tagAnalLoopholes Ch. 02

Loopholes Ch. 02


Author's note: 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!


Even though he didn't attribute any strictly transcendental meaning to it, Sunday still felt somehow sacred to Nick. It was the day when he allowed his lazy side free rein, the morning when he slept in and stayed in bed till noon feeling neither guilty nor compelled to do anything at all except relax and nap or maybe, at most, sit up and read, possibly while listening to music. Luckily for him, his aunt Leslie had never had a problem with any of that while he was growing up, which Nick deeply appreciated.

That particular Sunday morning, the first since Nick had returned home for the summer holidays, was going to be no exception. In fact, since his aunt had left early and would be gone all day to attend a friend's wedding in a nearby town, Nick's cherished day of rest looked particularly promising. Not that he would have minded spending time with his cool aunt Leslie, but having the house all to himself opened the gates to pleasures other than just enjoying a relaxing day of doing nothing at all, pleasures such as those he had sampled just a couple of days earlier in Tessa's bedroom during her father's birthday party.

In truth, fucking his sweet ex girlfriend's beautifully plump booty had been a much more meaningful experience than Nick had expected. Even though in theory it was supposed to be just a way to show her little sisters that anal sex was a perfectly viable and very pleasurable way of keeping their virginities intact, Nick and Tessa's passionate sodomy had stirred a whirlwind of affection and emotion in both of them, reaffirming their obvious compatibility in bed and once again demonstrating their ability to make each other cum like crazy through butt sex.

Inspired by their steamy reunion, Nick and Tessa had been texting all through Saturday, joking and chatting and teasing each other playfully all day while he spent time with his aunt and she was busy helping out with the organization of a church event. Seamlessly shifting into naughty mode, they had ended up sexting late into Saturday night, with Tessa sending him pics of her juicy bubble-butt and close ups of her dainty fingers teasing her tiny pink rosebud while Nick replied with images of his rock-hard cock as he stroked it all over its massive veiny length. Eventually, their sexting session reached its peak when Tessa gifted Nick with a video in which she got on all fours on her bed and then proceeded to lustfully masturbate her anus with a robust dildo while furiously frigging her nectar-drenched clit until she reached a squealing, gushing climax.

Even though he knew that he couldn't hope to match the insane eroticism of that video, Nick still sent Tessa a few shots that captured the orgasmic effects that her unexpected virtual show had had on him. Those pics, which depicted Nick's huge meaty truncheon lying on his toned abdomen in a gigantic pool of his creamy and insanely abundant seed, were actually so gratifying and arousing to Tessa that she had kept caressing her virgin pussy long after their interactive masturbatory session was over. Meanwhile, as he drifted off to sleep with a smile on his lips and afterimages of Tessa's glorious bubble-butt lingering in his mind, Nick felt a stirring in his semi-hard cock as he pondered on the final text she had sent him, the one in which she said good night and suggested that he should get some rest to be ready for a 'surprise' she had in store for him the next day.

Understandably, as he celebrated his Lazy Sunday in bed, napping and listening to music, Nick couldn't help but linger on Tessa's promising text. Since he had mentioned to her that he would be home alone all day, Nick assumed that Tessa's 'surprise' would probably involve her showing up at his door after church so to he could make love to her fabulous booty. The mere idea of immersing his huge boner in the warm, dick-hugging snugness of Tessa adorable little asshole was enough to make Nick's chubby schlong stiffen to aching rock-hardness, but he stoically refrained from jacking off, deciding to save every drop of cum for his ex girlfriend's curvy bubble-butt instead.

Knowing that Tessa would be in church for most of the morning, Nick didn't bother texting her nor did he expect her to text him during the Sunday service. Nonetheless, he did decide to strategically end his lazy time a bit earlier than he would have done under difference circumstances. Getting out of bed with a spring in his step, Nick smiled to himself as he took an invigorating shower right around the time he estimated pastor Jay's service to be almost done.

Much to his satisfaction, Nick's predictions were confirmed moments after he stepped out of the bathroom with a towel wrapped around his midriff, when an incoming text made his cell phone chime. Grinning broadly, Nick barely had the time to read Tessa's message, which simply said 'Your surprise is here', then the doorbell rang. Not bothering to reply via text since he would see her within moments in person, Nick simply dropped his phone on the desk and rushed downstairs to welcome Tessa in, remaining naked except for his glasses and the towel around his waist.

His semi-hard boner was visibly tenting the towel as Nick opened the front door with a genial smile and said: "Hey there, Tess-uhm-ssa's sisters?! What the..."

Chuckling and grinning as they enjoyed Nick's befuddled expression at seeing them instead of Tessa, Sharon and Sally shared a complicit grin before turning to Nick and chirping in unison: "Surprise!"

Blinking in stupor, understanding by that reference and by the suggestive looks on the twins' faces that they were indeed there at Tessa's prompting, Nick was so blindsided that he just stood there at the door, almost naked and with a prominent boner which the towel wrapped around his waist actually highlighted rather than hide. For their part, the twins seemed to be quite comfortable with the situation they had orchestrated with the blessing and help of their cool big sis. Dressed in their Sunday best, Sally wearing a light green sleeveless dress and Sharon sporting tight fitting black pants with a white blouse, the pastor's younger daughters giggled impishly as their identical blue eyes kept shifting between Nick's obvious erection and the priceless look of genuine shock, eager anticipation and glad surprise painted on his thin, handsome face.

"So, are you gonna let us in any time soon, Nick?" Sharon finally said, tapping her sensible pumps on the doormat and grinning impishly while she drank in Nick's tall, lean physique beaded with trickling water droplets. "Your aunt is not home today, right? Tessie said she had a wedding to go to or something."

"Uh... Yeah..." Nick mumbled, his brain gradually adjusting to the fact that Tessa had actually sent her gorgeous blonde sisters over to his house as her 'surprise' for him!

"We're not too early, right?" Sally asked, fixing her blue gaze onto Nick's bespectacled eyes as she anxiously bit her soft lips, inadvertently making him recall just how amazingly skilled at sucking his big cock that mouth had proved to be just a couple of days before. "Like, we didn't wake you up, or anything? Tessie said you'd probably still be in bed but you'd be awake by this time, so..."

"Oh he was awake alright, probably imagining Tessie's big booty making a surprise visit and bouncing away on his boner! Look at that big thing there, it's literally holding up the towel!" Sharon chuckled, elbowing her twin. "You were expecting Tessie to be here instead of us... Right, Nick?"

"Yeah, well, I guess you'll just have to settle for our subpar asses instead..." Sally interjected with a sort of timid yet sexy shrug and a swift smiling glance at Nick that managed to make his boner flex harder and prevented him to come up with a reply. Her half-apologetic and half-playful tone turned to a teasing purr as she stared straight into Nick's inquisitive eyes and concluded: "Our butts are not big and juicy like Tessie's, but at least you're getting two. And we're both anal virgins, as you know..."

"Hey, easy now. Your asses aren't subpar at all, girls!" Nick firmly stated, snapping out of his aroused befuddlement for a moment, only to immediately stop dead in his tracks as the implied meaning of Sally's words fully sank in. "Whoa... Wait a second, what do you mean exactly by 'you get two'? I get two asses?! Your virgin asses?! Seriously?"

"Let's get inside, Nick," Sharon chuckled, winking at a bug-eyed Nick while she stepped past him and walked into the house, followed by a giggling and enticingly flustered Sally. "You may wanna sit down for this one..."


As calmly and composedly as possible given that his raging hard-on was tenting up the towel in his lap in such a ponderous way as to look borderline comical, Nick sat back in the armchair and let out a long-drawn-out sigh.

"So, let me recap this just one more time..." he said slowly, looking at Sally and Sharon as they both smiled playfully at him from their seats on the couch in front of him, "You two want me to pop your butt cherries. Right here, right now. Both of you. Correct?"

"Yeah, that's exactly right!" Sharon nodded with a grin. "Of course we're talking strictly anal here, our pussies remain totally off limits. I mean, we're still good girls after all..." the pastor's daughter concluded, winking teasingly at an ever more aroused Nick.

"After watching you and Tessie the other day, well, we made up our minds. We really want you to be the first guy to fuck our virgin assholes, Nick," Sally declared, playing excitedly with her long blonde hair, her blue eyes sparkling with evident desire even as her sculpted cheeks blushed an adorable rosy hue. "Will you do it, Nick? Please... It has to be you, we wouldn't do it with just anyone."

"Holy fuck! I can't believe it..." Nick mumbled to himself before meeting the twins' expectant stares. He had to take a steadying breath before he could finally say: "Yeah. Yes, of course I'll do it. As long as you're both absolutely sure about it. Are you?"

"Yes!" the twins confirmed in eager unison, nodding their blonde heads vigorously in agreement before Sally added: "Sharon was already pretty much ready to do it any time, but for me it was your little demonstration the other day that did it... I mean, you made Tessie cum so much with your big cock pounding her ass, it looked so hot... Now I actually can't wait to try it!"

At the mention of his amazing ex girlfriend, Nick couldn't help but murmur: "Wow, Tessa knows and she's okay with this... She actually set it all up... Incredible!"

"Oh yeah, Tessie approves one hundred percent," Sally confirmed with a giggle, going so far as to extend her slim arm to show Nick her cell, letting him have a glimpse at her latest chats with Tessa. "We were just texting about it. See?"

"It was kind of her idea, really..." Sharon mused, distractedly twirling her blonde chin-length hair around her slender fingers as she spoke. "She even helped us train our buttholes yesterday. We used her dildos and her buttplugs all day, and she gave us all kind of tips and stuff... It was nice of her, really, and she was even super okay to let us use you as our first!" Sharon concluded with a chuckle, looking at the rigid, towel-hidden pole between Nick's legs."

"Tessie is so nice..." Sally chimed in, turning to her twin as she pondered. "I don't know if I'd be so cool about letting my ex boyfriend fuck my sisters in the ass. I'd probably be all mean and resentful and jealous, I think."

"Oh me too, definitely," Sharon agreed. "But Tessie is not like that at all. She's, like, super generous about everything. Tessie's really great... I mean, look at the awesome dick she got us for our first time doing anal!"

After giggling at her sassy twin's quip, Sally regained her composure and looked at Nick with a half-naughty and half-guilty smile on her lips that only made his erection flex with eagerness under the towel. "Sorry, Nick... I guess we're sort of objectifying you a bit too much, uh?"

"No, it's okay," Nick chuckled along with the pastor's twin daughters before concluding in his characteristic matter-of-fact tone. "I can definitely live with being objectified if it means that I get to deflower your sweet little asses. I'm all in for it."

Despite the honest seriousness imbuing Nick's words, or maybe because of it, Sharon and Sally burst out laughing and kept tittering for a bit, meanwhile looking knowingly at each other and unashamedly stealing glances at their big sister's ex boyfriend's toned body and blatantly erect albeit still towel-clad pole. Eventually, once that tension-breaking fit of laughter was over, Sharon exhaled and spoke for both herself and her twin.

"Alright, then. Now that we've cleared everything, we might want to get started. Tessie's gonna cover for us with our parents for a bit, and today there's this big meeting thingy at the community center. There are lots of people from other churches and stuff, so we probably can get away with disappearing for a couple of hours. We'll have to get back there at some point though, so we can't waste too much time on, like, formalities and such."

"Right," Sally agreed, straightening her dress and smiling brightly as she stood up, immediately imitated by Sharon. "So, Nick... Shall we go to your room?"

Grinning goofily as he pushed his glasses up on his nose with his forefinger, Nick took a moment to admire the twin paragons of youthful, wholesome beauty standing before him before he replied. Then, staring into Sharon and Sally's expectant faces in turn, he stood up too, letting the towel fall to the floor to reveal his massively erect cock in all its imposing, meaty hardness.

Over the pastor's daughters' matching gasps of awe and desire, Nick grinned broadly as he enjoyed the way their twin blue gazes instantly shifted to his crotch and locked onto his overswollen dick. As Sharon licked her gorgeous lips and a long lustful moan escaped Sally's O-shaped mouth, Nick calmly said: "Okay, girls. Let's do this."


The thought of calling Tessa or at least texting her to thank her for the insanely hot surprise she had arranged for him did cross Nick's mind more than once as he watched Sharon and Sally nonchalantly shedding their clothes and letting them drop on the floor of his bedroom, giggling and casting him impish glances all the while.

Leaning against his desk and distractedly stroking his huge boner, his bespectacled eyes hungrily drinking in the twins' long toned legs, flat tummies and flawless alabaster skin, Nick couldn't help but chuckle as he realized that he was caught in a weird sort of paradox. The less clothes Sharon and Sally wore, the more grateful he felt toward Tessa; at same time though, he was thinking about the pastor's eldest daughter less and less the more of her gorgeous little sisters' naked bodies he was being allowed to see. All things considered, Nick thought while his smile broadened, that was a very good paradox to be stuck with.

By the time Sharon and Sally had removed their bras to reveal their perky tits and then swiftly turned around with their backs to him to slowly peel their white cotton panties down their athletic legs, Nick's attention was entirely focused on the priceless vision of the twins' taut, heart-shaped butts being unveiled for his visual pleasure. Though smaller than their big sister's gloriously plump booty, Sharon and Sally's asses were masterpieces in their own right, as far as Nick was concerned. The most exciting detail about them was the fact that, albeit on a smaller scale, the twins' perfect little bubble-butts showed the same cock-hardening roundness and protruding fullness that he had always love about Tessa's epic booty. In truth, all three of the pastor's daughters had been blessed with an ideal waist/hips ratio, which was always associated with the type of mouth-watering butts that a devoted ass man like Nick couldn't help but adore and lust after.

Looking over their shoulders to see a panting and entranced Nick intent on stroking his massive pre-cum leaking boner more vigorously as he devoured their sweet asses with his bespectacled eyes, the twins nodded at each other before proceeding with the final move of the plan they had concocted to blow the mind of the lucky assfucker they had chosen to pop their anal cherries. Tittering excitedly, still facing away from him all the while, Sharon and Sally climbed onto Nick's bed and got down on all fours side by side, their elbows resting on the crumpled sheets, their backs arching as they tilted their round little bubble-butts up, docilely offering them to him.

A lustful gasp escaped Nick's mouth at that sight, and it wasn't just because of those two curvy asses presented to him so invitingly, nor because, in that position, he could fully see the treasures hidden in the twins' buttcracks and thus feast his eyes on their smooth virgin pussies and their pink little assholes. No, it was more than all that: much to Nick's glad surprise, both Sally and Sharon had preemptively thought about getting their untouched rosebuds ready to be deflowered by his huge cock, as was revealed by the image of their rubbery little sphincters stretched tautly around the bases of a pair of buttplugs.

"Holy shit! Oh fuck, girls, that's so hot" Nick panted, walking closer to the twins' bent over bodies as if in a trance.

His rock-hard schlong was pulsating with need and his brain was sizzling with horniness as he immediately recognized the silver buttplug stuffed in Sally's anus and the jeweled one dilating Sharon's orifice. Both toys belonged to Tessa, as Nick knew very well, having seen them jammed inside her ass many many times, especially in the early days of their relationship, when they were both lewdly invested in the hyper erotic task of preparing her virgin little butthole to accept his massive truncheon.

Upon recognizing the bases of those two specific buttplugs embedded within Sharon and Sally's hineyholes, Nick didn't only get even more wildly aroused than he already was, but he also felt like the emotional connections between himself, the twins and Tessa were being strengthened. Nick was well aware that his ex girlfriend had developed quite the collection of toys during their relationship after she discovered how much she liked anal, so he knew instantly that her choice to give the twins the very first two buttplugs she had purchased did carry a deeper meaning, which wasn't lost on him. It was a silent yet unequivocal way for Tessa to give him her blessing, her ultimate seal of approval on his taking her little sisters' anal virginities.

Feeling at the same time fluffier and hornier as he kept staring at the twins' plugged pink buttholes, Nick eventually chuckled as he asked: "You had these up your asses in church too, right?"

"Oh yeah, Tessie insisted on it!" Sharon confirmed with a mischievous grin and a wiggle of her heart-shaped rump.

"She told us that she used to do it all the time when you two were together," Sally went on, swaying her gorgeous little bubble-butt side to side, gently brushing her sister's protruding rear in the process, "so that you could fuck her ass right after the service was over. That's so naughty and hot!"

"Yeah, that was always one of her favorites..." Nick musingly commented as he rested his right hand on Sally's perky ass and his left on Sharon's taut tushy, instantly starting to caress and knead their smooth, perfectly round buttcheeks.

As Nick's fingers roamed all over the flawless curves of their identical booties, Sharon and Sally couldn't help but purr in unison, thrilled as they were to feel the hungry yet reverent touch of their sister's ex boyfriend's hands massaging their asses. Unsurprisingly, the girls' soft coos spiked up into full blown moans of pleasure as soon as Nick's digits reached the bases of the buttplugs stuffed into their virgin rosebuds and he started playing with them.

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byZenZerker© 6 comments/ 44956 views/ 40 favorites

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