"If I win... I want to pop your cherry," Derrick looked anxiously at Kerry, waiting for her reaction. He was being awfully bold, but it was true. It was halfway through the summer before they left for college, they were both virgins... and she was the girl that he'd always been the closest too. Sure they'd keep in touch, but they wouldn't see each other as much. And he cared about her, maybe he was doing this as a bet, but heck, might as well if that was how he could do it. He'd rather lose his cherry to someone he cared about.
To his relief, Kerry smiled at him. She'd actually been expecting something like this ever since their bets had started to push more boundaries, "Fine," and she'd come prepared, "If I win I want to take your virginity."
Derrick was confused, "Isn't that the same as what I get if I win?"
"Oh no," her grin broadened and she took the item she'd brought with her out of its bag and placed it on the table, "If I win, I want to pop your cherry with this."
Staring at the strap-on, Derrick came to the sudden horrifying realization of what she meant. Desperately he thought, I'd better win this one...
******************
To Derrick's utter relief, he did win, and he tossed the strap-on at her to put away. The thing had been haunting his vision the entire time it had been sitting on the table, and now he could finally get it out of his sight. He had a feeling he'd be seeing it again, next round, but for the moment he didn't have to think about it.
Kerry laughed, she wasn't too upset about losing, in fact she was kinda excited, "Let's go upstairs," she suggested, "I'd rather lose my virginity on a bed."
They laughed and teased each other as they went up the steps, trying to hide their nervousness. In the room, Derrick went still, very unsure of himself. Looking up at Kerry, he saw her shy smile and smiled back. Stepping forward hesitantly, he pulled her close to him and lowered his mouth for a kiss. It started off gently and then began to grow, until they were kissing passionately and their hands were running up and down each other's bodies. Inexperienced they might have been, but they'd been getting much more comfortable with each other lately and with each other's bodies; both of them started to undress each other.
Laying Kerry out on the bed, Derrick started to explore her body with his mouth as she ran her hands over every part of him that she could reach, the gentle way that she scratched her nails over him giving him goose bumps up and down his body. Kissing her breasts he sucked her nipple into his mouth, rolling it with his tongue and biting down gently with his teeth. She moaned and her legs moved up against him as her hips thrust, pressing her wetness against his dick and her smooth silky legs caressed his sides. Groaning, he bit down harder on her nipple and pulled his head away so that it stretched and her back arched as she cried out in pain. It hurt, but it heated her passion too, so that when he did it to the other nipple she arched her back before he even started to pull, her body begging for it. When both nipples were swollen and aching from the rough attentions of his teeth he started kissing her neck and collarbone, making her shiver underneath him.
Pausing for a moment he asked, "Do we need a condom?"
"I'm on the pill, remember silly?" she smiled at him, "I went on it forever ago to regulate my periods."
"I know," he scowled mockingly at her, "I just wanted to know if you wanted one anyway."
Pausing to think for a moment, she shook her head, "No, I want to be able to feel you, and I want you to be able to feel me."
Closing his eyes, he tried not to groan at the way her words turned him on. Damn but she was beautiful, and she felt so smooth and wonderful underneath him. He descended on her for another kiss, his knees urging her thighs to spread and his dick bumping up against her wet slit. As they continued to kiss he brought one hand down to fist his dick, sliding it around the slick surface of her pussy. Her body jerked as it rubbed against her clit, and he pressed lower to find her hole. Once he was sure he'd found the right location, he pressed inwards.
Kerry groaned into his mouth and he paused for a moment. Only the very tip of his head was really inside her and he was practically sweating with the pleasure and the need... but her comfort first.
"Are you ok?" he asked, slightly worried.
"Yes," she panted, "Just keep going... it only hurts a little, it's more like a stretching than anything else."
Only slightly reassured he nodded and lowered his mouth to kiss her. Pressing forwards into her slick walls, he thought he was going to die with the pleasant tightness of her. Fortunately she'd lost her hymen a long time ago and so there wasn't that pain to deal with, and she was quickly adjusting to the way he felt inside of her. It was an uncomfortably pleasurable stretching, everything about it was strange and yet exciting. No dildo or vibrator had every felt like this, he pulsed and twitched inside of her, strangely soft and yet incredibly firm at the same time. She clenched her pussy around him to get a better feel of the sensations and he gasped with shock at the exquisite pleasure that shot straight to his balls.
With one quick thrust he buried himself the rest of the way in her, her back arching up to meet him as he took the final plunge. Gasping, her pussy completely enveloping him, he just held there for a moment, unsure of his ability to move without cumming. Kerry was grateful for the momentary pause as her pussy adjusted, he was much wider and much longer than anything she'd ever had in her. The way he was lying on her made his crotch press up against her clit, and as he continued to lie there she could feel the little nubbin itch with need.
Frustrated with his lack of movement, she started move underneath him, her hips thrusting and her pussy clenching. It was strange and yet familiar at the same time; Derrick groaned as her body rippled underneath him, and he put his arms around her back and started thrusting with her movements, humping her gently at first and then slowly harder and harder.
Kerry spread her thighs wider as they started to really fuck, wrapping her legs around his waist and her arms around his shoulders, her nails digging into his flesh slightly as his dick parted her pussy lips. She fucked back, rubbing her clit against his groin every time he thrust home. For his part, Derrick thrilled to the fact that she was so involved and the way her pussy felt as it convulsed around him every time he got a direct hit on her clit.
Pressing himself against her smooth body, he buried himself in her and then moved his hips up and down, rubbing against her pussy lips and clit. Kerry cried out and humped back, her pussy quivering in delight. They found new and different ways to please each other; Derrick occasionally stopping as the jizz in his balls threatened to boil over. Always Kerry would start the movements again and he'd follow, helpless to the pleasure that she was giving him.
For her part, Kerry was a little frustrated with the way he was slowing down and holding back now, her pussy was ready to go and she could feel her orgasm fast approaching. She didn't want it slow now, she didn't want him to stop and gather his breath, she wanted him to fuck her hard and mercilessly and make her cum. An inner instinct told her that hard and fast was what would get her off right now, so the next time that he tried to stop, she didn't. In fact her movements increased and her pussy gripped his dick like a vise.
With a wild cry, Derrick realized that he wasn't going to be able to hold out this time and so he started again, pounding at her while she begged him to fuck her harder. They thrust against each other hard, grinding and plunging, until she suddenly went rigid against him and let out a cry of pure pleasure. He buried his dick into her and lost his breath at the intensity of her pussy convulsions. They massaged his dick, wrapped it up and let it go, squeezed him... pulling her even closer against him he ground his crotch against her clit and as her pussy rippled, spurts of cum shot into her body. In his rigid arms she shook and heaved, her nails scratching at his back as her orgasm went higher and higher, burning her up inside; his arms held her tight against him just as her pussy gripped his dick, and his groin was pressed firmly against her clit.
They were both breathless when their orgasmic pleasure finally released them, and Kerry had tears in her eyes from the intensity of hers. Derrick brushed them away with gentle fingers as he looked into her eyes and gently kissed her lips; his hips were still pressed against hers and she could feel the strange sensation of his dick shrinking inside her.
"Thank you," he told her and leaned down to kiss her again.
