Hmmm that's the ideal situation but have you watched the movie "Danish Girl"? It's about a husband who crosdresses and a wife who supported him.
There also blogs on tumblr like that? For support or fashion etc.
I used to follow fashion one about a husband and wife who did mirror pics for "look of the day" type posts. They even had their little girl in some of the photos and the husband posted a lot of good advice on what to look for when looking for a dress/heel/etc as a man. It was pretty cool.
Actually "The Danish Girl" is about a real transgender woman. The story of real-life Danish painter Einar Wegener who, in 1931, became the first person to undergo a sex-change operation.
to be honest, i think i'd actually like to have a cross-dressing boyfriend! we could have really funny banter:
bf- hey babe, can i borrow your skirt?
me- what? no!
bf- oh come on, why not?
me- because you look better in it than me!
idk, but something like that.