The Theft of Jessie Gray

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 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...