Loopholes Ch. 01

Laughing complicity together, Nick and Tess resumed their languid make out session as he lazily masturbated her needy butthole while Sally's throat and Sharon's lips took great care of his huge boner. Soon though, as the twins once again placed their mouths on either side of his shaft and resumed sliding their amazing lips up and down along his veiny length while slobbering and suckling on his dickmeat with renewed vigor, Nick finally had to break the kiss again to pant: "Tess, girls... I... Oohh fuck, it's so good! I won't last much longer like this. Just saying..."

Giggling while unlocking her arms from around Nick's neck to place her hands on each of her little sisters' heads, Tessa instructed: "Okay girls, you heard him. Enough now, or your anal lesson will be over before it starts!"

The twins let out long groans of disappointment as Tessa guided their cock-slurping faces away from Nick's massively swollen erection, but they didn't resist her. Their soft, pouting lips were still connected to his rampant dickmeat by shiny threads of saliva as Sharon and Sally looked up together at their big sister with puppy eyes and matching pleading expression that mixed cuteness and lewdness in equal parts.

"Aw, come on, Tessie!" Sharon complained, her tongue running over her wet lips, greedily seeking the aftertaste of Nick's sticky precum. "I bet he can stay hard after he cums. I mean, just look at this fat horsecock and these huge balls! Can we just suck him off and drink his cum? Pleeease?"

"And even if he goes soft we can suck him hard again, no problem! Please, Tessie, please... He tastes sooo yummy!" Sally eagerly added, her face flushed with arousal rather than shyness for a change, her hand moving steadily in circles inside her shorts as her pussy juices trickled profusely at the mere thought of blowing Nick to completion and drinking his seed.

"Hey, you two were just supposed to get him lubed up, remember?" Tessa mock-scolded her horny little sisters with a mischievous grin. Then, biting her lips and trembling with anticipation as she looked down at Nick's amazing cock all slick and dripping with Sharon and Sally's saliva, the pastor's eldest daughter theatrically stated: "Now girls, have a seat and get ready for the main event!"

As Sharon and Sally sat down on opposite corners of Tessa's bed, they both shot pleading doe-eyed glances at Nick, whose smile was as big as it was goofy while he shrugged and said: "Sorry girls, you heard Tess... And by the way, you were right before, Sally: you two can do stuff with your mouths that would put most pussies to shame. Seriously, you were awesome!"

As the twins giggled and smiled with naughty pride at his praise, Tessa turned around and got on all fours in the middle of the bed, placing her plump jiggly booty right in front of Nick's face, thus captivating his gaze immediately. Leaning forward, she extended her arms to reach into her nightstand and fish out the bottle of lube she kept in the top drawer, making her round asscheeks wobble deliciously in the processes. Then, slowly backing up until she was positioned docilely on her hands and knees at the very edge of the bed, Tessa tilted her bouncy bubble-butt up and out, arching her back and letting her upper body rest on the bedspread.

After savoring the long groan of desire that Nick let out at the sight of her luscious booty being offered to him like that, Tessa languidly turned her head to look over her shoulder at Nick and hand him the lube. Meanwhile, his mouth literally watering, Nick was already leaning forward and dipping his head down into Tessa's butt-cleavage, rabidly aroused by the sight of her masterpiece of an ass and high on the prospect of once again being allowed inside the warm, snug confines of her heavenly hineyhole.

"Okay, Nick. The girls have already got you all nice and wet, so now it's time to lube up my asshole too-ooh-oohh! Uuuhh god, Nick... Oooh babyyy, yesss! Uunghhh yeaaahhh..."

Tessa's words vanished in a long ecstatic whimper as she was suddenly overwhelmed by the combined feel of Nick's lips suckling on the gummy rim of her pink little rosebud while his wet tongue licked and probed its way into her sensitive sphincter. With his face buried between his ex girlfriend's curvaceous asscheeks, Nick sank his fingers possessively into the soft meaty globes of her bubble-butt and held them nicely apart as he went crazy on her pliant orifice, lapping away at her tiny backdoor like his life depended on it. Mixed with the heady scent of her pussy juices, the familiar flavor of Tessa's vanilla shower gel wafting from the flawless skin of her cushiony booty and lingering all over her asscrack filled Nick's nostrils within moments, bringing back hosts of naughty memories and arousing him even more. Kneading and squeezing her epic bubble-butt while its smooth, full plumpness encased his face, Nick made Tessa squeal incessantly as he treated her to the most intense rimjob she had experienced since their break up.

"Oowwhh... Ooohh my god! Uuuh Niiiick, yeeees, lick my aaaaass! You're so good at it, it's soooo fucking good, babyyy... Yes, yeeeess I love iiiit! Uuhh,yeah, like thaaat!"

Trembling like a leaf under Nick's toe-curling analingual ministration, Tessa could feel her pussy juices dribbling in rivulets down her thighs while her rubbery orifice twitched around Nick's amazing, pleasure-gifting tongue. When he started lengthening his swipes, lapping wetly from her winking little asshole all the way down to her pulsating clit and back again, Tessa was swiftly hit by a stabbing climax so sneaky and yet intense that it left her panting and writhing like a stranded fish, much to the visual delight of her entranced sisters. Thrilled by the sight of Nick's passionate ass-slurping performance, the twins were diddling their virgin slits with such urgency that they didn't even bother removing their shorts and panties completely, leaving them partially and hastily pulled down and bunched up around their shapely, athletic thighs.

Stunned to witness Tessa cumming just from having her asshole skillfully eaten out by an ever more aroused Nick, Sharon incessantly caressed her nectar-slick pussy and budding clit as she mumbled: "Wow, that's so fucking hot! I had no idea you could have an actual orgasm from that kinda stuff..."

"I know! It's making me cum just to watch him lick Tessie's butthole!" Sally replied, feverishly circling her clit while she brought her other hand from her drooling slit up to her mouth, so that she could lick up her own sweet juices, as she always did when masturbating.

Still deeply engrossed in his oral worship of Tessa's adorable pink butthole, Nick smiled contentedly as he gobbled down his ex girlfriend's trickling girlcum and enjoyed her super sexy mewls of release. Far from being done, having always loved to get Tessa's tiny little rosebud ready for his huge cock almost as much as he loved actually buttfucking her, Nick kept munching on the pastor's eldest daughter's irresistibly cute hineyhole with gusto, only breaking his persistent ass-slurping swipes and sphincter-poking tongue strokes to tease her clit with a few swirling licks here and there. Still, Nick did occasionally break his butt-eating routine and moved his face lower for a few seconds so that he could clamp his mouth onto Tessa's soft, sopping labia and stab his tongue into her virgin pussy in a sexy parody of a deep, sloppy French kiss that allowed him to get a real good taste of her scrumptious nectar.

All the while, drunk with the constant wavelets of pleasure that surged from her super sensitive, masterfully licked anus and then coursed throughout her bent-over body, Tessa couldn't seem to stop cumming and moaning and squirming on the bed as Nick drove her crazy with his fantastic tongue, licking her lovingly and expertly like only he ever could. Another massive, unexpected orgasm smashed into the pastor's eldest daughter when Nick suddenly unclasped his mouth from her asshole after a long and deep bout of poking butt-licking strokes and glued his lips to her clit, sucking on it while easily pushing one then a second digit into her thoroughly-readied, spittle-slippery sphincter.

"Uuhhh! Oohh fuck yeeeess... Uuhhh Niiiiick!" Tessa yelped breathlessly, clawing at the bedspread as Nick devoured her engorged love button while fluidly sawing two fingers into her tight yet eager butthole, coaxing more of her liquid pleasure to gush from her pussy and drench his face.

Sharon and Sally were whimpering and fingering themselves to climax too while Tessa's lust-addled brain was taken over by an unquenchable need for more, a thirst that she had only known before with Nick and that could only be sated in one way. Straining to speak coherently as her twitching little asshole clutched around his gliding fingers and her untouched pussy drooled unstoppably into his clit-pleasuring mouth, Tessa eventually managed to lift herself up on her elbows, look over her shoulder at her ex and haltingly speak.

"Nick... Oohh Niiick, pleeease..." Tessa whimpered, her voice husky with desire. "Nick, baby... I need you inside me now. Uuhh fuck, your fingers, your tongue... It's all soooo good! But I need more... I need your cock in my ass, baby, I want it so much... Please, fuck my ass, Nick!"

Recognizing that tone, loving the mixture of sincere need and sexy wantonness in her voice, Nick pulled back and straightened up, disentangling his face and digits from Tessa's sweet holes. His mouth and chin were shiny with her juices and he was breathing hard as he removed his remaining clothes, his raging boner meanwhile throbbing and pointing right at Tessa's fabulously plump ass. Meeting her glazed-over gaze as he adjusted his glasses, Nick felt all fluffy inside while he smiled back at a beaming, beautifully horny Tessa. Aching to make the both of them happy by burying his massively hard cock deep into her ass, Nick swiftly grabbed the bottle of lube and poured a healthy dose of it all over the pastor's eldest daughter's spittle-glinting, pulsating little butthole.

Holding the gummy edges of her sphincter apart with his fingertips to make her adorable forbidden orifice gape slightly, Nick held the bottle close to Tessa's winking butt-ring and squeezed long dribbles of lubricant straight into her anal chute before he slid two digits into her oily anus and started twirling them around, coating her smooth inner walls with the slippery fluid. As Tessa hummed and wiggled her round bubble-butt in eager anticipation, Nick pressed his stiff dickmeat against her soft pussy lips and humped slowly up and down along the fleshy groove of her labia, lathering his already spit-dripping length in her overflowing juices.

As Sharon and Sally leaned closer to have a better look, their hands never leaving their respective pussies, Nick looked at them in turn and expanded on Tessa's anal teachings by saying: "Girls, if you want my advice, never let a guy stick his cock in your ass if he's not willing to get you nice and ready with his mouth first. It's not just about lubing you up either, I mean, actual lube is still mandatory. It's more about appreciation, or asspreciation, if you will..." Nick chuckled at his own cheesy joke, before concluding in his deep, matter-of-fact tone: "I just don't think that a girl should give her butthole to a guy who doesn't want it enough to kiss it properly."

"Mmhh, yeah, that's so true..." Tessa murmured dreamily, enjoying both the feel of Nick's huge cock sliding wetly between her juicy labia and the stimulation of his ass-prepping fingers sawing in and out of her anus while he kept adding more and more lube and lovingly applying it to her needy hineyhole, sensuously widening her tight sphincter with his usual gentleness and care. "And one last thing, girls," Tessa added between soft moans while she reached one hand to her clit and started lazily circling her fingertips all over it, "the most important tip I can give you is this: never stop rubbing your clit, especially the first times you do anal. Mmhh, never stop... Before, during and after... Playing with your clit while getting fucked in the ass will make you cum like crazy, I promise you. Just wait and see..." she concluded with a mewling giggle.

As soon as Tessa was done talking to her little sisters, Nick slipped his fingers out of her well-readied anus and applied a generous amount of lube to his raging shaft, greasing himself up from tip to root. Then, nestling his huge purple glans against her glinting pink sphincter, Nick cupped Tessa's magnificent asscheeks in his hands and kneaded them lovingly. As he pulled her fleshy buns apart, squeezing their full bouncy roundness in his palms with possessive joy, Nick locked gazes with Tessa. He only needed to questioningly arch an eyebrow at her to get a bright smile and an approving nod in response, obtaining the confirmation that she was indeed ready.

"You're so amazing, Tess..." Nick murmured as he instinctively leaned down onto her curvy, bent-over body until he could place a trail of butterfly kisses on her neck and shoulders, making her giggle contentedly as she undulated her bubble-butt side to side and pressed her bulging tits more firmly into the bedspread, teasing her own puffy, sensitive nipples.

Straightening up again while always reverently caressing her sumptuous booty with his hands, Nick exhaled deeply as he got ready to press forward and push his throbbing schlong into Tessa's tiny, lube-glossy butthole. Sharon and Sally were holding their breath as they stared in awestruck silence at the incredible sight of Nick's shiny, obscenely big glans prodding at the miniature opening of their big sister's pink asshole. With her fingers slowly circling her clit, Tessa exhaled languidly in response to the feel of warm, meaty pressure on her anus and relaxed her winking little orifice as best as she could while Nick's bulbous tip pushed gently but firmly forward against the slick, small entrance of her forbidden hole.

A general gasp of pleasure and surprise filled the room as Nick's fat purple cockhead bulged out for a moment against Tessa's pouty pucker and then suddenly punched through, slipping inside her well-greased backdoor. While her rosy butt-ring dilated docilely around his invading pole, opening up for him and sucking his swollen knob into the clingy warmth of her hungry anus, Tessa let out the sexiest, softest gasp of bliss, echoed by Nick's low moan of sodomizing pleasure. The capitulation of the pastor's eldest daughter's slick orifice was so sudden and complete that a couple of inches of Nick's girthy length popped inside her ass along with his bloated cockhead before her distended sphincter contracted in momentary protest, clamping down firmly around his shaft. Immediately, Nick stopped his butt-jamming advance, giving Tessa's convulsing anal muscles time to adjust to his veiny, rock-hard schlong.

"Uunghh... Oowwhh yeees! Oh my god, Nick... Uuhh yesss... You're in my ass! Oooh your cock is in my ass again, baby, I can't believe iiiit! Uuhh, you're so big inside meee, it's sooo good!" Tessa mewled deliriously as she felt her asshole getting stretched out and filled up to the very limit by the familiar meaty thickness of Nick's huge truncheon.

"Fuck, Tess! You're so tight, your ass feels amazing!" Nick panted, his eyes hooded with delight behind his glasses as he held his dick as still as possible inside the pastor's eldest daughter's spasming, suctioning anus. Even though he couldn't do anything about the joyous throbbing pulsations that her cock-nursing butthole caused in his partially embedded boner, making it flex involuntarily inside her amazing ass, Nick tried to keep his roaring anal lust in check and concentrated instead on making his awesome ex girlfriend enjoy their first sodomy since their amicable breakup. "Are you alright, Tess? Just tell me if you want more lube or anything, okay?"

"Uhhh Nick, baby... I'm okay, really... Oohh I'm more than okay!" Tessa replied, her smiling mouth agape as she panted and mewled in anal delight. Her eyes were barely open as she focused on relaxing her anal muscles while at the same time she enjoyed the incredible, unique feel of having her tiny, ultra-sensitive asshole deliciously widened by Nick's massive truncheon. Whimpering as she beamed with naughty joy, Tessa locked gazes with Nick as she spoke in a husky murmur. "I'm totally fine, Nick, I'm just uuhh... Just give me a second to get used to you again, baby... Oooh god, this feels even better than I remembered! Your cock is perfect, so hard and big in my ass! Uunghh yeaahh..."

Tessa's words faded into ecstatic moans and her head spun crazily as constant jolts of pleasure centered on her well-rubbed clit mitigated what little discomfort radiated from her long-neglected and now finally cock-crammed asshole. Feeling tingles of pre-orgasmic delight all over her surrendered body, the pastor's eldest daughter couldn't help but purr in anticipation as she savored the butt-stretching presence of Nick's precum-oozing glans and the first inches of his fat shaft wedged into her asshole. Within moments, the intense roaring build-up she had always experienced during anal sex with Nick was already starting to mount deep inside her.

Barely aware of the sexy moans that her little sisters were letting out in the background as they watched transfixed the very point where her stretched out butt-ring was wrapped tautly around Nick's enormous shaft, Tessa had a look of adorable dopey tenderness in her eyes as she glanced back over her shoulder at her ex's thin, handsome face. Meanwhile, she kept haltingly speaking to him as if through a sweet and pleasurable fog, just letting the words flow as her anal bliss grew.

"It's been so long, Nick... Oooh so long without this... Your cock in my ass, it's perfect! I missed it, baby, but now... Ooohh Nick, I want you inside me so bad right now! Uuhh, baby, I need you deep in my ass, please... Uuhh! Just go slow, okay? Go slow but don't stop, Nick, pleeease! Make me feel full of you again, baby... Fill my ass and make it yours, it's all yours... Only yours..."

Going all fluffy inside at those lustful yet sincere words, his heart thrumming in his ears while his stiff boner throbbed inside the clingy ring of Tessa's overdilated sphincter and his ass-jamming cockhead spurted a huge dollop of precum right into the steamy, velvety smoothness of her narrow passage, Nick smiled as he lovingly cupped the pastor's eldest daughter's bouncy, incredibly round buttcheeks more firmly in his hands. Unable to reply to his former sweetheart's irresistible pleas with mere words, Nick leaned over Tessa's arched back and dipped his head low until his lips met hers and their mouths were glued together in a torrid, loving kiss.

Draped over her curvy frame, smooching her rabidly as she lewdly sucked his tongue into her panting mouth as if it was his cock, Nick started pushing his hips forward, carefully easing his fleshy pole deeper into Tessa's epic ass. With small, measured in and out motions, Nick gradually crammed more and more of his veiny length inside the warm, tight sheath of Tessa's rectum while never breaking their steamy soulkiss.

Patiently filling her butthole a millimeter at a time like he had done so many times before, Nick took notice of every little contraction and minute pleasure ripple coursing through his ex girlfriend's cock-hugging rectum, savoring all those incessant anal caresses but also using them to determine how Tessa's exquisite asshole was adjusting to the butt-stuffing presence of his thick, rock-hard dick delving into her tiniest, most delicate and sensitive orifice. Knowing her as well as he did and having sodomized her as much as he had, Nick easily managed to attune his slow yet relentless penetration with the increasing relaxation and acceptance of Tessa's willing anus: as soon as her warm, slippery anal walls started to squeeze and spasm around his massive truncheon, he immediately stopped and allowed her narrow chute to adapt, only to resume his butt-drilling incursion once her incredibly snug yet ever willing rectum relaxed and was ready for more.