1. Wanna Bet? 2: Higher Stakes


    Date: 5/25/2015, Categories: Mature, Taboo, Voyeur, Author: brianbigdogsmith, Rating: 100, Source: xHamster

    asked. “That you’ve slept with?” “Less than Todd.” Aside from Faith and Lara, there were a few girls from school, and one girl from Lara’s school. “Less than ten,” I answered honestly. “Then how do you know you’re better?” she said smugly. “I think you might be overestimating abilities.” “I’ve been with girls who’ve also slept with Todd… fuck, sometimes I’ve watched. And they come back asking for more from me, not him. I’m not trying to brag or anything, I just know I’m better. I could prove it to you, if you wanted.” She still looked skeptical, so I said, “But if you don’t, I lose a little money. Or, here’s an idea… we could bet on it, if you want.” “Bet on it,” Jeanette said doubtfully. “Sure. If I don’t make you cum at least twice, I’ll…” I groped trying to figure out something. “I don’t know, but if we screw, I win my bet with Todd.” A lightbulb dawned. “I’m not going to need this car anymore. So I’ll give you mine when that happens.” Her face scrunched up in disgust, but it was kind of cute disgust. “What do you think I am, a whore?” Interesting question, that was. See, I couldn’t imagine any girl wanting to date Todd after spending more than a few hours with him, except for the fact that he has a nice car and a well-paying job. If that was the reason Jeanette continued to date him, in my opinion, she really was kind of a whore. But I could give her the benefit of the doubt and assume Todd could be charming when he wanted to get into a girl’s pants. So I figured I ...
    should deny it. But then again, some girls didn’t mind being called a whore. Some even enjoyed it, when you wouldn’t expect it. I had a flash of inspiration, then. “No, I don’t think you’re a whore,” I said. “I think you’re just like Todd described you. A good girl. Always wanting to do the right thing. Always getting treated like dirt by guys who don’t give you the loyalty you give them. Always secretly disappointed when you see the sluts and whores seemingly so much happier.” The initial idea had been unformed, just a feeling, but as I groped around, the words just came. “Always envying them, wishing you could be like them, just once, but you’ve got so much wrapped up in being the good girl, you’re afraid to try and change.” She hadn’t interrupted me yet, so I continued. “You probably don’t really want to change, not totally, but you wish you could let loose just once, be the bad girl, be the whore, find out what it’s like. As long as nobody ever found out. So you know what, fuck the bet. I’m offering to make those fantasies come true. Have sex with me, be a whore for a few hours, and I will give you this car after I win the bet with Todd.” It was risky, but somehow, I had a feeling I was right in my assessment of Jeanette’s character. Sometimes I think I’m a little bit psychic, and have this insight into the parts of people’s inner selves they wouldn’t want to admit to anybody else. Either that, or I have a way of talking people into believing things about themselves. Whichever ...
«12...676869...9495»