My Transgender Day: A Transitional Farce in Five Brief Acts

An emotionally and physically tiring game of juggling

I am a late-in-life transitioning transgender woman. “What does that mean?” I hear the gender-uninformed cisgender person ask, possibly followed by: “What is cisgender?” To speed along the story I have put a brief glossary of terms below.*

I started my day with great plans that required multiple character and wardrobe changes. The new reality of my life demanded it. For personal and professional reasons I must continue to present as male most of the time.

It really sucks.

For sixty years, my role on the stage of life as a male lead was dictated to me by a rigidly binary world. It indoctrinated me into the role of Male from the moment of my birth. With a crack on my ass, the delivery doctors proudly informed my parents:

“Congratulations, it’s a boy!”

There was no looking back. The doctor and the world declared my gender as male.

Only they both got it wrong.

I was born with a birth defect.

Mother Nature had decided to wave the Magic Wand of Biodiversity over my mother’s womb causing my body to form male while my brain was wired female. Being born in the 1950’s was not the best time to be transgender. No one knew that the concept of transgenderism even existed. The word “transgender” wasn’t even used until the late 1960's.

The first 60 years of my life were both fruitful and distressing for me. I lived my male role to the hilt: sports, fighting, dating, career, marriage, family, empty-nesting, and visions of retirement. I truly believed that the doctor and the world were right. I accepted my male role as real.

That belief came to a screeching halt in my 60th year. Mother Nature had planted a gender time bomb that finally exploded and it shattered the gender lie.

I wasn’t a cisgender male, I was a transgender female.

Believe me, I didn’t want the new role. I refused to accept that it was real until the intensity of that denial almost killed me. Gender dysphoria (see glossary below) is an unforgiving bitch.

My need to continue to present male against a massive drive to present female is a daily battle for control. It is a difficult world of compromises.

The majority of my days are spent looking male and thinking female. To keep from blowing up, I periodically need to look female and think female. It provides me with some entertainingly bizarre days. Thankfully, I have a sense of humor because today was one of those days.

To make the day interesting, I made two female appointments, the first to get my hair done (notice I did not say “hair cut”) and the second, I had an introductory physical assessment at an all-female gym, all after a intense male day at work and a male end to my entire day.

ACT ONE: Being the professional male

The day started classically, get up, shower, shave, and put on a suit and tie. I despise shaving and I despise wearing a suit and tie. Being a transgender female it is the most emotionally abrasive choice of clothes I could choose.

Having done it for my entire adult life, I mindlessly went through the motions as my mind repelled from the process. I headed for my office. I dressed for the role of MALE BUSINESS EXECUTIVE.

I looked and acted the role with the ease of a TV sitcom pro who has had 60 years to improve his acting craft. I was entirely in character…except as I passed women on the street, I checked out their shoes, jealous of their cute dresses and how their makeup looked. I didn’t have any interest in their breasts or butt…clearly, I am not a cisgender male, I am just acting the role.

In the office, I am APLHA MALE, able to close deals and command attention in every meeting I attend. People come to me for decisions and no one questions them. I walk with confidence and surety with each step. I am the model of male privilege…and I hate every moment of it. I would drop every male privilege I had in a second to just be who I am inside but no one knows it. I provide a convincing male role to the world.

I left work. Home is just a subway ride away.

ACT TWO: Emma Undercover in Guy Sweats

I was going to drive to my hair appointment and I wasn’t comfortable driving as Emma in NYC rush hour traffic. What if I had an accident? I didn’t want to have to explain myself to the NYPD with my deep male voice in a cute dress. I don’t think they would understand and knowing my luck they would be Irish Catholic Trump supporters. I wasn’t taking the chance.

I opted for a wardrobe change as WORK OUT GUY. As I left my house and sat in my Jeep, I was safely 100% male looking. I drove with male confidence, without fear or a sense of threat. I was a powerful and entitled male driving in the thick of traffic daring anyone to cut me off.

With a quick 20-minute drive and a 10-minute pattern of looking for a NYC parking spot, I was all set for my next wardrobe change.

ACT THREE: Emma Blowing in the Wind

I was wearing my women’s yoga pants and bra under my WORKOUT GUY costume. Like Superman, I was ready to change into…well not Clark Kent…more like Lois Lane but I didn’t have a telephone booth handy. I did have my Jeep. In my backpack, I had a really cute dress, my makeup kit, and selected jewelry for my Emma hair appointment. All I had to do was find a parking spot near the hair salon.

I was hoping for a quiet spot to do my wardrobe change….yeah right, as if that was possible in NYC…

I finally found a parking spot but it was next to a construction site. If you are parking in New York City, beggars can’t be choosy. If you find a legal spot, you grab it, regardless of your fears about construction workers and changing clothes in your Jeep as a transgender woman.

I didn’t care if anyone was watching. Time to finally be me, Emma.

Changing in the driver’s seat with a steering wheel in your chest is not the most convenient place to change clothes. It can be virtually impossible but gender dysphoria, when channeled correctly, is a superpower. Ignoring the homeless guy eating his lunch sitting on the curb across the street, I ripped off my sweatshirt like Houdini escaping from a straightjacket. Realizing I was just sitting there in my bra, like a fashion ninja, I quickly slipped on my dress.

Once properly dressed, I felt totally at ease putting on my makeup using the tiny vanity mirror built into the sun visor of the Jeep. I guess the manufacturer didn’t expect too much vanity in the deep woods but there was enough mirror on the Jeep to accomplish my goal, I was Emma finally.

I exited my Jeep in time for a gust of wind to catch the hem of my dress. With unexpected speed, my hands were able to limit my Marilyn Monroe moment of exposure.

The brief walk to the hair salon was a walk of freedom for me. I felt totally me, totally Emma. The dress was a release from my male prison. I wasn’t male, I wasn’t androgynous, I was female and I loved it.

I walked into the hair salon to a chorus of “Hi Emma!” and a couple of “cute dress!” from the women who knew me. I was among friends, allies, and members of my tribe. Michelle, my hairdresser, looked over at me smiled warmly, and said: “I have never seen you in a dress before and you look so cute!”

I couldn’t get enough “cute” compliments. It felt so validating after such a male day. It helped me purge “male” out of my system. The rest of the appointment was more of the same female-reassuring experience that I couldn’t get enough of. It was like having my gender needs quenched after walking for years in a binary male desert.

After the hair appointment, I walked back to my Jeep with a smile that no one could chisel off.

ACT FOUR: Emma the Olympian

In the past week, I sent emails out to three female gyms to see if I could arrange a personal trainer. I made it clear that I was a post-op* transgender woman. I didn’t want to create unwanted stress for other women that a transgender woman could trigger. I respected their space and their needs.

Happily, I got three positive responses. It gave me hope for the future. I selected the one that I felt an immediate connection with and made an appointment for a physical evaluation right after my hair appointment. I needed a quick wardrobe change. Once in my Jeep, it was time for “Emma in a dress” to “Yoga Emma”. Fortunately, my yoga outfit was under my dress so there was no worry of public nudity.

It was a short drive to the gym…this time as full Emma, makeup, yoga outfit, and all. Yes, driving felt different. I felt more tentative and very much aware of my driving. That vulnerability continued as I parked a few blocks away and walked the dark street to the gym. I realized that my male confidence was gone. I wasn’t afraid but I was very aware of my surroundings and the people nearby. I was Emma, a woman alone on a dark street.

It was a very unpleasant sensation, one that I have felt before in public as Emma. I think it would be the same whether I was a cisgender woman or a transgender woman.

The light of the gym was a very welcomed sight.

For ninety minutes I was grilled about my body, health, and exercise history. I then answer a myriad of transgender questions. I was the first transgender woman the trainer had ever met. It was fun to answer them because she was so sensitive to what she asked. I found out that she was a professional ballet dancer and my heart skipped a beat. I told her of my childhood dream to be a ballerina. We immediately bonded and I scheduled a regular weekly workout.

ACT FIVE: Boringly Male Again

Walking the dark streets as Emma again, my antenna was super-sensitive to the world around me again. Once in the Jeep, I wiped off all of the makeup and pulled on my male sweats. I drove home wearing the armor of male invincibility but at the same time, feeling immensely sad inside.

It was an emotionally and physically tiring game of juggling my female gender and male gender presentation act. I reminded myself that it was still necessary but I hated that I was painted into a gender corner because of the circumstances that I had to accept.

I then started laughing while I drove.

What an absurd and farcical world I inhabited. I actually had fun getting it all to work successfully in one day but I was exhausted by the time I got home. I should trade the Jeep in for something bigger to change my clothes in…

Emma Holiday

• Late-in-life transitioning transgender woman: a person who was born physically male but has a female gender who has spent a lifetime suppressing their reality until they couldn’t any longer in their 50’s and 60's.
• Cisgender: a person whose gender identity corresponds with the sex registered for them at birth
• Gender Dysphoria: according to The Diagnostic and Statistical Manual of Mental Disorders, Fifth Edition, Text Revision (DSM-5-TR) used by mental health clinicians and researchers, gender dysphoria it the psychological distress that results from an incongruence between one’s sex assigned at birth and one’s gender identity. Think of it as a screaming fire alarm in your head that gets louder the longer you ignore it. It’s your brain telling you something is wrong. There is a conflict between your physical body and your gender-wired brain.
• Post-op: a transgender woman who has had either an orchiectomy, volvoplasty or vaginoplasty surgery.

Thank you for reading my work. Please also read:

My writing has three specific goals:

1. Writing is my therapy. I have a very limited outlet for my thoughts so I write to find a way to process the most profound experience in my life. I need to understand and I need to accept myself to move forward.

2. Being transgender, for me, is a very lonely existence and if I can share some of the things that I feel and think as I go through the process of transitioning with others who are transgender and, in some way, lessen their pain and sense of loneliness, then all of this public exposure of my personal thoughts is not a waste.

3. I write to help cisgender people understand that all trans people want is to be simply understood, accepted, and treated as a normal person.

We are.