"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.
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.
My other fuck buddy that summer. We mostly got stoned and had sex in the basement of his parents’ house. His penis had a mushroom head, which was a lot of fun to play with.
Harry and I share the same birthday and decided to have sex during our joint birthday party, because… why not? Sadly, he had whiskey dick and I got bored and went back to the party.
The bartender at a ski resort in South America. We had sex on the floor of the restaurant where he worked after it closed. The foreplay lasted so long that I had to beg him to finally start having sex with me, which was a pleasant change of course from the drunken sex I had been having with the residents of Frat Row.
The first time we had sex, Felipe told me he was surprised that I didn’t wait until I was married, and for some unknown reason, I kept sleeping with him. The combination of his extreme jealousy and complete lack of personal hygiene were dealbreakers in the end.
Mike and I dated for the last couple months of his senior year. I was head-over-heels for him but he was a commitment-phobe who also couldn’t keep it up.
Nick was a friend-of-a-friend who showed me around New York while I was interning there for the summer. The sex was mediocre and he was weird about it afterwards. He was the only Asian I’ve ever slept with.
Mark and I started hooking up after a friend told me that he loved eating girls out. He wore bandanas and had a long beard, which he wore braided, with plastic beads on the end. I would sneak off to his room in the morning and he would make us tea and then go down on me for hours on end. We never had sex but his amazing tongue deserves some recognition.
Nizar was sitting behind me on my red-eye flight to London, where I spent the summer interning. It was right when Lost was really popular and he was a sexy Sayid look-alike. After many mini-bottles of wine I ended my long dry spell by joining the Mile-High Club with him in the bathroom. The sex was really fun, but a day later I woke up with a UTI and learned first-hand the benefits of England’s National Health Service.
Jamie was my insta-boyfriend during my summer in London and was the first person to make me come during sex. Thanks to him I will forever have a preference for men who are uncircumcised.
The fall after I came back from London I went down to NYC to spend a night with Nizar, hoping for more adventurous sex like what we had had at thirty-five thousand feet. Despite the fact that we had talked about getting it on in various public places, he sequestered me in his crappy apartment in Midtown and treated me like an object. I didn’t trust him; and I grabbed my things and left while he was in the bathroom.
Quentin and I ran into each other while skiing over Thanksgiving break. We hadn’t spoken in a few years but the sexual tension was running high. After the holidays, he came to visit me back East at school and let me peg him in the shower while my roommates made dinner down the hall.
Jim was Catholic and a virgin. I broke it off when I realized the only reason I was dating him was the challenge of taking his v-card.
We had sex while I was rolling and he made so many weird faces that I thought it was his first time. When I asked about it later he told me that he had been tripping on mushrooms, which accounted for the weird facial expressions and lackluster performance.
We met via Craigslist while I was looking for a room to rent in Boston after graduation. I didn’t end up renting a room in his apartment, but we spent quite a few nights together regardless. The sex was awesome and fairly kinky (he liked feet), but we kept it a secret because he was on-again-off-again with his crazy girlfriend.
Matt was Parker’s roommate. In hindsight, it’s a good thing I didn’t move into their apartment.
Alessandro was a sexy Italian guy a friend brought to one of my roof deck parties. He wanted to eat ice cream off my body and I obliged, but he chose pistachio, which had chunks of nuts in it. I vividly remember him kneeling between my legs, stopping every once and a while to chew the nuts he was lapping up from between my legs. Gross.
Abdul and I met at the birthday party for a guy I had recently started dating. He had a huge dick but didn't know it, which was an absolute gold mine. He ate pussy like a champ and we spent most of the summer getting stoned and having sex on my roof deck. He let me take a picture of his dick that I keep on my phone.
He was sexy but had OCD tendencies and sex made him nervous. When we decided to call it quits, we had sex one last time and I got my period by surprise and bled all over his sheets. Whoops. Inside, though, I thought this was hilarious; a nice “fuck you” from my vagina.
Eric was my most serious relationship to date. I was in love with him, which led to many mind-blowing I-love-you-gasms, but the sex was very vanilla. I think he was terrified of buttholes, which sucked because I have tend to have a thing for them.
Guillaume was a cocky French hipster I met at my favorite dive bar a few weeks after my breakup with Eric. We danced to Talking Heads and The Smiths and I perched on a handrail outside and made out with him while he smoked a cigarette. His penis looked like Mike #1’s, which made me nostalgic for high school, but the sex was lousy so I faked an orgasm and left in the middle of the night while he snored like a freight train.
Noah was the official rebound after my breakup with Eric but turned out to still be in college. We hooked up for a bit, but he jackhammered too much for my taste and I was too lazy to show him what I liked.
Things with Luke were too good to be true: He was gorgeous and I was completely smitten with him, but he was another virgin, more religious than the first, and was actively searching for a wife. I did enjoy the frottage briefly, but filled the penis-in-vagina void by sleeping with other people.
He had recently quit his second job to be in a second band, and I thought that I could have the best of both worlds by sleeping with Tim and spending time with Luke. In practice this just made me feel like a shitty person, so I ended things with both of them the day before I left for Burning Man.