Well, I took a big, baby step today.
For my first bra I got a barely there crop top. I also made myself a pair of silicone nipples to go with it.
One big concern I have about my new change is revealing the new me to my neighbors in the apt. complex I live in. I have lived here for 2 years and they all know me as a man.
Today I wore my bra under my man clothes. I wore a white tee shirt so that it could be easily seen in the Vegas sun, under my shirt. I went out several times to walk my dog. I got plenty of looks and second looks, but not once did I feel the least bit of embarrassment. Next time I may try adding heels to the look.