Kerry put the dreaded strap-on onto the table again, grinning, "Same as last week," she told him, "I win, I get your cherry."
Derrick gulped, but countered valiantly, "Fine... but if I win, I get yours."
The obvious challenge didn't make her hesitate an instant, she'd known what she was getting herself into the moment that she'd even brought anal into the picture. It was something she'd always been rather curious about anyway, even though it was something that she thought was kinda dirty, the naughtiness of it had always turned her on. And fair was fair if she was making him bet his ass, she might as well have hers on the table too.
*********************
Derrick trudged upstairs heavily, following Kerry's swaying ass. Cold comfort that he might have had that if he'd won... he was very unsure about how he felt about this. On one hand, yeah it was with a girl, on the other hand, he'd never wanted anything near his ass. Social stigma maybe, but it was also supposed to hurt and he didn't really see how anything painful could be sexually exciting. If she hadn't made him bet his he probably would've never suggested that she put hers up for grabs.
They kissed as they stripped down, and even though he was extremely nervous about the whole ordeal, he couldn't help but get hard as they touched. Setting up some pillows in the center of the bed, she had him lay face down on them, his hard cock rubbing up against the pile. Some of his hardness dissipated as he watched her put on the strap-on, a smaller cock fitting into her pussy. It wasn't very big really, he knew that they made much bigger ones, but right now it seemed awfully threatening.
Smiling at him, her breasts swayed gently above the protruding dick as she lathered it with lubricant, making it slick and shiny. He watched with trepidation as she got behind him... his body tensed in anticipation and then shivered with reaction as she ran her hands down his back. Suddenly something wet touched his anus, but it wasn't big hard and rubber, it was soft and very wet, laving over his sensitive skin and awakening pleasure nerves that he hadn't known existed. Groaning he realized that she was licking his anus, something he'd heard about but had never thought anyone actually did. It felt fantastic.
Moving his hips with her tongue, he could feel his dick getting rockhard as it brushed against the pile of pillows, and his ass swayed with her movements. His legs spread apart a little more as he relaxed, he hadn't realized that his ass was such a bundle of nerves and pleasure points! Once he had really started to get into the licking, Kerry moved up and pressed the cold, slick head of the dildo to him. As she started to press in he groaned, his ass stretching over the thick rubber. It didn't hurt as bad as he'd thought it would, but it did make him cramp a little. She paused as it reached two inches into his body, massaging his shoulders and just moving it back and forth slightly. Inside of her the smaller dick moved and the clit stimulater tickled her pleasantly.
With little but firm strokes she slowly worked her way into his ass, and she wondered what it must feel like in there... what it would feel like if she had a real dick. Derrick was breathing heavily, his firm ass opening up slowly and every stroke digging deeper... to his surprise he was getting completely hard again. He'd begun to lose some of his hard-on as she'd first pressed the tip of the dildo against his tight hole, but now it was coming back with a vengeance. Somewhere inside him, when she pressed against one particular spot on the interior of his ass, it sent jolts of pleasure straight to his balls and dick. To his surprise, he realized that he was humping back against the invasion, even though it made his ass clench a little in pain... it still felt good on the whole.
It was slow progress into Derrick's tight ass, Kerry was just enjoying the sensations of the dildo inside her as well as watching the progress of the dildo into Derrick's tight hole. She'd sometimes enjoyed using a mirror to watch herself fuck herself with a dildo, but this was the first time she'd ever seen anything going into someone's ass. Running her hands over his hips and butt, she felt incredibly powerful as she began pumping in and out of his body, feeling the way he trembled underneath her.
Reaching around him she grasped his dick in her hand and he jerked back against her, impaling himself further onto the rubber dong. Sliding her hand up and down his dick, she jerked him off as she fucked his ass, and Derrick was feeling wonderful... whatever discomfort was still lingering in his ass was rapidly disappearing with the pleasure of her hand moving up and down on his dick. Even the slick movement inside his body was erotic, pressing in on him, invading him... he wondered if this was what girl's felt like. If this was how she had felt when he took her cherry... vulnerable and yet turned on, anticipatory and anxious, and incredibly erotic.
Her other hand reached around and cupped his balls, tugging on them as she humped him from behind. Now he was moving in rhythm with her, pushing back against the probing dick. The strap-on was rubbing her deliciously as she and Derrick moved together, he was getting much more into it than she'd guessed he would... she wondered exactly what it would feel like to have something inside her asshole. The enjoyment he was getting from it made her think that it might be good for her too... feeling incredibly lusty she began pummeling his ass harder, thrusting deep into his ass with powerful strokes. It was a lot of work, more work than she'd ever guessed a guy had to do from behind, but it felt good too... her clit was rubbing non-stop against the nubby surface of the stimulater.
As she got closer to her orgasm her strokes inside his ass got rougher, and her hands gripped his dick and balls, squeezing like she meant to milk him. The way the dildo invaded his ass made him gasp and jerk forwards, pressing her hand against his groin and pulling his balls away from his body. When she came, she fell forward and completely buried the dong in his ass, rubbing her body up in down with little movements and making the rubber bounce inside him. The steady friction and the tight squeeze on his dick and he was cumming all over the pillows that he was laying on with his ass clenching around the probing rubber.
*****************
When they sat down to watch a movie later, Kerry's eyes glinted with laughter as he gingerly lowered himself onto the sofa.
"You just wait," he told her, having caught the expression, "I'll get you."
Smiling serenely, she surprised and delighted him by scooting closer and snuggling her head onto his shoulder, completely unafraid of the 'threat'.
