The Theft of Jessie Gray by AnonTheMouseKing

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, 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.

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