My initial coming-out to my parents was kind of convoluted. I came out right after my suicide attempt and having had to move home from college. I wrote them a rather brusque letter (which is how I tend to communicate anything serious to my parents) after already having purchased a packer, a binder, and men's underwear and having them shipped to my house. Needless to say their reaction was not the best. They were concerned about how my mental health was affecting things. They never really accepted me, but they did eventually give me my packages.
Over the next few years I would continue binding and packing, but that was about the extant of it. I've always had short hair and liked guys T-shirts, so I would continue to express myself that way too. But as far as any social transition, that was the extant of it. I went to a small Christian college so I really didn't have much of an option.
In the meantime, my younger sibling came out as trans to my parents too. It was kind of rocky for him at first, but after a little bit, they accepted him pretty well. He is more vocal than I am, so I got a bit jealous of how relatively easily he seemed to be able to talk to them and get them to understand.
A couple years ago now, I asked my parents to start seeing a new therapist. I didn't tell them that one of the reasons I wanted to see this particular therapist was that he worked with transgender people. And we have talked a lot about my identity and my relationship with my parents.
A little less than a year ago, I re-came out to my parents (in another letter, ofc), better explaining my current identity and how I recognize that certain issues may cause them to question that. And after that, they have started using male pronouns for me at home (I didn't change my name, so that wasn't an issue). The next battle is a physical transition, which they're still not totally on board with, mostly because of financial reasons. However, this post has made me feel thankful for how far we've come.
My sibling was actually the first one I came out too. As much as I've ever been close to people, he's probably my closest friend. He's always been very pro-LGBT. Around the time that I came out to him as trans at first, he told me that he was (at the time) a lesbian.
As far as my extended family, I haven't told any of them. Some of them I'm not too worried about; one of my dad's sisters-in-law in particular is very liberal and LGBT-friendly. Others, like my uncle on my mom's side are more conservative. I've come out to a lot of groups of acquaintances of mostly people with whom on not close anymore on Facebook, and I'm hoping to come out to my relatives soon. We'll just have to see how that goes.
