I told my boss and it has been overall a good decision. I am treated differently but I would do it again.
I made an appointment. We sat in a park like setting. He was nervous because I wanted to talk in private, not in a meeting room, his office on in the cafeteria. When I sat down he said, ok now what is it, his voice was a bit uneven.
He is a little sexist and a little bigoted. I gave him 3 books which he never read. He thinks being TS/TG is like being gay or so his comparison was given. He really thinks women's thinking is not as logical as male.
I would go for the friend tactic, that is what I did. I must say, I discuss some TG light topics and he stairs at the floor. He can not look at me when I am discussing how I am doing, with specifics.