Wanna Bet? Read online

  But if she was going to be honest with herself, sex with Derrick was a topic that was constantly on her brain. When she was hanging out with him, when she was out with her girlfriends, when she was alone. She thought about sex, her virginity and Derrick.

  And eventually came to the conclusion that she wanted him to be the one to take her virginity. The bets were just an excuse. She was falling for him, really falling for him, and she couldn’t admit that to him because she really didn’t know whether he felt the same or if he was just using these bets to further his sexual experience with a girl that he cared about and felt comfortable with. Either way she knew that he cared about her, she just wasn’t sure if it was in a romantic way. But she knew that she wanted her first time to be with him, the first guy that she’d ever fallen in love with.

  Of course, being secretly in love with her best friend was no walk in the park. She not only had to hide it from him, she had to hide it from their friends too. Janice in particular had become a trial.

  ******

  “You know Kerry,” Janice said irritably when they were at their Girls Night Out Happy Hour, “I keep trying to hang out with Derrick lately but it seems like he’s spending all his time with you. Is there something going on between the two of you?”

  “No more than usual,” Kerry said somewhat evasively. Then, remembering Janice’s interest and her own decision to lose her virginity to Derrick, she decided that she might want to be a little more clear. “Well, maybe a little more than usual. We’ve kind of been… very friendly lately.”

  “How friendly?” asked Missy sounding curious. “Are you guys dating?”

  “Oh no,” she said immediately. After all, she couldn’t claim that without it getting back to Derrick and it’s not like either of them had ever talked about anything like that. She didn’t want him to think that she was desperate or trying to force him into anything. “We’ve just been… you know. Fooling around a little. Expanding on our bets.” She gave a small laugh, feeling uncomfortable at explaining just how much their bets had expanded. After all, as Missy had just reminded her, she and Derrick weren’t dating and she didn’t want her friends to judge her for the dirty things she’d been doing with her best friend.

  “Well, you know I would never poach on your man… but is he your man?” Janice pressed. “I mean, I don’t want to be a bitch about it, but if you’re just stringing him along then he’s better off with someone who actually wants to be in a committed relationship, like me.”

  Kerry finished her drink and set it down abruptly. “I have to go to the bathroom.”

  As soon as she disappeared her friends started giggling.

  “God she must think I’m the worst friend ever, but this is so working!” Janice said gleefully.

  “We’ll explain later,” said Missy. “She’ll thank you then.”

  “Let’s hope so! Are you going to call Derrick tonight?”

  “Heck yeah! Expanding on their bets… ha! Those two are just looking for an excuse to get together and we’re going to give it to them.”

  *****

  Derrick wasn’t exactly thrilled to see Missy’s name come up when his phone buzzed, figuring that he was due for a drunk call. He knew very well that the girls were out tonight having a grand old time. Hopefully Kerry hadn’t spilled too much about what was going on with them. Everything was still new and uncertain. He really wanted to ask her out on a date, and he’d been trying the past couple weeks, but somehow every time they went out to dinner it ended up just being like friends hanging out rather than something romantic. She wouldn’t even let him pay for her meal most of the time. But he didn’t want to push it either.

  Maybe if they lost their virginity to each other. Or after they lost their virginity to each other. Because he knew that’s where they were headed. And he knew that Kerry wasn’t seeing anyone else, she would have told him. He definitely wasn’t and he didn’t want to. It might be cliché, but he was falling head over heels for the girl next door, the girl that he knew best and had never seen in that light.

  It might have taken a small kick in the pants from their friends giving up on setting the two of them up together and moving on to trying to set Kerry up with someone else, but it couldn’t be too late. He hoped.

  “Hey Missy.”

  “Derrick hey! Do you have a minute to chat?”

  Surprisingly Missy’s voice didn’t sound at all slurred or even overly chipper like she’d been drinking heavily.

  “Sure, is everything okay?” he asked, a little worried. “Do you girls need a ride or some help or anything?”

  “Oh, no, nothing like that. I just wanted to talk to you about Kerry. Janice and I are worried about her, she was acting a little weird when we were talking about you tonight,” Missy said and Derrick winced, wondering what had been revealed. “She didn’t say much but… she didn’t seem to like Janice’s interest in you and she wouldn’t let any of the guys that came up to us buy her a drink.”

  Guys were trying to buy Kerry drinks? Well of course they were. She was wonderful and gorgeous and a guy would have to be an idiot not to want to buy her a drink. Sheer jealousy ran through him at the idea of a guy successfully hitting on Kerry. Followed by a rush of pleasure that she apparently hadn’t let any of them.

  “Look, Kerry’s one of my best friends, and if you’re just stringing her along then I think you need to let her go, okay?” Missy said, sounding very determined. “I know you care about her, but you two have been spending all this time together and I think you’re the reason she’s turning down other guys. If you really aren’t interested in having a relationship with her outside of friendship then you need to tell her that so that she can meet someone else. Brad’s really interested in getting to know her better.”

  “Brad better back off,” Derrick snapped immediately. And then coughed to cover his all too revealing reaction. “Look, Missy, I appreciate your concern and I’m sure Kerry would too but it’s really none of your business.”

  “It’s my business if you hurt her,” she replied, just as firmly as he had. “Cuz I’ll make it my business.”

  “You’re a good friend,” he said, sighing a little. Rubbing his hand over his face, he knew what he had to do before Kerry’s friends stepped in and convinced her that he was stringing her along. If Kerry really was turning down other guys then maybe he wasn’t delusional in thinking that there was something more than friendship here. “Look, consider it handled okay?”

  “What does that mean?” Missy asked suspiciously.

  “Just that I’m going to clear things up with Kerry,” he said. If things went badly then he didn’t want their friends to know, not unless Kerry decided to tell them. That was her prerogative. “Thanks for calling Missy, I’ll talk to you later.”

  “Fine. Just… don’t hurt her. Let me know when I can give Brad the go-ahead. Bye.” She hung up before he could snarl at her to tell Brad the go-ahead was never coming for him. Probably just as well.

  Putting down the phone, Derrick rubbed his face in his hands. The thought of Kerry going out with Brad made him want to punch things. Preferably things named Brad. Yeah, okay, so things with their bets had gotten a little screwy. But there was no way that Kerry was just using him to further her sexual experience. She had to have the same feelings for him that he had for her, the ones that went a bit beyond just regular friendship. Even being best friends.

  Every time they got together, things went a little bit further. He knew what the next natural step was. And man he wanted it. Not just in the normal, male “I want to have sex with a gorgeous woman” way – although of course that was true as well. No, Derrick wanted to claim Kerry and make her his. He’d make it special. Romantic. Everything she could have ever wanted.

  If she didn’t protest the bet of course. And if she didn’t want to take that kind of bet then he’d have his answer.

  He really hoped that his best friend wasn’t about to stomp on her heart. Not that he’d let her know if she did. After all, it wouldn’t be Kerry’s fault that he’d tried to step beyond the parameters of just friends.

  *******

  Today Kerry had come prepared. They were watching a soccer game (football the majority of the world) and she had a surprise for Derrick that would really up the ante. But she was too nervous to bring it up first, because if he wasn’t ready to take that next step then she didn’t want to be the one to push the boundaries quite this far.

  “So what do you want to bet?” she asked, not sure whether she was more scared or hopeful at the wager.

  Derrick turned to face her on the couch, his face serious, and her heart started pounding in her chest as those dark eyes stared into hers. This was it. She could feel it. Women’s intuition was really good for a lot of things, especially big moments like this.

  Reaching out with his finger, Derrick stroked it down her cheek and Kerry sucked in a breath. Suddenly everything felt so much more intimate than it ever had before.

  “If I win, I want to make love to you,” he said, his voice quiet and serious. Maybe part of her should have been more upset that her first time would be because of a wager, but that’s where they’d been leading to all this time. It was still too hard for her to admit her feelings to him, much less to herself, but she could admit that she wanted this. Badly.

  Still. She wasn’t about to let him wager something that big without having a stake of his own on the table. So she gulped and nodded. And then smiled, almost wickedly. Derrick gave her a wary look, recognizing that smile and realizing that he might be in a bit of trouble.

  “And if I win then I want the same thing, but I want to do it with this,” she said as she reached into her backpack and pulled out the box that she had ready there. Fortunately she’d positioned the bag at her feet next to the couch, knowing that it might come to this.

  Seeing his eyes pop open as he looked at the picture on the box made her giggle.

  “Seriously?” he asked, sounding a little choked. “That’s something you’re actually interested in?”

  “I’m interested in doing just about anything with you,” she said honestly. And then blushed as she realized how much of her true feelings she’d revealed to him with that one sentence.

  Hearing that definitely made him feel a little better though. Kerry wasn’t looking to humiliate him or anything, she just was a very adventurous kind of girl apparently. It had never really been his kind of thing, but to be honest this opened up a whole new gateway of bets that he’d never even considered before. While he’d upped the ante in one way, she’d done more than just match him, she’d blown him out of the water. He found himself grinning at her as she looked back at him in relief, obviously happy that he wasn’t going to be mad at her for the surprise.

  Hell no. Not with the opportunity that this would give him for future wagers. Kerry was going to be his, all his. And he was willing to be all hers since that was what she apparently wanted. Anything for Kerry.

  Although, of course, he really hoped he was the one to win tonight. While he might be willing to do anything for Kerry, a strap-on still made him understandably nervous.

  ******

  To Derrick’s relief, the team he chose won. And Kerry didn’t seem disappointed at all about losing, if the way she crawled onto his lap and immediately started kissing him indicated. Curving his arms around her waist, he hugged her tightly to him, grinding his cock up into her splayed crotch, as their tongues entwined. God she tasted so good. Her warm, soft body pressing against his was heaven.

  As he pushed himself to his feet, readjusting her so that she was held in his arms, Kerry broke off the kiss and looked up at him with big eyes. Her arms wrapped around his neck as one of his supported her back and the other curled under her knees.

  “Where are we going?” she asked.

  “The bedroom,” he said, grinning at her. “You didn’t think I was going to do this here on the couch did you?”

  “I’m not sure I was thinking at all,” Kerry said with a wicked smile, her eyes full of warmth and promise. Even though they hadn’t said the words, he was pretty sure that she felt just as strongly about him as he did about her. He was about to tell her so when she nuzzled her face into his neck and bit down gently on his pulse point. A stabbing lust lanced through him and he groaned, hurrying down the hall to the bedroom.

  Once inside he let her legs go so that she could stand on her feet and then he went still, feeling very unsure of himself. After all, this had been a bet, he didn’t want to push her. Kerry put her hands on his face, pulling his gaze to hers as she smiled shyly up at him.

  “It’s okay, I want this,” she whispered, a pink blush heating her cheeks. Then she went up on her tiptoes and kissed him again.

  Derrick was lost, her reassurance sweeping away any residual hesitation. He kissed her as if he could drink her in, as if he could brand her with nothing more than his lips and his tongue. The heat between them flared and exploded, curling around them as if they were in the center of a bonfire, their hands running up and down each other’s bodies. Inexperienced they might be, but they’d been getting much more comfortable with each other lately and with each other’s bodies.

  They slipped off of each other’s shirts, stumbling towards the bed and leaving a trail of clothing behind them. By the time they got to the bed the only thing left were Kerry’s panties. Derrick groaned as he lay her back on the bed, his hands roaming over her silken skin. Everything about her was perfect. To make them both more comfortable, for the moment, he left her panties on as he began to explore her with his mouth. In return, Kerry was touching every part of him that she could reach.

  Kissing her breasts he sucked her nipple into his mouth, rolling it with his tongue and then biting down gently on it. She moaned and her legs moved up against him as her hips thrust, pressing her sodden panties against his dick, her smooth legs caressing his sides. The feeling of her wetness against him, even through clothe, was driving him utterly wild.

  “Oh that feels so good!” Kerry cried out as Derrick suckled hard on her nipple, drawing the tender bud into his mouth and lashing at it with his tongue. She rubbed herself against him, now wishing that she’d had the courage to remove her panties so that she could feel his flesh rubbing through hers. Even through the cotton of her panties it felt incredibly good to have his stiff rod sliding between her lips. Clasping his head to her breast, Kerry arched her back and cried out again as he bit down harder on her nipple, pulling his head away to tug at the rosy nubbin. It hurt a little, but it heated her passion too, so that when he switched nipples she arched immediately, her body begging for the tug of his teeth. When both nipples were swollen and aching from the rough attentions of his mouth, he started kissing her neck and collarbone as she writhed beneath him.

  “Please Derrick, I want you,” she practically begged.

  It was the best moment of Derrick’s life, hearing those words falling from Kerry’s perfect lips. He groaned as he moved his mouth to cover hers, stopping her from saying anything further because if she did he might embarrass himself right now. They kissed ardently as he began to slide her panties off. Eventually he had to remove his lips from hers.

  Kneeling between her legs, her creamy thighs spread open to reveal the pink petals of her pussy, shining with arousal, and her neatly trimmed thatch of brown curls, Derrick felt absolutely riveted. His eyes ate her up as if he was burning her image to a CD so that he could take it out and look at it over and over again.

  His intense scrutiny embarrassed her; she felt incredibly vulnerable with her body naked and spread before him, knowing what was about to happen.

  “God you’re so beautiful Kerry, so perfect,” he whispered almost reverently, his hands sliding up her legs. His head dipped down and Kerry moaned, spreading her thighs wider as she remembered the intense pleasure she received the last time he’d used his mouth on her. Which had also been the first time.

  The wet glide of his tongue up her center made her hips jerk in reaction to the pleasure that rippled through her at his tongue. He groaned low in his throat, almost a growl, as he began to feast on her, teasing her pussy with his tongue. Lapping at her juices, he explored her intimate crevices, purposefully staying away from the little pink bud at the top of her slit, which was peeking out from underneath its hood.

  Kerry’s hand fisted in his hair, tugging at him and trying to draw him to that tempting pearl. “Derrick please, I’m so close…”

  “Good,” he said, pulling himself up on top of her. She would have screamed with frustration except that all the air seemed to have left her lungs as his weight settled on top of her. The blunt head of his cock nudged against her soaked folds, teasing them as he moved his hips in little circles. Looking down into her eyes, Derrick lowered his head for a gentle kiss.

  She clung to him, her hands on his neck and shoulders as they kissed tenderly, softly, seducing each other with their tongues. Although she pushed her hips towards him, Derrick didn’t connect the way she wanted him to. Instead he pulled away.

  “The condom’s in my pants,” he said. Immediately she tightened her arms around him.

  “I’m on the pill. I went on it forever ago to regulate my periods.”

  For a moment he hesitated, although his eyes light up with excitement at the idea of being so intimately connected to her. “Are you sure you don’t want one anyway?”

  Kerry shook her head decisively. This was a decision she’d already made.

  “I want to feel you inside me,” she whispered seductively, running her hands through his hair. Derrick moaned, his eyes glazing over with instant desire and she felt a pulse of sensual power beating through her. Pulling his head down to hers so that their cheeks brushed together, she whispered her next words directly into his ear. “I want to feel it when you cum in me.” Then she bit down on his earlobe.

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