The Transgender Cinderella Effect

Mila Madison

It is something that just about every transgender person who has begun their transition could relate to. The first time you present as your true self. It is the moment when you first publicly defy the expectations that society has thrust upon you. You begin to accept yourself and the moment comes when you first leave the house as you, or at least the version of you at that point in your journey.

The first time I went out in public as myself was a trip to the Stonewall Inn. Yes, very cliche to make your debut in the place where the LGBTQ+ movement began, but it was the safest place I could think of at that time. My wife and I had spent the day before finding clothes and makeup for the big night. I was lucky to have her as most people in my situation didn’t have someone to help them through it all. It took us hours to get me to the point that I was presentable as I battled raging dysphoria and a lifetime of fears over being my true self. There was also a sense of danger to the whole process. The possibility of running into some kind of bigot who would possibly cause me harm was very real. I was nervous, excited, and terrified all at the same time.


All things considered, we couldn’t have done a better job at the time with my presentation. My hair was so short and my body had no shape to it whatsoever. I was a couple of weeks into hormones, and my appearance hadn’t begun to change as eventually it would. I had to trust my wife who kept assuring me that I looked good. For me, the person I was seeing in the mirror looked absolutely ridiculous, but I also knew that was the dysphoria. I was going back and forth between enjoying the moment and catching a glimpse of the woman I was hiding all my life and seeing some kind of monster in that mirror. We finally reached the point when it was time to go, it was already getting late, and this was the best version of me we were going to be able to present.

We hopped into the elevator and made our way through the hotel lobby. I could have sworn that everyone was staring at me, but it was probably all in my head. We jumped right into a cab and made our way to the Stonewall. I was literally shaking the entire time. We finally reached the Stonewall where they were checking ID’s to get in, and all I had was my male license. I presented it to the woman at the door who stared at it then slowly looked up and said, “Damn girl, you look fabulous.” It put me at ease and we went inside.

My wife and I had a few drinks and we did some dancing. I finally let my guard down. It was awesome. We even got hit on and some guy tried to get my number. For at least a moment, there was hope that I would be able to successfully transition. Finally being seen as a woman was an exhilarating experience. It was also the first time I experienced what I would eventually call the “Cinderella Effect.”

Now what I am referring to is that there was a shelf life to my presentation. There would always be a point where I would be uncomfortable and my dysphoria would set in. No I wasn’t turning into a pumpkin at midnight, I was falling apart in my presentation and losing my confidence. It would be the point where a lifetime of testosterone exposure would begin to rear its ugly head. It was when I would start to see stubble on my face or something else that would trigger a downward spiral of dysphoria. It was at that point when I felt I had to get home at all costs, I would literally feel as if I were in danger.

In the beginning it was a shelf life of about two hours before this happened to me. Though my first night at Stonewall was a success, my wife and I made sure we weren’t there long before it all went south. Over time I began to learn to use makeup on my own. I watched a million YouTube videos and learned how to use my makeup to battle my dysphoria. With just a simple contour here and there, I was able to chisel away at it. My makeup became my shield, and it gave me the confidence to leave the house. Eventually that shelf life would become four hours, then six, and eventually even more as my body began to change with hormones and I improved with makeup. I got better at finding clothes that helped me to reduce my dysphoria instead of enhancing it. Everything got better with time.

Now I am sure there are cisgender women who are reading this while saying that all women go through this. And yes, in a way they all do, otherwise we wouldn’t have 12 or 24 hour makeup products and setting sprays. But for me this is not about vanity, it is about safety. It is a personal fear that I am in danger if I were somehow clocked or outed for being transgender. For a cisgender woman, having a hair on your chin can be embarrassing, but most likely you won’t get physically attacked for it. For me there is a certain life and death pressure when it comes to how I present myself.


My wife can leave the house and run to the store with no makeup on while just wearing sweatpants. Though she may not be expecting to be crowned as Miss America at that moment, she doesn’t have to worry about being killed just because of the way she looks. This is something I just can’t do. No matter how many times someone could say I would pass without makeup or dressing a certain way, I simply don’t believe them. I have a fear for my safety, even if it is in my own mind, and for me it is very real.

Over time the window before I experienced the Cinderella effect would lengthen even more. When I started out I would have to re-apply my makeup and go over my face with a razor half way through an eight hour shift at work. Thankfully with hormones and laser I have been able to last an entire day without going through a dysphoric spiral. This is something I am pretty sure we all go through at some point point. I am also sure trans masculine and non-binary people experience their own versions of it. We all come in different shapes and sizes. Anyone who experiences dysphoria can have different things that trigger it. Some of us are lucky to have it easier than others. Some of us can’t make ourselves feel better with clothing and makeup. Some of us are strong enough to not even care.

I wonder if a day will come when I no longer feel like there is shelf life to my presentation. I also wonder if I will ever feel safe enough to just leave the house without having to put on that shield that makes me feel safe. I do know that it gets better with each passing day in my journey. There are still bad days however; the one’s where I can’t even leave the house, but the good ones outnumber them. As my transition continues I further realize that in a way I will always be transitioning. There will always be something I am striving for or a point I am trying to reach. I am learning to accept this fact and enjoy the journey.

Comments (6)

I hope with another couple of years under your belt, you feel safer now. Fear is toxic, and it's something many cis women often have to spend years overcoming, too. I never had a lot of it, but there were moments walking home alone at night that absolutely did trigger me in a way I'd never been as a man. (Even if maybe I should have thought about that.) Random violence is just that, random, and we should all live our best selves without making fear our master.


Today, I wear little more makeup than lipstick and eye makeup. I pull on some leggings, add a top, and off I go. Like any woman I navigate the world. I do love getting gussied up for a special event but in the meantime I’m just me. I’m so grateful for all of this!


I also well recall the early days, especially after I went full time. I dreaded going out to the grocery store, or pretty much anywhere so I clumped my outings. I’d apply all the makeup, worry about the outfit, and “I’m goin’ in” would float through my mind.


some instinct.


I am sorry to say that. No presentation in the world will save you from being attacked. None at all. There is no 100% passing. Ever.

The only thing that can keep you save is your spine, (a convincing show of, or real) confidence, good company and

TU Articles