I first came out to my girlfriend (at the time, now fiancee) back in around 2011 when I began questioning, so she's been through this whole process with me. I then told my brothers and her sister. Slowly started coming out to close friends and other students (including my roommate at the time) and my instructors at my college I was in at the time. I then came out to my fiancee's family first, starting with her parents, then her siblings, and more recently her young neices and nephews (they immediately started using he/him and my proper name - kids are way smarter and more accepting than most people think). I finally then came out at work, and everyone uses my proper name and pronouns with very few slip-ups, and they're all very accepting, especially since almost half of us are somewhere in the LGBT+ community.
And lastly, I came out to my parents and my grandparents. I waited to tell them, not out of spite, but because I knew they would take it the hardest, and I proved myself right. My mom is accepting of my physical transition, but not my social, which is weird that she's supporting my desire for HRT, but refuses to use my proper name and habitually 'forgets' to use the right pronous. My grandparents, on the other hand, are conveniently ignoring it. They don't even try to use anything right, and my grandma even told a friend of mine that she will never call me by my proper name and I will always be a girl to her. Yet, this is the same woman who is lamenting that I'm not as close to her as I was as a child (I wonder why???

)
On the other other hand, my dad, whom I haven't spoken to in around 6 years until very recently, is completely and totally accepting of who I am, consistently using the right name and pronouns, even when I'm not around, apologizing when he slips up, and continuously letting me know about LGBT+ events at his work, including taking part in an event that was called "I'll Go With You", where you pledge to be there for trans people if they ever need support using the right restroom (he did this before I started talking to him again). He also got me a pocket knife with my proper name engraved in it for Christmas, even before he knew of the significance behind the knife itself.
But I digress. It's just very interesting how sometimes the most unexpected people are so supportive of you, y'know?