... and it went well, to make a long story short.
He's gay, so I figured it couldn't go too bad, even considering a lot of the TG community has to endure discrimination from the other LBG groups. We've known each other for about six years now, but only got close until recent. I told him very casual; I was telling him how my female friends (including one girl I'm hoping to formally date) jokingly tell me my nail polish makes me less of a man. So then I asked him if he did anything "girly", such as wear their clothing, makeup, accessories, etc. He said he only played with nail polish when he was younger (funny thing is he's not the type of gay guy that can give you fashion advice - he's pretty much a masculine guy, he just happens to like men). I told him I put on a few of my mother's dresses when I was a preteen and teenager. Then I told him I needed to get new shoes to show off my painted toenails. He suggested some nice flip flips, I told him some nice open toed stilettos instead. He stared at me; then I told him I would need a dress to match the shoes. He just smiled.
"Does that make me any less of a man?" I asked. "Not at all," he replied. "You just have a feminine side you like to express sometimes." He pretty much nailed it. He went on telling me he wasn't really surprised, as he thought my androgynous male mode wasn't womanly enough to suit me. It's nice that he doesn't see me any different than before.
It's so nice when someone knows and accepts you!
That's two down, a few more people to go
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