I'm surprised, through all his visits, one didn't include a doctor friend to start him on hormones and talk about other surgeries. At what point does he say, enough is enough.
I'm Delia, I have been crossdressing since I was 8 or 9. I have been lucky enough to have some wonderful experiences. When I was younger I was caught dressed in my sister's clothes, this led to a 'relationship' that lasted a few years.