I hadn't really planned on coming out of the closet this soon (will be months before I start HRT at best), but since only talking to a therapist feels lonely, I decided to talk to an "older" (as in their fifties) couple who are good friends with both me and my parents. They're nice people, tolerant and able to keep secrets. I was still pretty shaky though. But it went better than I could ever have imagined. They were knowledgeable, understanding and supporting. They did however say that I should come out to my family sooner rather than later, not only to give them more time to adjust before I change visibly, but also to give them the chance to support me and participate all the way. Difficult to argue with that. They also made me realize I'd feel miserable if I were to spend my Christmas break at home, not being able to tell them. And they'd probably not appreciate me coming out while opening presents.
So I decided to come out to my family when they visit me; my sister, in-law and niece (who's too young to understand anything right now) were here last Saturday, and my parents are going to visit me next weekend. I also decided to come out to some of my closest friends, and some more remote ones that I only know online, but who can't out me to anyone. It's going way better than expected, I'm amazed.
I started with an online friend - the only one who actually had an adverse reaction. Or rather, no reaction at all. He ignores me now. Oh well. I rarely talk to him anyway, could be he's just trying to figure out a response. A day later, I went on to another online friend, who would be a bigger loss. She's had a sort-of religious awakening, so I was a bit nervous, as you never know what that entails. But she just said something along the lines of "so you're a woman, no big deal. Nothing wrong with that". Turned out she has several transsexual friends. I also told another online friend, and she hasn't responded yet - but at least she told me she would keep quiet and that she needed to process this for a while before saying anything. She'll come around.
Then I told my ex-girlfriend, from ten years back. We're still good friends, but of course this was more awkward than the online friends. But she was completely supportive, too. And she had suspected me for battling with myself for years, for different reasons. So she wasn't too surprised - she just hadn't guessed the specifics. She's awesome.
Later on, I wrote a long manuscript to prepare myself mentally for closer family. I let my study counsellor (who also follows up health issues) read it. His job is being supportive, so no big surprises there. I didn't use my manuscript for my sister and in-law, though. It turned out too long. I always had a problem keeping my texts short. So I just told them how I felt during puberty, went on to early childhood, and then my period of denial after puberty, and how the last few years have brought me out of denial. It went amazingly well. They both told me they loved me, that they'd support me no matter what, and to not fear my parents. My sister said they (my parents) would walk through hell for me, even if they need some time to adjust. She also remembered a lot of the things from my childhood, so she wasn't that surprised.
After they left, I realized I wouldn't be able to concentrate about college stuff that day, so I decided to visit my best real-life friend. She had her sister visiting, so I talked to them both at once. They were also completely supportive and understanding. They had not suspected, but they were still not shocked. It was like the most natural thing in the world. We talked for a while, then we went on to solving math problems, looking at cat pictures and talking about random nonsense like we always do (yes, we're weird). Today, the sister contacted me and just wanted me to know they both thought I was courageous to come out to them like that, and they appreciated the confidence. She also said she actually looked forward to my transition, that she thinks it's right for me, and that she can't wait to take me shopping

I told her that made me very glad. I had tears rolling down my cheeks.
So basically, this is going so much better than I feared. I hadn't planned on telling so many people this early, but I'm so glad I did. I dread speaking to my parents a bit less now. It still scares me, and I spend big parts of my days thinking about it. But at least it's only a few days left, and my confidence has grown because of all those other talks. It feels like things are going my way for the first time in my life. Now I just hope it will continue like this for as long as possible; I'm sure there will be more negative reactions when it's time to come out to more remote acquaintances and family. But that's not something I need to worry about yet. So I'm happy.