No Friend of Mine

Josh removed himself from her mouth, then collapsed beside her on the queen-sized bed, panting.

Jessie couldn't believe what had just transpired. She still had the taste and feeling of his dick in her mouth; she had never expected him to be so well-endowed. She slid her tongue around her lips, capturing any semen that may have tried to escape her hunger.

"That was... something," he sighed happily, then turned over to lay on his left side, facing her. "But as I said before, I'm still a virgin. I have to go all the way."

She noticed that he was starting to get hard again, she could feel his dick pressing against her leg. Raising her eyebrow she asked, "Am I really your first time? Are you sure you want it to be me?" She used her restraints as leverage to turn over onto her right side so that she could speak to him face-to face.

"Yeah... Jessie, you're one of the most sexy chicks I've ever seen, and I've wanted to do this with you ever since I met you."

"Flatterer." She playfully attempted to kick him off the bed with her left leg.

Unfortunately, he had quick reflexes and caught her leg. He used it to pull her over onto her stomach. "I'd fuck you like this, but I want my first time to be in the missionary position. Fucking someone from the back just seems so impersonal." He scooted up close to her so that when he brought her leg back over to right side, he was once again between her legs. He put his arm around her back, lifting her slightly from the bed while he unclasped the bra he had tugged down earlier and tossed it to the side. "I practiced that by stealing a bra from the girls' locker room." Her torso was now bare, her breasts the centerpieces.

He leaned over and hovered above her face, "I meant it; you're so fucking sexy, you know that?" His lips pressed against her in an open-mouthed kiss. His tongue probed her lips, trying to find an entrance into her mouth. At the end of the bed she felt his now newly erect penis bump into her, distracting her for a moment. But a moment was all he needed.

His tongue burst through her defenses and started to explore her mouth. "Mmmfk!" she exclaimed, surprised. She had been about to part her lips freely when she had been distracted. Feeling her mouth being forced to accommodate him once again, his breath was hot and tasted like cinnamon. She wanted to make him work for it, so she tried to move her tongue away, but his would simply find hers again and intertwine in a slippery embrace, determined to taste her until he was satisfied.

He softly ended the kiss, and retreated. She panted, her breasts rising and falling with her breaths.

She saw him situate himself and grab the base of his cock. His other hand was used to pull her underwear to the side, exposing her wet pussy to him. He guided his cock toward her and rubbed it up and down her slit, eventually pushing a little so that he was in between her lips, being coated in her juices. The head of his cock found her entrance and began to press itself into her.

"Josh, please don't hold back," she begged, as she felt her pussy crave him.

"Don't worry, I'll make sure it's good for both of us," Josh said distractedly. He decided that the time was right, so he pressed his cock against her entrance in earnest. It slid inside of her without much resistance. Jessie gasped. She was so wet by now that even though he had the biggest cock she had ever taken, it managed to move easily inside her.

He groaned in ecstasy and started thrusting in and out of her. She had thought he was fully erect, but realized that she was mistaken as she felt him slowly swell inside her. It was so big it filled her up entirely and hit places she hadn't realized were there. Some of her juices dribbled down her taint and trickled across her asshole. She didn't want to make any loud noises in case someone passed by her room, but she couldn't help but let let small moans escape her lips. Her milky breasts bounced back and forth as he pounded her with reckless abandon.

There was something titillating to Jessie about the fact that she was in such a vulnerable position. Her hands strained against their bonds, but to no avail. Her body was his and she was powerless to resist.

She felt his hips rubbing against the inside of her thighs in rhythmic motions, one of her legs being held under each of his arms. His balls slapped against her taint, reminding her of what was to come.

"Fuck... Jessie. You're so wet. it feels so good. I think I can put it all in now."

She was confused for a second until she felt him shift to a better vantage point and press the entirety of his cock inside her until he was completely enveloped up to the hilt. She let out a groan, and her legs twitched. She didn't know how much more of this she could take, she felt like she was on the brink of bursting. He pumped his thick cock inside her pussy, making her gasp involuntarily at each intrusion.

His pace quickened, mimicking the desperate strokes he had used to face-fuck her earlier. Her eyes widened when she realized what was about to happen, but she wanted wanted the feeling of him releasing his thick semen; she had tasted it before, but it was not enough. Her legs wrapped around his waist and crossed behind his back, as if begging him to stay inside her when he shot his load.

"Jessie! Oh Jessie! I'm going to cum inside you! I'm going to cum inside my best friend's sister! Oh God! Fuck!" He used his thumb to rub her clitoris in circular motions as he pumped faster than ever before.

This sent her over the edge as the clitoral stimulation intensified the pleasure to which his cock was subjecting her pussy. They came together as his cum spurted into her tight, fleshy prison. The heat seeping deep inside her, she climaxed a second time, tightening her pussy around his dick in a vice-like grip. This coaxed a second spurt of semen to be released inside her. They laid like that for a few moments, entangled, each trying to recover from the climax they had shared.

"For a first time, I didn't expect you to last so long," she exclaimed, breathless.

"I've been practicing holding back," he replied. "So... you think we'd ever do this again?"

"With a cock like that? You can count on that. Next time I might make you beg for it, though."