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I met him at work when I had just turned 18. Over a course of a couple months, we started meeting up with each other to get high. I admitted to him one night that I was still a virgin. Like the gentleman he was, he offered to take my virginity. So in the backseat of my 1995 Cavalier parked in a Catholic church parking lot, I gave him what I thought then was a special piece of myself. We stopped talking to each other a week after it happened. He ended up dating a close friend of mine and they have kids with each other.
The first guy I really regret. I met him on Hot or Not and texted him for a few weeks. When I first met up with him, he was nothing like I expected. He was short, had a weird smell, and he really couldn’t hold a conversation. Regardless, I did not know how to say no. So on his couch, I let him have sex with me. When I asked him to wear a condom, he said he was allergic to latex and I didn’t know what to say. I spent a day at Planned Parenthood with my best friend afterwards, just to make sure everything was okay. Thankfully, it was.
I had a crush on Matt for a while during school. Once we finally graduated, we started seeing each other at parties. On the fourth of July, we ended up sleeping with each other. I was expecting more romance or passion or something. Instead, it was a few quiet minutes with our shirts still on. I found out he had a girlfriend afterwards.
Guy #2 that I truly regret. The first guy I ever slept with more than once. I met him at my best friend’s wedding. He introduced himself to me as the brother of the bride. He was kind and funny and had a mysterious vibe about him. A week later, he invited me over to his house for dinner. Afterwards, as we sat talking, he pulled off my pants and inserted himself inside of me without asking permission. When I told him to stop, he did and apologized. When I left, he sent me a long text about how fucked up he was because of his time spent in the army.
Foolishly, I forgave him and saw him again. Only to be guilted into bad sex again. After a month, I gained courage to tell him I was no longer interested in any sort of relationship.
Jake was the first guy I met when I started college. He was shy and quiet, but when he did speak, he was cute and funny. His hands shook when he held me for the first time. When we decided to have sex, he was nervous and didn’t really know what to do. Thinking back, I should have known that he was a virgin. After two minutes of what I would barely consider sex, he stood up and said to me, “I think I better leave.” And he put his clothes on and walked out my door.
After two weeks of unanswered calls and texts, he finally admitted to me that he was embarrassed to tell me that he was a virgin. I felt incredibly sorry that I didn’t have feelings for him when I took his virginity. But I couldn’t fake any feelings for him, so I ended things early on. He cried.
I met Evan at a concert at my college. I was alone and he offered to walk me back to my place. He had a faint smell of liquor on his breath. As we walked, he talked to me about all his favorite bands and everything he loves about music. I invited him inside and he stayed in my bed with me and we talked until the sun rose. I was in awe of how kind he was and how he didn’t expect any sexual favors from me. He was the first man to show me respect. I ended up making the first move early that morning. It was the first time I truly enjoyed sex.
We ended up dating for a few months, but he ended things to go back to his hometown a couple states away. We still talk every once in a while and I’m reminded that I still have feelings for him.
He was my rebound. He was smart and had a great career. I was attracted to how put together his life was. We agreed to only have sex with each other, no feelings attached. He gave the best head out of any guy I’ve been with and truly loved doing it. He would make me come numerous times and expect nothing in return. The sex was a little lackluster, but his mouth made up for it. Best orgasms ever.