tagFirst TimeWanna Bet?

Wanna Bet?


Kerry and Derrick had been friends for a very long time, both of them were very competitive and a long time ago they'd gotten into the habit of making bets. Over the years the bets had become more and more sexual, they'd been each other's first kisses, he'd been the first person to see her breasts... now they were both 18 and they had an entire summer before they were separated by attending different colleges. The bets had become more and more interesting; since neither of them were seeing anyone they felt pretty free to challenge each other. And Kerry had to admit, her bets with Derrick were much more interesting than anything she'd done with any of her boyfriends, and for some reason she felt a lot more comfortable with him than she had with them. Maybe it was because of her closeness with Derrick - and his with her - that neither of their relationships with other people had lasted very long, but she was content with that. Besides, it was kinda fun to have the same person be all of her firsts... she'd never gone farther with another guy than she already had with Derrick, although it was really intentional, that was just the way it happened.


"WHAT?" gasped Kerry, completely shocked. Ok, so the bets had been getting more and more sexual but this was a little bit of a shock. Usually Derrick didn't seem so confident when betting, and especially not when telling her what he wanted.

"Yeah," he said, leaning back in his chair and brushing his dark hair out of his eyes, "The Red Sox win and you suck me off." Dark eyes looked at her challengingly.

"Fine!" said Kerry, she'd never been one to turn down a challenge, of any kind, "And if I win then you have to eat me out!"

Derrick laughed, "Kinda sounds like I win on both ends!"

Smiling sweetly, if slightly maliciously, Kerry replied, "Except that you'll have to go home and whack off if I win."

They both laughed at that, good-natured teasing. Watching the game was particularly exciting, with both of them flirting with each other. She could tell that he had a hard-on all throughout the game, and she had to admit, her pussy was getting wet thinking about the inevitable end. One way or another, their relationship was going to be stepping up another level.

By the ninth inning, Kerry was sitting on his lap and his hands were up her shirt, playing gently with her tits. She realized that if she lost, she was probably going to have to go home and get herself off afterwards, she was getting so horny from this. The stakes were higher than ever, and his hands playing with her nipples weren't helping anything either. She should probably stop him, the only time that he'd ever gotten to play with her tits was when she'd lost a different bet, but it just felt so good... and one way or another one of them was going to see more of the other's body than they ever had before.

Kerry realized that the Orioles were going to lose, but she didn't feel at all unhappy really. In some ways, she was now going to get her curiosity satisfied, she'd always wondered how big he was and what he looked like.

Derrick was thrilled as they turned off the TV and she settled onto the ground in front of him, in between his legs. As she started to undo his pants he requested hopefully, "Take off your shirt?"

Kerry thought about it for a moment... well he'd already been playing with them for long enough during the game. She took it off. He could feel his dick flexing in the confines of his jeans as he watched her heavy breasts swaying, topped with very hard pink nipples.

When his dick sprung free, Kerry gasped a little under her breath. It seemed very large, she took it in her hand and wrapped her fingers around it, pumping a little. Derrick was breathing heavy, and he reached down to take one breast in each hand, thumbing her pink nipples. Trying to ignore the sensations that made her want to concentrate on her own needs, Kerry leaned forward and flicked her tongue against the head of his dick. It was a little strange, and she was feeling a little hesitant, but she also liked the way he gasped and shuddered as her tongue licked at him; it gave her an incredible feeling of control.

"Feel free to play with yourself," he breathed as he watched her pink tongue start to lick along the sides of his dick. Kerry shot him a look, no way was she going to give him the pleasure of seeing her pussy AND her play with herself while he was already getting head from her. He grinned as he realized that she saw through him completely, oh well. It had been worth a shot.

Not that he had a whole lot of concentration for watching at the moment. Groaning as she finally got up the courage to press her lips at the tip of his dick and slowly open them and sliding down; he couldn't believe how spectacular she looked with her pink lips sealed tightly around his shaft. With just the head in her mouth, he jerked with sudden sensation as her tongue laved over it, caressing the pee slit and rubbing against the underside of his mushroom. Ever so slowly her head started to descend, and his grip on her boobs became like suction cups as he kneaded and massaged them in response to the incredible wet sensation of her mouth as it enveloped him. Very lightly her teeth would graze against him, but not at all painfully; his favorite sensation was the way her tongue rippled against him as she allowed him to press farther and farther into her mouth.

Eventually she couldn't take him anymore, her gag reflex just couldn't handle it, and so she wrapped her hand around the part his dick that she couldn't fit into her mouth. Bobbing her head up and down, she found a rhythm with her hand that allowed her to move both at once. Of course the part of him that was in her mouth felt the best, but this was still the most exciting thing that had ever happened to his dick. It felt wonderful, wet and soft and he could feel all of her mouth just moving against him as she bobbed up and down. He wished that he could fit all the way in, but even without that he was incredibly happy.

The sight of Kerry on her knees in front of him, her lips wrapped securely around him as she bobbed up and down and her tits jiggled, that in and of itself was enough to start his balls boiling. With every stroke she became more and more competent at finding what felt the best, her free hand started to massage his balls gently as she continued to stroke. The unevenness of her inexperienced bobbing and fisting just added to the sensations. When she tugged gently on his ball sack he clutched her tits harder than ever and groaned loudly.

Smiling at this obvious success, Kerry started tugging again, still gently but also a little harder than she had the first time. Derrick starting jerking and writhing in the seat as she pushed herself even further onto his dick, trying to ignore her gag reflex.

Thoughtfully, he gasped, "Kerry, I'm gonna cum..."

To his shock, instead of pulling away, her efforts redoubled. She wanted to swallow his load. That was enough to send him into immediate orgasm, her mouth as far down on his dick as she could get it as she frantically swallowed his cum. Her hand never stopped moving on his balls as she sucked every last drop from him, making him jerk as her tongue slid over the pee-slit in a quick cleaning swipe.

"That was incredible," he looked down at her, awed as his limp dick slid from her mouth. Kerry just smiled back up at him.

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