Becoming Roberta

Years ago, I went out with a girl who was very kinky. I can't use her real name, because she is married now, but I will call her Christine. I liked a lot of the kinky stuff we did, especially being dominated and humiliated. She always wanted to see me have sex with another man, but I was very hesitant, and I never did. Yet she made me curious, and, over the years, I wondered if I would really enjoy it.

Although Christine is married, we recently started hanging out again, only as friends, of course. But we talk about sex a great deal. About three weeks ago, she came over, and I told her I finally had decided to try sex with a guy. I put an ad in the local email meet market, stressing that whoever it was would have to overcome my hesitancy by ordering me around, and there was not a single good reply. Guys offered to suck my cock, no reciprocity needed, or they said my picture was cute, let's get together, but nobody called me a bitch or a little girl, which I had specifically asked for in the ad.

This seemed to turn Christine on a lot, and she encouraged me to keep trying. I kind of thought I wouldn't, but our conversation really turned me on. My cock was hard, and I was trying to get comfortable as I was sitting.

Finally I blurted out "Look, Christine, you'd better go, because I really need to jerk off."

"Why not do it in front of me?" she asked.

"Are you sure your husband would approve?" I asked.

She shrugged. "As long as I don't touch you and you don't touch me, what can he say about it?"

"To tell you the truth," I said, "I feel a little weird masturbating in front of someone."

"So go into the other room and do it," she said. "If I peek in, it's not your fault."

So I went into the other room and took out my hard cock, getting it nice and wet with saliva. I rubbed it good, until I shot a big load onto the floor. I was very turned on by the dark figure of Christine in the door, which I could see out of the corner of my eye.