Does the fear fade? It depends. On what? Lots of variables.
The are lots of factors that make being trans harder or easier for each of us. Number one being social concerns. If we have social support then everything is far easier. And social support can come from family, friends, or strangers within the larger community. With more social support, then obviously the more the fear will fade. As one can come out and find connection instead of rejection. As well who accepts and who rejects can influence everything, a spouse who accepts, a parent who accepts, but then a friend rejects, who cares, but flip it around and it becomes far more difficult.
Okay, so some other factors that can play important roles, passing ability - sucks but it is reality that the easier one passes the easier their experience can be, not always but it can help. One's employer - it is now federally not legal to fire someone for being trans, but not all employers will embrace the changes and can make things very difficult. Finances - transition is expensive, heck even cross dressing was expensive for me, but nothing comes close to the more than 20k I have spent on electro for my face alone.
So.... much of what I have mentioned has only really occurred during my transition, which is a different experience than simply being trans and only going so far as to crossdress. Over my cross dressing "years" yes the fear got slowly easier and easier to handle. That only happened though by me first being willing to feel the fear and do it anyways. I proved my fears to be wrong.
