This hasn’t happened for me yet, but I’m getting close (I think). I have been hinting a bit here and there with my wife (although her reactions are still less than encouraging) and my younger daughter. I’ve also considered discussing it with my younger brother and one of my band mates. I consider them to be the most open minded of my circle.
The biggest issue I have (besides potential outright rejection) is that I feel like I should tell my wife first, but I think it would be easier to tell the others. This is the quandary that I’m stuck in of late. I feel like I’m going to burst and need to tell somebody after 50+ on and off years of crossdressing!