When someone asks me a specific question about attempting to go full time as a trans woman, I have a simple answer for an ultra complicated deal: Get your "pretty in pink" rear out of the mall and into real life. After a while you learn if you really want to tip your gender into where you always considered it to be. And then cross the magical, mysterious and highly scary line from being a cross dresser into living as a transgender woman.
Before I put myself up on a pedestal, my journey was hugely pushed along by friends who refused to accept than anything I was-trans and a woman at that. I was pushed into situations such as an NFL Monday Night Football game, a "lesbian wing girl" and of course, a trip to Mardi Gras. Even still, all of those were just experiences and not everyday life.
Recently, I have read several posts calling for cross dressers to come out- be counted and how do CD's fit in with the transgender community. In my never humble opinion, totally. With reservations of course.
My easiest example to relate to all of you is the story of my deceased wife calling me a "terrible woman" back in the mid 80's. I thought she was nuts and said the public didn't think so. She explained (bluntly) she wasn't talking about how I looked at all. Fast forwarding thirty plus years, I searched, searched and ultimately ran like hell from the fact I was indeed transgender. Since she has passed of course I have no problem with saying she was right!!!!
But-in no way is cross dressing a "gateway" process to becoming transgender. All cross dressing will do is provide an avenue to explore your own "genderality." Plus, there is absolutely nothing wrong with expressing yourself as a cross dressing male! After all, what is the real harm?
So, good luck with tipping your "gender scale." For years I knew which way mine was going and was afraid I could never get back. Then I discovered I didn't want to.