Masculinity, Femininity, and Being a Transgender Tomboy

I wrote a sentence on Reddit awhile back in reply to a comment of mine. The sentence struck a chord with me because I realized that I always knew it to be true, it never occurred to me until I said these words…

I never felt more out of place in life than when I was surrounded by my closest friends.

My best friends are three guys, two of whom I have known their whole lives, the other joined us in junior high. We are more like brothers than friends, literally so in that we all pledged the same fraternity in college. We all have similar personalities and almost everything in common, so why did I write such a statement and how can it be true?

Because it is.

I realized I was trans when I was 12 years old, they found out when I was 25. To them, I was always a heterosexual, cisgender male, and there was never a sign that anything was different. The reason behind that is that my interests have always been more masculine. I am a big sports fan, I love superhero and action movies, I love history and geography, I read theology for fun, and I am a self-described beer snob. If I had to sum up the initial reaction of my friends when I came out to them, it would be: surprised. However, none of those things made me a man. I also have more feminine interests as well. I love musicals, chick-flicks, makeup and dresses, going shopping, and pampering myself. None of those things make me a woman.

Early in my days of therapy my therapist asked me, "What does it mean to you to be a woman?" I answered something like this "Having this innate sense of femininity and womanness. It doesn't matter how masculine or feminine the activity, that sense is there." For example, when I am plowing through foes in Skyrim, I have always felt more like Joan of Arc or Xena than William Wallace. I see more of myself in Daenerys Targaryen than Jon Snow. As a kid, we used to sing a Sunday School song about wanted to be like Daniel or Ruth, I liked Ruth better. I looked to Esther more than I did to David.

On the other hand, I was boyish enough to have a therapist and me wonder if transitioning was not right for me. I even tried, albeit with some success, to identify as a guy (though never called myself cis), and not transition. It also helped me get that mentality when soon after I made that decision I ended up working with an effeminate pre-everything transwoman.

According to society, and even a good percentage of the trans community, I shouldn't exist. Transwomen do not talk about sports, wear men's/androgynous t-shirts, and we are not tomboys. I could place most transwomen I know, and I am aware I'm generalizing, into two categories: Quiet and nerdy or loud and hyper-feminine. In many ways, I often feel as if I have not found my place in our community as an outgoing tomboy.

Society seems to place this pressure on us transwomen to be extra feminine, more so than our cis sisters. It almost seems to say "If you're doing this, you have to go all the way." While dresses are cute and makeup is fun and makes me feel pretty, do you know what else is great? When I am lounging around my house in basketball shorts and a tank top. There is not a single way to dress, look, or be a woman. I do not know how many times I have said this to newer transgirls who were like me in that they were not very feminine.

I always bring up the same two points that people told me last summer when I was deciding to transition. One, cis people, while some may question it on occasion, do not obsess over their gender for years. Two, cis people actually actively enjoy being their own gender. For them, it is a black cat in a dark room that they enjoy having around. For me, I never related to either of those points. My gender was not an afterthought, and it never blended in with my male persona. When I lived as a guy, at best I tolerated it.

I have realized in about the year since I started down this road that what is masculine versus feminine is poor language. It is too binary and stereotypical. People are people and are going to have their own preferences, interests, and style. I started watching Queer Eye recently. One of the things I noticed is that the Fab 5's goal is to make the person into their best self, or at least a better version. Looking back, that is what transitioning did to me and all transgender people. We are still the same people, though in some circumstances, freer to express certain traits and shed others.

If you are reading this as a trans person who feels the need to fit into a certain box, don't. That is doing nothing different from the box which you spent years longing to break free from. If you are questioning things, do not worry about not being feminine or masculine enough. Those doubts are coming either the gatekeepers or those who put others in boxes. If you want to be a transgirl who is a tomboy or butch, you go girl! If you want to be a transguy who is more effeminate, you got this bro! You do you and do not let anyone stop you.