So I've been slowly testing the waters with coming out. As of now I am 100% out as gay, though the only ones who I have come out to as trans are my parents and one of my closest friends. Then between those two the only one who knows I'm pursuing transition and made appointments to start HRT is the aforementioned friend. My parents have been awesome. They were great when I came out as gay and when I came out as trans they said all the right things. Basically they said they don't want to tell me what path to go down, they want me to figure out what is going to make me feel happy and fulfilled and the will support me 100% whatever that is. Also my dad has his own medical practice and I'm on the practice's health plan. He said if I do decide to transition he'll make sure to switch the office health plan (and therefore mine) to one that covers SRS... Which is kinda amazing. I am very VERY lucky I know that both for the support and the insurance thing.
That said, when I was seriously flirting with transition about a year ago I could sense their sadness about it. They never ever said anything but I could feel it and it definitely clouded my decision making. I do plan on telling them before I actually start HRT but I'm not there yet... Though the clock is ticking down... I got two weeks before E time. Though they know the gender issues exist. Apparently my mom had an idea that I may be trans and not gay when she found my hidden stash of women's clothing in my room when I was 16... Which I had no idea she had found.
Anyway, tonight I was at another close friend's place. We got on the topic of trans people when she brought up a cousin of another friend (getting confusing I know). Basically we were at a shiva call for the mother of our mutual close friend and her cousin was there who happens to be FTM. The friend tonight was bringing that up and she was saying she never in a million years would have guessed he was born female (and she correctly gendered him the whole time) and that she just 'saw him as a pretty cute dude.'
So I used this opening as an opportunity to sorta suss out her feelings about trans people. Basically she ended up saying that she thinks it's a biological issue, and that she couldn't imagine her brain being at odds with her body and how terrible that must be to deal with day to day, and then said 'and you can't change the brain so you have to fix the body to match the brain.' She also said that she thinks trans-women are just women cause clearly they are women mentally and vice-versa that trans-men are just men to her.
I ALMOST told her tonight, but chickened out. But at least I now know she'll be accepting when I do tell her. She was one I was a little worried about cause she comes from a Christian conservative family, but no one in her family has ever taken issue when I came out as gay and then in this conversation her mom chimed in and agreed with her on all points in regards to trans people.
I have four people who I would say are my closest friends. One I'm totally out to and she knows I'm starting HRT and doesn't care, one is the one this anecdote is about, one is the one with an FTM cousin whom she fully embraces so I know she won't care, and one is a straight dudes dude. Naturally at this point the ONLY other one I'm worried about is him, but he also seems in previous convos to be pretty trans-positive.
Hoping this continues!