Sorry, this is gonna be long, but here is the situation as it stands now...
I am indeed only 24, but I think I already have enough regrets for a lifetime. I wish I had the courage to just be myself from an earlier age, but these feelings and my poor relationship with my parents when I was very young made me hide and attempt to rid myself of them. Unfortunately this has caused a pattern for me that makes me feel unsafe if people know things about me. I am much better now, but I would hide trivial things about myself from everyone around me, people wouldn't really know what my favorite color was much less my gender dysphoric feelings.
While the past year and a half have been spent slowly dismantling my front, that I have put up since at least 7, it is still difficult for me. Even on this forum I have had lots of struggle with my personal demons to do things like post pictures or talk of my experiences, It actually took me 8 months of saying to myself I was going to join before I got the courage to do even that. I am making progress but, my pace isn't great.
My wife has seemed a bit puzzled by my behavior over the past year, I am back to wearing makeup everyday (which was the case when we first got together 6 years ago) and I am slowly allowing her access to how I actually feel rather then what I think she wants to hear. She has given me several hints that she knows something is up, and bless her heart she has given me hundreds of opportunities to tell her even though I just don't feel ready yet.
A few nights ago we were talking about the effects that hormones have on people's bodies as one of my friends (A former marine) seems to have some crazy high T and she made note that I didn't seem to have very much. I told her that indeed as I can tell I have much less than the men in my family (I actually have a bit of natural breast tissue, no addams apple, my brow bossing isn't even close to my brothers, a higher voice than my mother much less my brother, etc).
After I made note of this she said "You probably should have been a girl." To that I replied "Yes, my life would have been much happier if I had". I was expecting her to push a bit more, and if she had, I may have told her, but with that she decided to go to bed. I can't help but think that she has a better idea of the situation than I previously thought.
In any case, I really shouldn't tell her until I am employed again, I want to prepare for the worst, and I don't have anywhere to go, I haven't spoken to my parents in years, and all of my friends are poor like me. I know it is selfish, but I really can't be honest if it means the risk of homelessness again, the last time I had that condition I was a child and I vowed that I would never, ever allow it to happen again. I don't think she would leave or kick me out but, there just isn't really a way to accurately predict how she will react.
I am sorry this was long and rambling, but It really helps to tell someone about this.