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Joe was a guy I liked in high school when I dated his best friend. We went on a few dates and I was totally smitten, but I think he dismissed me. We ran into each other a year later and went out a few times. Having sex with my high school crush was more satisfying than the sex itself, not to mention I had no idea what I was doing. Two years after that, I gave him a blacked out blowjob after a night of free drinks and haven’t seen him since.
Kyle was my friend’s cousin who I was into after he found my clutch that I drunkenly dropped on the bar dance floor. We “dated,” for several months during college in which time we mostly went out, got super drunk, and hooked up. I think we went to a restaurant one time. We didn’t have sex for a few months which drove me nuts until he found out I was on the pill. This is also around the time I found out he was a pregnancy-fearing Republican Catholic. Communication skills were lacking to say the least. It wasn’t until I got more experience that I realized how quickly he came, but I still always had fun.
Dan was a cute and sort of mousy guy that I went back to a few times over the course of my college years when very drunk. I originally slept with him to make Kyle jealous (I’m wincing here too), and he could never stay hard when we were together. He told me I had a “perfect body,” though so I was content to keep him around.
Nick was one of the few guys I’ve ever been with because I saw him and was like, “WHO is that?” He was shy, muscular and had a huge dick. The sex was good, but again, with later experience, I realized he was a selfish and lazy lover. We were super into each other for a while until he decided to get back with his ex-girlfriend.
Max was the ex-boyfriend of one of my roommates. We ran into each other at a bar while I was trying to get over Nick and trying to get drunk. The sex was average, forgettable, and I woke up hungover and hot. He seemed like the type who would have dated me from there, but I wanted nothing to do with it.
One night stand, twice repeated. Both times I was super drunk and he kept calling me a slut, which was annoying, even in a sexual way. But he was rough with me and I liked it.
This one will always hold a special place for me. My first ever foray into online dating, we met in the fall and had a brief romance before he moved to Colorado. He was very sex positive and we had a lot of fun together — he loved to eat pussy and was open to the toys I wanted to try. We also would choke each other and the first time he slapped me while fucking me I was surprised, but loved it. Slapped him right back. I was crushed when he left, and even went to visit him once. Our visit was an intense few days of constant sex and dancing around feelings. Those feelings have faded, but I still talk to him now and again and wouldn’t rule out anything for the future.
He had a big dick and fucked me on our second date, a few times after that, and then said it was too soon for him to be comfortable having sex with someone. Dude, what? Calm down. He tried to reconnect with me a few months later but I wouldn’t meet up with him.
Met Liam on OkCupid. He was so skinny that his lung once collapsed. He was also a poor actor so he didn’t have any air conditioning or sometimes electricity. We spent a lot of time watching things he wanted to show me on Netflix while I waited patiently for the sex portion of the evening. The sex was average, but there was something specific about the way he would pull my hair that I liked.
John and I met on Tinder. This is where I first developed my love for hipsters I fear. He made odd light fixtures, had a beautiful apartment and roommate, and a dysfunctional dick. He was rude to me, and came before he was ever inside me. I gave it a second shot and then walked away.
Paul and I met from OkCupid after he messaged me from his headless, kink profile. He had a beautiful apartment, solid career, and a duffel bag of toys in his closet. The sex itself was just fine, but I enjoyed playing with new things like his nipple clamps, Hitachi, and whip collection. We were actively planning a threesome when he became possessive and I suddenly lost interest. He continually tries to recruit me to sleep with him and other girls, but I hate how he tries to credit himself for my sexual exploration.
Maura & Carl
While I was seeing Paul, I decided to try a threesome as the auxiliary girl/unicorn. I met Maura on OkCupid and began sleeping with her and her boyfriend Carl. This was my first experience with a woman, and additionally with a couple, and it completely changed my view of sex and my understanding of my sexuality. I slept with them both individually on occasion but it was the 3-4 hour threesomes that drew me in and kept me in orbit even as drama and emotions got in the way. By far the best sex I have had to date.
Maura & Josh
Maura met another guy, Josh, and invited me to join. Josh is a boisterous bro with a drug habit and attentional deficits, but is fun just the same. I’m now back to juggling the etiquette of threesomes, but finding myself too drawn in to care.