Cowboy Joe DJ SHEYWOLFS fuhusband's blog: "Wanna Bet?"

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."

Kerry and Derrick began their bet as usual... although they were getting much less creative. Either way they were going to have some kind of sex - Derrick wanted to spank her and then take her in the pussy AND ass, Kerry wanted to tie him up and play with him. Neither of them even really cared if they lost, they both knew that they were thoroughly going to enjoy the afternoon... and it was a good thing too. The end of summer was coming closer and they would be going back to their separate colleges soon, a sad prospect but also an inevitable one. Sitting on the couch, neither of them could have said who started it. They were idly caressing each other of course, teasing touches designed to arouse, get each other going... waiting for the end of the bet had become a lot more fun of late. Derrick slid his hands under her shirt and brushed against her breasts - a teasing gesture that backfired on him when he found that she wasn't wearing a bra. Sliding onto his lap, Kerry ground her ass down against his already hard dick, feeling it press against her asscheeks. One of them started kissing each the other, maybe they both started kissing at once... it intensified and deepened as Derrick began to press her back onto the couch, his hands sliding back up her shirt and caressing her breasts. Moaning she pressed up against him, spreading her legs to feel him pressing against her groin. Pushing him back away from her, their lips reluctantly parting, she smiled and said, "Aren't we going a little fast for before the bet..." "Maybe," he grinned at her, "But I don't really mind, do you?" "Nope," she smiled back and then grabbed the back of his head, pulling him back down for another kiss. They began pulling at each other's clothing, passionately caressing and kissing... it was almost a new experience because they were now both equals. No one had won or lost yet and it was exciting to exchange pleasure for pleasure, not working towards anything but just taking enjoyment in the other's body. Derrick got a sudden idea and pulled himself off of her, turning around so that his dick was poised above her lips and he began pulling her legs apart and lowering his head and his dick. Realizing what he was about Kerry giggled, but opened her mouth to accept his lowering member, moaning around the fleshy shaft as his tongue began to lick at the junction between her thighs and her body. They sucked and slurped, taking enjoyment in giving the other pleasure and also in taking their own; Kerry shuddered and her legs closed over his head as he began to press his tongue into her pussy hole, wriggling it inside of her. Rubbing her hands along the backs of Derrick's thighs, Kerry caressed his ass, her fingers searching out the small crinkled hole. He groaned as she found it, her fingertip rubbing and pressing against the sensitive nerves that were bundled there, making his dick throb in her mouth. As he pressed further into her throat Kerry was a little nervous, but found that in this position it didn't bother her gag reflex as much. Sucking harder she made little circles over his anus, pressing down gently on the hole. All the teasing and fore-play was too much, not to mention the fantastic feeling of her throat actually massaging the mushroom of his dick. Losing control, he let his hips press all the way down, sliding his dick into her throat completely as he began to cum. Kerry swallowed frantically, surprised at his sudden climax but willing to go along with it... she started to run out of breath but he finished cumming and pulled up off of her before she could panic. Gasping a little for breath, she smiled at him as he crawled between her legs and said, "You're turn." and buried himself into her pussy. Her hips jerked as he began feasting on her body, sucking and nibbling on her flesh. Using that first lift of her buttocks he slid his hands under her and kept her hips up, using the extra space to slide his tongue from her pussy down to her ass. Teasing the small crinkled hole he wet it with his mouth, making her moan and writhe in pleasure as her pussy burned with excitement. Moving his mouth back up to her pussy, he slid his hands out from underneath her and began pressing a finger into her excited pussy hole. Coating it with her juices he pumped it in and out a few times, rubbing along the inside of her body. Pulling it from her heated aperture he moved it slightly lower and began pressing it against her asshole. It was a tight squeeze as he began to fit his finger into her ass, continuing to lick her dripping pussy, it clasped his finger and gripped down hard. Kerry moaned as he pleasured her, it felt like her pussy was itching with passionate fire that needed to be scratched and quenched. The one finger seemed very large in her ass, pressing inwards and filling her, creating a pleasantly full sensation that went along with the exciting stimulation to her pussy. Pumping her asshole with his finger, Derrick found her clit with his tongue and flicked it, making her hips jerk and her ass come down hard on his invading finger. Sucking the little bud into his mouth, he bit down and began to roll it with his teeth while her body started to shake. Opening her mouth into an ecstatic "O", Kerry thrashed and her ass clamped down hard on his finger as she came. It was quite a sight to watch from between her legs as her breasts jiggled spastically and her face contorted with passion, he felt himself getting hard again. As her orgasm slowed he pulled his finger from her ass licked up the remaining juices coating her pussy before coming up for a kiss. She could taste herself on his lips as they kissed deeply. Suddenly she pushed him away from her and looked at the TV, "Who won the bet?" The program they had been watching wasn't even on anymore. "I don't know..." he said slowly, a little distracted by his partially hard dick which was slowly growing as it pressed against his thigh. Turning her head back to him she smiled, "Do you really care?" "No." He grinned at her and she pulled him down for another passionate kiss. As his hands gripped her boobs, squeezing hard, she could feel his dick slowly growing along the inside of her thigh, almost as though it was purposely growing towards her pussy. Spreading her legs a little more she pressed her splayed pussy against his groin, moaning as her clit rubbed against his skin. Sucking on one nipple he pinched the other with his fingers, tugging on it like he was doing with his teeth. Kerry moaned and writhed underneath him as the heat in her pussy grew again, she was eager for the hard dick that she felt pressing against her. Pulling on his hips she tried to hurry the process along, but he held fast, just nuzzling his head along the outside lips of her excited pussy. Moving her hips up and down she tried to tempt him with the slickness inside, her sweet juices that were ready to cover him and ease his entry. Finally he began to press inwards, groaning under his breath as her tight hole opened for him and squeezed him deliciously. She was so wet that he slid in easily, a long quick plunge that made them both gasp with pleasure. Trapping him inside of her with her legs she began to hump back as he thrust into her, both of them moving in rhythm as they fucked. Her tits were smashed against his chest, hard nipples rubbing into him. Leaning forward for more leverage he slammed into her body, over and over, almost as though he was trying to drill her into the couch... she was almost surprised that they weren't moving the furniture with the force of his thrusts. They split open her shocked pussy, making her lose her breath with every powerful blow and she gripped him hard in pleasure. Every plunge filled her up and she clasped his dick as he receded, trying to keep him inside of her. Groaning, he held himself fulling inside her and ground against her body, rubbing her exposed clit with his groin and making her shriek with pleasure. Returning to his thrusts, he made sure to grind against her every few strokes, making her pussy burn with excitement. Pulling him even deeper into him with her legs as she tensed, he felt her pussy begin to ripple as she came, throbbing walls that closed around his dick. With five quick and hard thrusts that made her orgasm soar even higher, he plunged in a final time and began to empty himself into her body, arching his back with the intensity of his climax. Sometime later they both lay there, content and tired. Propping himself up on his forearms, Derrick looked down at her and kissed her, "I'm going to miss you." "I'm going to miss you too," she told him, "I missed you all this year." Then she smiled seductively, "You should come visit me... I'll make it worth your while." For a moment he hesitated before asking, "So... are we dating now?" Kerry hesitated too and then giggled, "Well, we definitely act like it." Looking down at her naked body with his dick still lodged in her pussy he laughed too. "You have a point." He grinned at her and they kissed again, finally both completely happy with where they were. More to come later I need a nap.

"So, if I win today, I want to tie you up and play with you." said Kerry, her eyes twinkling as she winked at Derrick. The idea of being totally at her mercy was both frightening and breath-taking... but he had his priorities too, "If I win, I get your ass cherry." And he leered at her. He was dying to take her in the ass ever since she'd had him, and although last bet he'd lost had ended up being thoroughly enjoyable, he still hadn't been able to stop thinking about winning. After all, Kerry did have a fantastic ass, and since she'd taken his cherry it was only fair that he took hers. This time, as they watched horse-race, she climbed onto his lap and let him play with her tits as they watched, her ass grinding down into his dick. He could feel her firm cheeks between the clothe that separated them and was very very hard already; pinching her nipples tightly he listened to her moan. There was also something exciting about losing, he'd have no control over what she did to him and really no say either... once he got her ass it might be something interesting to try out. Or maybe he'd go online and find something else to push her boundaries a little... even if it was just a different location or something that she hadn't come up with yet. He'd really like to surprise her with something. Kerry could feel his dick digging into the crack of her ass, it made her pussy leak with juices as she thought about the fact that she might be losing her anal virginity. After he'd ended up enjoying it so much she'd wondered what it felt like, especially after his tongue had licked her anus last time. It had felt so incredibly good, so unexpectedly sensational, and she was actually feeling rather excited to have him fuck her there. Still, tying him up would be fun too, and then she'd even get to do him in the ass again if she wanted. Or she could just tease him mercilessly; she smiled as his fingers played with her nipples, teasing him for a very long time before getting him off would be awfully fun. But it wasn't something that she would get to explore this time... his horse passed the finish line first easily. Derrick's hands gripped her tits hard as he whispered in her ear, "Your ass is mine." ************************ Upstairs he put her in the exact same position that she'd had him in for the taking of his ass cherry, a pile of pillows in the center of the bed to go under her hips, and one to go under her head. Because she was so nervous he started out by massaging her back and reaching around to cup her tits, squeezing them gently and rolling her nipples between his fingers. After all, he wanted her to enjoy this. Once he felt her tension starting to release he lubed up on of his fingers and began to press it into her ass. Shifting her hips, Kerry felt the finger begin to enter her... it felt very strange. And very big. Squeezing and wriggling she tried to adjust, feeling it go deeper and deeper into her body. It hurt a little, but not as bad as she might have though... mostly it just felt very very odd. A kind of pressure that she felt like she should be able to relieve but couldn't. Behind her, smiling, Derrick picked up the vibrator that he'd laid next to her legs and started to press it into her pussy as his finger wriggled in her ass, turning it on to its lowest level. Kerry moaned as something unexpectedly entered her wet pussy and started to buzz, it made her ass clench down on his finger again in reaction. That felt incredibly good... as he pressed the vibrator all the way in and started to fuck her ass with his finger she felt like she was stuff full. As a second finger entered her ass she groaned as it stretched, and he turned up the vibrator a notch. The pleasant sensations of its teasing vibrations went a long way towards distracting her from the slight discomfort in her ass. He enjoyed watching his fingers invade her tight slick hole, and even more enjoyed the way her ass moved and humped against them as the vibrator really started to get to her. Pumping his fingers in and out of her ass, he could feel the vibrator humming against them and wondered what it was going to feel like against his dick. Probably fantastic. Grinning in anticipation, he tried to spread his fingers a little, stretching her open even more... groaning, her hips shifted again. Turning the vibrator up another notch he removed his fingers from her ass and started to lube up his dick. Kerry wanted to tense up as she felt his hands caress and grip her ass cheeks, but the vibrator was doing its work too well, she couldn't tense up for too long because of the way it buzzed inside her. Putting the tip of his dick to her ass, he marveled at the fact that his large round mushroom head was about to make its way into that little crinkled hole. Pressing in, he watched as the wrinkles in the hole smoothed out as her ass opened up, until it suddenly popped over the head of his dick and closed tightly around the shaft. Both of them gasped; Derrick because this new orifice was so incredibly tight and exciting, and Kerry because her ass was now stretched very wide. Groaning, she wriggled her hips, his dick felt huge inside of her and she knew that he wasn't even very far in... the fact that she had a vibrator in her pussy wasn't help the over-whelming feeling of fullness in the lower half of her body. Derrick's dick twitched as the vibrations played over his sensitive head, he turned up the vibrator another notch and groaned, shoving his dick in another inch. Arching her back as his dick began to work its way into her tight hole, Kerry was having trouble reconciling the pain and the pleasure in her body; they seemed to be twining together in an unholy mix that made her pussy spasm. Slowly the vibrations spread over Derrick's entire dick as he worked it into her ass, and with just the last two inches outside of her body he couldn't take the slow pace anymore. With an apologetic groan he pressed all the way inwards, shuddering as her ass convulsed around his invading member. Kerry jerked backwards as the last of his dick buried itself in her body, causing him to thrust even more deeply and roughly than he'd meant to; but the little wave of pain and discomfort it caused was almost nothing compared to the pleasure. She felt completely full, her entire lower region stuffed and buzzing as the vibrator was pressed more firmly into her pussy by his position behind her. Moving her hips in a circular motion, she made both of them moan as his dick stirred her insides, and he began to pull out of her ass to begin steadily thrusting in and out of her tighter hole. Humping her backside, he ran his fingers over her back and down to her hips, trying to find the best placement for his hands; every thrust of his hips pressed the vibrator into her pussy along with his dick so that it was like there were two cocks each fucking one of her holes. And one of them happened to be buzzing erotically. Kerry pressed back harder against him, feeling the strangest sensation in her belly as he fucked her, like her entire lower region was tensing up for a fantastic release. As her hips moved back against his body he hunched over and reached under her, wanting to see if he could feel her tits... to his delight he could and he grabbed a hold of the swaying globes and squeezed. Shuddering, her ass rippled over his dick as he began to knead her sensitive tit flesh with his fingers, pinching the nipples and tugging on them. Thrusting harder, he started to really pound into her ass, sliding in and out of her slick hole with complete lustful abandon. With the vibrator buzzing in her pussy Kerry actually reached climax before him, crying out in passionate rapture as his dick continued to pound her asshole. Every thrust drove her ecstacy higher until she was shaking with the intensity of it... her ass gripped him hard as his dick began to pulse inside of it. She could feel every spasm as each spurt of cum passed through his dick, making the bottom of it pulse and swell against the rim of her ass before it spilled into her dark hole. Reaching down, she turned off the vibrator in her pussy before its tremors could become painful.

This week Derrick was feeling much more prepared, after all, last week he'd been through what he'd thought would be his biggest boundary pusher ever. He'd let Kerry take his anal cherry with a strap-on, this week he announced, "If I win, I want to take your ass, " and he leered at her. She giggled at his mock threatening look and tossed her head, "And if I win, I want you to fuck me..." his face brightened up and she laughed again, "and then eat me out after you cum." Now he just looked conflicted and she started laughing again. Making a face at her, he examined his feelings about this... well either way he was going to get a lot of pleasure, but he wasn't sure about eating out a pussy full of cum. Even his cum. Maybe even especially his cum. Well, no... now that he thought about it he felt more comfortable eating his own that someone else's... the thoughts were just all going circular in his head. Kerry watched him from the corner of her eye as she again wondered what it would be like to be taken in the ass. Having taken his anal cherry last week she was both excited and anxious at the thought of losing her own... still. She thought that her own challenge for this week was a good one, the expression on her face had said clearly enough that he didn't know what to think of it. Smiling, she leaned into him as they watched the football game, nestling her head on his shoulder. His fingers stroked little circles on her arm, giving her goosebumps. "You know..." he started and then stopped. "What?" she asked, tilting her head up to look at him, so that when he turned his face towards her they were only inches apart. "We're going to end up naked at the end of this anyway... so we could just start now..." he looked at her anxiously, waiting to see what she thought. Truth be told, it wasn't a bad idea. She was already horny, and the football game wasn't that exciting so far. Rather than answering him, she pulled his head down for a kiss. His lips were gentle at first and then they began to press harder on her, his body leaning into hers and pressing her down onto the couch. Sliding his hands up her shirt, he pulled it from her body as their lips parted and she pulled his off over his head; with his hands behind her back he fumbled with the clasp of her bra as their lips locked. Fingers massaged his back as he finally pulled the clasp apart and bared her breasts. With a slight moan he sat up a little and began to toy with the heavy globes, squeezing them with his hands. In response, Kerry reached up and started rubbing his nipples, teasing the tiny nubs with her finger tips and even pinching them a little. His dick was jumping inside his pants as his hips pressed against hers, trying to dig its way through the clothe to her soft pussy. Breathing heavily he lowered his mouth to her bare breast, making little circles on her flesh with his tongue, starting from the outer curve of the globe and slowly working his way inwards. Gasping, she arched her back as his mouth teased her, pink nipples were already hard and aching as he got closer and closer to them. She longed for him to take one inside his mouth, to suck and bite on the sensitive buds... her fingers squeezed his nipples tightly, echoing her own desires. When he reached her nipple, his tongue just gently flicked over it and she cried out with need, the desperate desire for firmer contact. Derrick smiled to feel her writhing underneath him, his nipples were burning and hot with the rough treatment her fingers were giving them... moving his mouth to the base of her neck he bit down gently and sucked, the way that she wanted him to suck on her nipples. They ached as his chest pressed against hers, the hickey he was giving her felt as though it was throbbing while he sucked her flesh into his mouth. Involuntarily her hips moved up against his, she could feel the wetness slick in her panties as she rubbed her crotch against his. As she moaned, she turned her head to the side, allowing him even easier access to the side of her neck that he was sucking on. The new position allowed to her to look at the TV and she realized that she was watching the last minute of the game. "Oh good," she panted a few seconds later, pulling him from her neck, "You lost, now fuck me!" And she pressed his head down to her chest where her nipples poked out, demanding attention and adoration. A wise man, Derrick obliged the implicit order, taking her nipple into his mouth and sucking it hard as he started to pull his pants from his body. Sighing in happiness as her aching nipple was finally being stimulated, Kerry could feel the wet slickness of her pussy getting even wetter as the pleasure rolled over her. Derrick pulled off her pants and panties and the cool air felt good against the hot wet flesh as she spread her legs and pulled him on top of her. They kissed as his fingers pinched and pulled at her abandoned nipple, making her back arch up against him. Releasing the little bud, he twisted slightly to his side so that he could grip his dick in his hand and get it into position at her pussy; the mushroom of his dick found her to be incredibly wet and slick, making him slip pleasurably up and down between her lips. She moaned against his mouth as his penis brushed against her engorged clit, making her hips jump. Eagerly he lined up with her pussy hole, pressing in and feeling its tightness trying to crush the bulbous head of his dick. Moving her hips up and down, she facilitated his entry, trying to use her legs to pull him into her faster and harder... he made her wait with a smooth, slow but firm slide into the wet hole. As his dick buried itself in her body she humped her hips up and down, rubbing her clit against his skin and making his dick twitch inside her body. "Fuck me," she begged, running her hands through his hair, "Please, just fuck me hard..." With a groan, Derrick obliged. He started pumping his hips with abandon, letting her take care of herself as he took pleasure in her body, enjoying the sheathe of her pussy and the way it encased his cock. Beneath him Kerry writhed and bucked, her legs spread wide - one of them thrown over the back of the sofa - as she rubbed against his moving body, greedily taking in every thrust to the maximum advantage of her lust. After all the teasing he'd done to her it didn't take her very long to cum, she cried out in ecstacy, her arms and legs pulling her close into him. He hadn't intended to cum so quickly, he'd wanted to put off the second part of the bet, and he'd wanted to enjoy her body some more... but when she started yelling out his name and her body tensed up like that, gripping his dick so tight... all resolve went flying out the window. Burying his head into her hair he thrust hard and held himself in her pulsating pussy, feeling his dick throb as it spilled cum into her. Kerry sighed in completion as she felt the last pulse of his dick, her body relaxing all around him. For a few moments they just lay there, she was happy to feel him shrinking inside of her, there was something incredibly intimate about it. But as he began to actually fall from her body she gently pushed him up. "Next part," she said, her eyes glinting with mischief. Derrick sighed and kissed her, caressing her lips with his own and delving his tongue into her mouth, although it was a bit of a delaying tactic she accepted the kiss and happily. Cupping her breasts in his hands he squeezed and kneaded them gently, slowly stoking the fires that had dwindled in her belly. As teasing hands manipulated her body she moaned, everything was still hyper-sensitive from her orgasm and so it felt ten times as stimulating as he thumbed her nipples. Taking his mouth from hers he leaned down and began to suck gently on her nipples, going back and forth and teasing them with his tongue and lips as he did so. Biting her lip, Kerry could feel her pussy awakening again at his gentle ministrations, her nipples were aching and happy to be soothed by his tongue. When he felt her start to writhe underneath him he abandoned her breasts and began working his way down her smooth stomach, kissing and caressing. Reaching her mound, he spread her thighs even farther apart and started licking the insides of them, he could taste her juices but not his own yet. Slowly he worked his way inwards and upwards where he could see his cum leaking out of her pussy. Deciding it was best to just dive in, he went straight for the hole with his mouth, sucking and licking... it didn't taste as bad as he'd thought it would. Mostly it tasted like her but with a slightly different texture, and not quite as sweet. Her hips bucked as he swirled his tongue along her slit, sucking and working her over. Pushing her legs up even more, he put them over his shoulders so that he could reach up and start playing with her tits as he ate her out, pinching her nipples while his mouth searched out her clit. Thrashing as he cleaned her despoiled pussy, everything was so sensitive that she thought she was going to die of pleasure when he nibbled on the outer lips before moving his tongue into the sweet pinkness between. When he stuck his tongue in her hole it felt like a small cock and she clamped down, spilling more juices into his mouth. Reluctantly he swallowed them, and was glad that their juices were mixed, mostly it just tasted like sex. Not that he really knew what sex tasted like, but it tasted like what he thought sex should taste like. Ignoring the ramblings of his mind he pressed his mouth further into her pussy and started sucking from the bottom of her pussy all the way up to her clit and then back. Getting a really wicked idea, from what she had done to him on their last bet as much as anything, he pressed her hips up a little more and this time when he traveled down her slit he kept going. Kerry's hips jerked upwards as his tongue touched her anus, electrifying contact of pleasure nerves that made her buck in surprise and exciting pleasure. "Oh God..." she moaned as his mouth followed her hips, pressing against the rosebud and licking and caressing... she'd done it to him last week to shock him, but she hadn't realized at all how good it felt. Braver than she had been, he stiffened his tongue into a little spear and pressed inwards, as her ass flexed he managed to push his way into her ass a little and smiled as she screamed with pleasure. His tongue wriggled as it raped her virgin ass, and she thrashed wildly, her body unused to this unexpected pleasure. Sliding his fingers away from her nipple and down her stomach, he pinched her clit and twisted; Kerry came with a loud cry, her ass tightening on his tongue and squeezing it out. As she thrashed in orgasm he continued to lick her asshole until she finally sobbed and her body went limp with exhaustion. Triumphantly he pulled himself up next to her and she looked at him tiredly. "That was hot." he told her, and she nodded agreement before closing her eyes and nestling against his shoulder.

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'.

"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.

This time Derrick had a little bit of a surprise for Kerry, "If I win, I want to watch you masturbate with this," he said, grinning at her startled expression as he put the large dildo on the table. It was a dark tan color, 6" long and 1" around; nothing too hefty although slightly longer than the vibrator she usually used on herself, "It's got a remote," he showed her as he continued to grin. Kerry just laughed at him, "Fine, but if I win, you've gotta eat me out while you masturbate." Squirming a little at the thought of having to show her just how much she turned him on, for some reason it seemed kinda embarrassing, he nodded. And they turned to watch the swimming. One nice thing about the Olympics, it gave them so many opportunities to bet. Derrick whooped and cheered as two of his picks came in first and second on the 200 butterfly, their chosen race. Flicking off the TV, he tossed the dildo to Kerry with glowing eyes. Just as she had found it exhilarating to strip for him when he was supposed to be masturbating for her, Kerry found that her body thrilled a little to the idea of masturbating in front of him. Deciding to give him a little show, she slowly stripped off her shirt and jiggled her breasts at him as she reached back to undo her bra. Rather than taking it off right away, she pressed her arms against her breasts to create a deep cleavage as she leaned forward and let the bra drop from her body. She could tell that he was already hard. Slowly she slid out of her jeans and then her underwear before sitting down and leaning back on the couch. Spreading her legs so that he could see her pussy, she started to toy with her breasts. Lightly running her fingers over her nipples, she squeezed her aching breasts, bouncing them slightly for him. Pinching her nipples gently, she tugged and her hips responded as she moaned. Derrick could see the juices starting to glisten between her pussy lips, and he wanted to dive in there with his mouth again. With one hand she reached down and brushed her fingers over her pussy before putting them up by her clit and spreading the lips with her fingers as she brought the dildo down in her other hand. Rubbing it up and down her wet slit, she lubricated it with her juices as her hips moved in harmony with the stimulation. Moaning, she started to press it into her hole with each slide, just a little bit, stretching out the entrance to her pussy. Breathlessly excited, Derrick pushed the button on the remote that turned on the vibrator inside the dildo to its lowest setting. Kerry shuddered as it unexpectedly came to life right on top of her clit. "Oh God," she said, as she pressed it firmly on the aching bud before running it back down her pink wetness. This time she pressed it a little more into herself, and rather than pulling it back out she started actually working it in and out of her pussy. Derrick felt faint with lust as he watched her pussy stretch open for the toy, its first few inches buzzing inside of her body. With every stroke its slick shaft pressed more deeply into her, and he turned up the intensity to the second of its six settings and put it on "pulse". Kerry gasped as the vibrator started to send the vibrations in short quick bursts, buzzing a little harder than it had before. She started thrusting harder with it, burying its entire length into herself and then pulling it out halfway before shoving it back in. This was a much more high-tech vibrator than the one she'd bought herself at the adult store. Her pussy slickly accommodated every thrust, her legs spreading even more so that Derrick could really see the dildo penetrating her. His dick was throbbing as he wished that it was his dick that was inside of her. Next best thing though... he turned the intensity up to the third level and put it on "wave". Now the vibrator went from the lowest to the highest in quick little waves that flooded through her, teasing and manipulating her pleasure spots. Shuddering, she held it inside of her as its waves got more intense - Derrick had pushed it up to level 4. Suddenly the dildo was out of her hands and moving inside of her, but she didn't protest when she realized that Derrick had taken hold of it. Instead she just reached up and started playing with her aching nipples, adding to the sensations that were taking over her body. Twisting the dildo inside of her, Derrick attached the clit stimulater to it and pressed it against the little nub. Kerry almost screamed with pleasure as the rubbery attachment buzzed against her, she could feel her orgasm rising deep in her belly. Seeing that she was going to be losing it soon, Derrick turned it up to level 6 and put it on twist, so that the end of the dildo started turning inside of her and pressing against her g-spot with every rotation. It looked like she was practically levitating as her body arched and she cried out, her breasts bouncing on her chest as she humped and convulsed with passionate cries, her hands clutching at the pillows. Derrick held the toy inside her, slowly lowering the levels of intensity so that her orgasm was long and drawn out but without ever becoming painful from too much stimulation - just like the girl at the store had told him to. When Kerry was finally calm, he was grinning at her as he pulled the vibrator from her slightly sore but very fulfilled pussy. Opening her eyes she looked at him, "Thank you..." Noticing that he had a slight problem of his own, she grinned and sat up, leaning over to undo his pants. Derrick watched in amazement as she voluntarily pulled his dick out and then pressed her mouth over him, sucking him down deep with her hand fisting the part that wouldn't fit. Almost as soon as she'd bobbed her head a few times, his over excited dick throbbed and he came inside her mouth, his hands pressing her down the furthest she'd ever gone as she swallowed frantically. "Thank YOU," he breathed as she finished.

Kerry laughed at the end of Jeopardy when her chosen person won, Derrick was smiling too. This time she'd bet him that if she won he'd have to eat her out. Sure, he wasn't going to get his own sexual satisfaction until later, but he'd been looking forward to getting his mouth onto a girl's pussy for the first time. Tell the truth, Kerry was actually more hesitant about it then he was; she'd never had a guy down there either. The only thing Derrick was worried about was that he'd be bad; but ever since they'd first made the bet where he'd risked eating her out, he'd been asking some of his friends and looking online for some tips and how-to's. He thought that he'd probably be ok. Getting laid out on the bed, Derrick started to unbutton her shirt, Kerry laughed and tried to close it again, "Hey, that's not part of the deal!" she told him. Grinning, "I have to get you in the mood though," and what a chance to get his hands and mouth all over her body! Smiling, seeing his point, she allowed him to finish unbuttoning her shirt and taking it and her bra off. Immediately he started massaging her breasts, getting his mouth onto her nipple for the first time. "Oh!" said Kerry in surprise as he began to suck on the tender pink bud; she could feel it turning into a hard little nubbin in his mouth, responding to the pleasurable stimulation. It felt very very different from having it pinched with fingers; his tongue licked it as he sucked and he even nibbled very delicately. Moaning, she arched her hips, looking forward to the new sensations which she was now sure awaited her when he ate her out; if a mouth felt this different on her nipple, surely it would down there too! Continuing to knead her breasts with his fingers, he transferred his affections to her other nipple, making her writhe a little on the bed. Damn but she looked sexy, all laid out like that and flushed with arousal. The nipple that he'd been sucking on was hard and glistening slightly in the cool air, he pinched it with his fingers as he began nibbling on the one in his mouth. Kerry was moving her hips against his body now, her pussy ready and wet with need. Keeping his hands on her breasts, he began to move his mouth down her stomach, licking little circles on her hot skin as he traveled. When he got to her pants line, he finally took his hands from her tits to undress her, slowly. He pulled her pants and panties off at the same time, looking up the length of her legs to that smooth pink mound. Beginning at her ankles, he started kissing up both legs, teasing her with his tongue. Almost whimpering, Kerry spread her legs to allow him easier access as his mouth went back and forth between her inner thighs; she could actually feel her pussy burning with anticipation. Arriving at that wondrous destination, Derrick kissed the top of her mound and then started licking around where her thighs and body met. Moving his mouth along her outer labia, he could smell the juices that were leaking down her asscrack, feel the way her pussy moved against him. Kerry was whimpering now, the feeling of his mouth massaging her outer lips was as different from her fingers as night and day, she wanted to feel his mouth on the inner flesh part, feel his tongue parting the lips. Carefully he started licking horizontally, and she almost cried out with frustration as his tongue barely flicked over the inner lips. Pressing her hips upwards she moaned . As her hips went up, Derrick slid his hands under her buttocks and grabbed each cheek, holding her slightly off the bed; then he finally dove in. Licking all the way long the inner slit, he tasted her sweet, musky juices. Kerry thought she was going to scream with pleasure as his soft tongue pressed against her slit, swirling around it in a completely foreign way. It felt so much better than she had ever imagined. Humping her pussy up and down on his face, Kerry could feel his tongue sliding into every crevice of her cunt, making tiny patterns on the flesh. When he actually stiffened his tongue and pushed it into her hole, she did cry out as it wriggled inside of her. Her hands found his head and clutched at his hair as he licked and sucked, feasting on her pussy flesh. Taking a trick that was given to him by a friend, Derrick slid his arms under her thighs and pushed her up so that her pussy was upwards towards the ceiling and his hands were full of her breasts. Playing roughly with her nipples, he sucked the outer labia of her pussy lips into his mouth and nibbled gently. Kerry went wild, thrashing and tugging on his hair, crying out his name and that she was cumming. Realizing that she was cumming even faster than he'd though, Derrick moved his mouth up to her clit and sucked the little bud into his mouth. Already in the throes of a passionate orgasm, Kerry screamed as her clit was stimulated, her pleasures heightening to peaks that she'd never thought possible. When he bit down gently on it, she screamed as the waves of ecstacy crashed over her, pounding her body until she finally fainted from the over stimulation. Surprised, Derrick looked up at her... she seemed to be unconscious but she had a look of extreme pleasure on her face. Well... he could always bring her to a happy awakening as well. Allowing her clit to pop out of his mouth, he started licking around her pussy again, cleaning it of the juices that had flowed from her while she orgasmed. Taking one hand from her boob, he brought it down and pressed it into her pussy. He didn't find her hymen so he figured she must have broken it sometime before, probably riding her bike or something... he'd heard of that happening. Marveling at the tight feel of her pussy around his fingers, he found a little ridged spot... according to his online reading, that was her g-spot. This was his first time with his fingers in any girl's pussy, but if there was one spot inside that felt different, and only one, then it was going to be hard to miss. He could feel his dick swelling even bigger as his fingers mimicked the sex act; he could only imagine how pleasurable sex must be... sticking his dick into a tight warm crevice like this. Gently rubbing his fingertips against the g-spot, he continued to lick and suck at the pussy flesh around her hole. Kerry started to moan and move a little in response to his manipulations, still unconscious, but enjoying it all the same. As his lickings and pumpings became more frantic, she started to come around, realizing that there was something inside of her... and that it felt wonderful. When she saw that only one hand was playing with her tit, she realized that he must be fingering her... and although that wasn't really part of what she'd requested, she wasn't going to complain either. The spot that he'd found inside of her was making her writhe already, and the memory of that incredible orgasm was enough to make her want more. Her pussy was already recovering and starting to itch with the need again. Derrick knew she was awake when her hands clutched at his hair again and her pussy moved more firmly against his mouth, tightening on his fingers. The first time her pussy closed down around his fingers he was shocked, he hadn't known she could do that! It seemed to feel good though, because she kept doing it as he rubbed her g-spot. Very quickly her movements got faster and faster, and this time he started sucking on her clit right away. Between the stimulation to her clit and her g-spot, Kerry was going off the wall with pleasure. When she came it was the hardest she ever had, but this time she didn't faint. She was expecting it a little more and her body wasn't as shocked by the onslaught. This time she rode out the entire intense orgasm, screaming and thrashing as her body rippled with pleasure. When it was finally over and Derrick finally withdrew from her pussy and came up beside her; she whimpered, "Don't touch me... I don't know if I can take it right now..." He smiled, "That's ok, do you think I could use your bathroom?" Kerry nodded, and he went off to relieve himself. She just lay on the bed, thinking that if he had touched her, she would have burst. Her body felt raw with pleasured stimulation, almost painful. Damn but that bet had been worth it. She'd been a little hesitant with the new places their relationship was going, but right now she was really enjoying it. And who else would she have been comfortable doing this with? No... this was good. And maybe next time it would be even further... she was starting to like the way they were pushing each other's boundaries.

"Ok," Kerry said, "So if any of the horses on my list win, you have to give me head." Derrick grinned, "And if any of the horses on my list win, I want to watch you masturbate." Kerry's eyes got wide, "Oooo... actually I like that one better! I want to watch you masturbate too if I win." "Really?!" Derrick was surprised. She laughed at him, "Hey, not all us girls are rampant sex-starved fiends... I've always wondered what it looks like when a guy masturbates. I'd rather get that one first, it's a good one." Of course Derrick always hoped to win, but this time he especially did so. Somehow masturbating in front of Kerry seemed more embarrassing than erotic... ************************* They were both screaming "GO GO GO GO!!!!!!!!" As two of their horses jockeyed for first... Kerry screamed triumph as Windfoot crossed the line ahead of the Red Baron and Derrick groaned. With gleaming eyes she turned to him, clicking off the TV with the remote, "Ok, so where do you want to do this?" Flushing, he mumbled, "Well usually I do it in the shower." "Ok let's go!" excited at her win, she grabbed his hand and practically dragged him up the stairs. In the shower, with the water spraying him, Derrick tried to get in the mood, "Kerry, I don't know if I can, this is just too weird having you watch me." She was sitting on the toilet watching him intently, fully clothed. It wasn't exactly the situation that wet dreams are made of. Sighing, she got up, "Ok, I see your point... you don't have a lot for stimulation here." Pausing, she bit her lip, "Well, you didn't win, but I guess it won't hurt cuz you will eventually anyway." And she started to strip. Derrick stared, surprised at her casualness about it. His dick started to twitch as she undid her bra and her breasts sprang free, perky with almost no drooping; his hands could remember the feel of them and his dick started to do a little more than twitch. As her pants slid down her thighs she looked up and noticed that he was standing at attention. Smiling she said, "Well this is certainly seeming to help." He could answer because as soon as she said that, she turned her back to him and started wriggling her ass at him as she slowly slid her pants all the way to the floor. She was wearing silky underwear that barely stretched over her firm cheeks, and his hand involuntarily went to his dick, slickly pumping it so to relieve the ache that it was giving him. Turning, Kerry started to watch him, but now he felt almost no awkwardness at all as her breasts swung slightly. Smiling sexily at him, she started to slid her underwear off and he could actually feel his dick pulsing in his hand. She watched as he slid up and down the shaft, his thumb rubbing against the head every time he got there, squeezing it roughly as he started to pick up speed a little. His dick was slick and wet with the water from the shower, and she found herself remembering what it was lick to suck on it. Licking her lips a little at him, the gesture wasn't lost on his sex-wired mind. Derrick groaned, using one hand to cup his balls as she had during their last bet, his hand never slowing its movement across his dick. Kerry was completely shaved on her mound and he thought he was going to pass out when he saw her pink pussy lips peeking out at him, hairless and gorgeous. Sitting back down on the toilet, she leaned back and spread her legs a little so that he could see her clit peeking out, the long wet pink slit, and even a glimpse of her crinkled asshole. "Is this better?" she asked, pouting her lips at him. "Yes..." he hissed, stroking his dick even harder. Wiggling her hips a little at him as she watched him jerk off to her naked body, she found herself wanting to touch herself in response. It was really kinda hot to watch him masturbate, and even hotter to know that he was doing it to the visual of her naked body; but since watching her masturbate was something he was using for a bet, it wasn't something she was going to give him for free. So instead she just concentrated on watching him jerk off, her eyes glowing and her breathing slightly accelerated. For his part, Derrick could see the way her pussy glistened with juices and her hard nipples let him know that she was turned on by all of this. For him, that just made everything even better and he could feel the familiar tingle in his balls. Watching her eyes glow as she watched him, he gritted his teeth and quivered. "Do you want to come closer and watch?" he asked, hoping that the answer would be yes. For a moment, Kerry hesitated and then she came over and got on her knees so that she was at eye level with his pumping hand. Looking up at him with wide innocent eyes, she said, "Spray it on me..." Turning with a groan, he obeyed almost instantly at the visual that made in his head. Spurts of frothy cum sprayed her across her face and then her tits, five streaks of white in her hair and on her body while his hand squeezed and he tried not to lose balance in the shower. Looking down at his handiwork, he thought again how beautiful she looked, and not just because she was naked and his cum was sliding down her body. Kerry smiled up at him, "Are you done with the shower? Cuz I think I need to get in." He tried to argue that he should be able to stay in with her - or at least stay and watch - but she kicked him out of the bathroom completely. She needed to get herself off.

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.