Finding it very hard not to tell people at the moment. I'm still planning to fully transition in June but telling people now means I will have more chances for socialisation presenting as female before full time.
Told an old friend yesterday - he knew me during my first rocky first transition attempt and even though I think I rattled him at that time he still stood by me. He seemed pretty OK with news of my second tilt, he's an easy going guy with a gentle outlook. Told three friends at once tonight (two women and a guy), two are people I've known for about 18 months and the other woman for ten years - they were all very supportive and happy for me - the two women want to take me shopping!
One thing I find really helps with the process of outing myself has been pictures - after I drop the bombshell and answer any immediate questions I get out the iPad and show them some of my better selfies... it stops their imaginations from running wild, picturing "whatever" they think I would look like based on their internalised perception of trans women. They get a chance to see me as I believe I will look and somehow it changes the overall reception to my news, it's as if the support goes up a notch or two. The other thing that helps is having a name ready, because it's one of those things that inevitably gets asked. When they hear the name it must help with the identification process or something.
Being several months along on HRT also makes a difference because I can point to various changes (like boobs). While keeping the whole thing fairly lighthearted I do still make it clear that this is a deeply personal and difficult choice and process. Plus I thank them deeply for their understanding... I certainly got a lot of hugs tonight! Sure, maybe they didn't really understand the full extent of what the deal is for me, but they're happy for me and supportive and that's all I can ask for really.
I don't expect the same level of acceptance from my family but at least I'm learning some useful techniques for when that day arrives...