I am somewhat in the same boat, talking about formally starting HRT with the VA as well as a private clinic. I have had a woman GP for my healthcare even before I knew I was trans and she was great and I didn't mind seeing her even though my trans wasn't an issue. She gave prostate exams and never once hurt me, the male GP I had before her hurt me several times giving that exam and has left me feeling very ill at ease about the prospect of a male GP for exams or especially this trans issue. Well, fast forward and I've had to own this for a while now and as uneasy as I was about the male doctor I was to see about HRT, turns out that as soon as he entered the room he announced he was gay and that he knew what a lot of the issues I was facing were about and I should put my mind at ease, he was there to help in any way he could. I was equally nervous about my dealings with the VA, but it turns out they were equally nervous about me! I'm in the Hill Country in Texas and it seems I'm the first self proclaimed trans person that they've had and a bit of a celebrity :-). They were asking all sort of questions about how should they address me and what did I want to be called and were all worried about some sort of perceived etiquette with the newly acquired trans person. In the end I was assuring them that I only wanted to be looked at like anyone else and no special handling was required and that Toni works with a Y or an I. I ended talking with a big, self proclaimed biker looking nurse who it turns out couldn't have been nicer. He said he had LBGT friends who he valued as good friends and nothing else mattered to him. So there you have a couple of pleasant outcomes in spite of our apprehension and the fact is that sooner or later you'll have to own this. Tell the truth and don't be sheepish about who you are. Give your caretakers the same opportunity you would ask of others and if you're not happy, be your own advocate and say no thanks and find someone else.