Jeremy
It was in many ways the stereotypical first time experience: we were both seventeen, both virgins, and in love. It happened right around prom. I came really quickly my first time, which makes me feel like a prodigy. Jeremy and I had sex exactly once. I was too paranoid to do it again because I wasn’t on the pill yet and I was afraid of the condom breaking. At least, that’s what I told myself at the time, but in retrospect, I think I also just wasn’t that attracted to him. We broke up before college — he wanted to get back together later on, but I didn’t. We’re sort of friends now and see each other every few months. Every once in a while I think that maybe I’d fuck him again, just to see if it’s any different.
Luke
My first serious, long-term boyfriend. We lived in the same dorm, I had a huge crush on him, yada yada. The first night we hooked up was so exciting — it was the first time I had any kind of experience with someone who liked me as much as I liked him. He basically taught me how to fuck, for which I’ll be forever grateful. He also was a total asshole dirtbag to me for the majority of our two-year relationship, which I was too naïve to realize at the time, and dumped me cold after I got back from a family vacation.
Mike
After Luke broke up with me, I decided to try to get back out there, sexually speaking. My first casual sex experience was with the president of a frat at my college. He was this big, built ginger who had all the necessary accouterments for his position, right down to the Animal House and Scarface posters in his room. Perfect. Mike was one of those dudes who had slept with half the girls I knew. He was also the ex of a girl I had just become friends with. The night after Mike and I fucked, his ex and I went out. She confessed to me that she still had feelings for him and wanted to get back together. Oops.
Nate
Nate was a rustic, woodsy type (hot), and also one of Luke’s best friends. We got to know each other because he lived down the street from me and had a television. My roommates and I would go over to watch TV and I started to become interested. I seduced him on Halloween night, after explaining that I had sprained my ankle and as such needed to stay on his couch. (Obviously, I didn’t end up on the couch.) The first few times we hooked up, he couldn’t keep it up because he felt guilty for betraying his friend. I really liked him, but I was reluctant to get involved since I had just had my heart crushed a few weeks earlier and needed some alone time.
Eventually all that blew over and we dated for nearly three years — still the best boyfriend, and the best cosmic, earth-shattering sex, I’ve ever had. It was the kind of sex where we would barely move an inch but it would feel outrageously incredible. I don’t even understand physiologically how that works, but that’s what it was like. We broke up when I moved away for grad school because neither of us wanted to do long-distance.
Isaac
Before Nate and I were officially together, I was trying to pretend I wasn’t into him by hooking up with other people. One of those people was Isaac, a gigantically tall engineering student with whom I had incredibly uneventful sex. He was in town with some friends who were staying at our house, and while we were fucking I could hear the sounds of two of his friends having sex on the rug in the room adjacent to mine. They were clearly having a better time than we were.
Alex
While I was lying back on my pillow being eaten out by Alex, I had an epiphany, and realized that I actually wanted to be with Nate after all. I shooed Alex out of my apartment, put on my pants, and ran to Nate’s apartment to bring him the good news.
Julia
She was a work friend I had a crush on. I have no idea why Nate was okay with this. Why is it not cheating when it’s a chick? Having sex with a woman was great; I want to do it again. It was really familiar and really unfamiliar at the same time.
Brady
The first dude I slept with after Nate and I broke up was an attractive law student I met at a New Year’s party in my hometown. We made eye contact right away, started talking, and left the party with two friends of mine — a couple — because one of them had a lead on where to find MDMA. We parachuted the M, hailed a cab. When we got back to his apartment, we ate homemade ice cream and apple crumble his chef roommate had left in the freezer, and then I ran around in an M haze smelling all their spices and looking at all their spatulas. Brady then put on Neil Diamond and we fucked for many hours. The sex was good. I didn’t see the glint of crazy in his eye until the next morning. Brady was recently recommended to me as someone I might know on LinkedIn.
Drew
My encounter with Drew marked the beginning of a phase I’m still kind of in, in which I fuck terrible undergraduates I meet at the bar in my little college town. My roommate and I went to the bar during a huge snowstorm and I found Drew, who was tall and blonde and Nordic with this gorgeous lithe body. At some point during the night, I guess I confused his Swedish heritage with his name, because I woke up the next morning thinking his name was Thor. This turned out to not be the case. The sex was terrible the first time, and it was still pretty bad the next.
Other Mike
A friend of my roommate’s ex-boyfriend, Other Mike was a husky finance bro from the city visiting his friend’s cabin for the weekend. I guess they came into town to soak up some local color. I fucked him because he requested a Sam Cooke song from the band that was playing and then asked me to dance.
Asa
Asa epitomizes the kind of insane privilege that haunts the college in my town. He had a heated towel rack in his dorm room and an oxy prescription from a quack. He also definitely always skipped leg day. I fucked him a few times because he was, surprisingly, kind of good at it. I run into him all the time. Even though I find him morally reprehensible, he could still get it.
Mark
This guy ruined me a little bit. He’s still the hottest dude I’ve ever fucked — he has this crazy jawline that makes him look like a more brooding Tom Welling, and an incredible body despite the fact that he never exercises and sits around all day. I met him on the train when I was visiting New York with a friend (who was also a friend of his from college). We had immediate, crazy chemistry. We had a magical night the first time we met and made out on top of a pile of records in his living room. We migrated to his bedroom and had gorgeous, passionate sex, although he came too quickly. We started messaging each other a lot, and dated sporadically for a few months whenever I was in town. He continued to come too quickly. I wanted things to get more serious but he stopped calling me — I think he realized I wasn’t cool enough to fit into his social group, who were all aspiring artists living the same boho Brooklyn life he was. I’m still not totally over it.
Robbie
A friend pointed Robbie out to me from across the bar and said we were from the same city, which is how I struck up a conversation. Robbie was a gigantic dolt with gorgeous blue eyes who played on the lacrosse team. The sex was super boring, and his body wasn’t as great as I thought a college athlete’s would be.
Other Drew
This was Robbie’s teammate, a super-muscular, super-hairy (which I love) dude who swung me around like a ragdoll and pumped away like I was a fleshlight.
Kyle
A professional soccer coach from some little town in England who lived upstairs from me for a few weeks in the summertime, Kyle was ten years older than me. I met him when I knocked on his door to borrow some olive oil and there was an immediate attraction. I ended up running into him as we were both coming home late one Friday night. He invited me up and I discovered, much to my delight, that he was incredible at eating pussy. He left to go back to England a few days later after telling me not to tell anyone what happened.
Avi
This night was a disaster. I was really wasted and feeling really lonely, which resulted in my taking home a dude I was completely unattracted to, even a little grossed out by. I don’t really remember if we fucked or not; at some point I started yelling at him and told him to leave. I think maybe he had just put the condom on and I realized I just couldn’t do it.
Sam
I met Sam at one of my favorite places to go dancing. They were hosting a 1960s music night that draws a really diverse crowd. He was that guy — the one who comes alone and spends the whole night dancing vigorously, and creepily, by himself. He was super gangly and his limbs were flying all over the place. Turns out he was an ethnomusicologist. When went back to his apartment, he put on some obscure reggae 45s and packed his vape, and we smoked as he fucked me on the couch. One of my fondest one-night stands.
Other Sam
A totally unremarkable townie I met at karaoke, blew in the middle of a field, and never called again.
Casey
This guy was the bartender at one of the nicer restaurants in town. We met one night at a different bar, and then I came to his restaurant with a friend to suss him out a little more. I knew I was going to fuck him when I saw him make a cocktail with egg white in it — there’s nothing sexier than a dude who can separate an egg with his fingers.
Dan
I had my eye on Dan all year. He was the bearded, kind of short TA for an undergraduate class I was taking. He was this total genius nerd type who wasn’t super attractive; I have no idea why I fixated on him, but I did, and I hit on him unabashedly every time I saw him even though he had a girlfriend. When they broke up, I started seeing him around more. We had sex one night when I invited myself over to his disgusting dorm room. After we hooked up, he started avoiding me.
Jordan
We met at my friend’s graduation. At some point in the night he told me that he took really heavy anti-psychotics, which didn’t bother me. Later when we were fucking, at some point he said something about hearing voices that were telling him to burn down my house. I think our fucking made him miss taking his meds. He left really early in the morning.
Connor
A totally adorable, wiry dude I met when I came home from grocery shopping one day. He and three of his friends rented a house down the street from mine for the weekend to get away from the city. I drove by and they offered me a shot of whiskey. I ended up hanging out with them all afternoon and all evening. Connor and I had great chemistry and he knew exactly what to do to make me come. I sort of want to see him again.
