The Theft of Jessie Gray

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The heavy, insistent beat of a relentless bass line cranked up entirely too loud pulsed back and forth between Lily’s ears and her brain. The teen had decided pretty quickly that Club 77 just wasn’t her kind of scene. A few of her school friends had dropped by for the place’s grand opening and spent the next few weeks positively raving about the party, but Lily wasn’t as impressed. The club was more rock than pop with a bit too much grunge and a bit too little flash. In the grand scheme of things, though, it didn’t matter all that much. With the mood they were in, she and Jessie could have celebrated in a disco parlour.

It was hardly the first time the two girls had gone out dancing together. They had, after all, been inseparable ever since the second grade when they first bonded under the thumb of their mutual bully, Deb Connors. From there their friendship had only grown. In fourth grade, they had each earned themselves a month long suspension for a prank their classmates still talked about in hushed tones. In the sixth, Jessie had dragged Lily along with her to volleyball tryouts and the pair had made their first team together. Come middle school it was only natural that Jessie was the first person Lily came out to around midnight one evening after the pair had spent several hours watching old movies and swapping more than a few practice kisses. While the blonde hadn’t returned her best friend’s affections, she had never held them against her either.

The pressures of high school might have broken some of their peers’ friendships, but they had only served to bring Jessie and Lily closer together. Every year the girls would tinker with their schedules to get into as many shared classes as possible. Not once but twice Jessie had even chosen to turn down a spot in their school’s top choir in order to stick with Lily in the general chorus. (Though, to be fair, her nerves had played into that decision as well.) Perhaps most importantly of all they had spent each and every fall and winter together as stalwarts of their school’s volleyball team. Even when the season ended and Lily went off to run track while Jessie focused on her photography (Lily had, of course, been her first model before the blonde decided she preferred nature shots) they hung out at least a few evenings every week. As such, it had surprised none of their teammates when the pair of besties had bailed on the volleyball seniors’ end of season party to go out clubbing together instead. Thanks to a pair of mediocre fake Ids coupled with some top notch flirting on Lily’s part, they were young veterans of several of their home city’s more youth oriented nightclubs.

It has been a hell of a run, Lily thought while she leaned back in their booth and waited for Jessie to return with another pair of drinks, and it just might be getting better. Even had she a genie all her own there wasn’t a single thing the teen would have wished to change about tonight. Sure the state tournament might have gone to hell in a handbasket, but a regional title was still the best result their school had managed in decades and the whole team had been riding the high all week. In such a euphoric mood, Lily had thrown caution to the wind and spent the night flirting more openly with Jessie than she had allowed herself to do in ages. To her utter jubilation, instead of Jessie’s usual flustered awkwardness the blonde had been responding with coy smiles and even a few giggles. Whether it was due to the joy of triumph, the buzz from their drinks, or something having changed between them in an indescribably wonderful way Lily honestly didn’t care. She was too busy seizing the moment and hoping against hope that the night might end with her and Jessie fooling around for the first time since that fateful night when they had last practiced making out.

The thought of what the two teens might get up to once back home was enough to draw tingles up Lily’s spine and a Cheshire grin to her lips when she caught sight of Jessie returning. It was going on two months since she had broken things off with her second girlfriend and the young lesbian was starting to get unspeakably horny. If Lily was being honest with herself, Kelsey had been nothing more than a rebound girl after She Who Must Not Be Named shattered her heart into tiny little pieces then stomped on them, baked them into a cake, and made her eat it, but if nothing else the sex had been spectacular. With that outlet abruptly denied to her, the teen’s libido had been enduring an endless feedback loop. For whatever reason her own fingers had never been as satisfying as another girl’s, and she was just dying to be eaten out.

By the time Jessie arrived and was sliding into their booth, her brunette friend was about as flushed as a girl could get. The blonde didn’t notice, though, and it wasn’t because the club lights were turned too low. Lily was well aware that her best friend was about as innocent as it was possible for a teen in the internet age to be. Puberty had hit her like a freight train, and it had been less than two years since that curse finally transformed to a blessing. She might be beautiful now, but being constantly overlooked during the lean years had left Jessie much too shy to handle the flood of attention she had inevitably received from what seemed like every guy with a pulse since coming into her own. So shy that Lily knew for a fact she had never so much as gone on a date, let alone started rounding the bases.

“Thanks, babe,” Lily greeted her friend once she had settled in, reaching across their table for one of the drinks as she did. “You got a few dances left in those sweet legs, or are you thinking it’s time to get out of here once we finish these… whatever the hell they are?” The teen shook her head in dismay at Jessie’s latest ***********ion, sending the short brown hair of her pixie cut bouncing. Four years since they had shared their first hard lemonade and she still regretted not holding out for a can of beer. Maybe then the blonde wouldn’t have wound up with a taste for weird fruity crap like whatever they were drinking now.

“Yeah, I think I am tired enough to call it a night. If that’s okay with you,” the blonde answered. “Will, uh… will Justin be home? You know what my parents think about us drinking.” Unless she was singing, or just particularly excited, Jessie’s voice was almost always soft and pretty. It was an unusually perfect fit for a shy beauty like her, and something Lily wouldn’t change for all the world. Against the atmosphere of a club, however… it did leave Jessie frequently bordering on inaudible.

“What about Justin?” Lily leaned in, the move drawing a slight grimace from her friend.

“Is he home?” Jessie tried again. Her voice was barely louder than the first time, but it was enough.

“On Friday night? Nah. We’ll have the whooooole place to ourselves,” the brunette flashed her bestie the finest mischievous grin in her arsenal, a true masterpiece honed over years of practice which drew just the blushing smile she hoped to see in return.

“Oh…” Jessie bit her lip for a moment, her blush only rising. “Uh, alright… we can go,” she finally agreed.

It was normal enough for the two teens to wind up alone at Lily’s place on the weekends now that she and Justin shared an apartment. Then twenty two years old, her brother had already been a grown man fresh out of college when their parents had passed away in a car accident freshman year and so had become her legal guardian. Unable to handle the memories or care for the large house they had grown up in, the two siblings had moved into a nice apartment just far enough away to feel different yet still familiar. They got on well enough that Lily had never minded the arrangement, and Justin’s job on the managerial fast track with a major firm in the city meant he was more than capable of taking care of her until she turned twenty one and gained control of her own trust. Between work and a long, serious relationship with his girlfriend of four years he had often been busy for one reason or another leaving the apartment vacant for the girls. The latter had recently come to an abrupt end, but Lily was pretty confident he would still be out doing something on Friday night. He always was.

Gulping down the last of Jessie’s ridiculous fruity concoction, Lily practically bounced out of her booth, followed a bit more sedately by her blonde friend. The pair quickly waved goodbye to a couple of Jessie’s cousins who they had happened upon earlier in the evening, then made their way out front. Rather than wait for a ride from one app or another, Lily flagged down the first cab she saw and they slid into the back, trying to ignore the musty smell of sweat and junk food wafting back from the driver’s seat.

Between a gruff driver and a trip too short for much of a real conversation, the girls instead spent the ride pulling ridiculous faces at one another and then giggling like the schoolgirls they would remain for just a few more months. Once inside Lily’s building, they spent the elevator ride trying, and dismally failing, to suppress their giggling so as not to draw the ire of the condescending old woman from up on five who was in the car with them. By the time they reached her front door, Lily’s heart was pounding in her chest at the thought of how she hoped the rest of the evening would go.

The exhilarated teen was so distracted she didn’t even notice the familiar sound of a tv greeting her, only stopping dead when she stepped through the door and saw Justin relaxing on their couch.

“Hey sis…”


For the past few weeks Justin had felt like he was stuck in the doldrums. His breakup with Gwen had been… unpleasant, and he was taking it hard enough to feel off his game at work and in his private life alike. In all honesty, their relationship had been on the rocks for half a year or more, but he had held out hope they could still work things out. In the end, though, what the two young professionals had wanted out of each other was just too different. So they had gone their separate ways. For good this time.

It wasn’t like the world was ending. He was still a young man in his prime, there was plenty of time to find someone else. And it wasn’t like his prospects were slim. He had a steady job with good wages and no ceiling on his advancement. He had been a high school athlete who was into intramurals at university and still kept care of his body. He was a charismatic guy and downright handsome to boot. All of these were very good things. Hell, he could probably land any girl he wanted.

It still hurt.

A few of his buddies had invited him out for drinks after work tonight, trying to sell him on one of the local comedy clubs that was supposed to be pretty popular. He had begged off, though, certain they would spend the entire night pushing him to get back in the game and trying to set him up with every unattached girl in the room. They meant well and he loved them for it, but if he heard George drop his lonely cousin’s name into conversation one more time… No, what Justin needed was a nice quiet night in to calm down and reset, so that was what he was doing. Lily was off somewhere partying with her school friends so he had the place to himself and could just chill. And miracle of miracles, it was working. By the time the apartment’s front door creaked open around ten minutes into the third movie of his ‘lighthearted fun marathon’ he felt better than he had in, what, months? So there was a casual smile on his face when he rolled his head to the side and glanced over towards the source of the giggling so suddenly intruding upon his peaceful evening.

His sister was the first to come into view, looking as she always did save for the fact her usual black jeans and leather jacket had been replaced by her slinkiest party dress, the one their father would probably have had a heart attack seeing her in had he ever had the chance. Lily had never been afraid to embrace every stereotype thrown her way, fitting the part of the sporty teen lesbian to a T. She wore her short brown hair in a wild pixie cut, shunned most makeup, and engaged in a relentless athletic schedule that kept her coltish body trim and fit enough to have easily drawn her brother’s eye were she any other girl. At the moment, she also happened to be sporting a rather irate expression that didn’t seem to mesh with the giggling from just a moment before.

About a second after Lily passed through the door she was followed by her best friend and dedicated shadow impersonator, Jessie Gray. The trim blonde had been tight with Justin’s sister for about as long as he could remember and he had watched with casual interest as she gradually grew into the kind of girl who turned heads. Standing at 5’9” or perhaps 10” Jessie was a good height, just a couple inches shorter than himself, with enough curves on her athletic frame to draw plenty of male interest even clad in jeans and a plain shirt that starkly contrasted against her friend’s provocative dress. Long, golden blonde hair fell down the teen’s back in waves. Up above, those tresses framed a pretty face with big doe eyes the perfect shade of pale, corn flower blue and a pair of nice full lips that more than a few of his friends had confessed to fantasizing about having wrapped around their cocks. Still, gorgeous as she was Justin’s interest had never been more than casual. It was no secret that his sister had it bad for her best friend and he had been in a committed relationship pretty much since the teens had hit puberty.

“Hey sis, hey Jessie,” he called over to the girls.

“Hi Justin,” the blonde answered, her smile seeming even more shy than normal, if that was at all possible. Were it not for the fact he had watched her act similarly with nearly every person she ever met, Justin would likely have spent the last few years under the impression Jessie was nursing one hell of a monster crush on him. With how shy she was in general, though, he had never read much into blushing greetings like the one he had just received. Lily, on the other hand, seldom greeted him with such a ferocious scowl. He really wasn’t sure what he had done to deserve her ire, but he was in a good enough mood to hold out his bowl of popcorn as a peace offering nonetheless.

“You girls want some butter and air? I just fired up an excellent movie.”

“No, we…” Lily started, but before she managed to refuse the invitation Jessie was already halfway over to the couch.

“Is that? It is! How did you know I was coming?” The blonde gushed, her face lighting up at the sight of her all time favourite movie.

“Hey, I’ll not turn down credit for happy accidents,” Justin chuckled, pulling the popcorn back onto his chest and shifting a bit to one side. “Hop a seat, blondie,” he offered, patting the now empty cushion beside him.

Still standing by the door with a grim expression Lily groaned in frustration, but if her best friend even heard the noise it wasn’t enough to change her mind. Jessie practically vaulted over the sofa’s armrest to land in the exact spot from which she had first seen the film in question several years prior. The blonde’s enthusiasm sent her bouncing into Justin and threatened to send his popcorn flying, but he somehow managed to both corral the bowl and keep it free of her hair. A true miracle, that.

“Whoa, easy there, kid,” he chuckled, turning back over towards the door. “Come on, sis, you know you like this one too…” For a second Lily looked like she was about to scream at him, but the moment fizzled out. Instead she just rolled her eyes with a huff and reluctantly plodded over towards the living area, falling into one of the vacant chairs with a visible pout. If this is what teenage daughters are like… Justin mused, shaking his head as he turned back to the tv.

Before the older brother’s eyes could settle back on the screen, though, he felt the none-too-gentle nudge of an elbow into his ribs. Glancing down at his side he saw Jessie shooting him a sad puppy dog look. “Could you start it over, please?” she asked softly.

“I don’t know,” he teased, dragging out every word. “That’s a lot of work. What’ll you give me in return?”

“Uh… I,” she glanced away, chewing on her lower lip as she tried to think up a suitable answer. Serious interest or no, it had always been great fun teasing a girl as easily flustered as Jessie and as he looked down at her, it occurred to Justin that his newfound period of free agency might just be the perfect chance to have some lighthearted fun at the shy teen’s expense.

“How about a kiss, huh?” he suggested, grinning as the blonde’s wide eyes darted back to meet his own. Her cheeks, already flushed from drinking, visibly reddened at the proposal. Much to Justin’s surprise, though, she didn’t back away.

“I, um…” her pale blue eyes didn’t waver, locked on to his own as she bit her lip hard. “Alright…” she murmured after a long moment, the word barely above a whisper.

Unexpected, Justin thought, but not unwelcome. For just a moment he gazed into Jessie’s eyes to make sure she meant it before leaning in to plant a kiss on her full red lips. A protest of “Justin!” came from his sister’s spot across the room, but their lips had already met before the word was even finished. A moment later and he heard her scoff and turn away.

Jessie stiffened as Justin’s lips made contact with her own, but a moment later she relaxed a little and fell into the kiss. To his surprise the teen wasn’t entirely passive, her lips moving with his own. There was no tongue involved and her mouth remained closed, but Justin could still taste the faint alcohol on her breath and, he thought, a hint of cherry lipstick as well.

Their kiss ended as abruptly as it had begun, Justin raising one eyebrow as he pulled away. Gazing down at her, he saw Jessie was breathing a little heavier than before and smirked. “Well now, what have you been up to lately?” he teased, voice barely more than a whisper. The teen didn’t reply, though, just blushing a little deeper and turning away.

“Alright, a deal’s a deal,” he announced in a louder voice, settling back into his spot on the couch. Picking up the remote beside him, he fiddled with its buttons until the movie was back at its beginning once more.

“Thank you,” Jessie’s quiet voice could barely be heard over the tv.

“No, no, thank you,” Justin answered, glancing down at her again. This time, though, her eyes were locked on the screen so his own only lingered briefly before returning there as well.

With that the trio settled in to watch their movie, its familiar glories playing out before their eyes yet again. Lily lay curled up in her usual awkward fashion on one of the two chairs positioned between the couch and screen. Most who witnessed the way she routinely contorted her body on such occasions were left flabbergasted as to how such a position could possibly be comfortable, but the teen always swore by the habit and those who knew her well had long since stopped questioning it. Behind her and out of view Justin had resumed his earlier position at the center of the couch, though he had straightened up enough for the popcorn bowl to perch in his lap rather than atop his chest. Beside him rested Jessie, but where the siblings were cozily nestled in she was anything but. Every minute or two the blonde would shift her position, curling up against the armrest for awhile, then tucking her legs under her body, then stretching them out towards the coffee table… Around twenty minutes into the film yet another round of repositioning saw a stray elbow catch Justin in the side and he decided he’d had enough.

“You know, Jes, it is remarkably hard to focus on the movie with you fidgeting like the dog that sat on the anthill,” he whispered, turning to glance at the teen beside him. “Just, c’mere already.” At the sound of his voice Jessie swung her head up to look at her host, but he was already reaching out to wrap an arm around her shoulders. The teen looked surprised at his move, but there was no protest forthcoming when he pulled her close. Instead she leaned in to rest her head on his shoulder, a smile decorating her pretty face as she directed her attention back towards the screen. Without thinking, Justin began to gently massage the girl’s arm, that casual intimacy prompting her to snuggle in closer and plant one hand over his heart.

Rather than tapering off as Justin had hoped, though, the teen’s fidgeting only seemed to grow more intense over the next half an hour. But where before her constant shifting had been an annoyance, now each move brought her in tighter against the well-sculpted body of Lily’s big brother, something he didn’t mind near so much. By the time her favourite film was halfway through its run the pretty blonde was practically clinging to his side, so close he could feel her every breath. Her head was nuzzled deep into the crook of his neck, her budding breasts were smooshed up against his side, and one of her long, toned legs had settled atop his own while the other lay coiled up beneath her. So close were their bodies that he could smell the faint trace of alcohol on her breath, that familiar presence blended with a subtle vanilla and a hint of, cinnamon? The scent of her perfume, he supposed, or perhaps a shampoo.

By that point the bowl of popcorn was long since emptied and removed from Justin’s lap, the movement when he sat up to discard it having drawn a fierce pout from his unexpected companion before she had taken the excuse to pull closer still. In its absence a, concern, had arisen. While hardly a predicament he intended to complain about, having a pretty girl draped over his side for an extended period was having a predictable effect on Justin. It seemed inevitable that sooner or later Jessie was going to notice the way her cuddling had left his pants tented, and having spent enough time around the shy blonde over the years he knew full well how awkward things might get when that happened.

Then again…

There was a pensive look on Justin’s face when he pulled his eyes off the tv screen and shifted slightly to gaze down at Jessie. He might never have paid the blonde too much attention while he and Gwen were together, but with that bridge seeming thoroughly burnt he took the opportunity to get a good look at his little sister’s best friend. She was undeniably gorgeous. A little young for him, perhaps, but not so much so as to raise many eyebrows, especially once they both had a few more years under their belts. It hadn’t been so long since the breakup that he was feeling particularly impatient, and he had stayed in because he didn’t feel like spending the night being hounded about finding a new girl, but what if that decision meant something had fallen right into his lap instead? Was he really going to pass up such an opportunity knowing that it might not come again?

The more important question, of course, was whether Jessie would return any interest he expressed. If he made a move and it went over poorly, well, heaven alone knew how bad the fallout might get between himself, Lily, and the blonde. That thought alone was nearly enough to stop Justin in his tracks. And it wasn’t like he had ever picked up a lot of signals coming from her… On the other hand, though, how likely was it really that a girl as shy as Jessie would go around advertising her interest in someone who she knew to be spoken for as he had long been? And how likely was it she would kiss just anyone then curl up so snugly together afterwords? Not to mention the strong rapport that had always existed between them. They had never had any difficulties getting along even when Lily wasn’t around. She would be furious, of course, there was no getting around that fact. But was that really a reason not to go for it? It wasn’t like Jessie had ever given much indication her position towards her best friend would ever change. Hell, if things worked out between him and the blonde it would practically guarantee the girls would never grow apart.

As, for the first time ever, Justin seriously mulled over the possibility of making a move on his little sister’s lifelong bestie, the girl in question let out a musical little laugh at something in the movie. He found himself chuckling at the line as well and, momentarily distracted, Jessie looked up at him. When their eyes met she flashed him a radiant smile before quickly nuzzling her head a little tighter against his neck and letting her attention shift back to the screen. What the hell. In that moment, Justin decided it was worth a shot.

Lifting his eyes back to the screen and smiling momentarily, he let the hand which had been casually massaging the blonde’s shoulder for the past half hour begin to drift a little farther with each movement. Were he still a horny teenager, Justin suspected he might have gone straight for Jessie’s tits. With the wisdom of experience, however, he was pretty confident doing so would be moving much too fast for her. Instead he let his hand wander until it found its way to her jeans. When his fingers first traced their way down the girl’s outer thigh and then back up a little further to the rear, Justin allowed himself the faintest of smiles at the slight hitch his move caused in the teen’s breathing. As tightly as their bodies were pressed together it would have been impossible to miss the way Jessie tensed or how her head pulled away to look up at him. He kept his own vision locked on the tv, though, waiting to see how she would respond to his exploration of her glorious legs.

The blonde said nothing, but her reaction told him everything he needed to know. Her pulse spiked, the beat of her heart easy to discern with the way their bodies were pressed together. That alone could have gone either way, but when Jessie made no move to pull back her answer was clear. If anything, the leg curled atop his own seemed to flex in what might have been an effort to draw him even tighter. Emboldened, Topkapı Escort Justin let his hand drift all the way to the blonde’s ass, wrapping around one cheek and gently squeezing. The motion drew a gasp, one barely audible over the film, but its sentiment was clear enough. Justin smiled broadly as he copped his first feel of Jessie’s ass, all pretense of innocence rendered moot. Even through her jeans he could tell it was every bit as firm and taut as he expected. Together the girl’s youth and athleticism were the recipe for a perfect rear and in her case the end result did not disappoint.

Once he was finally satisfied, Justin pulled his hand away from the girl’s ass and slowly traced a path around her hips and up to her belly. At long last he turned away from the screen and down to look into Jessie’s face. Her wide eyes gazed innocently back up at him, brimming with uncertainty. Even more adorably, she had sucked her lower lip in and was biting down on it so hard he was afraid she might just draw blood. When he leaned in to plant a chaste kiss on her forehead the teen’s eyes clenched shut and there was no missing the way her body shuddered against his own.

Those pale blue orbs flew back open mere moments later, though, when Justin’s hand started to slip under the waist of her jeans, locking directly onto his own. He offered the inexperienced blonde a reassuring smile as his fingers slowly slithered beneath the coarse denim and then, a second later, the soft cotton and clingy elastic of her panties. She gasped again, louder this time, as his hand brushed past her clit and began to explore the folds of her hidden flower. To his surprise, his fingers found Jessie already rather wet upon their arrival, the discovery leaving him to wonder whether the teen’s aggressive cuddling had gotten her worked up as well as him or whether it had instead been the cause.

Only after spending several minutes exploring between her legs did Justin finally slip one probing finger into the teen’s entrance. Jessie moaned at the intrusion, her voice dangerously loud given the company they were in. As fortune would have it, though, the noise was overshadowed by that of one of history’s foremost warlords utterly trashing a sporting goods store up on the screen. Still, the luck that had spared them could hardly be expected to hold.

“Shhhh,” Justin whispered, leaning in until their foreheads were almost pressed together. “Lily’s right over there, remember?” From the way Jessie’s cheeks flushed scarlet, it seemed she may well have actually forgotten they weren’t alone. Justin decided to take that as a compliment.

Pulling his head back up, the young man spared a glance over towards his sister, but his concern was wasted. She still lay curled up on her chair the same as she had since the movie started. For not the first time Justin thanked his lucky stars that his sister could be so rocklike once she got settled in somewhere. More than once he had played with Gwen much the same way he was now teasing Jessie without Lily ever catching on. Of course, it seemed the blonde was going to be a bit more vocal than his ex, but he could work with that.

Returning his attention to Jessie, Justin brought his free hand around to rest on the teen’s back. She gave him a quizzical look as he started to pull, but that quickly vanished once she managed to read his intentions. A moment later and her head was once more buried in the crook of his neck, but this time facing inwards. As she nuzzled up against him in search of the perfect fit, he could feel her arms moving to wrap around his body. One crossed his broad chest to clutch at the shoulder opposite while the other slid between his back and the sofa until she was clinging to him like a piece of timber from a wrecked ship.

Satisfied, Justin glanced up towards the front of the room and smiled as he did the mental math required to judge how long was left in the movie. There was no need to worry, though, plenty of time remained to teach Jessie a thing or two. Not wanting to waste any of his window, Justin started to work the hand he had down the front of the teen’s pants with greater purpose. While one finger explored the entrance to her pussy he shifted his thumb to circle and tease at her sensitive clit. He moved slowly and patiently, taking extra care both to keep his younger partner quiet and not to overwhelm her too quickly, but all the same his ministrations were more than enough to make her hips grind needily against his leg.

“You like that, huh?” he whispered into the blonde’s ear, feeling her soft golden locks tickle at his nose when he drew in close. Whether Jessie’s response was anything more than a whimper he couldn’t tell, muffled as it was by his neck, but there was no mistaking the way her head shifted up and down as she tried no nod. “Good, then you’re gonna love what comes later…”

Justin wasn’t done, though, not yet. Letting his eyes wander back to the television screen, he traced his free arm up the teen’s back to her head where it was to deliver the finishing blow. For just a moment he tousled Jessie’s hair affectionately, but then his fingers were diving and weaving through those golden tresses searching for the back of her neck. It took but a moment to find and then his close trimmed nails were scratching gently along her nape, the sensation sending shivers even he could feel rippling down her spine.

Jessie’s vulnerable young body shuddered against Justin as he worked, her mind no doubt overwhelmed by the various pleasures each tugging at her attention. It wouldn’t be long before she succumbed, that much was clear. Justin wasn’t vain enough to imagine it would be the girl’s first orgasm, no doubt she had done at least a little personal exploration already, whether it be lying in bed at night, or during a long shower, or somewhere else suitably private. Still, it was clear she wasn’t used to such attention and, to his modest surprise, he was pretty sure his probing finger could feel a particularly significant flap of tissue tucked away a little past her entrance. He couldn’t be certain, it seemed smaller than those he remembered from the few virgins he had the pleasure of deflowering in his younger years, but then perhaps that was how it had endured so much rigorous exercise.

The innocent blonde’s climax hit mere minutes after Justin had begun his efforts in earnest, and it was undeniable. Jessie’s body first trembled then writhed against his own as euphoria overtook her. A sudden jolt of pain made him grimace when she surprised him by biting down on the top of his shoulder in an effort to suppress her moans, but even that wasn’t enough. A loud, keening cry erupted from the teen’s throat, spilling out to overshadow the movie onscreen despite her best efforts. Well, so much for subtlety, Justin thought as his sister whirled around to face the entangled couple from her nearby perch.


Lily could scarcely believe her eyes. At first, she didn’t.

Up on the screen their movie had just reached the greatest history report in, well, history, when a sudden strangled scream coming from somewhere behind her startled Lily into action. Immediately she spun to search for the source of the noise only to freeze at the sight that awaited her. Jessie, her best friend in all the world, the girl she had spent years pining for, was wrapped around her own big brother like a snake around a tree and trembling in pleasure. It was unthinkable, it was unfathomable, it was impossible… and tonight, of all nights…

Mere hours before everything had been right with the world. The torch she had carried for so long, which so often had dwindled to the faintest of glimmers, was burning like a beacon as it seemed she would finally have that which she had longed for above all else. Jessie had been laughing and flirting and flashing those adorably shy little smiles… and now she was riding out the tail end of what looked like a spectacular orgasm on Justin’s fingers. Jessie’s first climax by another, maybe her first of any kind, and it had come at the hands of Lily’s own brother. There… there were no words.

Too shocked to speak, the young lesbian could only watch as the beautiful blonde she had so often fantasized about came down from the peak of her pleasure, the image of all her hopes shattering to so much dust searing itself into Lily’s brain. Utterly dumbfounded, her jaw fell slack and her eyes nearly bulged as the the waves of bliss wracking Jessie’s body gradually tailed off until her best friend was left trembling like the last lonely leaf clinging stubbornly to its branch against the autumn wind.

By her side Justin looked oddly stoic, grimacing as if he were somehow in pain, as if it was his heart being ripped out and torn to shreds before his very eyes. Lily could see where her brother’s hand had stolen between Jessie’s slender waist and the top of her jeans, disappearing into the promised land beneath which should never have been his. He didn’t so much as glance at his sister, eyes fixed on the screen as if he hadn’t just declared war. For her part Jessie’s face was hidden, buried in her partner’s neck as she lay there either dead to the world or pretending to be.

It was impossible for Lily to say how long she sat staring at the pair of traitors, her brother stoically refusing to look her way while his accomplice nuzzled feebly at his neck. Up on the screen their movie steadfastly soldiered on, somehow ignorant that it had been utterly upstaged. Finally, when the charade could drag on no longer, Justin made the first move. His sister watched in silence as he gently disentangled himself from her best friend and stood up, stretching his long arms out to each side and yawning. Yawning! Below, Jessie let out a little mewl of protest at his departure before sitting up herself, the gorgeous little whore at least having the decency to blush as she pawed away the long golden tresses which had fallen over her face.

Justin did no such thing, his face completely bland when he finally looked at his sister. “Ohhhh, it’s getting late,” he blinked languidly and spoke in a careless tone. “Pack away the movie, would you sis? It is most definitely past my bedtime, and I do believe I have company to entertain.” With that the bastard just turned away, reaching down one hand to help Jessie onto her feet.

Pack away the…

Pack away the fucking movie?!?

It hadn’t seemed possible, but somehow Lily’s jaw dropped even further as she processed those words. The sheer… utter… unbelievable gall of him!

A cocktail of emotions, rage and jealousy and confusion and humiliation and a thousand more besides all boiled together in the teen’s gut. But before any one of the countless curses fighting to break free of that inferno could push past the rest, the traitors were already walking away. They were walking away. So she did nothing. She watched with a face like stone and a heart to match as her brother led the love of her life through the door to his room and closed it behind them. Jessie had just meekly trailed after Justin, letting him lead her along by the wrist like a lost little puppy. Left alone in their wake, Lily could do nothing but stare after the unthinkable couple, stare at the bedroom door which had slammed shut on all her hopes and dreams.


As the entrance to his bedroom swung shut behind himself and his unexpected guest, Justin allowed a celebratory smile to blossom on his lips. After Jessie’s rather vocal display on the couch he hadn’t been sure whether or not he’d be able to get the blonde into his room without causing a scene, but lady luck was indeed smiling down on him. Lily, it seemed, had been too stunned to protest their departure, and now that he and Jessie were safely ensconced in the sanctuary of his room he very much doubted his sister would come charging in after them.

From the doorway it only took Justin a few quick strides to reach his bed, but that was time enough for him to already be pulling his shirt over his head when he plopped down on the waiting mattress. In what had to be record time, he proceeded to bend down and tug off his warm black socks, undo his well-worn belt, and finish by shimmying out of his crisp slacks and tattered boxers. Only after tossing away those final garments did he at last look up to see Jessie still standing wide-eyed and fully dressed before his bed, not so much as a single sock removed from her nubile body.

“You plan on getting in bed dressed like that?” Justin asked, smirking. At the sound of his voice Jessie’s head snapped up dragging her gaze from his crotch to his face then immediately turned away, the one cheek left facing him shooting right through pink on its way to scarlet.

“Relax, Jes, I promise I’ll only bite if you want me to.” The tired old joke drew a strangled noise somewhere between a laugh and a cough out of the teen, but it did its job all the same. Slowly, hesitantly, Jessie turned back to face him, though her eyes seemed eager to fall anywhere but on his own. “Would you rather I took your clothes off?” Justin asked tenderly.

“Oh!” she gasped, pale blue eyes finally meeting his own. “No… I… I will.” Very slowly, while her audience of one sat back and put on the most reassuring smile he could manage, the bashful teen moved her hands to the hemline of her top. Only after taking a deep breath did she start to lift it, hesitating for a long moment around the time the bottom of her bra came into view before clamping her eyes shut and swiftly pulling the shirt the rest of the way up and over her head. In an instant the designer garment was then abandoned, left to flutter lifelessly to the ground while its owner pulled her arms in to shield her supple breasts from view.

From where Justin sat those twin mounds looked a touch on the small side, but plenty perky. B cups most likely, though perhaps C. It was hard to be sure with them hidden away behind a plain, baby blue bra and two hovering arms. Justin had to struggle not to roll his eyes at how shy the teen had once more become when just minutes ago she had been cumming her brains out on his fingers, but he did his best to soothe her nerves with a gentle smile. “You really are quite lovely, Jessie.”

“Thank you,” the teen mumbled, turning her head away once more. “I’m not… it’s… thank you.” Her voice may have been faltering, but the praise seemed to breathe more resolve into her, enough at least to turn towards him and let her arms fall to the waistline of her jeans. Justin watched in silence as she clumsily fiddled with the button waiting there, her trembling fingers taking several seconds to undo the simple clasp. A moment later and the zipper beneath was being lowered, the sound like thunder against the backdrop of a silent bedroom. It took the blonde a few tugs and some shifts of her weight to get the tight denim past the curves of her hips and down onto her thighs, but from there it fell freely, every inch exposing more of her creamy thighs and long, toned legs.

A moment later and Jessie was stepping out of her pants to at last stand before a man with naught to conceal her youthful charms save her bra and a scrap of faded pink cotton stretched tight around her hips. Both colours looked lovely on her, the pale blue of the bra blending with her corn flower eyes and the pink of her panties complimenting her fair skin and the golden locks which fell past her shoulders. All the same, though, Justin was more eager to see her without them. He held out a hand and she stepped forward to take it, letting him pull her into his lap on the bed. Acting on pure instinct, the teen wrapped her powerful thighs around his body and her slender arms around his back.

The two new lovers’ lips met once more, this time with no reason to cut their kiss short. Justin’s tongue surged forward and his partner’s lips parted eagerly before him, opening her mouth to his exploration. While their tongues began mankind’s oldest dance, he reached around the blonde’s back to unclasp the bra which hid her breasts from him. Even without seeing them, it took Justin but a moment to undo the fasteners waiting there and then he was pulling it away, the act freeing her modest breasts to spill out against his chest. The nipples crowning Jessie’s chest may have been little more than nubs, but they felt hard as diamonds digging into his skin.

The inexperienced teen moaned and closed her eyes as the bra was pulled away, her body shuddering at the unfamiliar feeling of a man’s flesh against her bosom. With his partner helpless in his arms, Justin wasted no time in pressing the advantage. With one hand steady on Jessie’s back to keep her pulled tight against him he raced the other downwards to slip once more beneath her knickers and fondle her shapely ass. The blonde’s hips rocked at the intrusion, that motion causing her virgin pussy to grind hard against his cock with only a single, thin layer of fabric separating the two. One that wouldn’t be in the way for long.

It was then, as Justin sat kneading Jessie’s firm rear and chasing her soft tongue with his own, that he heard the muted thump of a door drawing closed. He knew from long experience that the only door in the apartment close enough to hear from his bed was… that of Lily’s room next door. So she had turned in for the night. In those brief moments before he and Jessie had retreated to his room, Justin had half-wondered if his sister might just flee, take his car and get as far from what was happening as those four wheels could take her. For a moment he felt a pang of guilt and wondered whether that would have been better. The walls in their home were not exactly soundproof and in a perfect world it would probably have been better for his sister not to witness what was rapidly approaching. But it was hard to stay guilty with a gorgeous woman in his arms, and Lily was old enough to make her own choices. One way or another, his sister would make her peace with what was happening. For now, all that mattered was him and Jessie, and he was beyond ready to push things to the next stage.

The shy blonde yelped as she suddenly found herself falling backwards, but she was in no danger. Justin had choreographed their tumble perfectly to leave her on back in the middle of his bed and himself looming over her. From his spot between her thighs he drank in the sight of his all-too-willing prey, making no effort at all to hide the way he appreciated her beauty. For the first time Jessie’s breasts lay bare before him and they were a truly glorious sight, a pair of perky little mountains each capped with an aerola the size of a quarter around a nipple which resembled nothing so much as the eraser atop an old pencil. Seeing them, there could be no doubt as to his next move.

Jessie was entirely unprepared for the fervor with which her first lover fell upon her breasts, grasping and kissing and squeezing and nibbling and doing all at once everything one might ever want to do in the face of such delicious targets. Entirely overwhelmed by Justin’s onslaught, the spasming teen closed her eyes and instinctively arched her back to present her bosom to his attentions. In doing so, her arms were sent flying wildly to each side where one hand ricocheted off the neighbouring wall while the other collided with the top of a nearby nightstand and sent several items tumbling off and to the ground.

The owner of that nightstand heard Jessie’s gasp a moment later, but with his face buried in her chest it wasn’t until he came up for air that he realized her attention was fixated on one of the few items not exiled to the floor. Curious, he followed her gaze and felt a wicked grin dawn on his face when he saw what had entranced her so. By chance, the innocent blonde’s hand had fallen upon a pair of fuzzy pink handcuffs, a relic of one of Gwen’s rare urges to experiment. Swiftly banishing the specter of his ex from his mind, Justin sat up a little and playfully cocked one eyebrow.

“See something you like, little girl?” he teased.

Snapped from her trance, Jessie’s face swung back up, cheeks blazing and golden locks flying all about. “I… uh… maybe…” she stuttered, her voice trembling.

“Oh? You want to try them on?” he asked playfully, then let his voice drop to a conspiratorial whisper. “Make your first time extra special?”

The blonde teenager’s blush deepened, her eyes flashing between the cuffs and their owner. Justin could almost see the cogs spinning in her mind, embarrassment sparring against forbidden desire against a backdrop of rampant arousal. Part of him wanted to tease her, to push her, but she just looked too adorable laying there chewing on her lip for him to ever interrupt.

At last, Jessie seemed to come to a decision, her eyes settling on Justin’s. “Um… alright…” she gave the tiniest of nods, her cheeks blazing brighter than ever before.

Justin did nothing to stop the wolfish grin that spread on his face, his cock throbbing against the quivering teen’s sodden panties. “Well, c’mere then,” he ordered, sitting straight up and reaching over towards the nightstand.

Jessie complied without speaking, sitting up and then shuffling around when prompted. She let Justin take hold of first one wrist and then the other, pulling them together behind her back. Two clicks later and the cuffs were on, not too tight, but enough that she wouldn’t be slipping out of them easily. When he let go of her wrists the teen tried an experimental tug, her breath catching just a little in her throat when they held and the reality of being restrained set in. Justin simply smiled and leaned in to whisper in her ear. “You’re mine now, cutie.”

Her only response was breathy and quiet, a simple “I know.”

“You’ll be a good prisoner?” Justin asked, wrapping one hand around the blonde’s belly and pulling her back against him. She let out a quiet gasp as the tug brought her body back in contact with his rampant cock.

“I will.”

“Good, good,” he whispered, suddenly so close he might as well have been kissing her ear. “I hope you like those, sweetie, cause I’ve got no idea where the key is.”

Justin could feel Jessie go rigid in his grasp at that news, her quiet whimper making him chuckle.

“Relax, I’m sure we’ll find it by Monday. In the meantime, though…” his voice trailed off as one of his hands came to rest against the small of Jessie’s back. A gentle push and the pretty teen was sent sprawling face first onto the bed, letting out a little yelp as she went.

Without the use of her hands to rely on, it took a few moments before Jessie had sufficiently extricated herself from the pile of pillows she landed on to peek back over her shoulder at her ‘captor’. By the time she did so his own hands had already found their way to her hips. Hooking one finger into each side of the blonde’s panties, Justin started to gradually tug the scrap of faded cotton down her body. Instinctively, she lifted her hips a few inches, presenting him a better view of her nubile ass and making his task a little easier in the process. She watched breathlessly as he stripped away the last shred of her modesty, the little pink undergarments drifting down past her thighs, then her knees, then her ankles, until finally Justin slipped them over each of her dainty feet in turn, snagging the socks waiting there as he went to render her entirely bare before him.

Once he had the teen’s underwear in hand, Justin simply couldn’t resist teasing her with it. Slowly and deliberately he slipped one finger through the hole which had so recently been occupied by her left thigh and let the the faded cotton drop to dangle in the air. From there it took only the slightest of motions to set her panties swinging side to side like the pendulum of an old clock. A wolfish grin spread across Justin’s face when he saw Jessie’s pale blue eyes fixate on the dancing fabric, tracing their path back and forth as if hypnotized. Her attention captured, he reached to the side and quietly slid open the drawer of his nightstand.

The pretty blonde did naught but watch as her unmentionables drifted through the air until they dangled above the open drawer. The spell they held over her was only broken when Justin finally let them drop, her eyes going wide as the trophy fell out of sight and was swiftly sealed away. There was no mistaking how anxious Jessie was when the blushing teen’s attention returned to her partner, not with how visibly she was trembling, so in the hopes of easing her nerves he leaned in to plant a tender kiss on her quivering lips. Her eyes closed as their mouths met, the shudder of her body unmistakable beneath him. When Justin pulled away, though, her breathing seemed to have slowed and he decided it was time. Taking a firm grip on her shoulder, he confidently flipped the teen over onto her back.

The newfound lovers’ eyes met as they came face to face, heat rising once more in Jessie’s cheeks. “Will it hurt?” she asked softly, gaze drifting down towards the fleshy rod which bobbed impatiently between Justin’s legs.

“A little, maybe, but I’ll be gentle,” he promised, reaching up to caress the blonde’s cheek. Her only answer was to give a feeble smile, saying nothing more and merely watching in silence as her partner took hold of one long leg, lifted it up, and slipped underneath to take up position between her thighs.

Justin was beyond eager to get started, after so very much buildup there were simply no words for how badly he wanted to ravage the innocent teen before him, but he also had a checkered enough history to know how much damage one bad experience could to a relationship. With how close she and Lily were, one way or another Jessie was going to be in his life for a long time to come and he didn’t want any regrets over tonight to strain things between them. Whatever fleeting enjoyment he might take in the moment, pushing the blonde too far too fast simply wouldn’t be worth it in the end.

With that knowledge at the Escort Bayan forefront of his mind, Justin fixed the hesitant virgin before him with a grave expression, one hand coming to rest steadily on each of her thighs. “You’re sure you want this?” he asked, studying her face closely. “We don’t have to do anything more tonight.”

Jessie didn’t give an answer immediately, clearly understanding the weight of the decision before her. Those pale blue eyes of hers peered up at Justin for what seemed a thousand heartbeats, the silence as she decided stretching on so long that he feared she was going to take his invitation to back out. Whatever answers she sought from his eyes, though, she must have found them in the end. At long last she gave a faint smile and a nod, shifting her hips so that her pale thighs spread open in invitation. Satisfied, Justin returned the smile warmly and moved forward to position himself against Jessie’s entrance, his gaze sweeping down her body as he did.

Below the teen’s pretty face a slender neck quickly gave way to the modest swell of two perky breasts, their nubile bounty thrust enticingly up towards him by the way the cuffs she wore forced her to arch her back. Further down Justin could see the perfectly flat belly of a fit young athlete who sported just enough fat to smooth out the contours of her well-honed muscles. Once they passed her navel his eyes at last came to rest on the junction of her long legs. She wasn’t shaved, not yet, but she was trimmed closely enough to possess naught but a thin carpet of golden fur which dusted her cleft and the area around it.

Jessie’s breath quickened as the crown of her lover’s cock neared her folds, growing even faster as it came into contact with the as yet unclaimed passage hidden within. She gasped when his tip pushed against that entrance, its slick lips parting to greet their guest. With his manhood properly positioned, Justin shifted his attention back up to the blonde’s face, fixing her eyes with his own. Taking a firm hold of her hip with one hand he raised one eyebrow in an unspoken question. The teen’s only reply was a timid nod followed by a nervous gulp, but that was enough. Satisfied, Justin put all his weight into one strong thrust that earned him the first few inches of her pussy, decimating the feeble resistance of her hymen in the process.

“Ow, OW!” Jessie’s entire body spasmed as her maidenhead gave way, seemingly torn between one instinct to latch on to her partner for support and another to push him away. At the same time her face contorted, mouth falling open, nose scrunching up, and eyes clenching shut. When they opened again a second later, those big blue eyes pleaded up at him, though for what she didn’t seem to know herself. “It hurts…”

“I know, sweetie. We’ll start slow,” Justin promised, reaching his free hand up to cradle her chin. Moving as gently as possible he leaned in to capture the young virgin’s lips in a kiss she met enthusiastically. The faint taste of alcohol still lingered in her mouth, though he doubted there had been enough in whatever she drank to dull the pain of her first time. Their kiss lingered for a minute or more before Justin finally began to gently withdraw himself from her passage. The quiet whimper with which Jessie greeted that move grew into a moan as he switched directions and began to work himself further in, but she didn’t pull away. Only after repeating that cycle several times did he finally break the kiss and draw back. “Feel better?”

“Uh huh,” she answered with a timid nod, biting her lip so hard Justin feared she might draw blood. “A little…”

“Good. Soon it won’t hurt at all.” That promise won him a weak smile from the blonde, her eyes sparkling hopefully. With the worst of it over, he began working himself a little deeper into her with every thrust. Jessie winced a little each time her lover gained ground, but from the quiet moans starting to fill the room around them he could tell she was beginning to enjoy it.

Only once the teen closed her eyes and began clumsily rocking her hips against his own did Justin pick up the pace, letting out his own groan as he was finally able to devote some of his attention to enjoying the act himself. Jessie was tight, tighter even than he had expected from past experience. Her snatch grasped at him ferociously, almost painfully, and with each inch of new territory he claimed it only seemed to grow tighter still. A less experienced lover might have let his passions run wild, but Justin took his time breaking the teen in, luxuriating in the experience he knew he may never achieve again.

By the time her first partner bottomed out in her, Jessie was completely transformed from the timid virgin he had deflowered just minutes before. Gone was her apprehension, replaced by unbridled pleasure as she moaned enthusiastically in time with each thrust, her perky little breasts heaving as the lungs beneath struggled to keep pace. Most satisfying of all, however, was the way her long legs coiled so tightly around his back that it was a challenge to pull himself back out after every stroke.

As her climax drew ever closer, Jessie’s voice rose in waves, her every moan cresting higher than the one before only to crash down and be surpassed by the next. When she finally peaked her face contorted into a look of rapture, eyes squeezing shut as a piercing cry escaped her soft lips. Her womanhood clenched down on Justin’s shaft like a vice, legs squeezing like boas around his back. As she tumbled down into an abyss of pleasure, her lover drew to a halt, content to simply enjoy the way her orgasming snatch massaged his length as she writhed helplessly before him.


A desperate moan escaped Lily’s parted lips and her tight pussy clenched in sympathy around her own drenched fingers as she heard Jessie’s orgasmic wail through the thin wall which separated her bedroom from that of her brother. The teen’s fingers were practically flying in and out of her own snatch as she bathed in the sound of her best friend’s pleasure, utterly oblivious to the wet schlicking noises that underlay her friend’s bliss and the ever-growing dark spot on the sheets directly beneath her parted thighs.

When Justin had made clear his intentions and led Jessie away into his room, Lily had sat in stunned silence for what felt like hours but may well have have been no more than a few seconds. By the time her floundering mind processed the fact that the love of her life was about to give herself to a boy, to Lily’s own big brother no less, any chance she had of interceding was already lost.

Once she finally recovered enough presence of mind to pull herself together, Lily’s first instinct had been to chase after the nascent couple, to scream and shout and destroy everything she could get her hands on until they were too distracted by her to… Fortunately, that instinct had been fleeting, almost instantly fought back by the knowledge that Jessie would never forgive her for ruining what should be a precious moment in such a fashion. They would still be friends of course, she doubted there was anything she could do to destroy that, but in all likelihood things would never have been the same between them again.

Her next thought had been the opposite reaction, to run as far and fast as possible and never look back. To pretend that nothing untoward was happening behind that plain white door and hope reality never caught up to her. She was nearly to the front door, had already retrieved the emergency car key from its home on the fridge, before that impulse too had been quelled.

In the end, it was Lily’s curiosity that won out. A base, twisted curiosity to be sure, but then, those were always the hardest to resist. For how many years had she lain in bed at night fantasizing about her best friend; imagined how the curves of Jessie’s body would feel, dreamt what sounds she might make once overcome with pleasure, how the the nectar of that hidden flower between her legs would taste, would smell… After all those nights lost in fantasy to have the chance to be just feet away while Jessie became a woman, how could she turn that down? Maybe… maybe she would even learn something… learn something which might help her win the blonde’s affections for herself someday…

It wasn’t curiosity alone which had lured Lily into her room, though. Not if she was being truly honest with herself. Watching Justin walk away, watching Jessie follow him… no matter how much she hated it, there was no denying the way that sight had stirred the old embers laying dormant in her belly and… below. It was something she had learned about herself the year prior. Something undeniable. Three times Alice had cheated on her. First at a party with some bimbo cheerleader who had spent the next week blabbing about it all over school. Then with one of her teammates from volleyball whose teary confession and pleas for forgiveness had floored Lily. Finally with the quarterback of the football team. An entitled, self-absorbed man-slut whose disgusting cum she had been shocked to taste polluting Allie’s twat. On fucking prom night.

All three times Lily had balled her eyes out on Jessie’s shoulder. All three times she had screamed her lungs out at the wicked redhead for whom torturing her seemed to be a game. But she had never broken up with the bitch. Because every time she discovered another affair, every time Alice didn’t answer her phone at night, every time she even thought about her wayward girlfriend stepping out, her traitorous pussy absolutely gushed. As dirty and pathetic as it made her feel, rarely in her life had Lily ever cum so hard as the nights she had spent laying alone in her bed wondering if her lover was out spreading her legs for someone else. So she always came crawling back, always accepted Alice’s hollow excuses, always forgave her latest tryst. She stuck with the bitch all the way until her foolish loyalty was inevitably rewarded the only way it was ever going to be, by being dumped a few weeks after graduation to make room for some new college skank.

Her evil ex may have been history, but as Lily watched Jessie disappearing into her brother’s bedroom she had realized the shameful appetites Alice’s indiscretions awoke within her were still there. Might always be there. So she had convinced herself not to scream, not to run, but to meekly slip into her room and embrace her shame.

When she stepped into her bedroom, Lily had been surprised to find that she could already hear some of the action next door. A few words here, a cunt-watering feminine gasp there, it was all much clearer than she expected. She had always thought that her brother’s ex was just shy about sex, that she preferred the privacy of her own home and that was why she had seldom heard the couple screwing next door. With as much as she could hear of Jessie, though, she started to wonder whether she had been wrong. The thought struck her that on the rare occasion she did notice any muffled grunts or moans it had usually been her brother she heard, not Gwen. Did that mean, then, that she had just been a particularly demure lover? That the walls weren’t as thick as she had always thought? The implications of that line of thinking had brought a fierce blush to the teen’s cheeks, but she did her best not to let them distract her.

Not wanting to waste any of the perverse show next door, Lily had wasted no time getting ready for bed, instead stripping right down to her knickers and diving beneath the mountain of blankets and quilts which lived on her mattress year round. Scarcely a second after nestling into the bedding her finger was already sneaking under the cheery yellow satin of what passed for her pajamas in search of the thoroughly primed cunt beneath.

From there the young lesbian had endured a roller coaster of emotions. She had gasped as she realized just what Jessie was ‘trying on’. She had fought back tears as she heard her best friend in pain from being taken for the first time. She had felt her heart rip in two, torn between jealous rage and earnest joy as she heard Jessie’s pleasure mounting, her once innocent friend’s moans coming clearer and clearer through the wall as Justin brought her racing towards a climax. Through it all, her well-practiced fingers never relented in their enthusiastic assault on her own womanhood.

And then it happened. Hearing the love of her life orgasm on her brother’s dick was just too much for Lily. As Jessie’s cries of pleasure washed over her, her own body followed suit. Lily’s entire lithe figure spasmed wildly under the mountain of blankets as she let out her own plaintive cry, the two teenagers’ voices harmonizing flawlessly for their audience of one.


Justin could scarcely believe his ears. At first, he didn’t.

Mere moments after Jessie began to thrash and squeal beneath him, lost to the ecstasy of a powerful orgasm, her vocalizations were joined by those of his climaxing sister a few feet away. They were a familiar enough sound on their own, while he and Gwen had shied away from doing much more than heavy petting on nights both they and Lily were sharing the apartment his sister and her girlfriends had never shared the same restraint. It could be a little awkward, to be sure, but he had figured that was simply the consequence of living with a teenager who didn’t put much stock in subtlety. Never before, though, had he heard her warbling cries while in the midst of an encounter of his own. And one with Jessie no less. Fortunately for all three of them, his newfound partner seemed to be entirely too far gone for her bliss-addled brain to process what was happening next door.

Still, there was no telling whether she would return to her senses before Lily quieted down, Justin was well aware his sister could be quite the firecracker once she got going. Fortunately, it wasn’t much of a challenge to think up a distraction that would keep Jessie busy. Much as he wished he could stay in the blonde’s still-fluttering womanhood forever, he swiftly pulled out, easily disentangling the tightly wrapped legs which had fallen limp during her climax. Once free of her snatch, Justin casually flipped Jessie onto her belly, the motion drawing an absentminded mumble from his young lover that he didn’t quite catch.

Nudging her thighs apart so he could slip between, Jessie’s first lover allowed himself to take a moment and enjoy the vista that awaited him between the former virgin’s parted legs. A thin trickle of crimson blood from her sundered maidenhead was dripping down the inside of one thigh and much of that wispy golden fur which obscured the puffy lips he was bound for was soaked through with her own fluids. As he lined himself back up with the teen’s entrance he noticed yet more evidence of her lost innocence coating his shaft, the red smears there stretching from its crown nearly down to its base.

Jessie groaned softly as that cock pushed its way back through her increasingly swollen entrance. Her hips, though, rolled eagerly against the strong body behind them and her pussy greeted its valiant conqueror with a clenching embrace, keen to pull him ever deeper. Justin’s first tentative thrust drew a feeble whimper from the pretty blonde whose senses seemed to be swiftly returning. He wasn’t quite ready to get back to pounding away at the teen, though, first reaching down to grab her hips. Jessie put up no resistance as he lifted her ass into the air, only shuddering appreciatively when he gave a second, stronger thrust to test the angle. Satisfied, Justin picked up where he had left off, quickly building up to a brisk pace which sent the bound teenager’s cuffed wrists bouncing frantically across her unblemished back.

The gorgeous teen was helpless beneath her lover, left to moan and quiver as he used his iron grip on her hips to leverage himself in and out of her body’s tight embrace. Within moments the sound of their enthusiastic coupling once more filled Justin’s bedroom; a cacophony of grunts and moans, the clap of flesh on flesh, and the shameless squelching of what he now suspected was not just one gushing cunt, but a second, somewhat muted, counterpart as well.

Having endured more than an hour of Jessie’s shapely body being pressed tight against his own even before getting her alone, watching her strip, and bringing her to a second orgasm of the night, Justin knew his own climax wouldn’t be far off. Already its first stirrings had arrived, his cock throbbing with the need for release. There was no question in his mind of what was to happen next, no thought of pulling out. Instead his hands tightened around the blonde’s hips and he pulled himself as deep inside her body as he could possibly reach before giving in to the primal call of his instincts.

Jessie’s breathy voice sounded almost frantic as she tried to get out a warning, “Wait… Justin, I’m…” but it was too late. Never before having brought a man to orgasm, she hadn’t realized what was happening until it was too late. Before she could so much as finish her plea, let alone try to wriggle out of her partner’s grasp, the cock inside her was already erupting. Between her bound hands and the iron grip with which Justin held her in place, the wide-eyed teen was helpless to do anything more than whimper as she received her first creampie. Time seemed to freeze while pulse after pulse of warmth blossomed within her and as it did she stared back over her shoulder at the handsome young man to whom she had gifted her innocence, pale blue eyes transfixed by the contorted rictus of unrivaled satisfaction which adorned her lover’s face as he baptized her young womb with his seed. Whatever doubts and fears might lurk in those beautiful blue orbs, Jessie’s womanhood drank up its gift greedily, fluttering in appreciation around the invader which had so thoroughly mastered it.

“Ohhhhh, damn I needed that,” Justin finally groaned out into the stillness that followed his release. Slowly, the haze clouding his vision cleared until he was able to make out the sight of Jessie still gazing back at him. After a moment, he released his hold on the blonde’s hips to run one hand lazily up and down her side. When it shifted away he nearly grimaced at the sight of the crimson handprint his vicegrip had left on her soft skin and hoped she didn’t bruise easily. It struck him that he had perhaps spent a little too long with Gwen who had always liked things a bit rougher than most girls and might need to temper his instincts. Hoping he hadn’t pushed her too hard, Justin looked up to meet Jessie’s waiting eyes. “That felt good, didn’t it?” he asked huskily, trying not to show his concern.

“It… uh… it did…” the teen seemed hesitant, but the way her cheeks reddened before his eyes made clear that the admission was true and so his worries faded away. She was a glorious sight, panting and sweating from the exertion of her first time with her loose blonde hair flung all about, but the look on her face was still anxious. “It’s just… I’m not, um… safe…” her already soft voice seemed to shrink into nothingness as she trailed off, corn flower eyes staring uncertainly up into his own.

“Shhhh, that’s okay sweetie.” Justin had expected as much, would have been downright stunned in fact had the shy blonde with strict parents ever been provided any kind of birth control. It was only to be expected that she be nervous, and if reassurance was what she needed that was what he would provide. With as warm a smile as he knew how to give, he once more ran his hand comfortingly along her side and spoke softly “It’ll be fine. I promise.”

Jessie’s only answer was a weak smile, but she leaned into his caress. She didn’t look entirely convinced, but nor did she seem keen to dwell on the issue. “Can you hold me? Please?” she asked softly, making to turn herself over once Justin finally withdrew his still stiff erection from between her legs.

With one firm hand planted squarely on her back, though, Justin brought the roll to a halt almost before it began, his intervention drawing a confused look from the teenager. “I’ll hold you all night, Jes,” he reassured her, “but I don’t think we’re done just yet.” As he nudged her back into position, Justin was unable to resist letting his eyes fall to Jessie’s freshly deflowered womanhood, drinking in that magnificent view. Her entrance was swiftly drawing closed after his departure, but all the same he could see a steady trickle of his cum leaking out, its normal pearly white stained to a hue of rosy pink. “A girl as wonderful as you deserves a memorable first time, not just a quick little tumble. Besides, there’s something else I think we should try…”

“What? What do you… OH!” Jessie squeaked like a cornered mouse as he brushed the tip of his cock against her puckered rear entrance. His grin only grew wider as the teen’s already flushed cheeks shot scarlet.

“That’s right, cutie. You’ve put so much work into this glorious ass, it’d be such a shame to let it go to waste.” Justin let his free hand drift to the girl’s rump, kneading one cheek briefly before pulling it gently aside to get a better view at his target.

“But, doesn’t… I heard…” There was no mistaking the way Jessie gulped at the thought of what her partner had in mind, her voice trembling. “People say that it hurts.”

“It depends on the girl,” Justin hedged, continuing to massage his partner’s rear as he made his case. “Some really like taking it up the ass.” That’s true, he thought to himself, more or less.

“I don’t know…” Jessie was biting her lip again as she gazed up at him, the effect undeniably adorable on her already gorgeous face.

“I think we should try,” he told her, trying to strike the perfect balance between confidence and encouragement. “If you don’t like it, we can always stop.”

That promise seemed to do the trick. “Well… I guess so… if you want to…” Jessie didn’t look eager, exactly, but it was enough for Justin. With a little luck she would enjoy it once they got started. And if not, well, she could always be taught to.

“That’s a good girl.” Not wanting the shy blonde to back out, he slid one hand beneath her hips to give her clit a little tweak. Her eyes closed and a little shudder of pleasure rippled through her body, whether from the words, the attention, or the combination was impossible to say.

“Please be gentle,” Jessie pleaded as the hand shifted back up to her ass.

“Of course,” Justin promised, her words bringing back echoes of his earlier resolution to keep his instincts in check. With one hand he kept a firm grip on the teen’s hips while the other worked to line himself up. “You’ll want to relax, otherwise this will hurt.”

“Okay,” she whispered, not looking all that relaxed. Justin didn’t stop, though, working his cock until the crown was resting against her starfish. Thankfully his shaft was still thoroughly drenched from her cunt otherwise there would have been no hope of getting in her without lube and he had none handy.

Justin’s first tentative push against Jessie’s stubborn anal ring drew a sharp gasp from the teen despite the fact that it lacked anywhere near the force required to actually enter her. His second, slightly harder, attempt drew another gasp followed by a demure little whine. For a long while their dance continued in much the same vein, Justin probing gently but with increasing force at the blonde’s rear entrance to get her used to the idea and sensation of what was to come next while Jessie fought to suppress her instinctive reactions, jumping a little less each time she felt his approach.

When her lover finally made his move and pushed the crown of his cock past Jessie’s sphincter the following shaft made it less than an inch into the teen before her tight passage clamped down around him. The girl’s yelp at the invasion of her rear had to be loud enough for Lily to hear in the room next door and then some, but beyond that lone cry any lingering reservations were kept to herself. No longer needing to guide his cock by hand, Justin reached back under his lover’s hips to seek out her clit. As tight as she was there was no getting around the fact that having her ass broken in would hurt like all hell, so he was going to need to keep her too distracted by pleasure to complain. It seemed to work well enough. The first tweak he gave Jessie’s sensitive little button upon finding it caused her hips to buck back against him and in so doing provide him the opportunity to slide a little further up her chute.

Over several long minutes Justin patiently worked his way deeper and deeper into the teen’s ass, savouring the experience and taking great care to minimize his partner’s discomfort. There was only so much he could do, though, and judging by the way she whimpered and whined it was clear Jessie was struggling to take his girth. Still, though, she soldiered on, and the longer they kept at it the less and less strained her voice sounded.

Justin, on the other hand, was in heaven from the start. It was hard to say which was more blissful, the way Jessie’s alluring body trembled beneath him or the way her vice-like ass clenched down on his cock in a vain effort to expel the invader. During their time together Gwen had seldom consented to letting her boyfriend take her up the ass and had never been terribly active to start with, so it had been many a year since Justin was last able to enjoy the sort of bliss he felt at that moment. There was just something about a sexy young athlete’s ass that was… incomparable.

Scarcely half his length had disappeared up Jessie’s rear before the first quiet moan signaled her increasing acceptance, even appreciation, of what was happening. “You like that?” Justin asked, leaning forward across her back even as her hips started to rock ever so slightly against his own. While he continued to tease at her clit with one hand, his other slid up and across her smooth back until he was delicately pulling istanbul Escort aside her soft golden hair to tuck it away behind the ear he was whispering into.

“It… oh… it hurts a little,” she murmured, her voice hazy as if she were struggling to concentrate on something that demanded more attention than she had to give. “But… it’s also… kinda nice…” The adorable expression on the teen’s face brought a smile to Justin’s, what with her little nose all scrunched up and her eyes squeezed shut. Before straightening back up he took a moment to plant a long kiss on her faintly flushed cheek.

“I’m glad.” He whispered. As he rose, Jessie’s new lover let his fingertips lazily trace their way down her spine, loving the way that act made her body shiver and her rectum clutch tight at his cock. When he eventually ran out of spine, his hand drifted to one side where it came to rest possessively on the teen’s rump. For a few minutes he pawed and kneaded at her firm curves, luxuriating in the way his lover moaned at his every caress.

Justin couldn’t hold himself back for long, though, not when there was so much more to try with his nubile bedmate. Given how well she was taking her first attempt at anal, to say nothing of the predispositions she had already shown, there was no doubt in his mind about what he wanted to try next. Out of nowhere the soft clap of flesh on flesh suddenly rang out through the bedroom, the noise overshadowed by Jessie’s startled yip which followed it a split second later. The teen nearly jumped out of her skin when Justin’s hand collided with her rump, that response to being spanked helping to drag his shaft a little farther into her body. She was still in the process of twisting her head around to to peer back over her shoulder when he delivered another playful swat, providing him the perfect vantage to watch a renewed blush blossom on one cheek.

“What are AH!” the blonde’s voice spiked when she was interrupted by a third spank, her big blue eyes going wide. Justin would have given anything to be able to freeze that moment in time, to capture the perfection made manifest which was his lover’s bewildered face. Her lithe body trembling, her pretty features flushed, in that moment Jessie was a work of art worthy of being put on display for all the world to see. But she wasn’t the world’s, she was his, all his and no one else’s. It was in that moment that any lingering doubts he had held about the wisdom of what they were doing fled from his mind. There would be no backpeddling, no broken hearts, he meant to play for keeps.

“Aww,” Justin cooed, punctuating the sound with another playful smack. “Does the prisoner not like her sentence?” he asked, adopting his best mock scowl. “I thought a hundred spankings was a perfectly reasonable punishment.”

Jessie let out a breathy little gasp at that, her body flinching slightly as her ‘captor’ delivered the next installment of the promised sentence. “Punishment?” The teen’s brow furrowed above her corn flower eyes, looking as if she believed she’d actually upset him. “What OH!… What did I do?”

“What did you do?” Justin leaned back and rolled his eyes up towards the ceiling. “Oh yes, there is supposed to be a reason for punishment, isn’t there?” he mused, absently patting her butt again as he feigned contemplation. “Hmm… how about… oh yes,” he let his eyes fall back to lock onto Jessie’s, a mischievous grin spreading across his face as he pronounced her ‘crime’, punctuating each word with a playful swat to her rear. “Being.” smack. “Unspeakably.” smack. “criminally.” smack. “Gorgeous.” smack.

All the anxiety that had risen up in the blonde seemed to drain away in a rush as she realized her lover was only teasing, leaving her to gaze adoringly up at him while she bit her lip in embarrassment. Every last glamour model, pop idol, and actress in the world could have paraded herself naked through Justin’s room in that moment and still he would have had eyes for none but Jessie. Instead of spanking her again, he reached forward to tousle her hair reassuringly and raised one eyebrow. “Does the prisoner wish to appeal her sentence?”

Mollified, the teen just demurely shook her head in response, arching her back as seductively as she knew how to offer up her taut behind for further punishment. When the next blow landed a moment later she gasped softly, then bit her lip and nodded in encouragement.

For the next few minutes Justin kept up a steady stream of firm swats to Jessie’s reddening cheeks as he got back to sawing his way in and out of her ass. He watched her reactions closely as he gradually put more force into both efforts, taking great care to push her right up to her limits and no farther. The freshly deflowered girl proved tougher than her partner had expected, though, displaying plenty of the same nervousness she had all night as he tested her but giving no indication that she wanted him to stop. Soon enough he was pounding into her at full force and delivering spankings hard enough to have left a fuzzy, glowing outline of his hand on each cheek.

In time, the sensory overload of her new lover having his way with her ass while he spanked her silly proved too much for Jessie to handle. Head down and eyes clenched tighter than they would have been were she riding the world’s most terrifying roller coaster, she yipped at every blow, pleasure and pain alike coursing through her body in a relentless competition. From the way the tremors wracking her body body were rapidly rising Justin could tell the blonde was racing towards another ferocious climax, so he steeled himself, grit his teeth, and fought to stave off his own orgasm until the time was right.

Nothing he tried, though, was enough to keep Justin from reaching the finish line first. With a groan like thunder he toppled over the edge, his throbbing cock delivering shot after shot of sperm directly into Jessie’s bowels as his strength gave out and his full weight came crashing down on top of the teen. Fortunately, the display was enough to bring his lover over the precipice with him. Trapped beneath Justin, her body trembled helplessly, ass grinding against his hips and clenching furiously around his shaft. Together their voices rose in harmony, her squealing soprano layered atop his steadily grunting bass until they both trailed off into silence.


Never in her short life had Lily’s cheeks been so red as they were while she lay panting in the aftermath of her climax. That rush of ecstasy had caught her entirely unprepared. Had she known Jessie’s orgasm would elicit so fierce a reaction from her own body she would have buried her face in the pile of pillows that rested at the head of her bed sooner. As things stood, though, that move had come far too late to salvage her dignity. With the way she had thrashed and howled out her passions there was no chance the couple next door could have failed to hear her. Justin knew what she had been doing, Jessie… Jessie knew… In that moment Lily wasn’t sure if she’d ever be able to face the two people closest to her again.

The shame of having been caught pleasuring herself to the soundtrack of her brother and best friend making love only added fuel to the inferno already blazing within her. As she lay there, eyes squeezed shut and face buried in pillows, she slowly realized that her hand was still idly toying with her sex. The lithe brunette groaned softly, hips grinding aimlessly against the mattress beneath her as she tried to restrain herself. But then, what was the point? She was far from satisfied, and could rubbing a second one out really sink her any lower in their estimation than she must already have fallen?

The two warring halves of Lily’s mind were still locked in furious battle when a feeble feminine moan fought its way through the thin wall separating her from the lovers next door and wormed its way into her ears. As soon as she heard Jessie’s cry and felt the way her own cunt clenched furiously around the stubborn fingers still lingering at its entrance she knew she couldn’t stop herself. Groaning quietly into her pillows, the teen gave up all pretense of restraint and let her fingers slide back into her sex.

As the newly forged couple next door picked up their pace once again Lily allowed herself to sink into a kind of trance. While her fingers raced in and out of her snatch she luxuriated in the sexy gasps and whimpers which poured forth from her dream girl to filter tauntingly through the wall between them. With eyes clamped shut she imagined Jessie was in her bed, that it was her drawing those sounds from the precious blonde, her fingers ravaging Lily in turn. Having shared locker rooms for the better part of a decade, the young lesbian had no difficulty picturing her best friend’s naked form, envisioning it entwined with her own…

Right as the teen was cresting a mighty wave of pleasure reality intruded upon her sapphic fantasies in the cruelest of fashions. All of a sudden the steady stream of breathy moans and gasps fueling her imagination was overshadowed by a flurry of harsh grunts and groans that had no place in Lily’s fantasy. The teen let out a little whine as her barely functioning brain realized what that meant, that her brother was about to soil Jessie with his seed. She had assumed Justin would have the decency to pull out, he was hardly ignorant enough to think her best friend’s strict parents would have their utterly innocent daughter on any form of birth control, but apparently she had given him too much credit.

Lily could clearly hear the love of her life try to warn Justin right before the bastard erupted inside her, but it was equally clear her warning had come too late. A minute later, perhaps less, and she heard her brother’s smug satisfaction as he congratulated himself on ruining the sweetest girl he had ever had the good fortune to meet, then again as he had the audacity to suggest he had done her a favour. Fingers frozen in her twitching cunt, Lily waited with bated breath for Jessie to denounce her brother, to protest his disregard for her wishes, to declare her eternal rejection of men in response to his callousness…

No such rebuke ever came.

“It did…” those whispered words, words which carried barely enough strength to reach Lily’s keen ears yet hit with the force of a cannonball all the same, sent ripples coursing through her trembling body. Jessie was never to be hers, was never to share her bed and her life, at least not in the way she had always dreamed of. No, the love of her life was fated to be Justin’s girl instead. Whether the couple themselves had yet made any such declarations mattered little, in her heart she knew it to be the truth.

For Lily was reserved a spot on the sidelines, a spot from which she was to watch as her brother made a life with Jessie, the very same life she had so longed for herself. It was no secret that Justin wanted to start a family, a big one more like than not, and the thought of him doing so with the love of her life hit like a freight train. In the wake of her brother’s recklessness, the image of her best friend heavy with child came unbidden to Lily’s mind, the teen’s own niece or nephew growing in her belly. A moment later another took its place, one of the radiant blonde smiling blissfully in her glorious wedding dress while Lily stood to one side with eyes downcast, the most miserable maid of honour in all the wretched history of that accursed post.

Cheeks burning with shame, the heartbroken teen buried her face deeper into the pillows before her, well aware this time that another climax was racing towards her. Justin, the big brother who had looked out for her since she was little, who had protected and cared for her in the years they spent alone, that same Justin had now stolen Jessie away from her. It was more than she could take.

Lily’s second orgasm of the night was even more ferocious than its predecessor, the exquisitely tortured scream that announced it’s arrival only prevented from echoing throughout their apartment by the fact the bulk of it’s strength was swallowed up by the pillows into which it was hurled. Just as fearsome was the force with which her hips torqued and her pussy clenched around the fingers which had been working it. With her face tucked away, the teen couldn’t have seen the way all the bedding piled atop her writhing form shifted and shook like the surface of the Earth amidst a remorseless tremor, but that meant little to the the dancing blankets.

Once her body at last drew still, Lily lay where she had come to rest for what seemed an eternity, unmoving save for the halting rise and fall of her modest chest. With eyes shut tight she lingered long in that haze that accompanied her shameful bliss, letting it seep into every inch of her being. Hearing Jessie and her brother making love next door was at once a thousandfold worse than anything Alice had ever done to her and yet felt right in a way her ex’s betrayals never had. Perhaps, then, she could in time make peace with what had happened. For the moment, though, cocooned as she was in her own little world of bliss, the tired teen had no desire to contemplate the future, only to drift away as sleep overtook her. She had almost done just that when a sharp noise pulled her back to her senses.

Ears perking up and eyes narrowing slightly, Lily started to push herself up from her mattress. That sounded like… her drowsy mind was still struggling to process just what she had heard when another sound echoed the first, chasing away all doubt. A jolt of adrenaline shot through the teen’s veins as the second time she caught a soft gasp following the unmistakable clap of flesh striking flesh. For a split second she froze, not believing the evidence of her own senses until the telltale sound of a third strike reached her ears, cutting off Jessie’s muffled protest in the process.

Was Justin hitting her? He wouldn’t. He couldn’t! If that bastard so much as laid a finger on Jessie she would kill him. Literally KILL him! In a flash the teen’s eyes snapped towards her desk, scanning for the well-worn pocketknife that should be resting there. Their father had given each of his children their first blade upon turning thirteen and she always kept it close, but where was the thing, dammit? It had been there yesterday! Grunting out her fury, Lily was just about to launch herself out of bed and towards the desk to search for her knife when a nagging voice buried in the back of her mind brought her up short.

Body tensed like a predator about to pounce, Lily strained her ears to hear what was being said in the next room over. Spankings… Punishment… Criminally gorgeous? Relief and embarrassment washed over the quietly groaning teen in equal measure as all the tension drained out of her weary muscles. Jessie wasn’t being beaten. She was being teased, toyed with. And who could blame her brother. The blonde was so easily flustered, after all, and that ass…

Lily slumped back into her bed, cheeks nearly as red as they had been in the aftermath of her first orgasm of the night. She could scarcely imagine the scene had she burst in on Jessie being fucked and spanked by her brother… Jessie being spanked… The thought of her blushing best friend on all fours, red ass being smacked over and over and over, was enough to set the butterflies in Lily’s belly aflutter once more. At the sound of just such a scene starting up again mere feet away the teen groaned softly, one hand snaking back towards her sex…


Silence reigned over the room next door, unbroken save for the freshly consummated couple’s quiet panting as they recovered from their inaugural romp. As soon as the haze clouding his mind cleared enough to notice his partner squirming awkwardly under his weight Justin rolled away to one side, his rapidly softening cock slipping out of the blonde teen’s sweat-slick ass with a wet plop. Coming to rest on his back near the edge of the bed, he let his head fall heavily against a stack of pillows and closed his eyes with a contented groan. He breathed deeply as his thundering heart gradually calmed, smiling at the heady scent their passions had left in the air.

A few moments later Jessie came to rest next to him, the former innocent perched somewhat awkwardly on one side with her still-cuffed hands trapped behind. Justin turned lazily towards her and let his eyes slide open once more to take in the glorious sight of his newfound bedmate. Her face was faintly flushed, her golden tresses mussed, and those pale, pretty eyes of hers gazed hopefully across the inches which separated them. So radiant she looked, with a shimmer seeming to hang all about her, that it was as if an angel had come down to sleep beside him.

“Hey…” he murmured, a gentle smile adorning his lips.

“Hey…” she answered, the corners of her own twisting up in answer.

“You liked that, didn’t you?” Justin’s voice was all quiet confidence, his words more statement than question. They both knew the answer.

“I… uh… I did. Yes.” Jessie’s eyes drifted down towards his chest, the question drawing out a slightly darker shade in her cheeks.

“Well, well, well,” Justin mused, letting his grin grow a little wider. “Who would’ve thought a sweet little thing like Jessie Gray would ever cum so hard from being tied up, spanked, and butt fucked, eh?”

The blonde squeaked at that, her corn flower eyes going wide and flying up to meet her lover’s, then flitting away again just as quickly while colour rushed to her cheeks. “I don’t… that’s…”

But Justin cut the teen off before she could turn away, reaching out with one hand to caress her cheek. “Aww,” he cooed, lifting her face back towards his own. She nuzzled against his hand a little, seemingly without even realizing it, and slowly lifted her gaze to meet her partner’s. “It’s tough, isn’t it? Being a good girl who wants be treated like she’s bad?”

Jessie’s mouth started to open as if she meant to speak, but then she paused and just bit her lip instead, answering only with a hesitant nod. The teen, so recently a virgin, just oozed an almost impossibly alluring blend of uncertainty and vulnerability, so much so that Justin fleetingly contemplated pushing for an encore before letting the urge pass. It could hardly be more clear that Jessie was but a sheltered neophyte in the art of lovemaking, one who knew just enough to recognize her own ignorance. She was like a fresh batch of clay, soft and yielding as she awaited the expert hand which would craft her into the perfect work of art she was always meant to be. Between her natural instincts and his own guiding hand, Justin had no doubts at all that his sister’s best friend could be molded into the perfect woman for him. And in all his life he had never found anything he wanted so fiercely as to do just that.

Shaping her, perfecting her, it wasn’t a process that would happen overnight, but already Jessie had so much of what all he could ever hope to find in a partner. She was fun and easygoing, someone whose company he doubted could ever become tiresome. She was quite pretty as well, and seemed to have a natural inclination towards submission that would make her a treat in bed. Most important of all, though, was that she was sweet and kindhearted, the sort of girl who would make a wonderful mother for his children.

That last reason was why Justin’s previous relationship had collapsed in the end. Once upon a time Gwen had seemed the love of his life, but as they grew older it became ever clearer that she simply wasn’t that interested in starting a family. Not nearly so much as he had been, at least. No, she had always been too invested in her career to engage in such frivolity, too focused on the next promotion. The more he had raised the prospect the more hostile she had become until the argument hung like a thunderhead over them at all times, erupting into more and more fights during which she would throw words like ‘incubator’ and ‘broodmare’ in his face. In the days since their final shouting match Justin had started to realize that his and Gwen’s relationship had always been doomed.

With Jessie, though, he was sure things would be different. In all the hours he had spent with the blonde and his sister never once had he heard her discuss the sort of grand plans for the future that some like Gwen and Lily clung to, the sort that would drive her to constantly put off living her life. Even better, with as timid and pliable as she had already proven herself it would be a simple task to convince his new lover to take the plunge sooner rather than later, especially if the matter could be presented as fait accompli. So long as she stayed off the pill and they continued sleeping together Jessie would eventually fall pregnant, and he had no doubt she was far too gentle and caring a soul to ever contemplate the alternative once that happened.

Justin was reasonably confident that the blonde’s parents wouldn’t be much of an obstacle either. With her and his sister having been tight for so long he knew the Grays quite well already and the older couple had always been very cordial to him. Fortunately they were rather traditional folks, not the sort to make a fuss over their daughter seeing a man a little older than her or providing them grandchildren a little sooner than expected. So long as they saw Jessie was happy and her father never found out exactly what his little girl would be getting up to in bed, Justin was confident he would have their blessing. The match would certainly appeal to them more than one with his sister, at the very least. She… would be more of a problem. Then again, judging by what he had heard coming from her room, perhaps not so much of one as he might have thought.

“Justin?” a soft voice shook him out of his musings and back to the present. “You look…” For a moment he could see a hint of concern lurking in the girl’s eyes, but it faded as he smiled at her.

“Sorry, sweetie, just lost in thought.” He leaned in to plant a kiss on Jessie’s lips, the teen accepting her lover’s apology enthusiastically. “Now where were we…” he trailed off dramatically, flashing a playful grin at her before she could even begin to remind him. “Oh, yes. I was about to promise to spank you every day, whether you deserve it or not.”

Jessie’s breath caught as she heard his words, their implications clear. She swallowed nervously, but there was a sparkle in her pale blue eyes as she spoke. “You mean…”

“Of course,” Justin’s hand had drifted to the teen’s side while his mind was wandering, but he lifted it to cup her cheek again as he spoke. “Only a madman wouldn’t want you as his girl.”

“Then, I…” She swallowed again, her eyes searching his own as if she were peering into his very soul. “I was good?”

Justin had to bite down hard on his tongue in order to stifle the laugh he felt rising up at her question, certain it would be taken the wrong way. How Jessie could possibly think any man would be disappointed in her was utterly beyond him, but in a way he was glad to hear it. If her lack of confidence was truly so severe, then that would make his efforts to shape her as he willed all the easier. So he didn’t laugh, and he didn’t tease. Instead he stared straight into his newfound lover’s azure eyes and spoke as warmly as he could. “You were wonderful, Jes. More precious than all the stars in the sky.”

The smile that blossomed on Jessie’s face in that moment was like the first dawn on a new world. In that instant Justin knew he would do anything for the angel laying beside him. He would make her the perfect woman for him, yes, but he would also make himself the perfect man for her. Never to falter, never to stray, and never to let her down, he would be there for her so long as they both drew breath and beyond. With that solemn vow firm in his mind, he leaned in and planted a kiss on her forehead.

“So,” he whispered as he pulled ever so slightly away, “are you gonna sleep in those cuffs, or should I get the key?”

Jessie gasped, her head pulling back until she could look up at him. “You said you lost it,” she pouted, the soothing of her fears allowing the faintest hint of playfulness to emerge in their place.

“And you should have seen the look on your face,” her lover chuckled. Ever since she had been little, Jessie had always been an easy one to tease. As he cocked one eyebrow and stared at her, Justin idly wondered whether her daughters would be the same way. He hoped they would. “Well…”

His new girlfriend chewed on her lower lip a moment, looking as if she was torn. Finally, though, she nodded twice. “My arms are getting a little sore…”

“Alrighty then, turn around and I’ll be back in a sec.” Justin took a long moment to savour the view before him as Jessie spun around and presented her shapely backside before reluctantly rolling out of bed and ambling across the room towards his desk. When he slid back into bed half a minute later it was with the key in hand and a moment after that Jessie was free, his girlfriend rubbing softly at her wrists where the fuzzy cuffs had left faint marks.

“C’mere, you,” Justin murmured, reaching out one arm to wrap around the blonde’s shoulder. She let out a happy little purr as she rolled over, immediately nuzzling her face tight into the crook of her boyfriend’s neck. Within seconds her free arm had snaked across his broad chest until her hand lay over his heart and her leg had drifted over until it lay resting atop his own. For his part, Justin let his hand drift down until his palm rested in the small of Jessie’s back and gently pulled her body snug against his own. Like that the newly united couple drifted off into sleep together, each of their dreams about the happy days that were sure to come.

The End

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