I feel that there are two main ways to go about this, the verbal and the visible. The verbal is where you tell people before it's visibility apparent. I'd say this is the most common way as people generally feel they need others approval and acceptance so they know they'll be there for them in their time of need. Though sometimes they will be flat out rejected but then will know they will be going it alone, at least to begin with.. in time family can turn around and accept.
The other is visible, this is where you just start to in a sense desex yourself, move into the grey area and become androgynous. Painting over pink with blue is much harder than changing it to purple first then blue! I consider this to be less of a shock to the system for those that know you... it's a subtle change that they may not realise at first and just consider it to be who you are.. there is a quote "the art of persuasion is at best a slow process", that's no doubt misquoted but the jist of it is there.
Basically someone will not be so shocked by a seemingly natural change than a sudden change, they're more likely to point it out to you "wow you seem so much more confident these days", "you really don't take crap from anyone these days do you". Little things like that. If they say you should grow your hair out then just tell them you prefer it this way, then the day will come when someone will ask you why you seem so less feminine and you can tell them it's just who you are and that you've seen a doctor about it etc.
