My name is Drew Riley, artist of the Gender Portraits series. Adolescence is a self-portrait created as the first painting in a set of four self-portraits chronicling stages that I went through in transitioning. The series of self-portraits serve to tell more than my story, they also serve to talk about the journey of transition in general as it relates to all of our lives.

The first stage in transition, which I have called adolescence, is perhaps the most well known. For trans-feminine people, it is often called the “princess phase” because of the individual’s often excessively girlish presentation. But more importantly, regardless of gender, it resembles the teenage adolescence that everyone goes through at some point in their lives.

If a person is transitioning at an early age, a lot of this stage will coincide with the normal course of youthful development. However, if a person transitions in adulthood, the transition creates a second stage of development that can create a lot of unforeseen complications.

I constantly have people tell me that their friend or partner is transitioning, and while they are supportive, they wish their friend wasn’t so… As they trail off, searching for non-judgmental words, I already know what they are about to say. I was that friend. Most transgender people have been that friend.

During the adolescent phase, a transitioning person’s personality might seem less authentic for a time. While this change can be shocking to friends and allies, it is important to remember that the transitioning person isn’t adopting a superficial personality. Instead, they are manifesting temporary symptoms of a complicated journey that they are embarking upon.

Imagine you are ripped from adulthood, and become a teenager again. You are going through the pains of figuring out who you are, what you like, how to dress your changing body, and how to socialize in new arenas. Except this time, none of your friends are going through the same thing. You don’t have your parents or family to ask for guidance. In fact, in this scenario, nobody knows that you are a teenager. They all think you are, and expect you to act like, an adult with everything figured out.

Most of this time for me, was spent in private. It’s common to be closeted for a large portion of this stage. I went through boxes and boxes of clothes, hidden in secret places and dumped out when nobody was around. I had entire evenings of trying things on, and practicing being female in front of a mirror. Sometimes, if I felt daring, I would go out and run a quick errand still dressed up, in a state of exhilaration and terror.

My looks changed regularly. A lot of it was fantasy fulfillment. I had a lifetime of wardrobe lust to get out of my system. Ruffles, lace, silk, beads, petticoats, stockings and more were forbidden fruit that I was now smuggling from their garden. My reflection in the mirror got to be the teen goth I envied, the prom princess who never got her night, the pleated plaid punk girl hidden in my heart, and a gaggle of others. I didn’t care what fit, or looked good, I was just chasing an experience.

I can’t properly express how emotional this time was. Putting on an outfit filled me with an electric comfort that both soothed and energized. Stepping out the door, dressed womanly, brought on the kind of terror that turns the gut and brings on nausea. Packing my secret stash of clothes away coincided with an endorphin and adrenaline crash, and a wave of shame.

Then, there was confusion. The questions were endless. “Why do I want, no need, to dress this way? Is this an addiction, mental confusion, my identity or a simple affinity for a certain aesthetic? What would happen if anyone found out? Would I be happy living this way? If I look toward the future, do I imagine myself as an old woman or an old man? If I am a woman, what kind of woman am I?”

I would go online and research as much as I could to help find answers [excitement]. Then I would delete my browser history [shame]. I would convince myself to meet another gender nonconformist, like myself [excitement]. I would over compare myself to them, and fear being put in the same boat [shame]. Like I said, this was an emotional time.

As I started to come out to people, and show friends what I was doing, it was suddenly apparent that things about my wardrobe and makeup were awkward. But I didn’t know how to fix it. I also didn’t know how to carry myself, talk or act. I would often overcompensate by acting like a caricature of a woman. I missed the childhood of social training that the average woman receives, and I was going through a self-taught crash course. Proving my womanhood in front of my friends made me a ball of nerves, and in my questioning state, I was vulnerable and defensive.

As already stated, I wasn’t completely blind to social friction, or to feeling out of place, but the magnitude and the source of the discord often eluded me. Like a genuine teenager, I couldn’t recognize how ghastly my choices were until I grew out of them. While this might have frustrated people around me, it did me a great service. My ignorance allowed me to enjoy the majority of my self-discovery. If I had been too aware, and avoided any adventurous departures from a sane, adult woman’s wardrobe and actions, I would not have transitioned into a well rounded person. I would not have gotten all the pent up sparkles and frill out of my system. I would not have futzed over my mannerisms until my own personal poise became natural. Lastly, I would not have found the more extreme sides of my feminine personality because some of those adventurous departures ended up hitting the mark.

I did have a strong advantage in my journey, and that was a good support network. When I finally came out to other people in my life, I ended up with friends and partners who encouraged me with low judgment. They allowed me space to explore myself, and graciously didn’t hold mistakes over my head. I even had a few mentors who gave me gentle guidance that was invaluable.

Even though the adolescent stage of transition lends itself to closeted isolation, I don’t recommend going through that journey entirely alone. Some solitude is necessary for safe, creative experimentation, but true self-discovery cannot be carried out in a vacuum. I dressed up and fantasized in private for over a decade, and I evolved very little during that time. Once I took my transition to the outside world, the changes came quickly. How people interact with others makes up a large part of their personality, and is the pathway to the next stage of transition.

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