tagToys & MasturbationWanna Bet? Special Chapter

Wanna Bet? Special Chapter


author's note: this story was written at the request of a fan who was disappointed that Derrick never lost this bet; i hope this is everything you wanted!


Kerry and Derrick were contemplating their last few days together when he remembered something he'd wanted to do before they left for school. Sure they'd still be dating, but in the tradition of this fantastic summer he'd wanted to do it before they left; one last thing, and the only thing that they hadn't really done.

"Hey honey," he whispered to his girlfriend as they watched the movie.

"Mmm?" she was a little distracted as she was fiddling with his dick inside his pants, not actually interested at all in the movie.

"I've been thinking about that bet you lost, the one where you said that if you'd won you'd want to tie me up and play with me... would you still like to do that?" His question was well rewarded as her eyes lit up and she turned to look at him.

"Really? You want that?" Kerry's voice was joyous and she gave his dick an extra hard squeeze, making his balls ache.

"Oh yes," he moaned, "I know I'll probably pay for it when you're playing with me and I'm not getting any release... but I want it bad..." Her hand was moving even faster on his dick when suddenly it let go and he was left gasping.

"Let's go,"she said, her eyes sparkling with mischief and Derrick wondered just what on earth he had gotten himself into.

On the way up the stairs he said plaintively, "You know, you could finish me off first and THEN we could do this."

Kerry just snorted, practically dancing with excitement as they made their way to the bedroom.


She tied in him a large X onto the bed, his arms and legs spread out. Humming merrily she went to her closet and pulled out a large box, bringing it over to the bedside.

"And just what do you have in there Missy?" he asked, raising his eyebrows at her.

Grinning back at him she replied, "Just some fun toys and stuff... I'm not going to use everything on you, but I thought it'd be fun."

And with that she stood over him and began to strip down, jiggling her tits at him and turning to wave her ass in his face. Practically dancing on top of him, Kerry could look down and see his lustful expression and the way his dick jerked in excitement. Kneeling so that she was straddling his body she began to play with her nipples, pinching hard and moaning as she tugged on them.

Derrick was feeling very unfulfilled, "Aren't you supposed to be teasing ME?" he groaned.

"Aren't I?" her eyes were sparkling as she began to rub her whole breasts, squeezing the tender globes and leaning over so that he was only inches away from her pink nipples. Trying to lift his head so that his lips could reach her breasts did nothing. Turning around, she practically put her pink pussy into his face - but again, not close enough that he could actually reach it with his mouth. It was pure agony for him to have this gorgeous body so close to his and not be able to touch her... and she wasn't even touching him! This really hadn't been what he'd had in mind, although he had to admit that it was extremely effective! His dick had to practically be purple in the head with all the blood rushing through it.

Moaning, he tried to thrust his hips upwards to come into contact with her body; to no avail. Instead he could only watch as her hand slid to her pussy, playing with the soft wet folds and teasing the little clit. Her fingers slid into her pussy hole and he moaned, only able to watch and yearn. The smell of her arousal filled his nose, she was so close and yet he couldn't do anything about it! Being tied down like this was arousing, but he wasn't so sure that he liked it so much anymore... straining he tugged on the knots but she'd really tied them well.

After a minute or so of watching her fingers plunge in and out of her pussy, Derrick was almost relieved when she climbed off of him and rifled through the box. She put a small vibrator, two strange looking suction cups that were attached by a tube and had a little squeezie ball, and a cock ring. Climbing back onto the bed beside him she began to run her fingernails from his shoulders to his groin, just very lightly and without any real pressure at all. They traveled around his nipples, but never touching, and neared his dick before veering away. Moaning he wished that she would just touch the spots that needed it so much... and then she did, her fingernails barely grazing her nipples and the head of his dick. It was so much worse than when she had just avoided the pleasure spots; but now to touch them with such a light teasing touch... he felt like his body was just going to fall apart or something.

Slowly the touch became harder, and his dick jerked in response as her fingers pressed on his nipples. He sighed a sigh of deep relief as her fingers lingered, pulling and tugging insistently. Then she leaned down and sucked each one into her mouth, spending some time nibbling and biting on each. Picking up the strange suction cups she placed one over each of his nipples and squeezed a couple times on the ball. It felt like his nipples were being firmly pinched, burning a little as they were sucked into the vacuum created in the suction cups.

"What are those?" he asked, looking amazed at his pinched buds.

Kerry grinned at them, "I use them sometimes when I'm masturbating and I want to feel something on my nipples. I was wondering if they'd word as well on a guy."

"Oh yeah," he moaned as she reached out and tugged on them, pulling his nipples upwards inside the little cups.

Her hands traveled down until they were gripping his dick, and he moved his hips frantically, trying to get as much relieving stimulation as possible. It felt like his dick was going to pop off; and the situation just got worse as she put the cock ring over his aching member, squeezing the base of it in a ring of rubber. Then she took him in her mouth and he thought he was going to just die... it was the most amazing feeling he'd ever had. Every part of his shaft and head seemed to be ultra-sensitive and he gasped as her hands closed over his balls, squeezing them gently and tugging them away from his body.

Moving his hips he felt totally lost in a haze of sensation, closing his eyes and just reviewing his body; the sharp pinch on his nipples, the hands playing with his balls, and the warm wet mouth on his aching dick. Along with the firm grip at the base of his dick that was going to keep him from cumming until she let him. Suddenly there was a slickness at his ass, pressing inwards, and he groaned as she turned on the vibrator, pushing it firmly into his anus. It felt incredible, stimulating the little bundle of nerves there... he wondered if this was what girls felt like when they used vibrators. If so, he could understand the attraction; his ass was pleasantly full and buzzing, making him shake a little with how badly he wanted to cum.

Straddling his body, Kerry lowered herself onto his throbbing dick, moaning at how hard he was. Biting her lips she fucked him hard, using her own hands to play with her tits and she bounced up and down. Although Derrick was enjoying the fantastic show, he was feeling a little frantic at the impending ache in his balls, the cum that wanted so badly to just spurt into her body and was being denied... Laying there, tied down, all he could do was watch as she began grinding down onto his dick, screaming that she was cumming.

Sighing happily, Kerry looked down at him with flushed cheeks as her first orgasm slowed; tugging on the tube connecting the nipple suckers she made his dick twitch inside her. Closing her eyes she began her movements again, fucking him slow and hard this time, all the while tugging on the suckers - and even reaching back to turn the vibrator up a little more. Derrick was thrashing on the bed underneath her, increasing her enjoyment that much more; especially as he started to plead for release. It gave her a rush of power that she hadn't had since the last time she'd won one of the best. With a wild scream she jerked on top of him, cumming again as he watched.

Opening her eyes she found him looking intensely at her, and she smiled wickedly back. Moving her body hard and fast, she fucked him again, making his balls ache with pent up cum, he wanted so badly just to be able to take her and throw her down on the bed, fuck her hard while her legs waved in the air. As she continued to torture him she turned the vibrator up to full blast, making his hips jerk underneath her and push his raging dick deeper into her pussy. When she began her third orgasm of the evening he screamed his frustration, and then screamed again in pleasurable pain as she ripped the suckers from his nipples. They felt raw and throbbing in the air and he twisted, pulling at the ropes.

With her orgasm slowing she suddenly pulled off of him, sliding the cock ring off his dick and pumping it with her hands. Derrick gasped in shock, his dick suddenly freed of the pressure at the base; thrashing wildly against the bonds holding him down, his body shook as cum sprayed her face and tits, shooting straight up into the air and onto her body. It felt like he was cumming forever, the best orgasm he'd ever had, like all the jizz in his balls was shooting straight out of his dick.

When it finally stopped, his dick sore but contented in her hand and his spunk dripping down her cheeks and boobs, he sighed with relief. Opening his eyes he looked over her new appearance and smiled.

"That looks nice," he commented, and she grinned back at him, starting to untie the ropes. Watching her he said, "You know, my dick is not just a toy for you to play with."

"Of course it is honey," she smiled, "It's a toy attached to a bigger toy." And she gave him a firm kiss on the lips.

On the way to the shower he smacked her ass, "I think I might be falling in love with you."

Stopping dead in her tracks, she looked up at him, beautiful with his cum still on her. After looking into his eyes she smiled again, "What a coincidence."

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