If there were no restrictions, such as familiar consequences (being ridiculed and/or exiled), no consequences on income ability etcetera, and I would be like starting a new life with all new friends and identity, never to return to the past life, then lets just say I would go a lot further. This is a kind of fantasy type thinking where one controls all the variables, so its fun to do as an exercise in thought.
For starters, I know I would get a total, professional make-over. The kind that makes almost any male passable-looking. And, I would learn to do these make-overs on myself. I would do my nails, toes, get my ear's pierced, and grow my hair long and have it styled fem. I would wear sexy, but not over the top types of outfits.
Extrapolating, and guessing/predicting a bit I would say that once I was presenting as stated above, I could see a whole mind-shift could start to happen. I might want to do HRT, breast enhancement and so forth, and I wouldn't be surprised if other aspects of my behavior changed. For some, and it's scary to think that maybe for me, once you go far enough down a certain road, a type of obsession could set in. Call it addiction. Or, call it just ones true self coming out? It's hard do know where the line is. It could be you would just adapt to a new, but different normal lifestyle.
This was an interesting, scary, and fun question posted by the OP. I will now go back and read what others have written.