Virgin Territory

Dear Mistress Maeve,

My girlfriend is a virgin, and I have never taken anyone’s virginity. Even though we’ve never had intercourse, we’re very open and communicative about sex. Of course I want to make love to her, but I’ve kept it to myself in an effort to not pressure her. However, she recently told me that she wants to make love to me. I want it to be special for her — something she won’t regret after saving herself for so long.

I know that it can hurt slightly when a woman first makes love. I have no idea what level of pain this is, and I’m kind of nervous about it. I would like to use a condom, but I’m also nervous about the latex and lube making it hurt more. I guess I’m mostly worried about her trusting me more than I could ever really know; I want to bear that trust without dropping the ball.

Thanks for any advice,
The Virgin Virgin

Dear VV,

Kudos to you for taking this situation seriously. A lesser man would simply do the deed, high-five his friends and look forward to the next conquest. When a woman manages to hold on to her virginity through her young adult life, it’s only fair that her first experience be a good one. As long as you truly care for this girl and see yourself staying with her well past this experience, I say go for it. However, if you’re not ready to take this relationship to the next level, do her a favor and keep her virginity intact.

And please — wear a condom. Her virginity doesn’t ensure your health, so play it safe. Besides, a little latex and lube will help things along. As for the pain factor, it varies from woman to woman, from mild discomfort to blood and tearing — a lot depends on the size of your member. Go slowly, communicate and assure her you’ll stop if she feels uncomfortable.

And keep in mind — this will not be your shining porno moment. No matter how open she is about sex, her first time should be more like The Notebook and less like Debbie Does Dallas.

With a cherry on top,
MM