheeks, with his lips clamped wetly around her adorable virgin sphincter and his tongue buried as deep as possible into her steamy anal passage, Nick redoubled his efforts and began rolling her slippery clit between his fingertips while he gloried in the slim blonde's obvious appreciation of his rimjob. As he gluttonously feasted on Sally's ass and teased her clit into climax after crashing climax with his talented digits, Nick was glad to notice from the corner of his eye that Sharon too was having quite some fun. Her husky moans and the desperate intensity she put into masturbating her ass with the buttplug while furiously diddling her clit showed that Sharon wasn't just mechanically doing what Nick had instructed her to do in preparation of her anal deflowering. In truth, watching her twin get her ass eaten by Nick was stoking Sharon's anal lust immensely and thus increasing her desire to get sodomized for the first time.

By the time Nick removed his skilled tongue from the snug confines of Sally's nibbling little anus and pulled his face back from between her shapely buttcheeks, the pastor's usually timid daughter was writhing and panting in ecstasy, so pleasure-weakened that she was barely able to remain in position on all fours. Treating himself to a long girlcum-scooping tongue swipe on Sally's drenched pussy that made the moaning girl shudder all over, Nick swiftly retrieved the silver buttplug, lathered it in Sally's trickling juices and then gently inserted it back inside her twitching, saliva-slick anus before her rosy pucker could seal shut on itself once again.

As Sally purred and let herself fall forward to lie on her tummy so that she could rest and savor her sizzling afterglow, Nick turned toward Sharon. With her ass tilted up and her face pressed sideways on the bed, Sharon was feverishly working her clit with one hand while with the other she methodically worked the jeweled buttplug back and forth into her rubbery little asshole. A litany of soft moans escaped Sharon's parted lips as she pulled the tapered toy all the way out of her anus until it escaped her gripping butt-ring with a lewd pop only to then swiftly be pushed back in until it was jammed completely inside her tiny orifice. As he admired the slim girl so intently pumping the buttplug in and out of her virgin asshole over and over again, Nick felt his rock-hard boner flex powerfully between his legs, rearing to get some action.

A lustful grin broadened on Sharon's gorgeous lips as she looked over her shoulders at Nick, her impish gaze meeting his bespectacled, inquisitive eyes. Still savoring the scrumptious sweetness of Sally's girlcum saturating his mouth along with the fruity aftertaste he had encountered while devouring her cute little asshole, Nick chuckled as he asked Sharon: "Did you guys use cherry flavored lube, by any chance? Because it would be very appropriate if that was the case..."

"Yep, you got it! We used one of Tessie's edible lubes when we put the buttplugs in. It was her idea, she was sure you'd like it," Sharon said with a wink. "The bottle is in my bag. I'm sure we'll need some more to get that monstercock of yours into our poor little assholes!" she concluded with a giggle, unconsciously running her tongue over her lips as she stared at Nick's monumental erection.

"There will be time for lube later," Nick replied as he positioned himself right behind Sharon's offered little booty, "but for the moment I'll just moisten you up like I did for Sally. Sounds good?"

"Yeah, definitely!" Sharon agreed enthusiastically, shaking her curvy rump and purring with eagerness as one of Nick's hands covetously cupped her round asscheeks while the other grasped the base of the jeweled buttplug and slowly but surely pulled it out of her clingy anus. As the plastic toy was removed completely from her clutching anal sheath with a sexy popping sound, thus leaving her pink sphincter gaping and twitching, Sharon let out an unhappy groan. Instantly missing the satisfying sense of fullness in her ass, Sharon wasn't disappointed for more than a couple of seconds. A thrilling shiver of anticipation ran up her arched spine as soon as Nick's hot breath hit her dripping wet pussy, while the awareness that she was about to feel his pleasure-gifting tongue on both of her virgin holes made her head spin with arousal.

Casting a quick glance to her side to take in Sally's heavy-lidded eyes and goofily smiling face, Sharon couldn't help but snicker. "Well, Nick, she sure seems to have liked what you did to her, a lot! I mean, look at her: she's totally owwhh... Oohh fuuuck... Uuhh yeess, Niiiick!"

The sudden feel of Nick's warm tongue replacing the lifeless toy inside her anus and the slick rubbing motions of his fingertips on her drenched clit instantly interrupted Sharon's train of thought, her words breaking into long husky moans that matched the lapping and slurping and munching attentions that Nick's mouth was devoting to her virgin pink rosebud. Just like her sister, Sharon was joyously overwhelmed by the delicious naughtiness and by the sheer forbidden bliss of getting her gummy sphincter dutifully licked and her virgin little butthole tongue-fucked by a devoted booty lover like Nick.

Unlike Sally though, Sharon didn't abandon herself completely to the pleasure of getting her ass eaten by Nick, managing to keep her mind more or less focused on the main event ahead while she enjoyed his masterful rimjob. Still, as impatient as she was to finally get her virgin anus deflowered by his impressive dickmeat, Sharon allowed herself one big butt-centered orgasm that sent her sphincter spasming around Nick's skilled tongue before she brokenly blurted out her raging desire to be properly sodomized.

"Uuhh fuck, Nick! That's so good, but... I want your cock in my ass now. Your tongue is driving me crazy, my asshole is sooo tingly! Just lube me up and stick your big dick in me, Nick, I want you to fuck my ass so bad!"

Thrilled to the core by that wanton invitation, Nick extracted his tongue from Sharon's pulsating little orifice and peeked over her heart-shaped tushy to smile and nod at her as she looked back at him with hooded, lust-glazed eyes. Without wasting a second, Nick darted across the room and retrieved the bottle of lube from inside Sharon's bag. As soon as he was once again positioned behind her upturned little bubble-butt, Sharon reached eagerly back to spread her taut round asscheeks open for Nick, who immediately uncapped the bottle and pressed it against her well-licked, saliva-glinting backdoor and then squeezed, pouring a generous amount of the slick fluid straight into Sharon's winking anus.

The sudden cold feel of the lube squirting into her anal passage made the pastor's blonde daughter groan, but her momentary discomfort dissipated as soon as Nick clamped his mouth onto her engorged clit and started suckling lewdly, meanwhile sliding first one then a second digit into her tiny, slippery hineyhole. Smoothly pumping his fingers in and out of Sharon's asshole to properly coat the inside of her snug chute with lube, Nick kept nursing on her clit until he heard her mewls spike up into unmistakeable squeals of climax. Then, as Sharon's gushing pussy juices flooded his slurping mouth, he slipped a third finger into her twitching, oily butthole and resumed steadily masturbating her ass. Focused as he was on making those clit-nursing and sphincter-stretching preparations as pleasurable as possible for Sharon, Nick was caught by surprise when the bent-over track star managed to turn her broken moans of pleasure into a trembling yet determined plea for more.

"Uuhh Niiick... I'm ready, I'm so fucking ready for your cock! Do it, Nick, pleeease... Stick your big cock in my ass! Fuck my ass before I go crazy... Oowwhh yeesss! Sooo good!"

Still sucking away on her girlcum-drooling slit and nibbling on her engorged clit, Nick waited until Sharon's climax abated before removing his face from between her round taut buttcheeks to stand up behind her, his fingers still jammed into her warm pink orifice all the while. Sharon's begging invitation to get sodomized also managed to snap Sally out of her post-orgasmic grogginess, convincing her to sit up on her knees on the bed right beside her mewling sister so as to have a better look at her imminent anal deflowering.

Before Nick could reach for the bottle of lube, Sally's eyes locked with his bespectacled gaze and she started to speak, blushing adorably while casting him a half-timid and half-seductive smile: "Don't worry about this, Nick, I'll uhm... I'll lube Sharon's asshole for you. We practiced together with the buttplugs yesterday, so I think I'll do it right. Besides, well, I wanna be involved too, kinda... Is that okay?"

"Sure, absolutely!" Nick nodded in glad agreement. Resting his free hand on Sharon's flawless booty, he gently directed her to lie on her side, meanwhile taking good care to keep his three sphincter-stretching digits always crammed inside her snug, well-lubed anus.

Mewling and cupping her pointy tits in her hands, her fingertips playing feverishly with her stiff and super sensitive nipples, Sharon docilely followed Nick's instructions and rolled onto her side, with her legs drawn up to her chest and her round perky ass hanging off the edge of the bed. The sight of Sharon's virgin holes offered to him so docilely, her little pussy dripping with juices and her pink saliva-slick asshole stretched tautly around his fingers, sent the umpteenth jolt of arousal to Nick's massively thick and painfully hard boner, coaxing yet another glob of runny precum to ooze from his purple glans.

Before Nick even asked for it, Sally was already extending her arm and turning the lube bottle upside down right over his meaty erection, letting a long dribble of the slippery fluid splatter on his veiny shaft. To the sound of Sally's excited giggles and of Sharon's urgent moans of anticipation, Nick rubbed the lube all over his huge pole and then aligned his well-greased length with the pastor's daughter's offered asshole, meanwhile always stimulating Sharon's clingy sphincter with his fingers. The lewd image of Sharon's rosy orifice dilated around his three butt-prepping digits got even better when Nick pressed his bloated cockhead against the distended rim of her pink gummy pucker.

That sexy picture improved even more when Sally cupped one of her twin's round buttcheeks with her dainty hand and pried her taut globes apart a bit more, much to her own and Nick's visual pleasure. In response to the irrepressible chuckle and questioningly arched eyebrow that her facilitating gesture induced in Nick, Sally just shrugged and raised the hand in which she held the bottle of lube, tittering as she said: "Well, I need to a have a good view of the action to squeeze this stuff on the right spot!"

As Nick and Sally shared a quick complicit laugh, Sharon groaned in antsy frustration: "Come on, you two, stop wasting time! You got me so fucking horny, Nick, I want your big cock in my ass now!"

"Okay, Sharon. Here goes..." Nick said in his deep calm voice, slowly withdrawing his digits from her clingy anus even as he pressed his fat glans more firmly onto the dilated rim of her asshole, so that it was pushing against the very edge of her finger-plugged backdoor. "You're all lubed up and clearly willing, so it should go in easy. But I'll take it slow anyway, and you can stop me any time you want. Ready?"

"Yes, yes! Do it, Nick... Put it in my ass!"

While Sally held her breath and stared in rapt anticipation, Nick completed the removal of his butt-stretching fingers from Sharon's slippery orifice, leaving her adorable virgin asshole to gape and twitch as it almost instantly began to shrink. Before her pink little sphincter could wink shut though, Nick eased his bulbous purple glans into that quickly closing hole, managing to wedge his whole lube-shiny cockhead inside Sharon's snug, quivering anus. A long gasping mewl from Sharon marked the moment her asshole was invaded by a real dick for the first time. A jolt of pure excitement coursed through her body as Nick's fat tip filled her delicate rosebud full and forced her tiny anal opening to widen and accept him, her quickened breathing matching the intense pulsations of her butt-ring clamping firmly around his girthy shaft.

"Wow! It's in, Sharon!" Sally exclaimed, her mouth open in naughty awe as her eyes refused to move from the memorable sight of her twin sister's overdilated sphincter gripping desperately onto the very first cock entering her body. "Whoa, it's really in there... Nick's got his huge dick in your ass, Sharon! That's sooo hot!"

"Well, it's just the tip actually..." Nick pointed out with a shrug even as he brought his hand to Sharon's dripping little slit and started gently circling his fingertips on her engorged clit to help her mitigate the unavoidable discomfort of her anal deflowering. "How are you doing, Sharon? Everything okay? I know it's gonna sound ridiculous, but try to stay as relaxed as you can. You're doing great so far."

Looking up to meet first Sally's smiling face and then Nick's bespectacled gaze, Sharon panted as she savored the feel of having his massive cock jammed inside her super tight asshole. The feeling was incredibly intense and weird but not actually painful, plus the slow caresses that Nick was treating her pussy to were doing a great job of keeping an undercurrent of delightful clit-centered wavelets rolling, making Sharon's whole body hum with pre-orgasmic joy. Trying to keep her pleasure-glazed eyes open as her dick-crammed sphincter twitched and lewdly suckled on the very first inches of Nick's meaty pole, Sharon shared a quick but meaningful glance with her twin before letting out her halting reply.

"Uuhnghh Nick... I'm okay I guess... Uuhh fuck! It d-d-doesn't really hurt but... Uuhh your cock is just sooo big! Oowhh you're stretching my ass so fucking much, Nick! Ooowh yeahh, rub my pussy like thaaat... Uuhh my god, yesss, that feels so good!"

For a while, as Sharon's clingy little butthole slowly adapted to being dilated to the limit by his huge boner, Nick just held himself perfectly still and enjoyed the potent glans-nursing squeezes that the slim blonde's anal muscles were imparting on his firmly embedded cockhead. Soon enough though, helped by his incessant clit-frigging manipulations and by her eagerness to be sodomized, not to mention the preparations provided by Tessa's buttplug and Nick's own tongue, Sharon's gummy pink sphincter stopped cramping around his swollen tip and began accepting him within the slick, extra tight grip of her forbidden orifice instead.