In hindsight, the signs were always there…
No one’s home; mom will never know if I try on this dress from her closet.
I wonder what it says about me that I’ve always had an easier time making friends with girls than boys.
They want me to wear a leotard for the school play. It’s just part of a costume. I’m sure my excitement is just from being on stage.
My high school friends want to dress me up as a woman for Halloween. I’d better make it sound like I’m grudgingly going along with it.
It’s not fair, all the different options women have for clothes compared to men. I wish I were brave enough to challenge those standards.
Why do I gesture so flamboyantly with my hands?! I need to pay attention to that, watch my movements and posture to make sure I’m “guy enough”.
40ish years of telling myself that these thoughts in my head aren’t a big deal, or that I can just stuff them down and ignore them. 40-some years of bending myself to fit what I thought I was supposed to be, what everyone expected of me. 40 years of missed opportunities to explore what I really like and who I really am.
Apparently my mom saw something different in me, too. At one point she admitted, “When you were little, I swore you were going to end up being either gay or a priest.” (Why she thought those two options were mutually exclusive is a question for another day.) Ok, so she missed on both counts. But that would have been in the 1980s, before she had ever heard the terms “gender fluid” or “transgender.” Gay was likely the only point of reference she had for her little somewhat-effeminate son. Maybe she’d recognize it for what it is if she had more knowledge then.
Don’t get me wrong, I know I had it easier than many. To my knowledge, I didn’t suffer gender dysphoria. Or maybe I did when I was younger, and I just buried that along with the rest of it. And while I never liked how I looked, I wouldn’t even say I suffered body dysmorphia. It’s not that I’m uncomfortable or feel wrong as a man. Just… incomplete. And I thought that maybe if I just indulged it once in a while, I could get it out of my system. It seemed like that plan was working. For a while, anyway.

Shortly after the pandemic, I decided to see what this really was. I bought some clothes, largely in the fetish/kink realm. Then shoes. Then makeup. From there, I knew I liked how it looked and felt, but I couldn’t exactly go out anywhere in the clothes I was buying. So I started picking up some more public-friendly outfits. Then wigs. Then breast forms, and, and, and…
Seeing myself fully dressed for the first time outside of a kink point of view was eye opening. There I was, the woman that I had secretly always wished I could be. Or more accurately, the woman I had always been, but never taken the time to acknowledge. Suddenly the gender questions became all too real. If this isn’t a kink, if it’s not about a sexual rush, what am I doing? Who am I? What does this mean to the life I’ve been living for close to 50 years? How do I incorporate this into what I thought I knew of the world? Yay for trans-friendly therapy!
It’s been an interesting journey: sissy (I don’t much care for the term myself, but if the stiletto fits), to crossdresser, to now identifying as gender fluid. And I’m still fairly early in it, so who knows where I’ll end up or how far I’ll go – I’d be lying if I didn’t admit to pondering HRT. For now, I’m simply enjoying discovering who Samantha is and how much to involve her in my day-to- day life. I’ve never enjoyed clothes shopping before; now it’s an addiction. I’m also learning to crochet and sew so I can make my own outfits. I’m slowly expanding my circle of friends who know, while adding little bits of femme flair to my boy wardrobe. I’ve grown my nails and started painting them; started wearing little touches of makeup to work; and I’ll be getting my ears pierced soon.
There are still moments of doubt. What if this is all one heck of a mid-life crisis? What if the people I tell assume that’s all it is? What if I lose friends or family because of this revelation? What can I say: I overthink everything. But I recently saw a quote from Arlene Dickinson that hit home hard: “You can’t base your life’s decisions on potential future regrets.” So rather than dreading those “what ifs”, I’m trying my best to live my life in the way that feels the most natural and authentic. And I’m eager to follow this road wherever it leads.
What’s your story that brought you here? I’d love to read it in the comments! Or find me on Facebook (hey, I’m GenX, so of course that’s where I am) at https://facebook.com/samanthafromde