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If it's no big deal for her, you'll still need to be gentle and considerate, but there may be less emotional prep work involved. Obviously you can't completely prevent one of you getting hurt feelings or regretting what happened, but you can reduce the chances with clear, honest communication up-front. Are the two of you in a relationship, or is this a casual thing for you or her? Many guys face this emotional challenge early on in their dating lives before they have had any sexual experience with women and when they are still virgins. Hence, we have a gendered and heteronormative conception of virginity:

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Until I dated him.

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Guys' Take On: Girls Who Are Still Virgins

Regardless of your partner's attitude towards losing her virginity, in terms of the physical act itself, it's going to pay to take things slowly. And then, once he and I started getting serious, they were convinced that he was going to "give it up" to me. In a brief case study, a number of women were asked to list the pros and cons of dating men who are virgins and men who are abstaining. No, not just with you: It would be really unusual to come across a virgin my age, and I don't tend to date women that are a lot younger than me.

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