Loopholes Ch. 03

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Meanwhile, despite being thrilled about their newly discovered passion for buttsex and their daily climax-ridden anal romps with Nick, the twins were getting worried. In a matter of days they would be going to camp, and that meant not having Nick around to give them those precious, anally administered doses of dickmeat that they had already come to crave so much. Unlike Tessa, who could at least conceive of going without assfucking for some time, even though she hated to do so now that she had finally been reacquainted with Nick's awesome booty-drilling schlong, the twins were panicked about having to quit their anal addiction cold turkey. Spending two weeks at camp and relying only on Tessa's assorted buttplugs and dildos to keep their needy buttholes satisfied was simply not an option for either Sharon or Sally: the way the saw it, it was obvious that, if they were leaving for camp, then Nick would have to tag along too.

Unsurprisingly, when Tessa informed them that Nick had finally agreed to come too, Sharon and Sally were so overjoyed that they didn't even contemplate the possibility that it might be the deep emotional connection that Nick shared with Tessa that eventually convinced him, rather than their own relentless pestering. Of course, the twins had already noticed how quickly and strongly the ties of love and friendship that bound their big sister and her ex were reasserting themselves; it was something Sharon and Sally had expected somehow, and they were glad to see it happening, given how fond they had always been of Nick. Still, they did like to think that a huge part of the reason why he had come to the decision to join them on their church-themed retreat in the mountains had to do with the sexy roundness of their toned heart-shaped butts, not to mention the complete access to their backdoors they were always eager to grant him.

Callipygian vainglory aside though, Sharon and Sally, didn't fail to notice how distracted Tessa was in the rare occasions when she video-chatted or texted with her boyfriend, Toby. At the same time, they saw Tessa getting more cheerful every day, with her most happy moments always occurring when Nick was around. The realization that they had never really seen their big sister so joyful with any other boyfriend apart from Nick led Sharon and Sally to wonder if, maybe, their recent involvement with him might be detrimental to the possible rekindling of a closer intimate relationship between Tessa and Nick.

That thought threw the slim blondes off a bit, but not too much. After a rather cursory but still well-meaning bout of soul-searching, during which they agreed that it would be much better for Tessa to get back together with Nick and dump Toby's lame ass as soon as possible, Sharon and Sally came to the conclusion that no, they shouldn't feel bad about their desire to offer their horny little buttholes for Nick to plow. After all, it had been Tessa's idea in the first place to have him pop their anal cherries, kinda, and it didn't really seem like Nick's obvious preference for Tessa and her spectacularly plump booty had changed in the least.

In fact, he seemed to be more turned on than ever by Tessa and her epic bubble-butt these days, regardless of how often he fucked their smaller but still gorgeous asses. As far as the twins were concerned, it could even be said that their involvement with Nick was actually helping rebuild his relationship with Tessa, sorta, at least in the sense that their cute heart-shaped butts served as appetizers for the main course: Tessa's big juicy rump. So yes, Sharon and Sally finally decided, it was okay for them to give in to their overpowering need to feel Nick's fat ass-stretching dickmeat sliding in and out of their bootyholes all the time, and it was even more okay for them to enjoy orgasm after gushing orgasm and bask in the feel of his abundant cum flooding their anal depths, filling their royally pounded anuses and soothing their snug anal walls with rope after rope of his creamy seed.

For her part, Tessa was not at all surprised when, as soon as she brought the twins up to speed about Nick's decision, they instantly replied that they had already figured out a perfect way to make it all work out. Without wasting a second, Sharon and Sally reined in their giggles and yelps of triumph and unveiled the carefully laid plan that they had been concocting for days now, a plan so well thought through that Tessa only had to put a few finishing touches to it.

In essence, the idea was to let Nick stay at their family's hunting cabin, which was near the camp grounds and could be reached via a trail through the woods. That way the three of them could sneak out and go there to have buttsex whenever they weren't busy with their jobs as councilors, the twins explained to Tessa with matching beaming smiles on their faces, making her chuckle and nod in ready agreement. To make sure that their plan would work, Sharon and Sally added that they had already contacted their aunt Jackie, their father's sister and the most frequent occupant of the cabin, and learned that she didn't plan to go up there any time soon.

One issue the twins had left unresolved but hoped that Tessa might smooth over was the possibility for all three of them to actually be exempted from having to sleep at camp and instead go to their family cabin at night once the daily activities were done. At that time of summer the camp was always at its most crowded, with people coming from various local churches, so, Sharon and Sally reasoned with Tessa, if they were to offer the director a small yet viable solution to alleviate the issue of bunking arrangements a bit, he might agree to it. That is, the twins pointed out, as long as it was Tessa who brought up the issue with him. After all, they insisted, Tessa was a veteran there, a trusted councilor, beloved by campers and staff alike, not to mention the fact that she was the sweet and perfect eldest daughter of the pastor whose great-grandfather had donated the land where the camp was built to begin with. If she was to make the right moves with the director, Sharon and Sally pressed on, she could easily pull it off.

Smiling knowingly at them, admiring both the fact that they had planned it all out and that they had done so while having absolute faith that Nick would eventually accept their call to come and sate their anal needs, Tessa answered her little sisters' expectant stares with a shrug that made her big boobs wobble under her top, an impish grin declaring her eager participation even before she spoke.

"Okay," Tessa said with confidence, "when we get there, I'll deal with the director. I got this, girls."

*****

As expected, convincing the director to let her and her sisters leave the camp grounds at night so that they could sleep at their family cabin turned out to be a fairly simple mission for Tessa to accomplish. All it took her was a day and a half of flattery and subtle manipulation, combined with a strategic usage of her generous and well-exposed cleavage.

A jolly old bear of a man with a bushy white beard and a big round belly, camp director Branson had been a good friend of the family for ages. Having being the girls' paternal grandpa's best friend, he almost naturally took on a grandfatherly role for Tessa and the twins after their grandfather's death. His preference for Tessa had never been a mystery: he always spoke very highly of her involvement in her dad's church, going as far as to suggest that one day she would be a great successor to pastor Jay at the lead of his flock. Beside the appreciation for her spiritual virtues though, Tessa never been blind to the fact that director Branson's lively gray eyes unfailingly strayed toward her ample bosom whenever they engaged in conversation. Based on that and on the fact that both his current and his former wife had massive boobs that made even Tessa's fleshy melons look like mosquito bites, the pastor's eldest daughter went out on a limb and guessed that Branson was a devoted tit man, and she used that key factor to her advantage.

Choosing to keep the camp regulation polo shirt unbuttoned and wearing the pushiest among push up bras she had, Tessa made it a point to be around the old director as much as possible from the moment she and the twins arrived at camp. Enticing him with sweet smiles and mesmerizing views of the soft, smooth upper slopes of her bulging tits, Tessa worked her magic on the husky director to the best of her abilities, weaving together biblical quotes and spiritual reflections alongside more mundane and practical observations about camp life and such, always keeping her epic rack as near as possible to Branson's hungry eyes.

Unable to resist the visual treat that were Tessa's young, huge yet gravity-defying jugs exposed to him so often and so readily, Branson couldn't help but give his full approval when the pastor's eldest daughter meekly asked his permission for herself and the twins to leave the camp at night so that they could sleep at their family cabin. The director's voice was thick with longing as he uttered a sighing and dreamy: "Yeeess!"

Moments later, Tessa retired to the nearest bathroom, pulled down her shorts and panties and jutted out her plump booty before taking a nice pic to send Nick, along with the good news that he could now leave for the cabin where, that very night, they would be together again.

That text and the sweet picture of Tessa's epic bubble-butt that came with it spurred Nick into instant action. His bag had been packed since the day the girls had left and he had already repeatedly gone over the directions to reach the dirt road that led to the girls' family cabin in the woods, getting ready to leave as soon as he got the green light. Within minutes of receiving Tessa's text, Nick was in his car, headed out of town with a maniacal smile on his face and a raging boner tenting his pants.

Even though it had only been a couple of days since the pastor's daughters had left, Nick already felt like he was on the verge of assfucking withdrawal, or something like that. Having complete access to three sweet little assholes had definitely spoiled him, and now the total removal of anal intercourse from his normal routine after the recent days of daily buttfuckfests was hitting him with a vengeance.

It was both paradoxical and ironic, Nick had thought when he tried to analyze his predicament. On the one hand, he simply couldn't stop reminiscing about all the booty-plowing he had done in the previous days, therefore getting rabidly horny. On the other hand though, jacking off to those vivid lust-inducing memories only served to remind him of how dearly he missed plunging his massive boner balls-deep into the cock-hugging tightness and delicious warmth of Tessa's welcoming rectum, or how gloriously naughty it felt to plow either Sharon or Sally's impossibly snug hineyhole and pump her steamy anal depths full of cum while the other blonde beauty waited for her turn, frigging her wet virgin pussy and masturbating her needy sphincter to get it nice and ready to be stretched out by his unyielding hardness as soon as it popped out of her twin sister's seed-flooded rosebud.

On top of that, Tessa and the twins had kept sending him a constant flow of sexy ass-centric pictures and videos since the moment they had left for camp. As much as he appreciated those naughty images, and he certainly did make good use of them during his barely satisfactory masturbatory sessions, the visual treats that the girls sent him only made Nick wish even more desperately that he could have those sweet round butts in the flesh right there and then with him, so that he could stuff them full of cock and hose them down with cum. Granted, most of the visual treats that the pastor's daughters sent him were quite tame, but among the many enticing yet relatively innocent shots of their booties, some sluttier and sexier gems did stand out, and those became the core focus of Nick's grim dick-stroking marathons.

Such favorites included a close up video of Sharon's gummy pink orifice clinging eagerly around her digits as she pushed first one then two then three slender fingers into her snug anus and held them jammed knuckle-deep up her ass while she frigged her clit to a pillow-muffled climax with her free hand. There was also a brief yet instantly cock-hardening clip of Sally sliding a buttplug out of her sweet little sphincter with a pop, leaving her lovely pink orifice to gape widely open and wink invitingly at him as it tightened shut on itself again, at which point, to the sound of her lustful gasps, she once again jammed the tapered toy into her needy hineyhole only to then repeat the whole process from the start. All the while, Sally was also lazily fingering her own pristine pussy, her mewls becoming louder as the video progressed, matching the quicker insertions of the buttplug into her lubed up backdoor and the faster slit-diddling rhythm of her fingers, until she came screaming, with the plastic toy crammed deep up her ass.

Still, Nick's favorite was a video of Tessa on all fours on a bed, her face pressed down on the pillow as she looked back at the camera over her shoulders, her big juicy ass tilted up and swaying gently side to side, just enough to make her gloriously round buttcheeks jiggle away in a hypnotic rhythm that entranced Nick instantly and made a stream of precum ooze freely from the fat tip of his raging erection. After a few seconds of gentle teasing undulations of her protruding booty, Tessa reached back with her hands and ran them all over the curvy plumpness of her soft bouncy globes, massaging her own rump with slow and sensuous caresses, kneading those fabulous asscheeks as she purred and smiled with her eyes half-closed. Then, when Nick's saliva was practically drooling on the screen of his cell phone, Tessa parted her meaty buns and revealed the tiny little pucker of her asshole in all its tight, adorable pinkness. At that point, after letting the camera take in the irresistible vision of her cute hineyhole, Tessa used the very tips of her forefingers to ever so slowly pull the rubbery rim of her butt-ring apart and force her forbidden hole to open up a bit, just enough to let Nick see it wink and pulsate and twitch with horniness. As if that lewd invitation wasn't clear and exciting enough, after a few moments Tessa looked over her shoulder and straight into the camera, smiling languidly as she said: "All my asshole needs now is your big fat cock, Nick..."

And with that irresistible line, the video shifted to a closer and closer view of Tessa's beautiful bubble-butt and gradually zoomed in tighter and tighter on her winking, delicious rosy asshole, until the clip faded to black on a promising close up of the entrance of Tessa's beckoning, barely revealed anal passage.

Needless to say, Nick had blown load upon massive load because of that specific clip featuring his bootylicious ex girlfriend, but then again all of the pastor's daughters combined and reiterated efforts to tease him with those digital surrogates of their beautiful asses had coaxed bucketloads of cum out of him. An added layer of eroticism was also implicit in the fact that, obviously, quite a few of those clips weren't selfies; the mere thought that the girls were actively helping each other shoot their videos to make them more enticing for him was enough to send flexing jolts of arousal to Nick's fat dick. Still, the fact remained that all those juicy vids and pics steadily increased his bottled up horniness while never providing him with what he really needed to relieve his simmering buttlust: a tight, willing little asshole to stretch out, pound hard, and bury his huge cock to the hilt into, so that his balls could properly empty of all their ever abundant supply of creamy sperm.

Given how generally vital to his overall well-being buttsex was and how frequently offered and deeply satisfying it had been since he had returned home for the summer, being deprived completely of anal intercourse led Nick to feel like the previous two days had dragged on with glacial and barely tolerable slowness, and no wonder. Luckily though, that was all over.

Now, Nick thought as he hit the gas and grabbed harder onto the wheel, staring at the mountain road ahead with a glint of crazed desire in his bespectacled eyes, now he was going to get what he so desperately needed and had been envisioning incessantly, either in his butt-focused daydreaming or in the saucy images that Tessa and the twins flooded him with. Now, less than an hour away somewhere in the woods up ahead, Nick was going to get his hands on the real thing and finally plunge his raging boner deep inside a sweet curvy ass. Or three.

*****

Having meticulously studied the route beforehand and with Tessa's directions indelibly etched into his mind, Nick had very little trouble locating the exact point where he had to exit the main road, travel deeper into the woods along a narrow secondary road and then take the winding dirt road that led up the side of the mountain to finally emerge in the broad, tree-encircled clearing where the pastor's family cabin stood.

Even before he killed the engine, Nick was already texting Tessa to let her know he was there. Within moments of his sending the text, she replied that she was on her way. Buzzing with anticipation and adjusting the tent that his chubby dong was causing inside his pants, Nick decided to make the wait more bearable by taking a look around and familiarizing with what he hoped would become his den of anal delights for the next few days.

Despite his innate aversion for outdoors activities (or, for that matter, any kind of physical exertion that didn't have to do with sex and was therefore, by his laid back standards, just needless discomfort) Nick was very much taken by the beauty of that secluded little spot in the mountains, and he particularly liked the amazing view of the forested valley that the cabin overlooked. The fresh air, the chirping of birds and the late afternoon sun helped Nick savor the situation more, giving him a glimpse into the reasons why someone would want to hike through the woods just for fun. And yet, his appreciation only reached a true peak when he stepped inside the cabin and discovered that there was perfectly functioning wifi and the kitchen cupboards were stacked with plenty of canned foods and other provisions.

The hunting trophies hanging on the walls and the rough stones of the fire place didn't particularly impress Nick, but the big comfy couch that dominated the living room along with a couple of plush armchairs and a fluffy-looking carpet brought a smile to his face, accompanied by mental images of how the girls might be arranged on the couch cushions or over the armrests to better offer him their sweet round butts. Once Nick went up the creaky wooden stairs and dropped his bag in the hallway, a whole array of positions and acts flashed before his eyes each time he peeked his head into one of the bedrooms, his huge dong hardening even more inside his pants. Grinning, he made his way downstairs again, all the while estimating how long it would take for Tessa to get there.

Given how horny he was, a mere passing glance at a photo on the mantlepiece featuring Tessa and the twins horsing around in a creek with their voluptuous aunt Jackie, all of them wearing skimpy bikinis, was more than enough to trigger even wilder fantasies in Nick's mind, leading him to include the girls' milfy aunt in his lewd daydreaming. Shaking his head to clear his steamy thoughts at least a little bit, he decided to go out and get some fresh air as he waited for Tessa to arrive. He dearly wished she wouldn't take too long, otherwise he would seriously have to consider taking care of his achingly hard erection himself.