Wanna Bet? Read online

  Wanna Bet?

  By G. Angel

  Published by G. Angel

  Copyright 2012 G. Angel

  This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you’re reading this book and did not purchase it, or it was not purchased for your use only, then please return to amazon.com and purchase your own copy. Thank you for respecting the hard work of this author.

  Thank you to all of my fans on Literotica who have encouraged and supported me!

  Table of Contents

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 1

  Derrick was walking through the party, feeling particularly bored, when he heard two of Kerry’s other friends just around the corner.

  “We have to do something about Kerry and Derrick,” Janice was saying, her high nasal voice almost too easy to hear. Anger rushed through him. Do something about them? God, were people never going to give it up? Just because he and Kerry had been good friends, best friends, for years and okay, so they’d made a few bets with each other that had occasionally had a slightly romantic or sexual bent, that didn’t mean that they would make the perfect couple. They both agreed on that even if no one else did. She’d been his first kiss and the first pair of breasts that he’d seen and touched, and she was beautiful and attractive as all hell… but… okay so he couldn’t think of a good reason for them not to be more than friends, but that didn’t mean that he wanted to mess up the fantastic friendship that they had.

  Why couldn’t people just leave them alone? They had a wonderful seven year long friendship, they were twenty years old, why did that mean that suddenly everyone thought they should automatically be a couple?

  Missy’s softer tones broke through his fuming. “I know. Brad should be here any minute now. Where’s Derrick? If we can keep him away from Kerry long enough then maybe he won’t be able to mess this up for her.”

  Wait what?

  “I’ll keep him occupied if I have to drag him off to a bedroom myself to do it,” Janice vowed, making Derrick shudder a little. The vulpine, super skinny, overly impressed with herself Janice always wore too much make-up with too high heels and too tight of clothing and she was so not his style. “Kerry needs to meet someone else and she can’t do it with Derrick always cock blocking.”

  “I don’t think it’s intentional,” Missy pointed out. Which was true. Had he been cock blocking? He didn’t mean to be. Okay, so granted, so far none of the guys that Kerry had dated were good enough for her. And he had no problem telling her so. He was also the guy that she went to when she needed to get an overly eager suitor off her back and he’d never minded pretended to be her boyfriend. She did the same for him often enough.

  “No, but it happens. At this rate she’s going to be a virgin for the rest of her life because Derrick’s obviously not into her but he’s not giving anyone else a chance to get into her either.”

  Wait… hey now… they were making him sound awful. Like he was deliberately messing up Kerry’s life. And he had to admit, the idea of her friends setting her up for sex didn’t appeal to him. He and Kerry had been each other’s firsts for so many other things, was part of him assuming that they’d be each other’s firsts in that area too?

  Now that he thought about it, it was a little weird that neither he nor Kerry ever managed to make it very far in a relationship. The farthest they’d gone sexually had been with, well, each other. And it was usually because of a bet. That’s how they’d kissed for the first time. And how he’d gotten to second base. It wasn’t intentional that the farthest they’d gone had been with each other. It had just kind of happened that way.

  And who was this Brad character that they were talking about? Did he know he was being set-up? Did he know that Kerry was a virgin? Is that why he was coming here to meet her?

  Hell no. An asshole like that didn’t deserve her.

  Swerving back the way he’d come so that he could avoid the plotting girls, he went off in search of Kerry. Maybe his cock blocking before hadn’t been intentional, but tonight it definitely would be.

  *****

  “He’s gone,” Brad murmured, giving Missy and Janice a quelling look as they giggled. “You two are lucky that he couldn’t see your faces, you’d have given the entire game away.”

  Janice rolled her eyes. “Whatever. It worked didn’t it? I told you it would.”

  “Good for you, but we’re not done yet. Get your ass out there and try to ‘occupy’ him so that he doesn’t get suspicious. Brad and I will find Kerry in five minutes,” Missy said, smacking Janice’s ass to get her moving.

  “Ouch! Yes ma’am!” Janice disappeared into the crowd, following the path that Derrick had taken.

  ******

  Kerry was shocked to see Janice hanging off of Derrick’s arm across the room, her breasts pushing up against his chest as she talked to him. For some reason she had the urge to go and tear her friend off of him. Which was stupid. It wasn’t like Derrick belonged to her, even though people so often thought they were a couple. They weren’t.

  Yeah, they’d kissed. And done some other stuff. But that was just because she hadn’t found anyone else to do those things with. No one that lasted past a couple of dates and kisses; guys just didn’t interest her in that way. It was hard to find a good guy when she was constantly comparing them to her best friend and they always came up short. Derrick was fun, funny, charming, easy-going and they rarely ever fought. Even when they got competitive with each other, it was always in a fun way.

  Heat bloomed in her cheeks as she remembered the last time they’d made a bet and ended up making out, his hands up her shirt as he played with her breasts. She had to admit, she’d kind of wanted things to go farther then. Her nipples hardened at the memory.

  She was just so much more comfortable exploring her sexuality with Derrick than with some random guy that she met at a party or through a friend. Derrick was trustworthy. Loyal. He never pushed her farther than the boundaries of the bet. But she didn’t want to ruin their friendship by bringing romance into it.

  Especially because he was a pretty popular guy and he seemed to feel the same way. Not that he’d ever gotten serious with another girl, in fact she was pretty sure that they’d both gone farther with each other than they had with anyone else. But that didn’t mean eventually he wouldn’t. And she didn’t like feeling jealous or insecure. So nothing beyond friendship between them. Dates were replaceable but best friends were forever. That’s how she saw it anyway.

  Even if seeing Janice all over him made her grit her teeth. It was just because she didn’t think Janice was good enough for him really. She didn’t understand Derrick and she wouldn’t want to. Janice was a nice person but she could be a little superficial; she’d never get her feet dirty wading through creek beds with him or enjoy getting mud spattered during a football game. But what if that was the kind of girl that Derrick actually wanted?

  Well that wasn’t the kind of girl that would make him happy in the long run. In fact, he was shooting frantic little glances at Kerry right now, obviously hoping that she would come rescue him.

  She was just about to head over to do so when Missy called her name and she turned to find her friend standing next to a very good looking blonde.

  “Hey Kerry! How’s the party? This is my friend Brad. Brad, this is Kerry.”

  Brad smiled, an easy going, almost lazy smile. She had to admit, he was extremely good-looking. Kind of the antithesis of Derrick actually. While Derrick had dark hair and eyes, Brad was blonde haired and bl
ue-eyed. He was wearing a button down shirt and khakis as opposed to Derrick’s normal attire of t-shirts and jeans with holes in the knees. And he was looking at Kerry with a kind of… intent in his eyes.

  “Hi, nice to meet you,” she said, feeling unaccountably nervous, putting her hand out to meet his. To her shock, he used her hand to pull her closer to him so that she had to look up to meet his gaze, rather than shaking it.

  “Very nice to meet you too,” he said in a lazy drawl, his eyes hinting that there was a secret message for her underneath the words. She blushed, unsure of how to handle herself, and was about to automatically look over her shoulder towards where she’d last seen Derrick, her trustworthy shield, when a heavy arm suddenly lay across her shoulders and pulled her away.

  “Hey sweetheart,” Derrick said, his voice sounding somehow deeper, his hand curving possessively around her arm. Being encircled and pulled against his side sent a feeling of relief sweeping through her. She didn’t know Brad well enough and she was uncomfortable with flirting with guys that she did know, so Derrick’s intervention made her relax. Immediately she curled his arm around his waist. “I was looking for you.”

  “Hi,” she said, smiling up at him. He smiled back at her but there was something in his eyes that she had never seen before, something almost threatening. Then he looked at Brad and his smile became razor sharp, but Brad was still looking at her, almost completely ignoring Derrick. “Um, Derrick, this is Brad, Brad, Derrick.”

  “Derrick is Kerry’s best friend for forever,” Missy said brightly. “He’s like a big brother to her.”

  Big brother? That wasn’t exactly how Kerry would describe it. Derrick was glaring at Missy, Missy was smiling brightly at Brad and Brad was still looking at Kerry with a small, little smile that made her blush. Was he interested in her? Even with Derrick hanging over her? That was unusual. Usually when Derrick showed up on the scene, other guys backed off. But it sounded like Missy was intentionally making sure that Brad knew Derrick and Kerry weren’t an item.

  “That’s nice,” Brad said, his smile growing. “Would you like to dance?”

  “Um…” Kerry glanced at Derrick, who was now practically seething. For whatever reason he didn’t like Brad, obviously, but she didn’t see anything wrong with the guy.

  “Derrick, how could you just ditch me like that?” Janice suddenly appeared on Derrick’s other side, actually batting her eyelashes up at him. As he turned his head to give her a smile, Kerry suddenly felt sick. So he could flirt with Janice, who was wildly inappropriate for him, and let her rub her boobs all over his body, but she couldn’t just go dance with Brad?

  “I’d love to,” she said to Brad, pulling away from Derrick. Keeping her back to him, she missed the enraged look that he gave Brad as the other man took her to the next room where people were dancing.

  As far as Derrick was concerned the rest of the party was pretty much pure torture, with Janice doing her best to block him from cock blocking Brad and him trying not to be obvious about the fact that he really, really wanted to cock block Brad. He was so not good enough for Kerry.

  It didn’t have anything at all to do with the fact that the bets between him and Kerry had gotten more and more sexual. Or that he wanted them to go even further. And the little voice in the back of his head that was saying mine every time he looked at her with blondie was just because he was protective of his best friend.

  Really.

  *******

  “What?” gasped Kerry, completely shocked. She’d been more than happy to come over to watch the baseball game at Derrick’s house, partly because she liked baseball and partly because she’d been eager to make another bet with him. Plus he’d been acting really strange at the party the other night and she wanted to know what was going on with him. Of course, when she asked him it was all she could do not to roll her eyes when he explained to her how wrong he thought Brad was for her.

  For one wild moment she wondered if he was jealous of Brad and if that’s why he’d upped the stakes so outrageously.

  “Yeah,” he said, leaning back in his chair and brushing his dark hair out of his eyes. “You’re so sure the Cardinals are going to win then you won’t mind taking this bet.”

  He grinned at her, obviously enjoying the confliction she was feeling. Kerry wasn’t one to back down from a challenge, but at the same time oral sex was much higher stakes than they’d ever played for before. This wasn’t just fooling around, this was getting serious. On the other hand, she really did trust Derrick and they’d done a lot of firsts together. The idea of being the first woman to go down on him, to lick and taste him… well it definitely had its appeal. As for turning it around on him, that had its appeal too.

  “Fine,” she said, smiling sweetly and leaning forward so that he could scope out her cleavage. “And if I win then you’re going to lick my pussy until I cum.”

  Kerry’s smile broadened as she looked down at Derrick’s crotch and saw the blatant evidence of his arousal at her words. The two of them just couldn’t help throwing down the glove for the other and she found herself really enjoying how her crass words had obviously turned him on. The lustful look he was giving her was doing a fair job of getting her engine going as well.

  “Kinda sound like I win on both ends,” he said, his voice husky. She licked her lips, which suddenly felt dry. God, they were really doing this. Already she could feel her nerves humming with anticipation.

  “Except that you’ll have to go home and whack off if I win,” she said, hiding her nervousness with a show of bravado. “I hope you’re reading for a time with Rosie and her four sisters.” She winked at him.

  They both laughed at that, lightening the sexual tension which was hanging heavy in the room. Watching the game was particularly exciting now, both of them flirting with each other and eyeing each other with sexual intent. Kerry could tell that Derrick had a hard-on the entire game and she had to admit to herself that her pussy was getting wet just thinking about the inevitable end. One way or another their relationship was definitely going to be changed by this, now that they weren’t just tip toeing around their attraction to each other.

  By the ninth inning Kerry was sitting on his lap and his hands were up her shirt, playing gently with her breasts. They just hadn’t been able to help themselves. She could feel the hard bulge of his erection pressing against the soft swells of her butt and she entertained herself by wriggling on top of him as he pinched her nipples. She was so horny that if she did lose then she’d definitely be going home to play with herself afterwards. Although part of her had thought that she shouldn’t have climbed onto his lap or let him play with her breasts, since that wasn’t part of the bet, the truth was that both of them wanted it. And either way it would be happening later, so why not enjoy themselves a little more during the game?

  The Cardinals lost, but Kerry wasn’t too unhappy. She was finally going to get her curiosity satisfied as to what Derrick’s dick looked like, what it tasted like. There would be other bets when she’d get her way.

  Derrick was thrilled as they turned off the television and she settled onto her knees on the floor 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 and shrugged before peeling off her shirt and undoing her bra. She had to smile as he groaned watching her strip, his eyes avidly eating up the sight of her bare flesh. Impishly she rubbed her nipples, loving the way he was practically panting at the sight of her heavy breasts swaying gently, her pink nipples hardening under her fingers.

  “Such a tease,” he said, but he didn’t sound unhappy about it at all. His voice became half pleading, half command. “Come suck me Kerry. I want to feel your mouth on me.”

  God that was hot.

  “I like it when you talk dirty,” she purred, rubbing her breasts against his legs as she finished undoing his pants. Derrick moaned, his dick flexing within the confines of his jean
s.

  When his dick sprung free Kerry gasped. It seemed very large. Slightly darker than his skin tone, the thick stalk jutted out at her, clear fluid gathered at the tip of the dark head, fully engorged with blood. She was fascinated by her first glimpse at the male organ, her fingers tentatively brushing against it. Derrick groaned and his head fell back as she wrapped her fingers around it. It was hot and heavy in her hand, the skin was satiny soft.

  “Oh God Kerry, you have no idea how good that feels… pump it a little bit… fuuuuck…”

  It pulsed beneath her hand as she stroked him manually, leaning closer to take in his musky masculine scent. Derrick was breathing very heavily now and he reached down to take one breast in each hand, squeezing the creamy mounds much harder than he had before. Trying to ignore the sensations that made her want to concentrate on her own needs, Kerry leaned forward and flicked her tongue against the small droplet of fluid on the head of his dick.

  Derrick gasped and his hips thrust forward, his fingers squeezing her nipples hard and she shuddered with the reaction. It almost hurt but it felt good too, to have him crushing the sensitive little buds like that. The taste in her mouth was salty and warm. She licked him again, this time taking a longer stroke around the sensitive head and enjoying his gasps and shudders, the way his fingers clenched around her breasts as he fondled her.

  “Feel free to play with yourself,” he said, his eyes practically glazed with pleasure as he watched her pink tongue start to lick along the sides of his dick. The teasing sensation was amazing. Kerry shot him a look. No way she was going to give him the pleasure of seeing her pussy and watching her play with herself when 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 the nerve to press her lips at the tip of his dick and slowly open them to slide down, he couldn’t believe how amazing her warm wet mouth felt around his shaft. It was the most incredible sensation, so much better than masturbating. He’d been waiting for this for so long, through the whole baseball game, that it was taking every ounce of his willpower to keep from exploding in her mouth immediately.