I've hinted in recent months to test the waters, with hypotheticals, he seems cool.
Just seemed concerned about what I was going to do about my deep voice.
He's a brother to me, actually I have adopted his whole family. They are all cool.
He has two sisters (identical twins), that I was 'kinda' friends with, I wanted to hang with them more and be platonic 'girlfriends'.
We used to be co-workers years ago, and tried starting a web development company together. I've counseled him as a friend through his relationships with women, and yeah, he's just a brother to me. He has his own junk to process, but he's my best friend, I let him make his mistakes as he lets me make mine, but if either is being a dumb*** then we call each other on it. That what friends do.
When I started hanging out with him years ago, he had moved back home for a bit and his sisters were around a lot. I had also started developing independent friendships with them. They moved away various places and lost contact for the most part with my friends sisters. I still talk frequently on the phone with my best friend. We are both software developers and we have a few indie game ideas between us.
He lives 1000 miles away, the only change he will notice is my voice actually. We only visit in person every year or so.
He and his family (sisters, parents) are actually some of the more "balanced" and "head screwed on right" people I've met.
That why I like them so much.
I'm pretty sure I'm stressing nothing.
But because of my male appearance and name and all that (still presenting as male til I get rid of facial hair and get good with makeup), friendships with women have always been tough to foster. Personally I'd like a female circle of friends, but on the platonic level things get segregated frequently, and I'm stuck with the guys talking about guy stuff and pretending to be interested. I just feel more comfortable and at ease around women, I always feel I have to be on guard around men. I find male-male friendships to be very adversarial. To me at least, It seems as if all males are playing one big game of king of the mountain. I don't like that game.