How to come out slowly? (Long self absorbed rant)

So I've told my fiancee that transitioning is probably inevitable for me and I feel much better for having told her, like to the point where I am barely depressed anymore, at least for now. Now I feel like I should be telling more people, but I am still not ready to up and "come out". I would like to do so gradually but am not sure exactly how to do this. I don't want it to be a huge shock.

I am thinking about telling my sister when I see her this Wednesday, but not really sure how to do so. It seems logical to tell her next since she has a vague notion of my dysphoria, at least socially. How I hate gender specific terms and haircuts make me borderline suicidal because I always end up with a pixie cut, I hate using public restrooms because half the time an old woman comes in and makes a scene because she thinks she is in the wrong one, I can't wear shorts because I won't shave, etc. I think she knows I don't identify as female (I've actually also told a couple of people this in the past, before I even knew this would be a problem) but never said I identify as male.

This seems less daunting because she has an idea, though it will still be surprising. Even my fiancee who I have erupted in tears in front of over this stuff many times in the past was surprised when I told her. It seems for most, identifying as male is a big jump from not identifying as female. When I say I am not female, they say "really? Interesting," but I already know this will be much different. This is the difference between a simple feeling and a lifetime of hormones and surgery.

Tl;dr: has anyone decided to come out one person at a time over like a year rather than the alternative, whatever that is? I've heard of people just changing their pronouns on facebook and making a status. I couldn't do anything like that especially since I'm not 100% sure about this. I'd also like to hear if anyone did come out all at once and if you regretted it. I want to kind of ease myself in. Maybe drop a few hints here and there. Tell an accepting big mouth and hope they let it slip to a couple people. I'm thinking of just telling important people that I am in therapy and am having dysphoria before telling them I may transition.

Thoughts? Advice? Tactics? Experiences?

---------- Post added 30th May 2016 at 10:20 AM ----------

Also, maybe this belongs in the coming out board...I just thought it was better off here because I've already comd out as gay and didn't get a negative reaction at all. I was hoping for advice specifically from trans folk because of the additional issues like how to best explain hormones and surgery and quell peoples' worries about my health and what not...

 

Hey thanks for the responses anyway. You just told them though? Face to face? I've also heard a lot of people advise the write a letter approach and I just don't know about that either. It seems like something that warrants a face to face discussion, at least with important people like family and close friends. But I do kind of want to ease into the discussion before I even truly consider medical transition or even just pronoun and name changes.

I'm a huge coward, can't even bring myself to tell people I am in therapy for depression and anxiety, let alone gender therapy...I have a bad habit of pretending to not have feelings so I also worry that I won't be able to express myself with the proper gravity that shows how unhappy I am, and then if I do either people won't believe me or they will start seeing me as a basket case.