Loopholes Ch. 01


Author’s note: The male protagonist here is the very same Nick from my ‘Buttfuck Buddies’ stories. The events described here take place a couple of years before the ones in that series.

This is a work of fiction. All characters are eighteen years or older. Don’t expect realism and you won’t be disappointed when you don’t find it! Enjoy!


Whistling the tune of ‘Moon Over Marin’ by Dead Kennedys, Nick slowly shuffled his way through the smiling, laughing people gathered in the spacious backyard of pastor Jay’s house for the minister’s birthday party and the traditional celebratory barbeque that came with it. Much to his own surprise, Nick had to admit that it actually felt pretty good to be back.

His first year of college had been much more interesting than he had expected and he had gotten pretty used to being on his own, yet coming home for the summer holidays and seeing some familiar faces was really nice. Although Nick had never technically joined pastor Jay’s flock and had always limited his participation during religious services to his duties as the drummer in the band, he was no stranger at all among the crowd of festive churchgoers. Everyone he met greeted him with kindness, asking how things were and telling him how nice it was to seen him again. In most cases, Nick knew for a fact that those sentiments were genuine.

Once he made it across the crowded backyard and reached the sizzling grill, Nick finally saw the pastor himself, laughing and chatting with other guests as he flipped burgers and sipped on his beer. As he marveled for the umpteenth time at the uncanny resemblance between pastor Jay and Don Draper from ‘Mad Men’, Nick approached the man of the hour and tapped him on the shoulder. As Jay turned and recognized him, Nick barely managed to wish the burly pastor a happy birthday before Jay exploded in a big laugh and trapped Nick in a bone-crushing hug that knocked the wind out of the young man’s tall, lanky frame.

“Nick! Good to see you’re back in town, son!”

After letting him go and asking him extensively about college and music and how he was doing, the pastor handed Nick a veggie burger and thanked him profusely for coming to his birthday party, concluding by adding in a conspiratorial whisper that the church band’s sound just wasn’t the same since Nick’s departure the previous fall.

“By the way, do you wanna play some songs later, when the rest of the band arrives?” pastor Jay asked, grinning broadly. “I’m sure the guys will be happy to have you jamming with them again.”

“Sure, no problem,” Nick shrugged, adjusting his geeky glasses. Unable to hide a hint of sarcasm from his tone, he then added with a snicker: “I assume you’ll join us too for some Rolling Stones covers at some point, right?”

“You bet I will! Maybe we’ll even do ‘Sympathy for the Devil’ this time!” the husky pastor replied, chortling and heartily slapping Nick’s slim shoulder before returning to grilling food and chatting with the other guests.

As he saluted the pastor with a nod and headed back into the crowd, Nick couldn’t help but laugh to himself and shake his head at the thought that the only man of the cloth he knew personally was also one of the least priestly-looking dudes he had ever met. Saying hello here and there at the members of the congregation that greeted him, Nick kept mostly to himself as he ate his veggie burger and washed it down with lemonade. Then, as he skirted around the edges of the vast backyard, he finally caught a glimpse of someone that he was genuinely looking forward to seeing again.

Smiling and chatting with everyone around her, with her chocolate brown hair pulled back in a signature ponytail and her hazel eyes sparkling with guileless joy, Tessa looked as beautiful as Nick remembered. Her green summer dress hugged her curvy albeit petite frame perfectly, enhancing the jutting fullness of her tits and the bouncy, plump roundness of her protruding bubble-butt. As he walked up to her, Nick couldn’t help but feel a stirring in his groin at the thought of all the times he had fucked Tessa’s beautiful ass and pumped her tight little butthole full of cum during their senior year in high school, when they were still a couple.

“Now this is what I call a sight for sore eyes!” Nick said with a smile as he approached Tessa from behind.

“Oh my god! Nick?!” Tessa exclaimed while still turning around, her eyes wide with surprise, a big beaming smile dancing on her sensuous lips as her whole face brightened up with excitement at the sight of her ex boyfriend. “I didn’t even know you were back yet! How… When… Oh, it’s so good to see you, Nick!”

Squashing her buxom jugs against his chest, Tessa squealed happily as she locked her arms around Nick’s tall frame and hugged him tightly. As Nick wrapped her in an affectionate embrace in turn, Tessa purred contentedly and turned her face up to meet his bespectacled gaze. Behind his nerdy glasses, Nick’s brown eyes were as almanbahis intense and mesmerizing as ever, giving Tessa the familiar feeling that he was staring right into her very being, seeing her and accepting her and liking her for who she truly was.

“You look amazing, Tess. As always,” Nick said, his deep calm voice and his matter-of-fact tone making Tessa shiver in his arms as a wave of memories hit her full blast, setting her heart aflutter. It hardly made any difference to her that she was technically still a virgin and that the two of them only ever had anal and oral sex when they were a couple: as far as Tessa was concerned, Nick was her first, and always would be. He was the guy who had made her a woman, her first love, and as such he would forever have a special place in her heart.

Tessa was still staring dreamily into Nick’s thin, handsome face as he asked: “Are you going to sing us something later, Tess? Please say yes… I don’t want to be stuck playing cheesy covers for an hour with your dad!”

“Come on, Nick! It’s his birthday, let him have some fun!” Tessa laughed, playfully poking Nick’s side as they disentangled from their hug. “But yeah, I’ll sing something. Daddy already convinced me to sing ‘Shine A Light’ and ‘You Can’t Always Get What You Want’, so…”

After letting out a resigned groan, Nick perked up and said: “Well, at list I get to hear you singing again, even if it’s just the Boring Stones.”

“Oh, shut up already! We both know you secretly love them…” Tessa teasingly snickered.

“Hey, easy now!” Nick chuckled, looking around in mock-alarm. “I don’t want your dad to hear that, it would ruin my reputation!”

Laughing and smiling together, Tessa and Nick forgot about everybody around them as they talked and talked and talked, catching up and reminiscing, happy to enjoy each other’s company and to be reunited again.

From their texts and phone calls and video chats, Tessa already knew that Nick was seeing some Mia chick from college, and, even if they weren’t officially together, it was clear to the pastor’s daughter that Nick was really into this new girl. Similarly, the silver promise ring on Tessa’s finger was a constant reminder to Nick that things were getting fairly serious between his high school sweetheart and the guy she had met at the local Christian University. Still, as if following an unspoken agreement, both Tessa and Nick avoided asking direct questions about the other’s love life, choosing to savor their renewed closeness instead.

Half an hour later, Tessa and Nick were sitting in the swing on the front porch of the house, chatting quietly by themselves away from the crowded party, when the arrival of a car pulling into the driveway followed by the sound of two high-pitched voices forced their attention away from one another.

Sharon and Sally, Tessa’s younger sisters, had just returned from their daily training session at the track and were talking heatedly as they walked up to the house. Both blonde and tall and slim like their mother, Sharon and Sally were identical twins, and though it was easy to discern them from each other once one got to know Sharon’s saucy tomboyish attitude and Sally’s reserved and dreamy nature, the only thing that set them apart at first sight was the fact that Sharon styled her hair in a cute chin-length bob while Sally let her golden tresses grow long.

As the twins made their way to the house, Nick couldn’t help but let his eyes linger on their long shapely legs, exposed as they were by their skimpy running shorts, and on the swelling of their ripe pointy breasts, enticingly showcased by their tight-fitting tank tops. Most of all though, it was the flaring curve that ran from the twins’ thin waists to their toned heart-shaped butts that drew Nick’s attention, making him smile as he told himself that Tessa’s formerly skinny little sisters had really filled out nicely in the last year, developing two very similar and equally delectable asses. Being very disciplined track stars and having inherited the pastor’s wife’s slender hourglass build, both Sharon and Sally were endowed with taut protruding butts that a devoted ass man like Nick couldn’t help but admire reverently. Still, as much as he was enjoying the sight of the twins’ round little bottoms swaying side to side as the girls approached, Nick knew that neither of those two perfectly fine asses could compare to Tessa’s luscious, jiggly, beautifully plump booty.

“I’m telling you, it’s okay!” Sharon emphatically stated, staring right into her twin’s blue eyes.

“How can it be?! It seems impossible…” Sally replied, arching her eyebrows in doubt and shaking her head negatively. “Besides, it’s literally wrong… Like, unnatural or something.”

“No it’s not! Lots of people do it and most of them like it too, you know that! Oh look, Tessie is with Nick!” Sharon exclaimed, elbowing Sally as she noticed their big sister and her former boyfriend waving at them from the porch. almanbahis yeni giriş “Perfect, let’s ask them! They should know!”

“No! Sharon, wait! Don’t…” Sally gasped, her eyes growing big with panic as she attempted in vain to stop her exuberant twin from rushing ahead and involve Tessa and Nick in the conversation.

“Hey guys!” Sharon chirped as she stood straight in front of Tessa and Nick, her arms crossed under her perky breasts and her head cocked to the side as she bluntly asked: “You two used to have anal sex when you were together, right?”

As Nick slow-blinked in momentary befuddlement, Sally groaned and cast her unsubtle twin a half-desperate and half-incinerating glance before burying her face in her hands. For her part though, Tessa just let out a soft laugh and shrugged, unfazed by her little sister’s characteristic directness.

“Of course we did, Sharon. I thought you knew that already,” Tessa placidly replied. Within a second though, she was glancing inquisitively at the twins in turn, automatically switching into her protective big-sisterly mode. “Is that what you two were arguing about? Wait… Is someone pressuring you to do stuff? Because I’ll kick them in the nuts myself if that’s the case! Did either of you get a boyfriend and forgot to mention it to me by any chance?!”

“No, Tessie, that’s not it,” Sally responded after sharing a shocked look with Sharon, both of them genuinely offended by the mere suggestion that they might hide something like that from Tessa, whom they loved dearly and had always worshiped as the awesome big sister that she was. “We’d tell you if we had a boyfriend, of course. It’s just that, well… It’s about anal, specifically…”

“We’ve been thinking about it, Tessie. Like, a lot,” Sharon stated drily before exhaling and starting to explain. “I mean, we’re going to college in the fall and we feel like we should be able to do stuff, you know, beside blowjobs… We both want to stay virgins until marriage, so anal seems like the only way we can compete with all the coed sluts who can just let guys fuck them in the pussy.”

“I still think blowjobs will do just fine, even in college…” Sally grumbled, glancing sideways at Sharon, clearly rehashing a common argument between them. “We give great head after all.”

“Oh my God, Sally…” Sharon sighed in exasperation. “How many times do I have to tell you: it’s not gonna be enough! Guys wanna fuck! Like, actually fuck, you know, stick their dicks into a hot juicy hole and pound away!”

“So? Guys have fucked our mouths before, haven’t they?” Sally persisted, tucking her long blonde locks behind her ears. “Nobody’s ever complained. And when we deep-throat them and they push real deep, well, it’s warm and wet and tight in there too, kinda like a pussy. At least, I think so…”

“Jeez, Sal, seriously?” Sharon half-laughed and half-groaned, turning to Tessa and Nick again for support. “Guys, please, would you explain to this silly goose I got in sort as a twin how real sex works? Nick, Tessie… Please? Come on, help me out here.”

Keeping his mouth wisely shut, his cock having swelled to an uncomfortable state of stiff chubbiness within his pants during the twins’ conversation, Nick laughed inside as he was reminded yet again of the many fun and naughty sides hidden behind the deceptively dull facade of churchgoing girls. Smiling meekly, he just raised an eyebrow as he looked at Tessa, leaving her to deal with that weird albeit arousing situation.

Sighing and rolling her eyes at each of her little sisters in turn, Tessa started by saying: “Okay, first of all, both of you shut up right now before someone hears you talking like cumsluts. I mean, really, you are the pastor’s daughters and so am I, and it’s his freaking birthday party! Second of all,” she went on, focusing her gaze on Sally, “Sharon is sort of right, you really can’t compare oral with anal. Having a man inside you, being penetrated… It really is something else entirely. And I mean for you, not just for him. And anal is actually very intimate, as long as it’s with the right guy.”

“Yes! Thank you, Tessie! See, Sal? I was right!” Sharon exclaimed, interrupting Tessa. Unable to contain her gleeful sense of triumph, she even started shimmying in place while pointing at her twin and playfully teasing: “Told you! Ahah!”

“Sharon, come on, there’s no need to rub it in!” Tessa chuckled before she resumed. “Sally, just be honest with me: what’s really bothering you about this? You know that lots of girls in the congregation do anal to save their virginity, and you know that I do that too. So what’s the big deal? Just tell me the truth, it’s okay.”

“I, uhm…” Sally started tentatively before squaring her slim shoulders and turning her slightly flushed face up to face Tessa, Nick and Sharon. “I just don’t believe it’s as good as people say it is. I think it’s weird and dirty and I’m sure it hurts, no matter what everybody say. I mean, pornstars almanbahis giriş are just acting, right? And as for the other girls in our church who say it’s okay, well, I think they’re just lying and trying to look cool. There, I said!”

“Aw Sally, really…” Sharon cringed, rolling her eyes at her twin.

In contrast to Sharon’s mocking tone, Nick’s deep calm voice was very serious as he said: “Skepticism… I like that. It’s a wise attitude, Sally. If you think about it, in your circles a doubting Thomas shouldn’t be that strange, am I right? Besides, his need for tangible proof didn’t prevent him from becoming a saint after all.”

Blushing a bit but smiling widely, Sally chuckled and nodded appreciatively at Nick, causing Tessa and Sharon to laugh along too. As the tension faded, Tessa ventured: “Sally, let me ask you this: would you think I’m lying if I told you that anal doesn’t have to be painful and it actually feels really, really good?”

Exhaling as Sharon stared tauntingly at her, as if daring her to call their beloved big sister a liar, Sally bit her lips and furrowed her brow before replying in a measured tone. “Well, Tessie, you see… It’s not that I don’t believe you specifically. It’s just that I can’t… I mean, I know you wouldn’t lie to me, but I can’t convince myself to believe that it’s true. At least not without…”

“Not without what?” Tessa encouraged her.

“Not without proof, I guess,” Sally concluded with a sigh. “But then again, it’s not like I can get any proof without trying it myself. And I’m too scared to try it without proof, so…”

“Yeah, that’s a nice catch twenty-two alright,” Nick agreed, grinning sympathetically at Sally.

After a moment of silence, Tessa spoke, her voice firm and clear. “Okay then, Sally. I’ll get you your proof: Nick and I will show you. We’ll have anal sex in front of you and you’ll watch us and you’ll see for yourself that it’s not painful or dirty or wrong. Would that work for you?”

“What!?” Sally gasped in shock.

“Oh yeaaah!” Sharon cheered, grinning broadly.

“Uh?!” Nick muttered, blinking while adjusting his glasses as if somehow ascertaining that he wasn’t dreaming. While his plump boner strained painfully within his pants, he breathed in deeply before asking: “Tess, are you serious?”

“Yes, I am,” Tessa confirmed with a guileless smile, her eyes sparkling, her beautiful face set in one of those expression of mixed innocence and naughtiness that had never once failed to turn Nick rabidly horny. “I don’t see any problem with that. It would be a simple demonstration, something to help my little sisters out.”

“I’m all for it!” Sharon declared enthusiastically before impishly adding: “I always wondered about you two doing it, it’s gonna be interesting to see you in action!”

“Tessie, but…” Sally mumbled, her blushing face having turned even redder at the thought that she had instigated the whole thing. “You have a boyfriend, and that ring he gave you… Wouldn’t this be, uhm, cheating? And doesn’t Nick have a girlfriend too?”

“Actually, no, I don’t. Not exactly, at least,” Nick specified, adjusting his glasses on his nose while shifting as inconspicuously as possible in his seat, attempting to fit his achingly stiff shaft more comfortably within the constricting confines of his pants. “What we have is… I’m not sure how to define it, but the agreement that Mia and I have is of a strictly non-exclusive nature.”

“See?” Tessa smiled at Sally before glancing affectionately at her ex boyfriend. “Besides, Nick is almost family, in a way. I mean, he’s like the son that Daddy always wanted, we all know that. I’m not sure if anal qualifies as ‘cheating’ exactly, but even if it did, I’d be doing it with one of us anyway, so it shouldn’t count at all, sorta… And Nick definitely is one of us, right girls? One of us… Like in that film we all saw together, remember?” she unexpectedly added, giggling as she recalled something she hadn’t thought about in a while. “There was that super weird part when they all chant ‘One of us, one of us’ and stuff like that. I can’t remember the title of that movie, crap! It’s on the tip of my tongue…”

“Oh you mean that crazy old black and white film that Nick made us watch? Sure, I remember it. Very weird, but kinda fun too,” Sally nodded with a grin.

“Yeah, ‘Freaks’. Good stuff,” Nick chuckled, remembering the time early in their friendship when Tessa and the twins had invited him over to the house to watch a movie of his choosing and he had introduced them to Tod Browning’s disquieting masterpiece.

Chuckling while recalling the eery mantra from the most iconic scene of the film, Sharon started chanting and stamping her feet in an attempt to somehow reenact that crazy, unforgettable sequence. “One of us! One of us! Gooble gobble! We accept him, we accept him! One of us!”

After laughing and chanting along with her twin for a bit, Sally still couldn’t help but eventually point out: “But wait a second, Tessie… Wouldn’t it make it worse to consider Nick as part of the family?! I mean, I guess it wouldn’t be cheating, in a way, but it would be incest then, and anal incest at that! That’d be even worse, wouldn’t it?”

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