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I was 14 at the time, way too young to be having sex. I had slipped out of my house to go watch my boyfriend’s band practice. I don’t remember if we planned this or not, but we ended up in his best friend’s bedroom going at it. I remember that it hurt. He accidentally hit his head on the wall, and was very gentle. A couple weeks later, we broke up, went our separate ways, and I didn’t get over it for a couple years.
We dated for around nine months. I was 14 going on 15. In my opinion, still way too young. I had only had sex once before him, and I ended up taking his virginity. Eventually it got boring and for other reasons, we ended up breaking up but are still currently very good friends.
William was my best friend. We were friends for around two years before we ever did anything beyond innocent rough housing. It’s safe to say he was my real first love. I took his virginity, and I wished I would have waited so he could have taken mine. We were freshmen in high school. Halfway through the friendship, he got a girlfriend and we continued to be friends till around halfway through the relationship. We used to smoke a bunch of weed together and we convinced each other that if we happened to kiss that it would be okay because we would have been high. After the first kiss, everything escalated from there. This was my one and only tragic love story. We never really reconnected after his girlfriend found out.
Andrew was a small time DJ. I met him through mutual friends and we had a friends with benefits type of relationship for about two years. He was verbally abusive, and I was feeling too low on myself to really do anything about it. We were friends apart from the verbally abusive parts. When things were good things were great. But, he was lazy. He didn’t believe in oral sex on women. The sex got boring and I got bored.
See, Dallas was 20. I was 15. Very illegal, I realize. Great lay, weird guy.
I always thought he was so beautiful. Until we had a very, and I mean very brief and steamy encounter on his bedroom floor. He’d “never had sex with anyone so attractive before.” Minute man.
Jason and I would do so many nasty things until the sun would come up. He was amazing. It’s the shy ones you have to watch out for. They are freaks in bed. I never thought I was so flexible before we were FWB. It was a short steamy stint. Only about 4 months. After a pregnancy scare, and a girlfriend he didn’t tell me about, things ended very quickly.
Matt was a drunk. He was the kind of drunk you bring to parties, but not a wedding. He always knew how to keep the party going. We looked out for each other. Our best friends were dating each other and whenever I stayed the night at the apartment he always gave me a bed to sleep in. Not very talented in bed, but he did give great back massages.
I’m a little person. I’m 5 feet tall and petite. Bobby was around 6 feet tall. He was so well endowed, I couldn’t even enjoy it. And he lost the condom inside me.
Chris was a sweet guy, we’d grown up together. We dated for about two months. He broke up with me on my birthday. Sex was average. It was a long distance relationship so we rarely got to really enjoy and explore each other.
He was a couple years older than me. I was barely starting high school. We had sex on my parents bed. He sweat so badly, sweat dripped into my mouth at some point and I will never forget it. Eventually he told me he wasn’t interested and we stopped contacting each other after his second year of college. A year or two after that, I ended up seeing him at a party with Jason which was terribly awkward.
We’ve been together for a while now. He made me realize after two years of just doing whatever I wanted, doing whomever I wanted, that sex was a beautiful thing. I will never go back to casual sex. In the end, casual sex wasn’t doing anything for me other than just ruining my self esteem and self worth. The sex isn’t always mind blowing, but most of the time it is and it’s wonderful. I’m really at a loss for words at how much I cherish the physical and emotional connection with him.