Wanna Bet? 2: Higher Stakes - Sex Stories

Wanna Bet? 2: Higher Stakes

... him and he has another friend named Mark. It’s led to annoying confusion in the past. “Oh, what’s up?” “You alone?” “Yeah, man. I’m driving my Beamer. Hey, if you’re offering another piece of your s****r, you’re going to have to wait till tomorrow at least.” “You remember what you said last time? Were you serious about that?” “What?” he took a second to think. “You know, where you said you thought Jeanette would shoot me down. You said you bet your car on it.” “That? It was a joke, man.” “Oh, so you admit I could get your girlfriend to fuck me.” “No way, man. Come on, you might think you’re some kind of sex god, but between you and me you ain’t had any pussy who wasn’t in high school, and you weren’t related to. You have no idea how to talk to a real woman. No way you could get a girl like Jeannie to cheat.” “So then it’s a bet. If you win, I won’t charge you to fuck Faith ever again.” “And if you win, you get my BMW? That’s hardly fair.” I knew it wasn’t, but I expected him to up the ante and bet something else. “Yeah, I knew you were chicken.” “Chicken?” “Well, you must not be too confident, right? Tell you what, I bet you I could get her by the New Year. I win, you sell me your car, legally. I’ll give you a hundred bucks for it.” “Yeah, fine, you’re on then.” He hadn’t demanded anything extra for his part of the bet. He really was dumb. “Two things before we start. First, you’ve got to give me a little information on her, just to get me started. Where she lives, where ...

... she works, what her hours are, that sort of thing.” “Fine,” he agreed grudgingly. “Second, this is a friendly bet, and we’re f****y. If I win…” He cut me off. “You’re not going to win, b*o.” “If I win, I’m going to be fucking your girlfriend. You’ve got to swear you’re not going to be pissed at me for that.” I wanted him to be pissed, really, but I didn’t want it to get to the point where he might do something stupid. “Are you k**ding? Like I’m going to get hung up over a slut? Jeannie’s a nice girl, but girls like her are a dime a dozen.” “And it’s not like you’ve been entirely faithful to her.” He laughed. “Yeah, you got that right. If I’m pissed, I’m going to be pissed because I lost my car, not Jeannie. But if I win, I don’t got to use a condom, either. I hate those things.” I thought about it. It wasn’t really in the plan, I’d promised my s****r that I was the only one who’d get to fuck her raw. Even beyond that promise, if somebody else did, I couldn’t be sure I was the one who got her pregnant. But then, I had no intention of letting Todd do it. “Fine. It’s a bet.” Over the next few days, I continued to fuck Faith on a regular basis, and always made a point to cum in her pussy, even if it had just started as a blowjob. The first time the next day, I’d convinced her it was okay because the pills she’d been taking before wouldn’t wear all off all at once. After that, I didn’t say anything, and neither did she, but I know she was getting worried. I noticed she now had a ...