I'm really frustrated with myself right now. This morning, I was thinking of telling one of my best friends, a girl who is like a sister to me, about me. I ended up chickening out and then turned it into an awkward conversation. I couldn't even find it within myself to hint at it.

Then later that morning, my sister (my actual one) calls me and tells me we can't meet up tomorrow at Winn Dixie. She says it's because she needs to save gas, but she lives a few blocks away from there and could just walk over. I think it's because I told her I don't want her SO to know about it and I want to tell him myself after I see her reaction. I mean, it's really nothing against him, but I just want to tell her beforehand.

I just needed to do a little rant because if I didn't I would have kept questioning myself with the why did I bother or the why didn't I just say it.

Don't beat yourself up about it. Telling people we love and are close to is a major deal, the fear and possibility of rejection and losing them is always there. I almost chickened out of telling my folks, in fact I was given a golden opportunity to do just that...but if not then, then when? I was days from starting work full time and they needed to know then and there. Yes, I really waited that long before telling them. In part because I was terrified but also I didn't see a point in letting them know until I was ready to make the change. I could have told them earlier I suppose but then everything would be in limbo, I'd still be presenting as male while I got myself geared up for transition. I mention this because I notice the ticker in your sig says "6 months until you're sure"...maybe you don't need to tell anyone until you are sure?

The ticker is kind of my way of saying that I'm making sure I am still gonna feel like this until my birthday. Not that I'm doubting myself or anything, because I know how I felt through out my school years. I just don't want to do anything and then feel regret about it.

I've told a select few and a couple understand that I have been feeling like this since school, just very confused about everything. There are a couple more select people I plan on telling, one being my grandpa who did raise me pretty much and he probably did notice it and the other being my sister, obviously. The current ppl who know are my dude friend who i'd trust with my life, my SO and my friend who actually showed me the site and everything.

I totally understand your frustration.  Coming out to some people is incredibly easy because if you get a negative reaction you really don't care.  But the people that are most important to us are hard because we are afraid to lose them.  Most will say if they don't accept you then you don't need them in your life.  But that doesn't help the fact that someone you really care for has rejected you.

The hardest for me was my wife.  I must have planned the conversation a thousand times but chickened out over and over.  When I finally did it, I started to tell her and then started to chicken out again but I had said enough that she wanted to know what it was and basically forced it out of me.  I can tell you it was such a relief I almost started to cry. 

You'll have other opportunities to tell your friend and sister.

I agree with Julie, the more important the person is the more dificult. Also, the first few people are tough just because coming out is tough, you are exposing a very personal side of yourdelf.

I told 7 or 8 people that I knew would be supportive before I told my wife. My wife I knew would not be supportive.