A transgender woman shares her story about the first time she tried to wear makeup in an attempt to see her true self. – “The Weekly Rant” with Mila Madison.

In the beginning of my transition, I remember the first time I tried to see “her.” The woman I had been hiding for my entire life, me. I had just come to terms with the fact that I was going to live my life as my true self, but I had no idea where to begin. I was full of self-doubt, filled with fear, and my mind was racing a million miles a minute. Though everything in my life leading up to this moment finally made some sense, I really did not know what was going to happen. One thing I did know however is that I needed to see this person who I had been hiding within myself. I though if I could see myself, it would add some clarity to this journey I had just begun, but I had never been so wrong.

Luckily I had my wife who wanted to support me through this process wherever it may lead. We were both at the stage where we wondered if we could really do this. For me, it was could I really transition. I wondered if I would ever be able to see this person who I was meant to be. For my wife, she wondered how she would feel once she saw this person. In our hearts we knew we loved each other no matter what, but we never put that love to test in the ways we had recently. Safe to say, we were entering a world of unknowns, but there was no turning back. These were answers we both needed to know to be able to continue forward together; otherwise we would always wonder what might have been.

“I was afraid of what I would see once I looked into the mirror.”

I booked an appointment with a woman who did hair and makeup for transgender girls who were beginning transition. It seemed like a good idea at the time. Before the appointment, my wife and I went to the mall and bought some clothes for me to try on as well. When we arrived, the woman who was going to do my makeup introduced herself. She was really sweet and supportive. She did everything she could to make me feel comfortable, but I was literally shaking. I was afraid of what I would see once I looked into the mirror. She started with a facial and proceeded to apply my makeup. There was no mirror for me to see what she was doing, which was probably a good thing as I may have freaked out. Next she styled my hair, which was no more than a little pixie cut at the time. She left the room and I put on some of the new clothes I had just bought. It was time for the great reveal.

I came out of the room and the woman escorted me to another area that had a big mirror. She gave me a minute to be alone while she and my wife waited for me to come out. As I looked up to see myself in the mirror, all my hopes to finally see her instantly vanished. I saw “him” and “he” was wearing makeup. It wasn’t that the woman did a bad job; it was just that it wasn’t me who I saw. My dysphoria kicked into overdrive. The bad thoughts rushed through my head like a waterfall. “I am never going to be able to pull this off,” I thought to myself. It was a makeup fail of epic proportions. My hope for a moment of clarity quickly turned into a moment of defeat. I looked absolutely ridiculous wearing this makeup, and the clothes I was wearing did nothing but highlight all that was wrong with my body. I was shaking even more than before I started. All the negative stigmas that society gives to us as transgender people began to enter my mind. That along with all the newly discovered pressures of being a woman in today’s society amounted to a major breakdown, as I lost all hope that I would ever be able to transition. I mustered enough courage to leave the room. My wife and the stylist both tried to help me improve the situation. We tried adding a scarf and whatever else, but to me there was no way to improve the situation.

A transgender woman shares her story about the first time she tried to wear makeup in an attempt to see her true self. – “The Weekly Rant” with Mila Madison.

Though I was defeated, my wife had a different experience. She saw the potential of whom I was going to be, and somehow it eased her mind. She knew at that moment that we would be okay no matter where the journey went. I was amazed that the experience was so different for each of us, but she also didn’t suffer from gender dysphoria as I did. I left the appointment discouraged and defeated, but I was determined to move forward. There was no going back for me. One day I would see “her” if it took me an entire lifetime to do so.

“It was a strange feeling as I was expecting my mother to pop out at any time and yell at me for getting into her makeup..”

In the coming weeks I would take it upon myself to get through these beginning stages of my journey. I would play with makeup, just like a little girl for the first time. I worked through society’s stigmas and the pressures of what the world tells us a woman should look like. In the beginning I felt guilty, as if I were doing something wrong. It was a strange feeling as I was expecting my mother to pop out at any time and yell at me for getting into her makeup or something, luckily she lived 40 miles away. Eventually I got over my fears. I watched a million YouTube makeup videos. I learned about contouring and all the different techniques that can be used according to the features you have that you like or don’t like. I experimented and I got better and better with it as time went on.

Eventually I began hormones and my face and body began to change. I learned how to use makeup as a way to reduce my feelings of dysphoria. The clothes I looked so awkward in began to fit as my body became more feminine. In time I began to see “her” as I had always dreamed. My wife seemed more attracted to me than she ever had been before, and it gave me more confidence. She realized it was the real me that she was always in love with, and our relationship grew stronger that it ever was before. Eventually I came out to the world and I became more comfortable living as the real me.

I learned that what makes a woman beautiful is not what is fed to us through advertising and movies. It is certainly not makeup. Women come in all shapes and sizes. Some wear makeup, some wear a lot of makeup, and some wear none at all. It doesn’t make them any more or less a woman. I found what made me comfortable. To be honest, I am not sure if I will ever get to see “her” completely in my lifetime. What I can tell you is that I see a little more of her each day. If you are at the beginning of your transition and you are feeling doubts or discouraged, I say keep going. Keep trying. You will get there one day. It is all part of the journey.

  • Lee Anne

    I came out at age 61. My face has wrinkles, my hair is thin, brittle and tends to hang limp. I wear minimal make up as too much just accentuates the person I saw for 60 years. But now, when I look in the mirror I see the person I was always meant to be, myself. I will never be glitz and glam.I will never “pass”. But I can, and do, walk with pride as I shop and go to restaurants with my wife of 20 years. (forget about getting make up tips from her. She uses less than I do). And that is what it’s all about. Finding ourselves and becoming comfortable in our skin. No matter how we look.

    • Emma Sweet

      Absolutely, Lee Anne, well said: “That’s what it’s all about: Finding ourselves and becoming comfortable in our skin.” Yep, that’s my goal, girl!

  • Ronin Sterling

    “It was a strange feeling as I was expecting my mother to pop out at any time and yell at me for getting into her makeup or something…”
    This hit home for me, as I have a vivid memory of my mother yelling at me for cutting my hair as a young child, much to her dismay given her assertion of very strict gender roles and conflation of long hair with womanhood/femininity.
    In my transition thus far as an NB person, there are often moments in my internal dialogue wherein I wonder who they (me) are and if I will ever see them (myself) and times where I see myself as them in reality. Then there are times when I hear in my head, despite the fact that I know better, all the erasive and defamatory ideas, conceptions, and stigmas society has for nb people.
    As bad as those make me feel, as all scary and consuming the dysphoria can be, the times when I see them(myself) are absolutely worth it.
    Excellent article.