Going from Tomboy to Transman

Grayson Bell
6 min readMay 10, 2019

Disclaimer: This article contains language that some transgender individuals may find triggering. I am writing this from my personal experience, and I do not speak for the entire transgender community.

As far back as I can remember, around the age of three or so, I’ve viewed myself as male. I couldn’t understand when my grandmother tried to explain that I wasn’t a boy, until I accidentally walked in on one going to the bathroom. However, even faced with that fact, I still preferred wearing boy’s clothes and keeping my hair short. Knowing how disappointed I was, my grandmother allowed it, although she kept trying to get me to wear skirts and blouses with big flouncy bows for special occasions. (I hated those bows!)

Transitioning was not a widely known option when I was younger. I had no choice but to shove myself into being female and ultimately embracing the identity of being a tomboy. I don’t even recall how old I was when I first heard the term, but from my perspective it fit well enough, however imperfectly.

As I grew older, I didn’t always present myself as butch. On occasion I did enjoy growing my hair long. I never was a big fan of wearing dresses or skirts, but sometimes they were fun. I learned to wear minimal makeup because when I didn’t, I’d get concerned questions regarding my health (as many women do).

The idea of being able to transition from female-to-male didn’t come to my consciousness until Chaz Bono came out as transgender, around 2009. I remember watching him with his parents on TV back in the 1970s. However, the idea of transitioning didn’t resonate with me at the time, for various reasons.

First, Chaz had come out as lesbian before coming out as transgender. He was attracted to women, and I was not. At the time I didn’t understand that gender identity and sexuality are not linked together. Second, I knew Chaz came from a wealthy family, and I assumed that transitioning would be prohibitively expensive. Third, I was about three years into my relationship with my now late husband. I didn’t want to do anything to ruin that relationship. Finally, my life was in a great upheaval at the time. In 2008, I was laid off from the company I had worked at for over 11 years, and I was having to rediscover who and what I was professionally.

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Grayson Bell

An autistic, gay, transgender man writing queer fiction and about LGBTQ issues, focused on the transgender community. (He/Him) http://graysonbell.net/