The Theft of Jessie Gray

"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..."