I was adopted so sometimes I wonder if maybe it's easier for my family to accept it. Overall, they've been fine with it, except for my brother-in-law. It told my oldest sister first, and she was very accepting. But then I told her husband, whom I had always thought was pretty cool and down-to-Earth when I was a kid. He simply didn't approve, but it didn't end there. When his daughter got married a year or two after that, he got sloshed at the reception and had an awkward drunken conversation with me on the ride back to the hotel. He urged me to tell my parents. Not sure why that of all things was on his mind at the time, but it was. Recently, he's made comments like "I just can't believe he has boobs now, I'm not sure I can handle that!" Note this was well before I started HRT. It got back to my mom who relayed it to me. And then last year they were down here at their time-share condo and my parents went and saw them. I was living in the same city but my mom urged me not to go because it might cause drama and she wanted to protect me. Then last Christmas I got a heavily-religious card and no money, despite the fact that they're well off and most other years have sent me money or a gift card. I'm assuming it was my brother-in-law's idea. I try to shrug it off but it still sucks. And what bothers me most is that it not only bothers him, but he actually thinks about it from time to time. I rarely saw or interacted with him in my teens and onward, so I'm barely in his life as it is, and yet he dwells on it. :/
Anyway, after I told my oldest sister I told my other sister and she seemed enthusiastic about it. I haven't talked to her much since (I keep in touch with my siblings through my mom) but I saw her recently and even though we didn't talk about it, she seemed to skirt around it and seemed generally supportive. My oldest sister had talked to her and told me that she was excited to have a younger sister like she always wanted.

And then there's my parents... I was so afraid to tell them, but once I was stable enough to live on my own and far away from them I sent my mom an email explaining everything. Surprisingly she was supportive! And she apologized for not seeing how hurt I was as a kid. She told my dad after some time, once she got up the nerve, and he seems accepting but hasn't really talked about it. I'm currently living with my parents while I save up to move next year, and they're helping me get to my appointments and whatnot and my mom asks me occasionally about how I'm feeling to make sure I'm handling the hormones alright. Still haven't told my brothers and I may never tell them, but my nephew is coming for Thanksgiving so if I tell him, he'll be the first male in the family that I've directly told since my brother-in-law. Hoping it'll go better...