I'd trust medical folks to be the least risky to out myself to. Made a pact with myself as a young man to never lie or prevaricate to my doctors. OTOH, I'm a middle-aged, white, cis, male, so I can hardly feel it from the viewpoint of a trans person. Also depends on the area. OTOOH, even here in the deepest South I don't see the medical people I've known and dated to hold that sort of prejudice. They just want to fix you and need the best data to do so.