This is a complicated question for me. I’ve always known I was “different”, I didn’t well fit the mold of a boy, I was too soft, too emotional, too empathetic; most traditional boy activities held little appeal for me.
I was always fascinated by stories of transformation, and felt very interested in any sort of gender bending or transgressive people or roles or activities I encountered.
But I had no labels or context in which to pull all that into some kind of coherent narrative for myself.
As I got older and learned more about trans folk and the possibilities of transition, I found the notion of pursuing transition appealing, but balked at the potential familial, social, and employment repercussions. I also told myself I’d make an ugly woman.
The watershed came a few years back (ca. 2015, at age 55), when in a therapy session I suddenly blurted out “You know, I’ve never much liked being a man.” My therapist, bless her, didn’t let me just sweep that back under the carpet as was my initial impulse.
We kept exploring the issue and eventually I came to the realization that something needed to change, so I started putting things into place to change my situation and get myself to an environment that would support me in transitioning.
I got there in April of 2018, started active transition that June, started HRT that September, and came out at my job that October and have been living as Stef 24/7 ever since.
I have never looked back and my main source of dysphoria today are the times when I have to pretend to be him in order to accomplish certain legal or financial tasks (I haven’t yet pursued legal transition, that’s the next big hurdle on my agenda).
And, guess what? I don’t make an ugly woman! I think I’m cute AF when I’m dolled up, and I increasingly see Stef in the mirror even when I’m not dressed explicitly en femme.