Everyone I've Ever Had Sex With: Female, 26, Boston

"His penis looked like Mike #1’s, which made me nostalgic for high school..."

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We met on our high-school robotics team and were each others firsts for just about everything. Our sex was pretty vanilla, aside from a few times when we filmed it on our flip-phones. We talked about trying anal, but never did. He was my first love, but we broke up when I moved across the country for college.

String of Anonymous Fraternity Brothers
I naively thought that sleeping my way around my new preppy liberal arts school would ease the pain of breaking up with Quentin. The only thing I remember about these drunken hookups is that they happened frequently and with people whose dance moves I was more familiar with than their names.

Miguel was another one-night stand, but notable because the lock on his dorm room was broken, so every few minutes someone would walk by and swing it open for all to see. While I definitely had an "...is it in yet?" moment, I faked pleasure because if everyone was going to watch, I wanted to put on a good show. It's amazing I didn't get a lasting reputation after that night.

Ryan was hung, but he lacked the skills that should accompany such a weapon, and accidentally harpooned me in the ass while he screwed me from behind. It hurt so badly that it brought tears to my eyes and I was afraid to poop for a couple of days.

Paul was a staunch Republican complete with an American flag tattooed on his shoulder. Despite the fact that we were complete opposites, our sex was awesome. He had a big, banana-shaped cock that would nail me right in the G-spot over and over.

Paul #2
Big man, tiny penis. The day after I met Paul #2 I told my mom I thought I might marry him. Then his a capella group serenaded me in the dining hall and I called my mom back to tell her I was wrong.

Rob and I met at my cousin’s wedding the summer after my freshman year. He had the biggest cock I'd ever seen (a record he still holds). It was almost scary. We fucked doggy-style in the back of his parents’ van, which left bad rug burns on my knees that got infected and left scars. I was glad I didn’t go to the brunch the next morning, because I learned years later that people had seen us from the balcony.

Back for the summer, replete with my newfound sexual freedom, Taylor was one of two fuck buddies I kept on speed-dial. He was my first real foray into kinky sex. Our most memorable moment was when my best friend walked in on us having anal sex while we watched the 2006 World Cup Finals.


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