I went to a women's clothes for men shop here in Chicago to look for high heels, no dice, I have gigantic feet at size 15 mens, which translates to size 17 in women's apparently. I'm not going to be able to find heels before halloween. D:
I DID find some awesome falsies, they take you from nothing to a C cup, they're made of gel and are super soft! I already wear a DD cup but with these inserted in the cups it's pushes me out of the cup such that I actually have cleavage now!

Better still, these inserts have serious nipples, they show through the bra and the dress, actually they're super noticeable to the point that I'm slightly self conscious about them.
I pushed out of my comfort zone, it's not halloween yet, but I dressed up completely. Put on makeup, wore my dress, panties, garter, hose, bra, falsies which is everything I have now and put all my stuff in my matching purse and went to the grocery store. Interestingly enough people stared LESS than they usually do when I'm dressed as a man but wearing a bra under my shirt, not sure why.
I was super nervous someone would say something, but the people who did see me smiled and nodded or what have you... the cashier was a guy and he was really friendly, but I had trouble looking him in the eye, I felt pretty embarrassed. I'm sure I'll get better at looking people in the eye as I get more used to being dressed up in public.