The Theft of Jessie Gray

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 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.