For me, the first few times were small things: the corner store for a soda and chips, the grocery for beer. It was really rough because I hadn't had a lot of experience at, really anything by that point. The big thing for me were the stares and looks. It took quite a bit out of me to work up the confidence to laugh it off. I won't lie, it still has an effect on me. I'm certainly not out to assert or challenge, but I have managed to become confident with who I am. Perhaps not with my appearance, but living as I do has brought noticeable improvements to my well being. Now when I get a look I allow myself to

instead of

or

; maybe a little

. I've come to accept, more than just understand, that the looks you get from people, the feeling you feel, that insecurity, that's exactly what those people are going through. Bewilderment, uncertainty, fear. Now when I get a look I can just laugh and it almost makes me feel a bit better inside, that someone else was made uncomfortable for a brief moment, share some of those years of struggle that came before the day break.
As someone who can sort of pass I still don't go out with "macho-confidence". I still can't flaunt, there are plenty of mistakes being made, and a distinct lack of wardrobe accessory. So when I do go out I go out with my two dearest friends, friends whom I trust fully, not a shred of doubt. When I'm with then the world melts away. The odd stares become distant blurs. When I'm with them I don't worry or fret. This lets my confidence flow out almost naturally, a cloak that makes you near invisible to those not looking. For instance, a doorman at a bar was confused when I handed him my license this last weekend. Confused that my license had a picture of a boy, a boys name, a little M next to the label "sex". "So you're a guy?" He asked. In a tone of bemusement I replied, "The way I was born."
First posties, yay! That was fun. Much more fun writing here than the ranty technical posts I've been forced to throw together on some of the internet's other districts.
Edit: Something silly, one of the challenges for a grammar fix was "Which is always red: Car, Fire Engine, Bus, Truck", Fire Engine being the obvious answer, However many times they are painted florescent yellow instead of red.