I tried on a dress for the first time yesterday and it was great. But I don't know what to do now. I would like to come out to my Mom to make things easier (hiding who I am sucks) but I don't know if she would be accepting. I'd really like something to wear in public without anyone noticing.
Maybe you can find a news article about a trans* person and ask her what she thinks about it to test the waters? Maybe you can experiment with undergarments, maybe neutral shoes from the women's section, or neutral women's clothing (like t-shirts). Stuff like that. You could also maybe do subtle jewelry like a necklace and if you need to you can always tuck it under your shirt. I found initially just the fact that something came from the men's section to help a bit. You know, just to start with!