You may be suffering from impostor syndrome, also known as I don't deserve this syndrome. There is a certain amount of guilt that goes with having it easy compared to all the hard luck stories you see around here and on the news.
Having to dismantle the life of a 50 year old alpha male in order to live as my real self has been anything but easy, but I can relate to you in one way, and this may help:
When I first graduated law school, passed the bar exam, and started practicing law, everyone in the courtrooms was super nice, and everything seemed super easy --especially after slogging my way through three years of law school in which two thirds of my entering class flunked out, and passing on the first try a bar examination in which 56 percent of the takers failed.
For that first year or so of practicing law, I suffered from a bad case of impostor syndrome. I kept waiting for someone to come up, say there had been a mistake, and ask me to hand over my bar card.
Now that I am living part time as a female, I start to get those same feelings again whenever folks treat me as female -- and of course there is the fear that I will get thrown out of a women's restroom.
So that may be what is going on. You may want to talk to your gender therapist about it.