Well, I did it!
It didn't happen exactly as I planned, I attended a vigil for national transgender day of remembrance, only roughly 5 people came other than me, all LGBT, and after all the heavy stuff was over we had a little open mic thing, and I came out to them there. They reacted great, they all said they where there for me, that I made a good choice by telling them, we group hugged, it was great.
I told my mum later that night, she said that she would accept me no matter who I was, and that it might be best to tell my dad over Thanksgiving.
Overall it went pretty good, glad I had you guys for support.
P.S. The guy I mentioned couldn't come that night (he was in Vegas) but I now know for a fact that he IS gay, so I'm probably going to ask him out soon after I join the group I mentioned.