Wanna Bet? Read online

  Almost whimpering, Kerry spread her legs to allow him easier access, too aroused to be shy 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 around her outer labia he enjoyed the scent of her, the juices that were leaking down into her butt crack and the way her pussy moved against him as she rocked her hips.

  The sensation of his mouth massaging her outer lips was as different from her fingers as night and day. She wanted to feel his tongue on the inner fleshy part, feel it parting her lips.

  “Please, Derrick, more…”

  Carefully he started licking back and forth horizontally and she cried out in frustration as his tongue barely flicked over the inner lips. Pressing her hips upwards she reached down to grab his hair, trying to pull him more firmly against her aching flesh. As her hips went up Derrick slid his hands under her buttocks and grabbed each cheek, holding her up slightly off the bed and he finally dove in.

  Licking all the way along her inner slit, he tasted her sweet, musky juices. Kerry thought she was going to scream with pleasure as his soft tongue pressed into 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 actually 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 the firm muscle wriggled inside of her. She clutched at his hair as he licked and sucked, feasting on her pussy flesh and the sweet honey coating it.

  Taking a trick from 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 before moving his mouth up to her clit and sucking the little bud into his mouth. Kerry went wild beneath him, thrashing and crying out his name.

  As he sucked hard Kerry screamed, her passionate orgasm heightening to peaks she’d never thought possible. When he bit down gently on the sensitive nub, his fingers still tugging at her nipples, she sobbed with the incredible stimulation as waves of ecstasy crashed over her, pounding at her body. She rode them out until she gasped and lay quiescent, Derrick’s tongue lapping at the juices that had spilled from her.

  But she didn’t know that he wasn’t finished yet. Taking one hand from her boob he brought it down and slid two fingers into her soaked hole. Kerry gasped as she felt the penetration, her eyes flying open with shock as she stared down her body to see Derrick still focused on her wet folds.

  Marveling at the tight feel of her pussy around his fingers, Derrick pumped them gently back and forth, enjoying the throaty cries that his touch elicited from her throat. He tried to imagine what it would feel like to have his dick encased in this warm, wet tunnel and almost exploded inside his jeans. The sensitive pads of his fingers found a small ridged spot. According to his online reading that must be her g-spot. This was his first time with his fingers in a pussy, but if there was one spot that felt different and only one then that had to be it, right?

  Gently rubbing his fingers across that little spot he continued to lick and suck at her pussy flesh around the hole he was penetrating. Kerry’s hips began to move again, following the pumping rhythm of his fingers.

  “God Derrick… oh my god that feel so good…”

  Man he loved to hear her talk. Her words motivated him to increase the pace, pressing harder on that little ridge spot. She writhed, her thighs tightening around him as an entirely new sensation began to build deep inside of her, a more powerful orgasm than the one she’d already experienced.

  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 for her though because she kept doing it as he rubbed. Her movements got faster and faster against him and he started sucking on her clit again. The two different kinds of simulation had Kerry going off the wall with pleasure.

  When she came it was the hardest she ever had, a wailing cry that turned into a hoarse scream of ecstasy as the rapture overwhelmed her. Her body rocked as she rode out the entire intense orgasm, her fingers entwined in Derrick’s hair as he finished her off, thoroughly enjoying watching her come apart for him.

  Slowly her body began to relax again, nerve endings tingling as her breathing returned to normal. Derrick withdrew his fingers from her pussy, making her moan a little.

  “Don’t touch me… everything’s tingling… I don’t think I could take it…”

  Derrick smiled, looking incredibly smug as he had every right to be. He also looked rather strained. “That’s okay, do you think I could use your bathroom?”

  Kerry nodded and then closed her eyes, thinking that if he had touched her again she would have burst. Her body felt raw with pleasured stimulation, almost painful. Damn but that bet had been worth it. No wonder she had been feeling rather jealous of the idea of someone else going after Derrick, after all the pleasure that he’d been getting from her lately, of course she wanted to get some from him too.

  In the bathroom Derrick braced one hand on the wall as he quickly released his cock from his pants. It only took a few hard strokes of his cock with the taste of Kerry still on his lips and tongue, the image of her writhing for him imprinted on the back of his eyelids and then he was gasping as semen spurted into the tissue he had wrapped around the head of his dick.

  Leaving the bathroom he returned to Kerry’s bed and crawled next to her, pulling her into his arms. He didn’t question his need to cuddle with her or the way that she wrapped herself around him. That was just what friends did sometimes. Okay so maybe they didn’t do it naked, but he and Kerry were special friends.

  “Kerry?” he whispered, stroking her hair. “Are you okay with this?” He wasn’t entirely sure what he meant by this. The cuddling? The bets? The ever changing boundaries of their friendship?

  “Mmmm hmmmm.” She nuzzled her face into his chest hair and he cradled her against him.

  They ended up falling asleep. Waking up together the next morning could have been awkward if they both weren’t running late. Moving quickly they got out the door, laughingly goading each other into hurrying. They’d had sleepovers before, just not naked ones.

  Oh well, Kerry thought. Shit happens sometimes. Maybe she should drop a hint to Janice that she and Derrick were having naked sleepovers. The other girl probably wouldn’t be so interested in Derrick if she knew that he was having naked sleepovers with Kerry. It would just be for Derrick’s sake, of course, since he wasn’t into Janice.

  Chapter 4

  When the summer Olympics started both Kerry and Derrick were thrilled. So many different things to bet on! They got together to watch the 200 butterfly, randomly choosing it from the many swimming events, and divided up the participating swimmers.

  This time Derrick came prepared with a little surprise for Kerry. They were getting closer and closer to what was seeming like the inevitable conclusion, but he wasn’t ready to completely give in yet and he didn’t think she was either. So he’d gotten creative with what he’d wager.

  “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. Smaller than Derrick, in fact. He held out his hand with a small black remote in it. “I’ll be controlling this part.”

  Kerry just laughed at him. “Fine, but if I win then you’ll eat me out while you masturbate for me.”

  “Well that just sounds awful,” he teased her. Kerry stuck out her tongue at him and he surprised them both by leaning over and kissing her, sliding his own tongue into her mouth. For a moment he felt her hold back and then she leaned in, kissing
him back and he groaned, pulling her hard against him and just enjoying the intimacy of a kiss with her.

  Pulling away, because he found himself wanting to do more, Derrick tried to cover how much that kiss had affected him. He didn’t want to ruin their friendship. “Better not stick out that tongue unless you’re planning on using it.”

  “Uh huh,” Kerry said, looking a little dazed. Had the kiss had the same impact on her that it had on him?

  Just then the race started and they both turned their attention to the television.

  Derrick whooped and cheers as two of his picks came in first and second. Flicking off the television he tossed the dildo to Kerry with glowing eyes.

  Just as she had found it exhilarating to strip for him when he was masturbating for her, Kerry found that her body thrilled a little to the idea of masturbating in front of him. Heck, she’d had trouble not doing so at the end of their last bet! The furtherance of the intimacies between them was both exhilarating and frightening. The most reassuring part was that Derrick seemed as into the escalating wagers as she was, he certainly wasn’t pulling back from them at all. And he wanted to see her naked. And playing with herself.

  Janice was definitely not on his mind, she thought a little smugly to herself.

  The echo of Missy’s phone conversation with her echoed in her head, but that wasn’t why she decided to give Derrick a little strip tease. It wasn’t at all. She just felt like doing it.

  Tossing him a teasing little smile, Kerry flicked her tongue out and licked her lips as she began to tug her shirt upwards, enjoying the way his eyes darkened with lust. The prominent bulge at the front of his pants declared that he was already very interested in what she was doing. His eyes were glued to the lacy fabric covering her breasts as soon as it became visible. Kerry had gotten in the habit of wearing her best underwear when hanging out with Derrick, just in case.

  Rather than immediately stripping off the bra, she pressed her arms against her breasts to create a deep cleavage as she leaned forward and unsnapped the back clasp. Derrick was practically panting as she let the lacy covering fall from her body and onto the floor. Slowly she undid the button and zipper on her jeans, turning around so that he could appreciate the slow uncovering of her ass.

  She was gratified to hear him let out a low moan as he realized she was wearing a thong, the thin strap bisecting the creamy swells of her ass. The jeans dropped all the way to the floor and she stepped out of them, heading over to the arm chair that was directly across from his seat on the couch and picking up the dildo on the way. Placing the fake penis on the chair, she turned around to watch his face as she hooked her thumbs over the waistband of her thong and lowered it to the floor.

  Derrick’s eyes were practically glazed with lust, his right hand pushed down into the front of his jeans, too turned on to even try and control himself. In his left hand he held the remote. Kerry had never felt so sexy in her life, knowing that she was the reason for that look on his face and in his eyes, knowing that she was the reason he’d thrown competitive pride away and wasn’t even bothering to pretend that he didn’t want to masturbate.

  Sitting down on the armchair she slowly spread her legs to the sound of another low groan from Derrick. Looking straight at him she leaned back in the chair, scooting her ass forward and letting her legs dangle over the sides of the chair, opening her body to him completely so that he could see how wet she was.

  “Fuck Kerry, you’re so gorgeous,” he said, his hand moving up and down in his pants.

  “Do you like this?” she asked, her voice husky as she trailed her fingers over her breasts before cupping them and squeezing the aching mounds.

  Derrick groaned again. “You have no idea how much I like watching you do that. Pinch your nipples for me Kerry, I want to see you.”

  “Mmmm.” The small sexy noises she made as she rolled her rosy buds between her fingers were driving him wild. “That feels good… I can feel it… all the way…” one of her hands started to slide down the soft skin of her stomach and Derrick almost whimpered “down here…” She brushed her fingers over her pussy before pulling them up by her clit. “OOooo I’m so wet.”

  Her nipples were hard as diamonds as she released them completely, using the hand that wasn’t in her pussy to grab the dildo. Derrick looked like he was ready to leap across the room at her and under his lustful gaze she found all of her inhibitions completely flowing away. She loved the way he was looking at her, like he was seeing some kind of sex goddess rather than his best friend.

  Circling her clit with one hand, Kerry rubbed the head of the dildo up and down her wet slit, enjoying the moist noises it made as it traveled through her center. Derrick’s breathing was getting heavy and the hand in his pants never stopped moving. Rubbing the dildo back and forth in 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 a little with each slide, stretching out the entrance to her pussy. Breathlessly excited, Derrick pushed the button on the remote that turned the vibrator on to its lower setting. Kerry shuddered with pleasure as it unexpectedly came to life right on top of her clit.

  “Oh… Derrick…” She pressed it firmly against the aching bud, her back thrusting against the wonderful stimulation, before running the dildo’s length back down her pink wetness. This time she pressed a little bit more of it into her hole and rather than pulling it all the way back out she started working it back and forth in her pussy, pressing it a little deeper each time. Derrick felt faint with lust as he watched her pussy stretch around the toy, its first few inches buzzing inside of her body. Thinking about what it would look like if that dildo was him, making love to Kerry.

  With every stroke its slick shaft pressed more deeply into her and he turned up the intensity to the second of its six levels and changed the vibration cycle to “pulse.” Kerry gasped as the vibrator started to pulse 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 halfway out before shoving it back into her fully.

  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 him inside of her. Groaning, he fisted himself furiously, watching and imagining what that gorgeous, wet pussy must feel like.

  Turning the intensity up again he clicked it over to the wave cycle. Now the vibrator went from its lowest intensity to the fourth level in quick little waves that flooded through her, teasing and manipulating her pleasure spots. Shuddering, she held it inside of her as the waves became more intense and her both writhed in sensual abandon.

  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 control of it. Instead she reached up and started playing with her aching nipples, adding to the sensations that were rippling over her body. She actually preferred him controlling the vibrator completely, adding to the illusion that they were making love.

  Twisting the toy back and forth, Derrick took a moment to add the clit stimulation attachment and press it against her swollen nub. Kerry almost screamed with pleasure as the rubbery attachment fluttered against her. She could feel or orgasm rising deep in her belly, her hands clamping down like suction cups over her breasts as she humped her hips up and down, working her way to a glorious climax.

  Derrick turned the vibrator to its highest level and changed its rotation to ‘twist’ so that the end of the dildo started gyrating inside of her, supposedly guaranteed to press against her g-spot with every rotation. It was half the reason he’d bought the toy. And the results were more than worth it to his eager eyes. It looked like she practically levitated as her body arched and she cried out, her hands releasing her bouncing breasts and reaching upwards to hold onto the headboard for dear life as she began to convulse.

 
As she screamed his name, Derrick groaned, rubbing his hand against the front of his pants as he watched her splinter apart in an incredible release. The smell of her pussy filled the air as she flooded. Holding the toy inside of her, he slowly lowered the levels of intensity so that her orgasm was long and drawn out without ever becoming painful from too much stimulation – just like the girl at the store had told him to do.

  When Kerry was finally calm, he was grinning at her in pure masculine triumph as he pulled the vibrator from her satisfied pussy; her folds still tender and sensitive from the ecstasy he’d brought her.

  “Thank you,” she said, breathing the words out on a sigh as she opened her eyes.

  “My pleasure,” Derrick said, his voice sounding slightly strangled. He felt like his cock was about to burst out of his jeans in an attempt to rub itself all over her wonderful body.

  Noticing the straining bulge Kerry grinned and sat up, leaning over to undo his pants. Completely surprised and speechless, Derrick could only watch in amazement and abject relief as she voluntarily pulled his dick out and pressed her mouth over him, taking his painfully hard erection into her warm, wet mouth. He groaned, his hands coming down on the back of her head as she sucked him deep, her hand fisting the part that didn’t fit into her mouth. Almost as soon as she’d bobbed her head a few times his over excited dick throbbed.

  “I’m going to cum,” he warned her, his hips straining upwards. Kerry just sucked harder and he moaned her name as his balls tightened and the cum came boiling up and into her mouth, her lips sliding down the farthest they’d ever gone as she swallowed eagerly. She kept suckling him until she’d drunk down every drop and he was beginning to soften inside her mouth.

  “Thank you,” he said fervently as she sat back up with a pleased smile on her face.

  Chapter 5

  Kerry and Derrick’s relationship seemed to have taken a bit of a turn after that. She could tell that he was still interested in pursuing the bets, but that he was nervous about it. After all, they kept pushing a little farther each time and it was like they were both dancing around the subject of actual sex. For the next couple of weeks they hung out at each other’s apartments, had occasional dinners together, watched some movies and did their normal friend stuff. They even watched some of the Olympics without making any further bets.