Sorry this post turned out a lot longer than I initially planned, skip to the bottom line part if you just want my main point

I would venture to say the first person you come out to is definitely the hardest (yourself). Then the first other person you tell is probably going to be still very hard because it's such new ground talking about it with anyone but yourself. But after that (and you start to get some supporters + positive experiences from telling people - - which WILL happen) it will become much much easier as others have said. You will find a rhythm with it.
I still haven't come out to ALL of my extended friends yet, but I've told about 30 or so of the close ones individually (it's a big group!), as well as my mom and step dad. It's really easy for me now, I don't even get nervous or pre-defensive describing my decisions about transition anymore. I just know that I want to tell everyone eventually and I look for opportunities to pull friends aside to have a nice chat with them and tell them something about myself that they didn't know. It's your chance to re-write history in a way

I have come to realize how blessed I am to have such an extremely accepting and forward thinking group of friends (and parents too!). I know that some aren't always fortunate enough to have that

Maybe I was just lucky in that department, but it seems like we all might assume the worst at first (I know I did) and it makes for some very nervous awkward initial conversations which could lead to potential downfalls. Try not to let nervousness or anxiety get to you, it will pass as you gain experience hand crafting your story for each specific scenario. Expect to be uncomfortable at first, but most importantly always try to show happiness about who you are... you are so very strong and beautiful for having the courage to even come out to yourself alone.
BOTTOM LINE
Exuding happiness and positivity about your future during the conversation is a major catalyst for acceptance. If you can see it from the side that being trans is not a curse and rather that you can finally be your true self, they will most likely be happy for you, too- if not totally stoked that you would share such a deep rooted thing with them. There are definite red flags to watch out for such as religion and/or homophobic tendencies, but I think on the whole people generally just want you to be happy.