I enjoy wearing women’s underwear. I don’t want to full-on cross-dress, but I really like the feel of having frilly panties on under my clothes.

How can I break this to a date so she doesn’t freak out when we start getting naked? — T.N., West Virginia

I wasn’t sure how to best answer this question so I asked Ilaria, a former cross-dressing man, turned woman, turned lingerie designer and lingerie fetishist for her advice. This is her flawless answer:

“I would suggest first asking her some subtle questions about gender role and gender identity to find out how accepting and open-minded to she is. You could start off with a lighthearted question about how she feels about stereotypical gender roles, blue for boys and pink for girls and gay and lesbian rights, etc.

Then perhaps a question regarding her opinions on sexual intimacy. Does she believe in strict gender roles in the bedroom, i.e., the man providing and the female receiving, or is sex a more mutually giving experience?

Then ask her if she has a kinky side, and talk about her about her fantasies. At this point, you should have a pretty good idea of how she feels about gender identity and a good basic idea of her sexuality.

If she seems pretty open-minded, then it’s looking good, and she might go for it! I’d begin by telling her that you have a kinky secret that you’d like to share with her, but remember that women love to hear about feelings.

Tell her why you like sexy panties, why you wear them, and especially how they make you feel. Then tell her how much you’d love to share those pleasures with her. Hopefully, she’d love to pleasure you in your panties.”

This column doesn’t constitute medical or professional advice. Always consult a qualified health care professional for your medical, psychological, or relationship problems.