Well it's finally time. This is the letter I fired off to the first couple of friends. It's the format I'm planning to tweak a bit before sending to my parents, so consider this its' dress rehearsal. Any constructive thoughts from the rest of you would be appreciated as well.
...
Dear [names withheld],
I have some news I wanted to share with you. Not having seen you for some time I'm not quite sure how to relate this in an easy manner, so if you'll indulge me I'll be direct and risk coming across a bit brusquely.
I have decided to transition my sex to make my external appearance match the gender I've always felt inside. In other words, I am transsexual and am planning to become a woman.
This has been anything but a quick or easy decision. Most of my life has involved a combination of hiding or repressing this part of me. For as long as I can remember I have lived in a state of abject terror that someone might discover this secret, and that has driven me in sometimes strange and often self-destructive directions to keep it hidden. But I've finally reached the end of my endurance for that kind of life. I need to finally make myself whole, face the fear, and come out as who I really am.
This is not going to be an instant change. The process is (unfortunately from my perspective) fairly slow. But, especially because it presents some unique challenges in terms of employment in addition to costs specific to the transition itself, I don't anticipate being fully transitioned in every aspect of my life for a couple of years. This means I cannot necessarily tell you which gendered version of me you might encounter at a given point in time during that period. But to avoid confusion you should know the long term direction is clear - eventually I will live my life entirely as a woman. The male "version" of myself will eventually go away for good.
I've always valued your friendship, even though my desire to hide my secret inner self caused me to maintain a lot more distance than I would have liked. I'd like you to understand that the distancing itself - the constant pushing away / running away - was the result of my inner transgender struggle. It's impossible to grow very close to anyone when you feel like you can't risk being yourself around them. In lieu of honesty I prejudged myself on everyone else's behalf, including yours. I decided everyone would reject me if they only knew the real me. And as a result real closeness to others was simply impossible for me. I'm trying to change that as much as anything else by this process.
Obviously this kind of thing is difficult for many others to understand and accept. I'm well aware that this may put you in an uncomfortable position in regard to our continued friendship. I just want you to know that I would like to keep your friendship - possibly even become a better friend than I've been able to be in the past. I'm always willing to answer any questions or address any concerns you may have.
With love and respect,
[name withheld] (who is becoming Diana)