How do I talk to my girlfriend about occasional crossdressing?
March 30, 2014 9:23 AM Subscribe
I'm a 30-ish heterosexual cis-male in a long-term relationship with an awesome woman. We've been together for about four years, have lived together for about three of those and I think we're both pretty happy with it. I want to talk to her about the fact that I sometimes like to dress in women's clothing and would like to get your opinions on how to approach that conversation. Snowflakey details inside.
Some background: Before I met my girlfriend, I'd sometimes wear women's clothing in private. This was an occasional thing and I had a small collection of clothing I'd wear every now and then. It wasn't a sexual kind of thing, it was just satisfying in some way. After thinking it over, I've come to the conclusion that I like it because it makes me feel pretty and there aren't many other ways to achieve that as a straight man (since straight men aren't 'supposed' to want to feel pretty).
The clothes I like to wear are fairly unremarkable. I'm not trying to play a role - it's just me in a dress. The clothing leans towards the feminine, but I think it's probably the kind of clothing that a woman of my age might wear.
Dressing up like this isn't a core part of my identity, although it's probably a bit more than peripheral. I got rid of my women's clothing when I moved in with my girlfriend. It would probably have been better to talk about it then, but it didn't seem important at the time and my attention was taken up with new relationship limerance, etc. I've thought about it on and off since then and finally got some new clothes, which I've worn a few times when my girlfriend's not around.
I don't want to hide this from her, which seems (and probably is) untrusting and disrespectful, but at the same time I'm aware that this might not be the easiest conversation to have, so I want to approach it carefully. I don't necessarily need for her to be OK with me doing this around her (although that would be great). She's pretty open-minded so I don't think she'd have a problem with the idea of people doing this in general, but I can understand she could have some concerns and worries with it happening in her relationship.
So how do I talk to her about this? Advice from people who have been on either side of the conversation is especially welcome.