I’m a 27 year old virgin who was raised in a Puritanical family to believe that Sex was dirty, evil and wrong; I masturbated when alone, watched porn when I could, but never tried to touch a woman for real because I believed that there was some pure virgin woman out there, waiting for someone exactly like me who, when we got married, would satisfy every sexual desire I had. But when I got to college I started to realize that both good girls AND bad girls have sex, and the mysterious, untouched, pristine virginal woman who would wait for years until marriage to have sex, basically didn’t exist. I’ve tried dating, but every woman seemed to view me as “friend zone” material until I recently found one on an online dating app who is perfect in every possible way. In two months of online interaction I’ve fallen head over heels for her, and next month I’ll be flying to her state to meet her in person and spend a week with her. However, she is not a virgin; in fact, she’s quite experienced and can’t wait to “have all kinds of naughty fun” with me. But I haven’t the slightest idea of how to please her! I told her I was a virgin, and she told me that’s okay. But, I don’t know how to do cunnilingus, I don’t know how to move from one activity to another, and I’m not sure if my penis is big enough to satisfy her. And my fear is, I will lose her if I don’t satisfy her on this trip. What should I do? Should I visit an escort so I can practice? Any advice you can give me is greatly appreciated!
This might seem weird coming from me, but DO NOT see a sex worker or otherwise make any attempt to lose your virginity before meeting up with your lady. You told her you’re a virgin, and she said that’s OK; it’s entirely possible that it’s even more than OK, and in fact may be something she specifically finds desirable in you. Some women like breaking virgins in; sometimes it’s a turn-on in and of itself, and sometimes it may be that they enjoy “training” a guy to do things the way they want them done. Now, it may be that your lady isn’t specifically interested in your virginity, and that she doesn’t care one way or the other. But it’s also possible she might feel kind of cheated if she was looking forward to that and you went and screwed it up without good reason on the eve of your meeting. Note: I am not saying that anyone “owes” a new partner virginity, or that sexual experience is a bad thing (and I am not going to be a pot describing the color of kettles). All I’m saying is that I see no valid reason for you to make a liar out of yourself when you may be fulfilling a fantasy of hers (which I think you’ll agree would be pretty awesome).
Don’t worry about not knowing what to do; trust me, she already expects that. Lots of men who think they know what they’re doing in bed actually don’t know shit, and since she’s quite experienced I’m sure she’s been with more than a few of those (incredibly annoying) guys. Believe me, sugar, she’ll be a lot happier in bed with a guy who admits he doesn’t know anything than a blowhard who pretends he does, but doesn’t. You say you don’t know how to give oral sex? Well, you’re in company with at least 80% of the male population there. Ditto not knowing how to guide the dance; that usually ends up being the woman’s job. And unless you have an actual micropenis, don’t worry about being big enough to satisfy her; if she were a size queen she’d already have asked you about that. Though your fears are understandable due to the garbage you’ve taken in from both your upbringing and the popular culture, it is a virtual certainty that they are baseless: you aren’t going to lose her because you aren’t Superstud with a magic penis (especially because there ain’t no such organ). That would be true even if you had a typical level of experience for your age, and it’s even more so since you were upfront about your lack thereof. Relax, have fun, and let me know how it goes.
(Have a question of your own? Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)
