I never really had one, except in private. Long ago, when my then girlfriend was out of the country, I found her corset in a drawer and suddenly wanted to put it on. So I did, and got depressed because I didn't have the big boobs sticking out that I wanted. I never told her I'd done it.
Years later, I got briefly involved online with a dominatrix. I went to Dollar Store one night and bought a big red bra and girl panties. I never had the guts to send her pictures, even though I'm sure she'd have been amused.
What did I learn? I learned that being a girl takes WORK. You can't just put on a corset or sashay down to the Dollar Store. You need to spend hours doing your makeup. You need to get every detail just right.
I failed at being a girl. But I did learn a bit about how hard it is to be one.
I've mostly lived my life as a straightcis man and now I regret it,I'd like to explore pegging, crossdressing, submission and all the other stuff I craved but didn't want to admit I was crazy for.