I have been married to my wife for 31 years now. And I told her about my clothing preferences while we were still dating. She is supportive, but with certain rules. Number one being that I keep it private and don't leave the house dressed except for Halloween (and shockingly attending Rocky Horror). Other than that I have kept a few rules of my own, trying to not push boundaries to far. For example not once have I ever asked for anything girly.
So imagine my surprise last week when my wife spotted me admiring a dress while we were out and asked if I liked it? I said yes, but it was okay and I was not planning on buying that day. She then looks at me and said "well, I have not bought you your birthday present yet... do you want this? They have it in your size."
You could have knocked me over with a feather. Of course I said yes. I had never had a denim dress before, and this was styled in one of the few 70's designs I like. Honestly, while I still wish she was more comfortable with the idea of going out as Kimmy, I really can't and won't complain.