Wanna Bet? Page 2

  “God Kerry, that’s so hot,” he said, drinking in the sight of her sweet lips wrapped around him so intimately. “You have no idea how good this looks.”

  The dirty talk really did seem to be turning her on as she gave him a pleased look, her breasts swollen and fleshy in his palms.

  With just the head of his dick in her mouth, he jerked with the sudden sensation of her tongue laving 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 breasts became like suction cups as he kneaded and massaged them in response to the incredible sensation of her mouth enveloping him. Very lightly her teeth would occasionally graze against him, but not at all painfully.

  He tried as best he could to let her control the motions as she took him deeper into her mouth, not wanting to overwhelm her. Eventually she couldn’t take any more of him, her gag reflex just couldn’t handle it, and so she wrapped her hand around the base of his cock. 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 amazing thing that he’d ever experience. It felt wonderful, wet and soft, and he could feel all of her mouth just moving up and down as she bobbed her head.

  He knew that whenever he masturbated after this, this would be the image in his head: Kerry on her knees with her lips wrapped securely around him and her tits filling his hands, flesh jiggling as she sucked him. With every stroke she became more and more competent at finding what felt the best, her free hand started to massage his balls as she continued to stroke. The unevenness of the movements between her mouth and hands just added to the sensation. When she tugged gently on his ball sack and just about lost it, his hips jerking upwards uncontrollably.

  Humming with pleasure at the obvious success, Kerry drove him wild as the vibrations played over his shaft and she tugged his balls again, still gently but a little harder than she had the first time. Derrick was writhing, his hands releasing her breasts and holding the back of her head, completely lost in the incredible sensation of her sucking mouth.

  “Kerry…” he groaned, trying to be considerate. “I’m going to 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, her tongue lashing the underside of his cock as she swallowed his cum. Her hand never stopped moving on his balls as she sucked every last drop from him, making him shudder with an aftershock of pleasure as her tongue slid over his pee-slit in a quick, cleaning swipe.

  “Holy fuck Kerry…” he said, breathing hard as she sat back on her heels, looking proud of herself. “That was amazing.”

  “Yeah, it was,” she agreed. The taste of him was still in her mouth and she had to admit, she didn’t hate it. Not at all. Actually what she really wanted to do is go home and play with herself.

  “So um, are you hungry?” he asked. And then blushed as he realized what he’d just said. “I mean, for food.”

  Kerry laughed. “Yeah, let’s get something to eat.”

  And just that easily they slid back into their friendship, almost as if nothing had happened. If Missy and Janice had been there they probably would have banged their heads on the wall.

  Chapter 2

  “Okay,” said Kerry. “So if any of the horses on my list win, you have to eat me out.” Since last weekend when Derrick had introduced oral sex into their bets she didn’t feel awkward at all about wagering it again this weekend. She kind of hoped that he’d keep the same stakes, she’d rather enjoyed giving head and she wouldn’t mind trying it again now that she knew what to expect.

  She was grateful that during the week their friendship hadn’t seemed to change at all just because they’d gone a step further with each other sexually. Although when they’d been out with their friends for dinner on Wednesday night Derrick had kept his arm wrapped around her shoulders and glared at Brad a lot. He glared at Missy and Janice too strangely. Although she’d felt like glaring at Janice a few times herself, she kept flirting with Derrick even though he obviously wasn’t interested. Maybe that’s why he’d kept his arm around her, maybe it didn’t have to do with Brad at all. But for some reason she seemed to like the idea of him being jealous better than him just using her as protection against Janice. It was kind of weird but she didn’t let her mind dwell on it.

  “And if any of the horses on my list win, I want to watch you masturbate.” Derrick grinned at Kerry’s obvious surprise.

  “Oooo… I actually like that even better! I’m changing mine, if I win then I want to watch you masturbate.”

  It amazed her how creative Derrick could be when it came to their bets and how he pushed the boundaries. She liked it. Sure, she wanted to know what it was like to eaten out, but at the same time she was feeling a little shy about having Derrick so close to that part of her. And she rather liked keeping their bets similar.

  “Really?” Derrick was surprised that she wanted something which seemed like it would benefit him more than her. Of course, the reverse could probably be said to be true, but he knew that watching Kerry get herself off would be a memory that he’d hold onto for a long, long time.

  She laughed at him. “Hey, I’ve always wondered what it looks like when a guy masturbates. I’d rather get that one first, it’s a good one. And if we keep betting like this, eventually you’re going to have to eat me out anyway.”

  “Have to, right,” he said, rolling his eyes at her. “It will be such a hardship.”

  “Whatever, you still don’t like losing.”

  Well that was true. Of course, he always hoped to win. But this time he especially did so. He’d rather eat Kerry out than masturbate in front of her. Somehow it just seemed… embarrassing more than hot to think about getting himself off with her watching because she was curious. If she’d said she thought it would turn her on then that would be different.

  ********

  “GO! GO! GO! GO!” They were both screaming as two of their horses jockeyed for first place on the final stretch. Kerry screamed in triumph as Windfoot crossed the line ahead of the Red Baron and Derrick groaned, falling back on the sofa in defeat.

  With gleaming eyes she turned to him, clicking off the television with the remote. “Okay, so where do you want to do this?”

  Derrick flushed. “I usually do it in the shower,” he mumbled.

  “Okay, let’s go!” Obviously excited at her win she grabbed his hand and practically dragged him up the stairs. “I can’t wait to see what this looks like.”

  He groaned again, allowing himself to be pulled along because he honored his bets, but he was so not feeling sexy right now. Plopping down on the toilet, fully clothed, Kerry watched him intently as he stripped down and got in the shower. It wasn’t exactly the situation that wet dreams are made of.

  Looking down at his flaccid dick, Derrick looked at her pleadingly. “Kerry, I don’t know if I can do this. It’s just too weird having you watch me. I feel like a science experiment. It’s not exactly a turn on.”

  “Okay, I see your point,” Kerry said with a sigh, standing up. “You don’t have a lot for stimulation in this situation.” Pausing, she bit her lip. “Well, you didn’t win, but I guess it won’t hurt cuz if we keep doing these bets then you’re going to see this soon 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, just as perky and gorgeous as he remembered. In fact, he could also remember how great they felt in his hands 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.

  “Well this is certainly helping.” She smirked at him. He couldn’t answer because as soon as she said that she turned her back to him and started wriggling her
ass in his direction as she slid her pants all the way down to the floor. The silky pink underwear was barely stretched over her firm cheeks and his hand involuntarily went to his dick, slickly pumping it to relieve the ache that was beginning to build.

  Turning, Kerry started to watch him but now he felt almost no awkwardness at all – he was too busy watching the gentle sway of her breasts. Smiling sexily at him, she hooked her thumbs into her panties and slid them down and he could feel his dick pulsing in his hand. She watched as he moved his hand up and down his shaft, his thumb rubbing against the mushroom head every time he reached it, squeezing it roughly as he started to pick up speed. His dick was slick and wet with the shower and she found herself remembering what it was like to suck on it. Licking her lips at him, the gesture wasn’t lost on his sex-wired mind and he moaned.

  Using one hand to cup his balls, as she had during their last bet, his hand never slowed his movement across his dick as he took in the full sight of her naked body. 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 of her labia, 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. He was going to masturbate to this scene a lot, he thought to himself as he tried to memorize every gorgeous detail about her body.

  “Mmm that’s so hot,” she said, lowering her voice sexily. “I like watching you touch your cock.” Derrick groaned, appreciating the dirty talk.

  Spreading her legs a little wider to give him an even better view as she watched him jerk off to her naked body, she found herself wanting to touch herself in response. It was really kind of hot to watch him masturbate and even hotter to know that he hadn’t been able to get it up until she’d gotten naked for him. He wasn’t just masturbating, he was masturbating to her. But since watching her play with herself was something he wanted to use for a bet she wasn’t going to give it to him for free. Instead she just concentrated on enjoying watching him jerk off, the water from the shower sluicing over the hard muscles of his body, the way his strong legs were braced to hold himself up as he cupped himself, his hand moving over every inch of his cock.

  For his part, Derrick could see the way her pussy glistened with juices, clear evidence of her arousal even if her nipples hadn’t been all puckered and hard. For him that just made it even better, even hotter, and he could feel the familiar tingle in his balls. Watching her eyes glow as she watched him, he gritted his teeth and almost 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 a contrived look of innocence on her face she said, “Spray it on me.”

  With a groan he obeyed almost instantly at her raunchy words. Spurts of frothy cum sprayed 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 his balance at the force of his orgasm. Looking down at his handiwork he felt one more pulsing jet rush through him. She looked beautiful and not just because she was naked and his cum was sliding down her body, although he really liked the way that looked too.

  Kerry smiled up at him. At first she’d been a little taken aback by the intense look that Derrick gave her, but then she realized that he was still looking lustful even though he’d just cum. Obviously he liked the way she looked and suddenly she felt sexy with his cum on her. But that didn’t mean that she could walk around for the rest of the day with this.

  “Are you done with the shower now? 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.

  Chapter 3

  “So what do you think of Brad?” Missy asked. She’d called Kerry up to invite her to a girls night out and the conversation had taken an inevitable turn to boys.

  “He’s nice,” Kerry said noncommittally. It was true, he was, but he didn’t really do anything for her. Not just because Derrick didn’t seem to like him, of course. But he just didn’t rev her engines enough. Sure, she and Derrick weren’t a couple or anything, but didn’t that mean that she needed to be more attracted to any guy that she dated than she was to her best friend? Otherwise it wouldn’t be fair to the guy. She shouldn’t be more excited about the best with her friend than about her dates.

  “Just nice? Cuz I think he’d like to ask you out.”

  “Just nice,” she said firmly. “Maybe you should hook him up with Janice.”

  “Mmm. I think she’s still interested in chasing Derrick,” Missy said. “Do you know if he’s interested in her? She said he’s been blowing kind of hot and cold and she can’t tell if he’s just playing hard to get or what.”

  The overwhelming feeling of jealousy that rose up in Kerry was almost shocking. It was just because she didn’t think Janice was right for Derrick, of course. Nothing else. Just because their bets had been getting more intimate physically didn’t give her a claim on him or anything. And she didn’t want one. Just… argh. She pushed her emotions away to be dealt with at a later date.

  “He hasn’t said anything,” she finally responded. Which was true. There was a hard edge to her voice. Did Missy hear it? She hoped not. With some effort she tried to make herself sound more cheerful. “I think he probably would have if he was though.” Dammit. Now she did sound possessive. Or jealous.

  “Hm. Maybe,” Missy said.

  “Maybe? What’s that supposed to mean?” Kerry snapped her mouth shut, horrified to realize how much like a jealous girlfriend she sounded. Derrick was just her friend. Her best friend. Whom she’d fooled around with a little. She had to remember that.

  “I didn’t mean anything really. Is there something going on with you and Derrick? I can tell Janice to back off if you want.”

  “No,” said Kerry stoutly. “Janice can do whatever she wants.”

  Why did saying that make her suddenly feel like it was hard to breathe?

  ******

  Going over to hang out with Derrick on Tuesday was a relief. They ate dinner, laughed, talked and when she mentioned Janice in passing he rolled his eyes and made a face. After that she felt much better and challenged him to a Jeopardy bet. They didn’t usually do bets during the weekdays but heck, why not. It didn’t have anything to do with her feeling relieved about his disinterest in Janice or anything like that. It just seemed like it might be fun.

  And Derrick was certainly willing to jump on board.

  Kerry cheered at the end of Jeopardy when her chosen person one and Derrick was smiling too. This time she’d bet him that if she’d won he’d have to eat her out. Sure he wasn’t going to get his own satisfaction until later, but he’d been looking forward to doing this with Kerry. In fact, he’d almost been hoping to lose, even though he would have enjoyed watching her masturbate for him.

  The only thing Derrick was worried about was that he’d be bad, but ever since the first time she’d wagered being eaten out he’d been asking some of his friends and gone looking online for tips and how-to’s. He thought that he’d probably be alright.

  Getting her laid out on the bed, Derrick started to unbutton her shirt.

  “Hey that’s not part of the deal!” Kerry laughed as she put her hands up to stop him.

  “I have to get you in the mood though,” he said persuasively. “I want to lick and suck on your nipples and get you all nice and wet for me to lick.”

  “Mmmm.” Kerry moved her hands to run them up his arms and onto his shoulders, liking the naughty talk. Truthfully she didn’t mind him getting his hands
and mouth all over her, she just hadn’t really thought it through. She allowed him to finish unbuttoning her shirt and get it and her bra off. Immediately he started massaging her breasts, lowering his mouth to her nipple for the first time. “OH!”

  Kerry’s back arched as Derrick began to suck on the tender pink bud, turning it to a hard little nubbin in his mouth as her body responded to the pleasurable stimulation. It was very different from having him pinch it with his fingers. His mouth was hot and wet around it, his tongue flicking it as he sucked. When he nibbled very gently she moaned in appreciation, running her hands through his hair. The sensation seemed to go straight between her legs, turning her on incredibly.

  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 this 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 other one in his mouth. Kerry was moving her hips against his body now, rocking against the leg that he had wedged between her thighs. His dick was aching to be freed from his jeans but this time wasn’t about him.

  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 he finally released her breasts to undress her, slowly. He pulled her pants and panties off at the same time, looking eagerly 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.