True Story: I Regret The Way I Lost My Virginity

Everyone says your first time should be with someone you love. Well, here’s something “everyone” didn’t tell you: just because you lose it with someone you love doesn’t mean you won’t regret it. I certainly do. While I loved Sam very much, it was not at all the right time. When I look back on it, I don’t have a pleasant memory.

I had a really tumultuous relationship with Sam for about six years on and off at the time, which probably was a red flag to begin with. But I was young and in love, and he was “the one.” The timing with us was always wrong. We’d both be seeing other people, but always gravitated back to each other regardless. We would stay up all night on the phone, bitching to each other about anything and everything.

One night we were talking, and the topic of sex came up. He was curious, I think, if I had slept with someone. I was shocked that Sam would even propose the idea that I would lose it to someone other than him. He was relieved; “Good because I love you, and I want to have that experience with you.” That’s funny because he wasn’t a virgin. He had actually lost it to my ex-best-friend, but that’s a whole other story that we won’t get into now. Read more…

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