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V-Card Diaries: Anna "We were hoping it would 'happen naturally,' but we ended up planning it out like a military operation"

Today we're highlighting Anna from North Carolina, who talks about losing her virginity twice - to a man and then to a woman. The second time was better, but she was also more comfortable with sex. If you want to tell your story, go to our submission form. You can find all our V-Card Diaries here. Tell us about yourself:

I'm a teacher and a writer with a background in anthropology.

How do you define virginity?

It's a completely personal definition - having had sex with both men and women, I would consider the first time with each to be losing my virginity.

Tell us your story

When I was 19, I lost the textbook penis-in-vagina virginity to my boyfriend, a man of my own age that I had dated for a year and who I was completely in love with. We had talked about having sex beforehand and while we bought condoms, hoping it would "happen naturally", we ended up planning it out like a military operation. It was painful and I didn't come, though I think my boyfriend did. Afterwards I fled to a friend's room, but since she was a virgin herself, she took me to one of her friends who was sexually experienced. Lots of hugs and encouragement ensued. Through practice, my boyfriend and I ended up having pretty darn good sex, if I do say so myself.

Interestingly, I later ended up losing my sex-with-a-woman virginity to the sexually experienced friend that I talked to on that first night. By that point I was in a relationship with her. My first experience with a woman was much more relaxed and pleasurable than my first relationship with a man. However, I think that difference had a lot to do with my increased understanding of my own sexuality and comfort with my body, which I gained through sex with men.

Any thoughts on virginity in our society?

Firsts are always important, but the concept has become detrimental to the individual's pleasure. I think most people, especially women, have a crappy or neutral first experience. And that's OK! Practice makes perfect, believe me. We shouldn't put virginity on a pedestal, and I think it's OK to share your body with people that you love and trust without it somehow detracting from your value.