Basically how I did it was the following:
I basically started a photo album called "My Transformation, In Pictures." For months and months, as I progressed with HRT, I posted a new picture every few weeks or so. I was losing weight at the same time, and always posted my updated weight along with my picture updates, so everyone just assumed that the "transformation" I was talking about was weight loss. Unbeknownst to them, they were watching me feminize right before their eyes.
Finally, after about 7 months of playing this game, I decided it was time to come out. So basically what I did was post a picture which included my already-B-cup boobs in an athletic body-hugging outfit, with a feminine heart necklace, along with the following message:
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"I've been debating whether or not to post this photo for a long time now... because I know what it's going to mean once I do. But you know what? I'm tired of this little game of "figure it out" that I've been playing recently. And above all, I'm tired of this act of normalcy. After 14 years of hiding who I am on the inside, this picture should make it pretty obvious exactly what kind of a life-changing transformation I've been hinting at for the last 10 months. Let's just say that there's a very good reason why I'm growing my hair out. And due to some significant hormonal changes, certain appendages have been growing while the rest of my body mass has been shrinking. (Holds breath and hopes for the best here.)
(and if this picture doesn't make it obvious enough... here's a picture of me in my Halloween costume, which should remove any doubt. http://i43.tinypic.com/2w312xw.jpg )
My childhood (gay) friend immediately rushed to my support. As did all of my friends from work who I'd already come out to months before. (Basically I was fired from my job, and right after getting fired, I'd heard that some people had been whispering about my increasingly-feminine appearance, so I just decided to come out on my workplace's Facebook page, so probably 40% of my friends' list knew already.) A ton of people told me that I looked great in my Halloween costume. A family friend replied "you're my friend, whatever." Another childhood friend sent me a PM to basically say "holy s***, dude."
The next day, following the picture coming-out, I changed my gender marker from male to female, and then posted the following official coming-out announcement:
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So, in case you haven't seen by now, as of yesterday I'm now officially out as transsexual. And it apparently came as a shock to many people, so I guess I owe all of you at least somewhat of an explanation. So here we go:
Basically, around the age of 12, I started feeling something called "gender dysphoria." Which basically means that I started feeling like my physical body didn't match the self that was in my head. For whatever reason, every single one of the changes associated with a male puberty made me feel detached, as if "no, this can't be happening, this shouldn't be happening!" And I stopped feeling comfortable in my own body. Every single time I looked in the mirror and saw body hair, heard a deep voice, had to fight against my newly-enlarged sexual anatomy, it made me feel like complete and total crap, and I'd look at the girls and just feel this deep-seeded feeling of longing, of "why am I not like them? Those changes that they're going through, that is what would feel right to me."
I've lived with this feeling as my default state of existence for the last 14 years straight, doing EVERYTHING in my power to get over it, including flat-out denial in the form of trying to become a fundamentalist Christian and pray away these transsexual desires.
Around last Christmas, I finally realized that it was never going to go away. Despite all of my best efforts, despite officially renouncing my transsexual desires at age 21 and declaring myself cured, I was just kidding myself. They ALWAYS came back. And at that point in my life, I had absolutely everything that I had always thought I wanted. I was finally done with school, I had a great-paying job now, I was well on my way to financial independence, I had a girlfriend, I was eagerly looking forward to a possible future family, I was established, and living the life I'd always thought I'd wanted, and I should have been happy in every single way. And yet I wasn't. Because no matter how great things were on the outside, I was still at war with my own body on the inside. I was still stuck in this "dull grey drear" mode where nothing ever seemed to bring me real joy. I was bitter and angry and snappy all the time for no reason whatsoever, and social interactions felt like a chore. And every single day I was still waking up in a body that I hated, not feeling the emotions that I felt I should be feeling, not feeling truly alive for a reason that I just didn't understand.
With that in mind, I decided that it was finally time to quit running from my transsexual desires and face them. And on January 8th of this year, I officially started hormone replacement therapy. And for the first time since I was 12 years old, I am FINALLY starting to feel happy in my own body again.
That's really all that there is to it. I was miserable for the entire 14 years of my life that I had testosterone in my system, and now I'm finally becoming happy with myself again. That's why I'm doing this. Because it makes me feel happy. Because I finally feel like my body is starting to match my internal identity again. Because I'm no longer at war with the body hair, and the male sex-drive, and my emotions finally feel right, and I feel happy on a core level where previously I felt miserable on a core level, even though now I'm WAY worse off in terms of life situations.
(there was also an Q&A at the end where I answered what I assumed would be some common questions about surgery, hormones, my sexual orientation, what my new name was going to be once I finally did legally make the switch, etc, but I don't feel the need to repost them.)
I was shocked at the sheer amount of people who gave that note a "like." Childhood friends, high school friends, college friends, my ex-girlfriend, friends that I'd met through her, work friends, and even some of my old teachers from middle school.
And to be honest... only one person seemed really surprised. (An old friend from my childhood secret club.) Apparently everyone had been assuming I was gay all of these years without anyone really telling me outright, so yeah, the response tended to be support with a side dose of "yeah, I could kind of tell, but it's glad to see you finally come out and be authentic about yourself."
And then about 5 months after that, once I legally changed my gender marker, I changed my name on my Facebook profile to my female name. My aunt wasn't happy about that. She wrote me a reply about how I should keep my birth name because I'm named after my great-uncle, and I needed to honor that. Friends immediately counter-posted about how they loved my new name. (I love my friends sometimes.

) [And my aunt later calmed down after I explained to her that I was still named after him, just using the feminine version of the name "Charles," Caroline, instead.]
Aside from that one protest from my aunt about my name, I didn't encounter any open hostility whatsoever. Anyone who didn't respond or "like" my trans-related posts pretty much just said nothing and haven't said anything about it since. However, a few days ago when I was looking back at my friends list, I noticed for the first time that 2 or 3 friends had quietly de-friended me without saying anything. So some people weren't okay with it, but they were too polite to say anything to me, and just decided to leave my Facebook page.
That's it. I've had some drama with my dad behind the scenes, but in terms of Facebook, it couldn't have gone smoother.
I deliberately decided to come out in as direct of a manner as possible, just outright changing my name and gender marker on my primary Facebook account rather than doing the two-profile method, because I didn't want to give people the option of clinging to the old false me while ignoring the actual me. And for me at least, it had exactly the desired effect. I treated being trans as nothing to be ashamed of, just an immutable part of me that they were going to have to learn to accept, since day 1, (and I tried to do it all in a very matter-of-fact tone rather than being confrontational or sensationalistic about it,) and people have responded that way right back, with surprising amounts of acceptance.