I’m a 50-something straight male who enjoys dressing in women’s clothing. I’m not transgender. I just have fun playing dress-up sometimes.
It’s never been an issue, as all my friends are open and accepting. I frequently go out in public in full drag. But I’ve recently started dating a new woman, and I’m afraid to tell her about my penchant for frilly shirts and high heels. She’s open-minded, but I don’t know if I’ll freak her out.
My buds have been begging me to dress up in full costume again. It’s been months since I’ve left the house in drag, but how can I break this to my girlfriend?
-- Constrained Cross-dresser
I’d like to commend you for not being afraid to show your feminine side. As a girl, I know I’m a bit biased, but women just have better clothing options.
That said, your fear of “coming out” to your girlfriend is certainly understandable. Depending on how conservative she is, she may or may not be able to reconcile dating a guy who likes to share her clothes. But if cross-dressing makes you happy, you can't deny yourself that pleasure forever. No matter what the circumstances, it’s always important to share the real you with a new dating interest. If you don’t, the relationship could progress to a more serious level and you’ll be even more repressed.
However, I wouldn’t recommend picking her up for the next date in fishnets and lipstick. You should first casually mention your love of cross-dressing to gauge her reaction. If she seems okay with it, show her some pictures of yourself in ladies' clothing. Then let her know you’ll be dressing up one night, and make your grand entrance when the two of you are alone at the house. If she seems comfortable, a night out on the town could come next.
However, if she isn’t comfortable with your cross-dressing, you should consider calling off the relationship before it progresses too far. Don’t stay with someone who can’t accept you for your true self.
Got a problem? E-mail Bianca at firstname.lastname@example.org.