I think it's a quickly changing landscape, gender in society and how we as individuals label (or refuse to) ourselves in what used to be a binary.
To give some context, I an a MtF transperson, and grew up in the same era as I feel you did. Transgender, or even transvestite, guests on talk shows were just grouped in with the 'freakshow' sort of guests, and I think that whole genre of television has been seen as the exploitative and dehumanizing charade that it is. But that was also one of the first exposures some of us had in that era to the blurring gender lines in society. As the transgender movement has progressed and taken a front seat in sociological discourse, I think we as a society have become more comfortable with expressions of self that don't conform to the binary set before us. We as a societal whole are in a transition, if you could call it that, from the strict straight and narrow world that we were born into.
I think it becomes pretty complicated when you, the individual, tries to figure out where you fit into all of this. In your post, you seem to have already had a lot of thoughts about the gender binary and how it applies to you, wearing pink as a big middle finger to society's roles for example. This is where I think it's up to the individual to decide where they fit, by looking into it themselves. Just know that you may struggle to find a place, and that place may change with time!
I also empathize with you on how the gender binary affects you, and how you see yourself. Who I am, as a person, is someone who relies on the gender binary to attain the label I personally want. I present as female in my everyday life, which shouldn't mean anything, but effectively it means I wear dresses and skirts, do my makeup, and put my hair up. This is me following the binary of what a female should do in our society, so that I am treated that way, but also because that's what I want. And what you want, I think, is the most important thing. I also, like you, prefer to play as a cute anime girl in video games, but I also am the kind of person who wants to play as a cute anime girl in real life. So I dress, and act, in a way that mimicks the mannerisms and style of characters I aspire to be like, because I personally find that appealing. They just so happen to be characters that subsribe to traditional gender roles (as Japanese games and anime are terribly traditional in how they present society).
To get this back to you, I think you should look more into the penis. Consider that a penis can also be feminine, if you want it to be, as you already seem comfortable stripping the gender binary off other things. Think of the sexuality of things as well, further on, if that's something you think you might want to explore. These are questions and ideas that many of us still haven't figured out, and there are a lot of academics centered around this issue, because the only correct answer for you, is the one that works for you.
Also know that there are so many people out there going through struggles similar to yours. Don't feel alone!
(anecdote, HRT didn't do really anything to my chest, so, still full of justice over here)
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