I have been on hormones now for about 3 1/2 months ( with a month break in between), and I have only told a few people about transgendered status. Out of the ones that do know, they have been supportive and helpful in any way they can. It is a wonderful feeling when the one's that are close wish to stay that way even though you might be changing some outside. It is a great way for you to determine who is really your friend and who is not.
I decided to tell one person at my work of what was going on with me, believing that I could trust them. Unfortunately, I found out last week I could not, as I found that they decided to go and tell other officers (I work security) even though I asked for it to stay between us. On the bright side, the person she decided to tell is going through the same thing I am, but in the opposite direction. The person who found out has been great in helping me with anxiety issues about work and my transitioning. I also found out that she had already told work of her transitioning and everything was okay. There was no loss of job, no harassment, just an acceptance.
So, today was my day off, but I found myself going in anyways to cover a partial shift for someone who could not come in to work. When I got there, my boss came to me and asked the question that everyone cringes when they hear it, "If there is something you would like to talk to me about, I am hear." When I heard that I just about panicked and ran, but instead I let the adrenaline just flow and I kept my cool. Turns out that the original person I told decided to tell more people, and when they were talking about it, my boss overheard. I quickly talked to the other officer who is transitioning, and she reminded me that everything would be okay. After a short talk with my boss there after, I was so relieved. He did not have a problem with anything; he just said, "As long as my people do their jobs, I have their backs, and I will help any way I can."
All in all, I had to do things that I was not ready for, but it turned out really well in the end. I overcame a huge obstacle in my transition, and I am not looking back. Oh, and an additional plus note, I always had to cut my hair short for work; no longer; I have been given approval to let it grow long again as long as I keep it up and above my collar while at work. : )