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"I didn't plan on having sex with a man, much in the way I didn't plan on losing my virginity to a woman. I met her when I was seventeen, the summer before my senior year in high school. We fell in love. Two years later I checked "lesbian" in the box and I did all the things one did when coming out in the nineties: I cut my hair short, I listened to Ani DiFranco, I put gay-pride stickers on my car, and I stayed away from men. In college, I minored in women's studies and took any opportunity to argue about sexism, classism, racism, and any other ism related to the plight of gender inequality.
My first girlfriend and I explored and studied sex like we were getting degrees in it. She penetrated my mouth, pussy, and ass with her tongue, fingers, and dildos that she strapped on. We tried all sorts of positions and developed a love or for role-playing. I discovered I liked pain and sexual submission. She discovered she liked power, control and inflicting pain — so much so that years later she became a he.
I never understood why men would get so flustered when I told them their pick-up lines would not work on me, I was a lesbian. Often, I was told that I needed to experience a "real cock" — theirs. But why would I want to work at getting something hard, just to have it possibly deflate, when a woman could strap on and fuck me whenever she or I wanted?
My first girlfriend and I explored and studied sex like we were getting degrees in it.
Then at twenty-six, after my second three-year relationship with a woman, I started to get curious and restless. I left my girlfriend, our one-bedroom house in City Island and our troubled relationship in search of something new. I was curious about a lot of things, even men, but didn't put "have sex with a man" on my to-do list. I figured if I was open to it, it would happen. And it did. The night I lost my virginity to a man, I told him the same thing I had told so many others: "I'm a lesbian; I'm not going to have sex with you." Except this time I didn't mean it. Many hours and many drinks after we met, I asked if we could go back to his place.
The sex was drunk and sloppy. By the time his cock was inside of me, it was seven a.m. and we were many, many sheets to the wind. He pumped me for about three-and-a-half minutes before he went limp and passed out. If I had still been a sharp-tongued lezzie who took any opportunity to tell a man off about his cock, it would have been the perfect time. But I didn't. There was something about him that I liked. Plus, my mouth was too chalky and my mind too confused to get the words out.