This story originally appeared on The Mental Illness Happy Hour Podcast blog on March 25, 2018. It was uncomfortably titled “The First Time I Dressed Up As A Transwoman.” I’d be remiss to mention the demeaning grammar of the word “transwoman,” which I did, immediately. It was not changed, clearly, so I’ve changed the title to something less commercially viable, yet more emotionally correct. This was hardly the first time I dressed up as a trans woman. I was dressing like a girl in secret since I was a preteen. The first time “I Dressed Up As A Transwoman” was Halloween 1986, when I convinced my mother to let me go as a cheerleader.
People have asked for my writing, or I have offered it for publication, and it has rarely gone well. I don’t want these experiences with difficult people to color my thinking. I was young and asked too many questions. I feel like I was homeless on the streets just a year ago, even though it was two decades ago, and since then I’ve changed gender at least once. These formative times of my life could be better summed up as “traumatic.” I want to share them, I want to be honest. I just want to mention here that these times were messy, and raw, and that I made a lot of bad decisions all on my own. This particular story happened thirty years ago though. I’ve changed and grown quite a lot since these shadowy times. Thank you for sharing in them.
In 1989, I was a sixteen year old with a mother who was a very heavy sleeper. Nights meant I could finally “dress” in the outfit I’d collected by sometimes unsavory means. Mostly from shoplifting sometimes at the mall down the road. A black skirt, high heels, and a simple blouse weren’t something I could just carry to the cash register and buy. I knew stealing was wrong, but I could finally soothe that nagging feeling. The purr that quickly turned into a roar, and me into a monster who yelled at my friends incoherently. Maybe because they all seemed so comfortable in their skin, and the eyes of society. I was angry, and dejected from a night of not fitting in, so I began dressing up as soon as I was home for the night. It was very late, and I was as drunk as I had ever been.
Up to that point I was buying cigarettes to share with my friends when they came over really desperate. In my cloudy haze I began to think I should go get a pack for myself. This was something I was absolutely mortified of normally, but right then I was feeling fearless. I decided I could take my Honda Elite scooter the six blocks, buy smokes, and be home in no time flat. I park it out front of the shop, but can I go in? Maybe the guy inside would make fun of me? I can only hope that’s not true, but my heart was racing. Next thing I knew, I was inside the brightly lit store. The clerk seems a little confused by my scared look, but with little hesitation, sells me the cigarettes. Easier to just get me out of the place, I’m sure. I left in a hurry, too.
I had done it! I had walked through life, dressed as my true self. As opposed to the walk around the block almost every transwoman has done. So relieved, yet still flustered, I jump on my cycle and tear out of the parking lot. I’m in such a hurry to get home, I speed through the stop sign. In my peripheral vision I barely registered the car speeding up from under the railroad underpass to my left. It hits the back of my scooter with a terrible force that throws me to the concrete. It’s like a thousand fists at once. As soon as I realized what’s happening, and the trouble I was in, I’m up and moving. The man in the car started to get out, and without thinking really, I began to scream “just go! I’m okay, I’m okay! GO! I really saw fear mirrored in the eyes of this poor guy, who might had been drunk as well, equally confused at all that was happening. He seemed worried, but relieved to extricate himself from such a crazy scene. Alone again, I go to lift my Honda Elite 180 scooter off the ground. I have put it down a couple times before, but this time the engine is literally hanging out of the back, so I wasn’t that surprised when it didn’t start.
In a feat of superhuman strength I drag the very totaled remains to the side of the road. After I shabbily covered the lifeless scooter with several sticks, I ran all the way home. I sprinted as fast as I possibly could wearing three inch heels which was pretty fast under the circumstances. Sobered up by the specter of death, I washed my face, changed back into my male uniform, and went quickly to sleep. I just wanted the nightmare to end.
It was far from over though. Without having a chance to dream, I woke up an hour later to my mom shouting the police were at the door. I grabbed a glass of day old water and drank it down quickly. It was either effective at masking the smell of beer, or the officer had sympathy for me. I could only imagine what I looked like. Remnants of mascara around my eyes, tears flowing. I didn’t mention dressing up or drinking that night. Half of an hour later, I was out of his car, and safe at home again. I was given a ticket for driving without a license and leaving the scene of an accident. It would be about fifteen more years before I would get the courage to live full-time. It is unfortunate because I had to experience a few hundred more nightmares trying to live as the guy I was most definitely not born to be. Now that I’ve thrived as a woman for almost a decade, I wish I could tell my younger self how less scary it is than hiding. Once I was out, and I was finished covering the tracks of misfortune and shame, only then could I find true agency, and start to heal.