I am a 28 year old virgin. I'm not religious, and it's not that I don’t want to have sex, because I do, very badly. I think that for whatever reason it didn't happen when I was younger (family issues and schoolwork prevented me from having a long term relationship in high school and college, and I'm not the kind of girl who has one night stands).
My problem is that I feel like as I date as an adult, sex is expected either very quickly or held off until two people are in an exclusive relationship. When I date, I find myself self-conscious about having not done it. If I tell the guy early on, he inevitably gets freaked out and runs away. Sex is a conversation that tends to come up in dating, and I feel like I need to be honest about the fact that I haven't done it.
This has been an issue for me for a long time now, and as I get older it only gets worse. Please help me before I become a thirty year old virgin. I'm starting to get desperate here, but really don't want to just jump into bed with the next guy who buys me a drink. I should add that while I'm no supermodel, I'm attractive enough that I usually have no trouble attracting comparable men.
Okay, so the question is “why is the guy running away?” You’re probably thinking it’s because he hears you’re a virgin. The way he interprets that information depends on the way you interpret it and feel about it. If you’re self-conscious and serious about your virgin-ness, then he’s probably going to assume that the decision to deflower you will have serious consequences and that sex with you is going to be emotionally complicated. Serious, complicated sex is like libido-kryptonite. It not the fact that you're a virgin, but how that gets interpreted.
I get that you’re self-conscious about being a virgin, and about what sex will finally shape up to be. Let me offer you 2 things to consider. First off, you can spin your lack of experience as a plus. Short of starting a fire or throwing up on your cat, you have no idea whether your guy’s performance was dismal or spectacular. There’s less pressure on him to perform. Him: “Yeah, it’s actually normal for a guy to cum really fast and on your leg.” You: “Oh, okay. Awesome.” Second, everyone is self-conscious when it comes to sex because sex is fucking awkward. Or awkward fucking. It doesn’t matter how many partners you’ve had. It always involves some degree of vulnerability and performance anxiety. So if you’re uncomfortable, it’s fine. Nothing’s wrong.
Try and be less serious and more playful about your virginhood. When the topic comes up, immediately accuse the guy of being a sex fiend, then offer a smile. When you’re forced to talk about it, get all serious all of a sudden, lean in, and tell him you have a secret. Tell him you’re a former gangbang queen. Have a laugh and then tell him the truth – that you never had sex because you were looking for a relationship but were too busy masturbating to take interest in anyone else. You get the drift, right? Just have fun with it and don’t be embarrassed about the truth. It’s really not the biggest deal. The guy will see that you have a good attitude and he’ll see that having sex with you might be some awkward fun.
The last thing you want to consider is what you’re expecting. If you’re waiting for a long-term relationship, well, those are rare in general, so it’s going to be harder to lose your virginity under that condition. It’s a choice you’re entitled to make and I wouldn’t tell you to compromise something you feel strongly about. If you’re willing to be flexible and, say, sleep with someone you’ve been dating for a month with whom you’ve developed a decent amount of trust and intimacy and with whom you can see yourselves dating through the following month, then your chances of finding someone to sex you will statistically improve. It’s a good idea to let the guy know what you’re expecting, especially since he’ll automatically assume you will want a long-term relationship.
Finally, if you haven’t sexed by your 29th birthday, then I’d suggest calling up a liberal-minded friend, sparking a conversation about sex over some drinks, and proposing that you both have sex once. Tell him that he won’t have to get you a present if he does. If you want to have more sex later, you can discuss it openly afterwards.