This question haunted me. I was a perfectionist in school and a pretty responsible adult, so the thought of letting someone down in bed was utterly humiliating. It’s also the sort of thing that gets worse in your mind with each passing year that you don’t have sex, and unfortunately, the humiliation manifested itself in a real way for me in the form of a quasi-breakup. I happened to fall for a guy in college who now I credit with destroying my self-confidence and rendering me incapable of intimacy with anyone for seven years. At the time, we were ambiguously inseparable – the type of couple that people were always wondering about. After over a year of back-and-forth (and other crushes in-between), I asked him what we were doing, and he told me that he didn’t want to date a friend. Unsatisfied with the answer, I asked for a better one, and he said that he wanted to be with someone who was more “experienced.”
Because of that shithead word and that shithead person, I missed out on fun sex in my early twenties. I let the idea of my inferiority – based on one person’s completely unfounded inference, by the way – control my happiness for seven years. The truth is, I was bad at it at first. Everyone is. And being an older virgin, you’re likely to be with someone who is more experienced when it actually happens.
Assholes like that one I mentioned usually reveal themselves if you trust yourself and consider the signs, and they’re definitely not worth sleeping with. There was a reason we hadn’t slept together when the question came up, and it wasn’t because of my inexperience — it was because of his selfishness. Being a virgin is a good thing to a good partner. Whoever you’ve decided to sleep with first should consider it an honor, especially because they’ll have a hand (and many other parts) in shaping your sexual future, too.
Communication is also incredibly crucial. If you’re feeling insecure, it’s OK to say something. If your partner’s mood is shot by your honesty, then fuck them. (But don’t actually fuck them, if you know what I mean.) More than likely, they might take the opportunity to build you up, to tell you why they think you are sexy, and you should listen to them, because they’ll be telling the truth. If you’re not sure about how to do something, ask. Asking the question means getting the answer, and getting the answer means learning something.