Firsts
Yes, I am aware of what’s going on in the streets of my country. But I’m still going to submit what I already wrote.
Being Trans is all about Firsts. As most older transwomen were raised male, we don’t get the firsts that GGs experience. (I’m going to focus on transwomen here, as I can’t speak to the transman experience.) But we do have our own firsts, usually experienced alone and with a sense of Fear, Shame, and Wonder.
First time wearing pantyhose/bra/lingerie.
First time fully dressed as a Woman.
First time trying makeup.
First time going out into public as a Woman.
First time out Alone as a Woman.
There are so many firsts, and they make us what we are. Each has their own unique experiences, but isn’t it amazing how many of these we have in common? How we all understand the feelings?
I have written many times about my first time in public as a Woman on Halloween 2008. But I have never written about my first time out wearing something feminine. I have never forgotten it, but it wasn’t exactly public.
It was early spring, 1980. I was in 8th grade. I had this horrible compulsion . . . I knew I was supposed to be a girl, but I wasn’t. And the girls in my school, they were all blossoming. Becoming women. And I wasn’t. I so desperately wanted this for myself. I wished someone understood, but, in this pre-Internet age, I was the only “freak” like me in the world.
Growing up in Spring City, there was a driveway leading to a church parking lot across the street from my house. That church, like most of Spring City, was on a hill, so the downhill side of it rose fairly high. And on that side, there was a painted steel fire escape, accessed by an alley between the church and a house. It went up the equivalent of five stories. The neighborhood kids often climbed it during the day; playing hide and seek or whatever. Me, I climbed it quietly at night sometimes, as it offered quite a view of Royersford across the river, especially at night. The lights of Main Street curved down the hill, maybe a mile away, but seemingly in another world: a world as foreign and inviting as any in my overactive imagination. My world back then was barely more than a few blocks. My Junior High School was over in Royersford, and attending it “doubled” the size of my world.

The Fire Escape Today. The fencing and barbed wire were not there back then.
It was early spring, and there was a misty drizzle falling, muffling noise and adding to my isolation. My homework was finished, and none of my friends were around. So, while my parents watched TV (I forget where my brother was, but he wasn’t in his room,) I sneaked upstairs to my parent’s room and borrowed one of my mum’s bras. I then grabbed two rolled up tube socks from my drawer, and sneaked them all out in my coat pockets. I couldn’t believe I was doing this.
I walked through the parking lot and around the church. Making sure no one was watching, I ducked down the alley and climbed the fire escape as quietly as I could. When I reached the top, I sat in the small doorway ledge attached to the landing. Then, I sat a while, looking at the lights of Royersford through the rain.
I took off my jacket and my t-shirt (that’s all I wore back then: t-shirts.) I put on the bra, which was too big, stuffed the cups with the socks, and put my shirt and jacket back on. Then, I sat quietly on the cold steel in the misty rain, which was getting just a little harder.
I retreated into the doorway as the rain intensified into a shower. I sat, feeling. . . feeling. . . a strange sense of calm melancholy. I was outside: exposed to the world. I was terrified of being spotted, yet there was the thrill of doing something “wrong.” And feeling so at Peace as I expressed my femininity.
I remember thinking of all the girls in my grade who were wearing bras right then as well. How lucky they were. Not understanding the challenges the new rushes of estrogen were inflicting upon them. All I knew is that I wished in my soul that I were going through those changes — that I would blossom like they did.

The Top Landing
I remember sitting in the white painted doorway, crying. Sobbing. . . like a girl.
I remember taking one last look down at the bulges in my shirt, and then stripping off my jacket shirt, and the bra. It was white, as were the socks. I stuffed them in my jacket pockets.
I sat looking out at the lights in the distance. I don’t know for how long. Eventually, I quietly descended the slippery steel stairs, and walked alone through the misty night back home.
My parents were still sitting where I left them, watching TV. They didn’t even glance at me when I came in; my hair soaked from the rain. I ran upstairs with my coat on, put the socks back in my drawer, and hid the bra between the mattresses of my bed. I put it back on a little later that night.
The next day at school, I was standing in the lunch line. A few people ahead of me was Mike, who lived on the same street as the church — maybe half a block up the hill from it. I saw him smiling, whispering in the ear of the kid next to him, and pointing at me. I smiled weakly — terrified that he had seen me on the fire escape the night before. I later learned that he whispered nothing to the kid. He was trying to make me paranoid. It worked.
Not long after that, using money saved up from my allowance and shoveling snow, I ordered my first piece of female clothing from the Sears catalog.
A bra. Same size as my mum’s. White.
I purged that first bra long, long ago. I remember burning it in the brick grill my dad built on the patio. I burned all of my female things on a sweltering hot early August day in 1983, while my parents and brother were down in Delaware for the week. I then put the ashes inside a garbage bag, and set it out with the trash the next day.
And immediately fell into a deep depression that continues in some form to this very day.
I have come a LONG way since that night 36 years ago. I suppressed who I was for over two decades. I grew into despised manhood. Tried my damnedest to die. Married and had a daughter. And eventually, accepted who and what I am: a Woman.
But, that wet night was really the first time I dared to express any shred of femininity.

Was it worth it?
Now I’m full time living my Truth. I own several bras (though none of them are white, Lorraine!) and I no longer need tube socks as I fill the cups nicely, thank you for asking. But I’m still experiencing firsts. I always will. That’s one of life’s great adventures — doing things the first time — exploring who and what I am.
What are some of YOUR firsts? I invite you to share your moments in the comments, dear reader. Share with us all how you felt that first time you challenged the forbidden. You never know whom it may help.
Be well.
You must be logged in to comment using the comment area below.
Category: Transgender Body & Soul
