My First Time is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your "first time" is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that's how sex stays fun, right?
Growing up, I always thought of cheating as essentially a bad thing that people did when their relationships weren’t working out. When I was 13, my best friend’s mom had an affair, and I remember being really shocked and scandalized by it. Her parents separated, and I saw how that fractured her life. When I was 18, my own parents split up because my dad had an affair with someone else. I saw the effect that cheating had in my own family structure, and I always told myself: I’d never do that to someone. I used to say things like, “if you feel like cheating on your partner, you should be honest with them about those feelings.”
Now that I’m older, I realize that parents are also humans, and I can understand why people cheat. When my dad cheated, I thought, H__ow could you hurt me like that? I felt personally victimized by his behavior. But now I understand that he was in a loveless marriage, and that he was unhappy.
The first time I cheated, it was a one-off thing. At the time, I was in a fairly new relationship with my partner, who I’m still with. Since we weren’t official, I was sleeping with someone else. I hadn’t told him about it—I didn’t feel like I needed to, given that we weren’t exclusive at that point. But about three months in, we had the chat and decided that we were going to be boyfriend and girlfriend, and so we weren’t going to get with anyone else. About a month later, I cheated on him for the first time: I kissed someone else on a drunken night out. I think my cheating was linked to my emotions about being in a new relationship. It sounds awful, but I thought, T__his might be the last chance I get to do this.
Selfishly, I thought that if I told him about it, he’d think, W__ell, she was pretty drunk, and we haven’t been going out for that long, so it’s not a big deal. But he did get quite upset. He handled it well, but it definitely set our relationship off on the wrong foot.
I wonder, in retrospect, if I was self-sabotaging the relationship because everything seemed to be going so well, and I was frightened. I felt like I didn’t deserve to be with someone so loving and kind, so I set out to ruin it. My last relationship had coincided with my parents splitting up, and I experienced a lot of loss all at once. I was really upset and hurt for a long time. When I met this great guy who treated me so well, I thought, D__o I really want to commit to someone again who might hurt me or leave me? My self-esteem was so low that I thought if I sabotaged the relationship, I’d be doing my new boyfriend a favor: He should be with someone better than me, not someone who slept around as much as I did, and who was so broke and unhappy. I didn’t want to color his life with all my darkness.
After the first time I cheated, I decided I wanted to take the plunge, face my insecurities, and be in a committed relationship with someone. I wanted to relearn intimacy and what it meant to have sex with one partner. But I cheated on him again about six weeks later with a guy I’d met at a course I was taking. We’d known each other for a while, and had always flirted and gone out and gotten drunk together. The course was coming to an end, so we went out drinking with a few friends. In the back of my mind was the thought that I might not see this guy again, so I asked him to come back to my house. We had drunken sex, and it was not that great. He left, and I immediately felt so guilty. I never spoke to him ever again.
I felt guiltiest about the fact that we had sex again in the morning, because I didn’t have the excuse of being drunk. I thought, I am the worst person in the world. I had sex with him when I was sober. During that second time, I was thinking, O__kay, one more time, and then I’m committing to my boyfriend. But I regretted it.
About a month later, things got seriously complicated thanks to that incident when I realized I was pregnant. It took a day or so for it to sink in that the person I'd cheated with might be the father. In addition to the guilt, I had to deal with all the emotions that come with an unwanted pregnancy. My boyfriend was so supportive when I told him about the pregnancy, and that I was getting an abortion, which made the guilt about a hundred times worse. All I could think was, Wow, you’ve really fucked this up.
About two years later, I told my boyfriend about the cheating. I’d thought about telling him lots of times before, but my friends had advised against it. They said, “You’re never going to see that guy again. It doesn’t mean anything—it’s better for him not to know.” But I was surprised at how much the guilt lingered for those two years. It just wouldn’t go away.
We were on holiday when I told him. We were in this restaurant, and it all just came out. I told him how sorry I was, and how it had been eating away at me, and I started crying. He was stunned, because we’d just been having a nice meal together. Then he said, “I’m glad you’re able to tell me about it.” Amazingly, he was okay about it. He said that he knew I’d been in a weird headspace for the first few months of our relationship, and he knew I’d never do that now.
I’m really glad I told him. I couldn’t handle the guilt any longer. At first, I regretted not telling him sooner, because he took it so well. But I think I told him about the cheating when I felt ready to tell him, so I don’t regret not telling him earlier. I needed the time.
I’d never cheat again now. I was stunned by the amount of guilt I carried because of a one-night stand. I can’t even imagine how much guilt you’d feel if you had a full-blown affair. I don’t want to carry that baggage around with me ever again.