I share a somewhat similar story to you in that i told my friends first, and came out to my family a couple of years later. My friends were great... mostly... I did lose a couple of friends, but at the end of the day, were they really friends that I wanted in my life? Probably not!
My mum and sister were accepting and things were fine there, my dad on the other hand wasn't so great, and it took quite a few years for him to be accepting, but we are great now, and he is fine with my fiancé as well. You are right, coming out it is a daunting experience and one that I unfortunately still find myself doing regularly in different situations. I think that's the most frustrating thing that people don't realise about being gay, having to constantly come out in different situations like work, or just meeting people, its draining sometimes... sometimes i can't even be bothered correcting people when they assume the gender of my partner!
Thanks for the thread, hopefully more people add their thoughts!