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Shane
That summer, after realizing my then-best friend wanted to kill me and wear my skin, I turned to the Strictly Platonic section of Craigslist to make new friends. Shane connected with my identification as an Afro-Punk and with my love of John Waters. After three months of cross-country emails and phone calls, we began dating when I returned to college in the fall. He had been my first everything—date, hand-hold, kiss — at the ripe age of twenty. We planned to do it during my first time at his apartment. Once things got hot and heavy, he put it in without a condom or any sort of warning. “No,” I said. “No?” he asked. “No,” I said, then he pulled out.
Andrew
After two years with Shane, I was ready for a nice guy. Andrew and I were a 99% match on OKCupid and shared an “INFJ” result on the Myers-Briggs Type Indicator. He constantly talked about crushing the patriarchy, which appealed to the neophyte feminist in me. An innocent search of his Yahoo! screen name had let me know he was eight inches. He would never finish, and it took all of my efforts to even get him hard. For us, sex was him staring blankly at the wall as he planked on top of me.
Jason
After his Clams Casino and Balam Acab filled DJ set, I took Jason home and let him go down on me. He had shown me that he wanted me, and, at the time, that was enough. It was Christmas the first time we decided to have sex. Not even the gas station was open for us to buy condoms, so he posted a Facebook status saying he needed a favor. Within minutes we had one. Once one of his friends had confirmed Jason’s rash and Planned Parenthood had confirmed my yeast infection, we both agreed no more condoms.
Leif
Eight months after things ended with Jason, I had answered Leif’s ad on Craigslist looking for 420 fun. He ended up driving ninety miles to see me. We smoked a few joints, and agreed we would each choose a pizza topping. He chose bacon. I chose pineapple. We watched Harriet the Spy then proceeded to have extremely polite sex. Suddenly, I felt his tongue in my asshole. I didn’t hate it. Not even a little bit.
Sean
Since the encounter with Leif went so well, I figured I would give casual sex another shot. Sean was the type of bro that found Frida Kahlo attractive, but would never admit it to his friends. When he suggested we watch a kid’s movie, I chose Hercules. I was amazed that someone almost three years younger than I was could kiss me with such a perfect amount of lip pressure. He was the first guy I had ever 69’ed with, and he contorted my body into all sorts of positions. I could hardly walk the next day, but it was worth it.
Drew
I don’t normally trust men in their late 20s who sleep in twin-sized beds, but I was horny enough not to care. Drew had a squeaky, nervous laugh and couldn’t hold a conversation, but he could pound me doggy style without ever slipping out.
Paul
Paul was visiting his parents for Thanksgiving. He had an eyebrow ring and was a political science grad student that had never considered The Smurfs as an allegory for communism. We smoked a few bowls, and I was higher than I ever had been. While he was going down on me, I imagined he was a girl, “Poker Face” style. When he tried to position me on top, I was sprawled on top of him too baked to know was happening. He left immediately after he came and gave me a pity kiss for my confusion.
Greg
Greg had described himself as “white with a vaguely ethnic look.” This meant his family was from Cyprus. My two biggest turn-offs when it comes to men are shortness and body hair. He was maybe 5’5” and had enough hair to look like he had on a sweater when shirtless. He had cooked steak with green beans and mushrooms. As soon as the food was ready, he pulled me into the bedroom. I would rather have eaten. When we tried doing it again after eating, he warned me not to touch the bedspread because the cat had shit in the bed.
Tyler
Tyler and I took shots of Fireball before doing the deed. When I asked him what Songza station he wanted to hear, he chose “Freak Nasty R&B.” I explained to him that “Oops (Oh My!)” by Tweet is a song about masturbation, and complained that Facebook had made my ability to remember birthdays obsolete. I had liked him, until he said he wanted to come on my tummy. The only word I want to hear less during sex is “potty.” When we were finished, he said he was “definitely interested” in doing this again, and gave me a kiss. I never saw him again.
