Around a year ago I started coming out as trans to my friends in real life. Previously I'd told mostly online friends (a few I met in real life, too) or some of my sex partners only.
Friday night we threw together a small party, and the cast ended up being people who I genuinely like a lot. Someone who I'd only known online but who knew a few other folks showed up. She's a sociology graduate and had asked me lots of questions online, but meeting me for the first time, she had a lot more questions. We all talked quite a bit about my GID. Mostly, there was a lot of sentiment about "Now that the topic is breached, DO WE USE HIM OR HER BECAUSE SERIOUSLY WE'RE F-ING CONFUSED WHAT YOU WANT AT THIS POINT TELL US SO WE DON'T OFFEND YOU" simply because I never really demanded anything from them.
To me, demanding female pronouns is something I've been afraid to do. I don't feel passable enough, even though I pass a lot. I told them as much, but after a few hours (and many drinks), I did flatly say I prefer female. And at some point in my vodka haze realized everyone was using them.
And I felt like a real person for the first time. I didn't have to worry, like I do while at work, that any random inflection or angle of my face would out me to somebody who's been calling me she - my friends understand and don't care, because they do care.
Feeling like a person is warm and fuzzy.
I realize that I don't demand female pronouns from people because of the same reason I don't dress up in overtly female clothes. I'm afraid of being denied; of failure.
I've had it pointed out that passing as female while working at a hardware store probably means that if I actually dressed girly, I'd pass a lot more.

I do have several people in my life who tell me that they don't see me as being gendered. There's no he or she, there's just Malename. Which is actually a nice concept - gender is such a screwy thing anyway, that it's nice to be liked and loved for being the person you are, not the gender you are. I am worried about fully transitioning in their eyes, but I'm sure as time passes it'll get easier.
My biggest fear, I think, really, is having a successful life after transition. And meeting the right people. And... the idea off losing women as lovers scares me too... because most women don't want to be with women, and I *still* find myself getting crushes and attraction towards girls. I figure it's going to be a lot of heartbreak when I fall in love with someone who says "if only you were a boy..."