Huh, I got in on this one a tad late.
Let's see... at 18, realized I was trans. Did absolutely nothing about it for almost 6 years subsequent, due to fears about people's reactions, etc. At 23, came out to one friend, who said I must be insane and should get into therapy at once to reinforce my gender (this was a fairly open-minded guy who was fine with my being supposedly a lesbian, but not with my being a man). Went crazy, dated some even crazier people, and just prior to my 24th birthday, went full-time to everyone but my parents. Had been dressing male and cutting my hair short since age 15 or so, though.
So timeline...
1) Bound with neoprene belt (ouch!), used men's restrooms, grew out what facial hair I had, and presented as fully male except to family.
2) Bought binder and elevator shoes (yes, I'm the moron who thought one had to be tall to be a man). Passed about 95%.
3) Chucked the elevator shoes, got married as a man (but only because the justice of the peace read our names for one another)
4) Stopped passing, despite not doing anything differently. Turned 25, and figured the length on female hormones was taking its toll.
5) Got on T so I could pass again. Within a month, passed flawlessly and haven't gone back since.
Yeah... that's all I've got. I've been on T for roughly a year now, though on and off due to financial strain. Oh yeah, and I guess I came out to my mom somewhere between #2 and #3... she came out to the rest of the family for me when I got married. My transition is sort of on hold for now, due to my impending divorce... ain't life wonderful? But hopefully within the next year or two I'll be having top surgery, and should be having my name changed LEGALLY within the next few months. Didn't have it changed before because in California, you can change your name & gender on your license with a doctor's note.
What was the hardest thing for me? Dealing with people's reactions. Apart from that first guy I came out to, the majority of my friends were totally cool about my being trans, but my family has been anywhere from deplorable to horrendous in their reactions. They still call me by my birth name, and refuse to think that anyone could ever see me as a man. They think I'm an aberration in the eyes of god... you get the picture. But it's worth being able to look at myself in the mirror without wanting to slit the throat of the person I see.
SD