Wow! Thanks for the reply's everyone, wasn't expecting this much feedback ^_^ I guess it's a subject that's weighed heavily on everyone here at some point or other.
Actually should have mentioned that I have kind of come out about it to one other person before, but while I was pretty intoxicated. I remember she was very positive about it but I quickly recanted when I sobered up the next morning and tried to put it down to being drunk, we've since largely fell out of contact due to moving about. So this still feels like coming out about it for the first time right now, even if technically it's not.
Since you all took the time to write and since I've been thinking about this a lot over the last week I'll attempt to respond to everyone here. Hmm this could make for a lengthy post.
@Peky, I know, it took me long enough to post it somewhat anonymously on a message board, I think I know a few people who would definitely react favorably, some (extended family) I'm certain would not, but mostly I'm apprehensive about the rest who might be shocked and think of me as weird from then on. That thought bothers me more than outright hostility for some reason.
@OBrien, good tactic

I could try to fem up my appearance a bit first as a way to break the ice ^^
@Reinhaven, nice to meet you

luckily I do have some female friends that I'm quite close to, I just don't see them nearly as much as my male ones, but when I can I think I'll definitely start with them for some of the reasons you gave. It's really just a case of building up the courage to do it at this point. I'm also incredibly lucky that my parents are very liberal on the topic, so I know I'm fortunate to have this much going for me there.
@Diana, all of them at once? yikes! I hope that went well, a one on one conversation is frightening enough at the moment thanks, you will have to teach me how to go into a trance tho

@Admin, I'm almost certain drunk is how I will eventually do it, it's how I came out about my sexuality, and thank you ^^
@Annah, what witchcraft is this 0_0 seriously amazing transformation! wearing woman's clothing or makeup in public is pretty much unthinkable to me right now, that must have taken a lot of guts, glad it paid of for you ^^
@Ausbelle, part of me kind of wishes that would happen, someone else spreading the news (or someone I know stumbles across the pics of me I posted on here), just so that I don't have to go through doing to much of the outing myself. Then again another part hopes nobody I know ever goes near these forums 0_0
@Kelly, I get that completely, because I had much the same experience coming out as bisexual (sans the facebook post, probably 70% of people who know me know about that now). Well it is some comfort to know every step won't be as hard as the first.
@Malachite, I do like the idea of dropping it into the conversation as casually as possible, much more than some grand statement.
@Bev2, writing out my thoughts on it might not be a bad idea actually, even if its just practice at this point, with the exception of writing this I tend to just let my thoughts stew in my head. Ah I can't wait until the thought of telling someone inspires boredom in me rather than fear

@JoanneB,

if all else fails I may try the Dr Seuss method of coming out ^^
@Zumbagirl, thank you for sharing your story, it sounds like you had to work every step of the way to make your real self a reality, I can see I've got quite a lot to learn ahead of me! I can't believe they fired you tho! I'm afraid my ignorance on the law in those cases is also quite glaring (well, I've seen Philadelphia ^^ not that that's exactly the same situation), was there any legal recourse you could have taken and did you? It sound's like it was definitely all worth it in the end tho, you sound very happy with your life now

@Misato33, That point, the no big deal stage seems a long way off yet, hope it comes sooner rather than later!
@Emily, you just made me kind of glad I didn't actually say anything the other night, I probably would have been a stuttering mess when the follow up questions came, hope telling your friend goes well.
@Tristan, Glad everything ended up well for you

but I do hope I can skip the drama that might come, I just want the coming out to pass and have the whole thing become a distant memory.
@Elspeth, what a unique situation, you and your son have your own mini support group in each other

I haven't even ventured as far as dressing androgynous, infact being somewhat repressed on two fronts (gender and sexuality) I always tended to gravitate to the least showy and dark clothes I could find, I've at least starting wearing some brighter colours now

Baby steps indeed.
@Jen, thanks, I do have some amazing people in my life luckily

and I'm fairly shy in person so I don't think letting them take control of the conversations going to be a problem
Was just thinking, I used to have a female friend who took to jokingly (but definitely affectionately) referring to me by a female name, when she started doing it in font of mutual male friends I (to save face) pretended that I didn't like it, when inside I don't think I'd ever been so happy, ouch how pathetic is that :/
Ok thanks again for the reply's everyone some really useful advice in there

edit: Eek! I use smileys far to much