I have a friend overseas who knows about this forum and is an occasional lurker here. She sent me this as a kind of observers contribution:
"Some thoughts from an occasional visitor, who while not completely conventional herself, does not entirely share your background, and so can't completely understand what you go through - but is never the less sympathetic and wants to help.
I read a lot of post about coming out, the drafting of letters, emails etc. The careful planning of meetings, the apprehension, sometimes the joy and relief, but all too often the disappointment.
One thing strikes me that you need to know and appreciate. How you word it, what you say, is of course important to you. Obviously you want to express your inner truth and turmoil. However as they say "it takes two to tango". Sometimes it just doesn't matter how you say it, or what you say, the person listening is just primed to either support and care for you, or they aren't, and no amount of polishing the words and picking the perfect moment will make that much difference.
Often it is more important to just SAY IT - than to wait until you have the perfect words, and the best moment. My partner of the last 25 years is Trans. She is now dying in a care home. For years we supported each other in the knowledge that we had plenty of time. Sometimes this meant that things went unsaid. Now however, every day, I try to make sure that I tell her the things that I need to say to her before we part, because one day soon, that parting will turn out to be our last. I can't predict when that will happen, but I try to make sure that when it does I do not end up with regret for the unspoken truth.
So my advice is - if you are trans stop allowing fear or some sort of false guilt preventing you from coming out.
Stop hiding behind finding the right moment, or the right words. Life is too short. If you want to be yourself, then be proud of that, and do it, but realize that you cant control other people's thoughts and reactions. If they are going to understand then sooner or later they will, and they are not, then nothing anyone can do will change that. Don't let their lack of comprehension spoil your life. It is yours to live, and not theirs.
Oh and one last thing. Please understand that while I'm sure being trans is not fun, it isn't the case that girls are always happy, and that life in the correct gender is all about fairy farts, puppy dogs, perfume and sweets.
Life is hard, bloody, and miserable for a lot of people a lot of the time, and while being trans doesn't make it easy, please don't imagine that the pain will stop when you are not trans. IF you transition, things will be different. You will solve one set of problems, but they will instantly be replaced by another set which will be no easier to deal with, just different.
What I am trying to say is, please do this with your eyes open. Do it because it is YOUR truth, and not because you imagine that life will be better. Do because it is who you are, rather than because you imagine that it will make you happy. Do it for yourself and not for the approval or disapproval of others. It is your life and your truth to live."