How does one start transitioning?

| Feb 19, 2018
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Her first dress.

So, how do you start? When your actual identity can no longer be denied and it bubbles up to the surface; when your hours and hours of fantasizing finally breaks thru and affects your day-to-day reality, how does everything begin, exactly? I don’t know how it was for anyone else, but for me, the answer is: Awkwardly.

Here is a picture of me wearing the first ever dress I ordered online. I am so geeked here. A savvy reader might even take note of my Rainbow Dash My Little Pony: Friendship is Magic socks to complete the ensemble. At this point, I still basically looked like a boy in a dress, but it was all I had, and I loved it.

I started to want to experience the world this way. Like, immediately. I asked Phoebe if I could borrow one of her spare purses and I walked a few blocks alone to go get us some Little Caesars. The feeling was amazing. I felt the breeze on my legs. The world looked different, hips swaying to and fro of their own accord. People looked at me differently. My body moved differently. It was me: unfiltered. I was euphoric. When I got back with the pizza, I was so jazzed that I insisted that I run out again so I could go get us drinks from the Ralph’s Grocery next door. Once there, I got smiles from strangers and I smiled back freely. We were just a bunch of gals in the produce section! I felt unsaid inclusion. I saw another trans girl in the store, and we noticed one another and gave a knowing nod. My brain was exploding with sparkles.

But, besides this undeniable feeling that it was just “right,” what did I really know about transgender people? I had never met one up until that point and, if my mother was to be believed, they were “deviant drug addicts that were destined to die alone”. I couldn’t abide that belief anymore, so I went to the internet, made a new Reddit account, and learned EVERYTHING I could. This is how I found out about HRT (I truly had never heard of it before). This is how I found out that there was a trans group that met at the LGBT center in Hollywood every Friday, and I started making a thing out of it. After living life presenting male all week, I’d come home from work Fridays, shave my legs, squeeze into a dress, and drive down to Hollywood in wedge heels (which is an acquired skill).

At my first meeting, I was VERY intimidated. Was I feminine enough? Would they take one look at me and say, “Nope! You are not trans enough to be here! BE GONE FROM THIS PLACE!”? It was not like that at all. I learned that there is no such thing as “not trans enough.” That’s just my lack of confidence in myself, mixed with imposter syndrome, with a twist of mental abuse reverberating from childhood. Anyone could feel this way, but that doesn’t make it true.

The real education came after the meeting when all of the people who attended went out to Denny’s together. Here, I learned some very interesting things. I learned the easiest ways to try to get on HRT ASAP. I learned that trans girls on HRT experience WAY more intense orgasms than before (as if I needed more convincing. . .) and it also changes the way that we process our thoughts, and even the way our skin feels. My mind was blown. And I also learned that there is no “right” way to be transgender and we all take our time defining ourselves and figuring out what that means to us. I learned, and am still learning, SO much from the transgender community here in Los Angeles, and I’m so glad to be a part of it. Everyone is ridiculously nice and helpful. Two of the girls there helped me get over my fear of using the proper bathroom and were basically my emotional escorts. I’m so thankful for them.

I also kicked around what I wanted my new name to be. At first, I thought of “September”, which was the name of one of the characters from my screenplay, Ladies, that I really identified with, but I eventually found that September was pretty much already her own person in my mind and I felt like I was just co-opting her personality. (That’s weird, right?)

Next, I tried calling myself “Penny” for a while. And I liked this one, especially if you recall the story about my necklace and my connection to pennies from my last entry. I thought that I’d found it, until a friend of mine pointed out that this was the name of the girl from The Big Bang Theory, and unless I wanted to be followed around by people doing the Sheldon thing of: *knock-knock-knock* “Penny!” *knock-knock-knock* “Penny!” *knock-knock-knock* “Penny!,” for the rest of my life, then I should probably pick something else.

Also when choosing, you don’t want to name yourself the same name of anyone you are close to or see on a semi-regular basis because that would be an awkward conversation:

Them: So . . .  you’re calling yourself my name now?

Me: Well, I’ve always liked it, so yeah.

Them: Did you name yourself after me?

Me: No. I just liked it. Unrelated to you.

Them: Am I a role model to you then? Do you aspire to be me?

Me: No. It’s not about you. I just like that name.

Them: Well, can I call you a nickname when you’re around me so people don’t get confused? It was my name first, so . . .

Me: Um . . .  okay. 

I just wanted to avoid all of that nonsense. I didn’t want a nickname, I wanted a name that represented me. Phoebe eventually came up with Natalie, which fit. I can’t explain it, but when I heard that name in this context, as a possible name for me, it felt different. Like, when you ring a large bell and, after the gong, you hear this sustained reverberation afterward. That’s kinda what that was like. Phoebe said: “How about Natalie?” and it just reverberated and echoed off the walls and hit me from like 3 different directions. “That’s it!” I said. And that was that. I made my middle name “Nicole” for two reasons:

1.) Because my sister’s best friend when we were growing up was named Nicole and she had always been one of the sweetest, nicest people I’ve ever met. I remembered her and Andrea letting me play a game called “Girl Talk” with them once when they were having a sleepover, and I got to imagine what it would have been like to grow up as my sister’s sister. I’ll never forget how much we giggled and had fun, as I pretended like I wasn’t having the time of my life, and

2.) My dead name is Nicholas. I liked still having some vestige of that name with me, because who I was is a big part of who I am. It’s not his fault he didn’t know anything. I’m not running away from who I was, I’m just running toward who I will be. I know some girls are triggered by their dead name and want no affiliation with it whatsoever, and that is completely fine. We are all just figuring out what feels right to us, and Natalie Nicole feels right. I don’t know why, it just does. Maybe because that was always my real name . . .

Pretty in pink.

Here’s a pic of me trying to figure out my style around this time. I couldn’t get enough of the pink (I still kind of can’t, but in the beginning, pink had been forbidden for so long that adorning myself in as much pink as possible bordered on a compulsion). And nothing says a ’90s girl more than a flannel shirt tied around the waist, or so I think anyway.

I also bought myself a bra early on. I would work all day with Phoebe, and when we got home, she’d immediately take her bra off, and I’d immediately put mine on. I just liked the feeling of it. Like a security blanket. A message to my body that I’m aware of what I am and am moving toward getting there. I gradually stopped wearing men’s clothes altogether. The fabric started to feel different and weird. I just didn’t like it at all anymore and was kinda done. I ended up donating all of my boy clothes to a goodwill (and this was before I found out about those transgender clothing swaps that are organized sometimes! I really missed out!).

What comes next was living under cover and coming out to my family, but those are tales for another time.

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Category: Transgender Body & Soul


About the Author ()

Natalie Nicole Dressel is currently a Grad Student in Writing for the Stage and Screen at Point Park University in Pittsburgh, and is also a graduate of Michigan State University with a BFA in theatre. She has 8 years experience doing stand-up comedy and is a graduate of the improv program at Upright Citizens Brigade in Los Angeles. She is proud of her recent appearances on Comedy Central's "Problematic" and Game Show Network's "Divided"; she also is a co-host of the program "We Didn't Start The Podcast", which is currently on iTunes, and is obsessed with Ramen shops.

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