No way, not willingly.
The last time I wore a dress was in the summer of 2001, long long before I even considered that I was trans. A friend of mine had bought all sorts of clothes she couldn't fit into, and since I'd had lost weight and could, she wanted me to model them. I agreed, and let her do me all up in makeup. This was something I never ever did, and so I figured, hey, why not just try it out?
Afterwards, when washing the makeup off in the bathroom mirror, I looked at myself and realized I looked like a guy in drag. It was startling, and after that I would never agree to anything of the sort. (that was also the point where I began to suspect I actually was a guy in drag, it's a shame so many years of denial followed)