I Slept With The Guy I Lost My Virginity To Again & It Was Awful

I Slept With The Guy I Lost My Virginity To Again & It Was Awful ©iStock/wundervisuals

It’s not abnormal to imagine having sex with the guy you lost your virginity to again somewhere down the line when you actually know what you’re doing in bed. After all, he’s the one who opened your eyes to the world of sex. However, actually sleeping together again years later won’t necessarily be a worthwhile experience — it certainly wasn’t for me.

  1. It made me realize he wasn’t as good at sex as I thought. When you lose your virginity, you have no prior experience to base it on so you naturally assume it’s good sex even if it’s actually terrible. It takes time to learn the difference between hot and embarrassing sex. Sometimes you have to accept the fact that you really don’t gel between the sheets — you’re actually way better off as friends.
  2. It changed my perception of losing my virginity. When I had sex with him again, it made me realize that he didn’t make me feel special at all during my first time. To him, it wasn’t a big deal, but for me, it’s something I’ll remember for the rest of my life. I was too young and naïve to recognize when a guy is simply horny, looking for any woman that’s willing to sleep with him.
  3. It brought me back to the past, and not necessarily in a good way. It’s never beneficial to go backward, especially when talking about past lovers. When we had sex again, I thought about all the great and not so great times we shared years ago, and I realized that he was more of a casual fling than a relationship. We didn’t have the foundation we needed to last.
  4. It made me regret doing it again with him. For some reason, I thought it would make me feel good about myself to be the one calling the shots this time — when we were younger, he was the one who broke off our “relationship.” However, after it was all said and done, I questioned why I even wanted it in the first place. I anticipated feeling like I finally got my sweet revenge, but in the end, all I felt was guilt.
  5. I didn’t feel any more comfortable with him than I did the first time. From the moment he walked into my apartment, I felt uncomfortable. We had barely talked after we ended our relationship and a lot had changed. Sometimes, welcoming people from your past into your current life is more trouble than it’s worth. You have to be picky about the people you surround yourself with because many of them don’t have the most genuine intentions.
  6. It didn’t last as long as I thought it would. When I was losing my virginity, the sex felt like it lasted a lot longer than it probably really did because I’d never done it before. Once I started sleeping with other people, I realized that sex can actually truly last if the guy has enough stamina. Of course, not every guy can last 30 minutes and that’s okay; it’s just nice when he surprises me. This guy clearly was incapable of that.
  7. It was awkward as hell. Reconnecting with my first lover is a difficult experience to describe. Even though we’ve seen each other naked several times now, I still feel like we barely know each other. This made the sex totally unenjoyable because I had no reason to go the extra mile to please him, and he certainly didn’t make any extra effort for me either.
  8. There was no connection. Without thoroughly knowing the other person, sex can feel extremely unfulfilling. Truly getting to know each other can do wonders for my sex life because we can learn what makes each other turned on over time. If I don’t have significant time to figure out my partner’s quirks, I’ll feel aimless during sex and I basically might as well not even bother.
Bolde has been a source of dating and relationship advice for single women around the world since 2014. We combine scientific data, experiential wisdom, and personal anecdotes to provide help and encouragement to those frustrated by the journey to find love. Follow us on Instagram @bolde_media or on Facebook @BoldeMedia