I went to my gender therapist today dressed for the first time. I've gone wearing womens jeans/boots and nails painted in past but today I decided I wanted to push myself a bit.
I wore black tights, black skirt, red blouse with a comfy sweater over it, and pair of black ankle high buckle boots. I had on minimum makeup, as I'm still bad at it, and can't stand foundation that looks heavy. I'd never pass, with my beard shadow, but that wasn't really the point.
I was comfortable and felt feminine, which helped me be a bit more in tune with my therapist. Had a lovely session, and felt really good on way home. I have things to start pondering, plans for transitioning, how that will look, and how it might proceed.
My biggest anxiety right now is how I come out to my best friends, probably the most difficult part of this whole thing. My best friends are pretty much guys guys. Known them for 20 years, since college. My gut reaction is that I'll lose most of them, which is going to pull a major rug out from under the support system I've built since adulthood. But who knows. That's for another day to ponder I guess.
Cheers,
-G