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.