It sounds to me like you're thinking a lot about the social boxes of "masculine" or "feminine" virtues and behaviors, and how our society expects men and women to act. Those things don't necessarily have anything to do with transness, though.
Here's how I'd put it...
Right before transition, I did a little test on myself to see if my desires were more to escape the social "box" of masculinity, or if I really did want to be female. And the way that I personally did this was basically to quit letting myself be hindered by societal expectations. I knew that I wanted to express myself in a more open, feminine manner. And so I did. I stopped faking the "dude" behavior and started being more open and nice to people. I wanted to wear more feminine clothes. And so I did. I adopted a more androgynous clothing style, and started wearing things like shorter shorts, v-neck shirts, panties, and more form-fitting jeans and shirts. I started openly talking about my more feminine interests with people, and basically giving myself the complete freedom to do whatever it was that I wanted to do, whether masculine or feminine, without any regard for what my physical sex dictated that I "should" do according to societal notions of normality. Plus I started losing weight, trying to get myself into a body that I was more happy with.
It was a big plus. I felt MUCH better about myself, more liberated, and people did start treating me in a MUCH friendlier manner. I was definitely happier. But in my case, even after the end of all of that, I realized that it wasn't enough. I didn't want to be a man wearing feminine things, communicating in that feminine way, and still living with a male body, male sex-drive, male emotions (or lack thereof,) and being treated as male socially. I wanted to be a girl doing those things. So finally I realized, it wasn't about my freedom of expression, it really was that I would not be happy unless I was female.
Have you asked yourself the same kind of thing? Is there any way that you can be happy as a male, if you just give yourself more social freedom to be yourself? Or is it really a problem so deep that even if you give yourself the complete freedom to do whatever you want, you still feel like you can't be yourself unless you're physically and socially a different sex?
Just something to think about. Try to separate out your gender identity from your gender expression. One doesn't necessarily have anything to do with the other.
