Wife ... but even then I could not completely comprehend exactly what being trans was going to mean for me and her over the long haul. 

I voted "friend", but the very first person I told was my medial Doctor.

Group of friends in high school while we where hanging out in the library after school. They had always made comments in the past that they thought of me as a guy anyway so I felt comfortable slipping it in while we were discussing an acquaintance that was "trying on" being transgender and making a show of it (the phrase "trying on" were her words). I said something to the effect of "people like that make it hard for people like me to talk about their gender issues without looking like all we want is attention". They agreed with me and let me know that they had my back and would never accuse me of seeking attention for attention's sake. Four years later and none of them have changed their tune on me.

I'm not actual transgender, however The first person i came out to that I was bisexual was my wife. The fun doesn't end there however, I did infact have a go at a female perspective of myself, and lets just say the results weren't exactly... astonishing lol. Nor did it really feel right to me, but hey that's what trying new things is all about 🙂

Technically the first person I told was the Trans Health Advocate at my local LGBT clinic. But she is on the behavioral health side of things. After her, like two days later, I couldn't hold it in any longer and told my two best friends. After them I couldn't tell the people in my world fast enough!

I actually came out to my friends Fiance first. I had known her for a few months, and her roommate/friend at the time was genderqueer/genderfluid. She had known this person for a long time so I knew that she'd be accepting of me if I ever came out to her.
I actually had tried to get her to guess that I was trans before i straight out told her as I was still too scared to say it myself, unfortunately/fortunately for me she can be a little slow when it comes to figuring things out so I ended up just getting frustrated and told her.

She is now one of my best friends and couldn't have chosen a better person to come out too first

For me it was a female friend I made online, though I never used a label we just talked about stuff. As for within my family it was my aunt that lives near me. She in turn told her husband and three kids. They all support me though and were more or less like "Whatever makes you happy. You know we will be here for you." Then I told my little sister and she told her fiance. That really only leaves some family I have in Dallas and a friend that moved to Florida. I think I will just let them be surprised.

I probably did things a bit backwards seeing as I am still 100% presenting as male. (pre-transition) I wanted to get it out there and know who was going to support me. I caught a little religious backlash from my sisters fiance but he is old school. He hasn't said anything about it to me or treated me differently, my sister just told me what he said to her. *Rolls eyes while making overly dramatic hand gestures "It is against God's plan...blah blah blah."*

I came out to my mom just recently that I am Transgender