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In her own words, Shakina Nayfack tells of her journey from young Jewish boy to outspoken theater actress

Transgender actress Shakina Nayfack stars in a New York Musical Theatre Festival production of "Manuel vs. The Statue of Liberty." She plays the Statue of Liberty.
James Keivom/New York Daily News
Transgender actress Shakina Nayfack stars in a New York Musical Theatre Festival production of “Manuel vs. The Statue of Liberty.” She plays the Statue of Liberty.
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I was 6 years old the first time I wore a dress in public, at a Super Bowl party with my mother. Another mom had brought a bag of costume dresses for the girls to play dress-up with while the boys watched football.

My mom is a fierce protector, and has since channeled that into becoming a fierce advocate. But at that moment she was really afraid of me being made fun of, so she got me out of that dress as quick as possible — and wanted to forget about it.

In “One Woman Show,” my first solo theater piece, I have a song about it called “Wear You.” The song tells the story of seeing that yellow dress and putting it on. The chorus sings, “I want to wear you, pull you over my head.” That was the first formative moment that I can recall.

Growing up, I didn’t have the language to understand myself as a trans person. I knew I felt like a girl, but I thought that just equated to being gay. I’m 34 and grew up in Southern California. I moved to New York in 2010. I lived the early years of my life as a gay boy, and I was out loud and proud in the ’90s, part of the Queer Youth Movement. I came of age as a sexual being during the height of the AIDS epidemic.

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Throughout my youth in the mid-’90s I was really gender nonconforming. I wore makeup and confrontational outfits. Every day was a battle zone.

In high school, I was slammed against lockers, pushed around, threatened. I’m 6-feet-2, but it’s hard to feel powerful when the world is set against you. I’m not a person who is prone to violence or aggression. These were tough dudes, even if they were smaller than me. When I was 16 years old, I gave myself a tattoo. It’s side-by-side male symbols. I figured that if I was found gay-bashed or dead that at least my body would declare that I was out and proud.

I grew up Jewish as Jared Alan Nayfack. My parents split up soon after I was born and I saw my dad every other weekend. We’ve gone from being estranged to really close. He was the first person I told when I realized I had to transition if I was ever going to be happy. When I decided that I was going to start wearing my hair long, he took me out to get my first high-end wig as a birthday present.

I’ve been Shakina since 2001. Shakina is derived from a Hebraic word that refers to the feminine presence of the divine spirit. I was in college in Santa Cruz. The big, formal announcement was the night of my graduation. I spoke about Shakina, the concept, in my speech, in front of my college. I wore a black gap dress and fishnets under my graduation gown. That was like slipping it in. I was literally cloaked.

When I came out as trans, and changed my name and pronouns, I was really afraid of changing my body. I didn’t want to be a big, hairy woman. So I devoted myself primarily to cultivating a sense of womanhood through feminism and spirituality before a physical presentation.

I wore women’s clothing. I shopped at Lane Bryant and they were lovely. They’d call me when something a little edgy came in. I used the ladies’ restroom in public. I felt like I was transgressing a social norm, but the discomfort created by that was everybody else’s problem.

Then I actually went back to being a dude for a couple years beginning in 2002 after a couple debilitating events — a sexual attack and a friend’s suicide.

Trying to be sexual and date was really difficult and dangerous as a trans woman, and I think it still is. I had an experience of sexual assault that was pretty terrifying.

Shakina Nayfack takes a selfie in Thailand before surgery.
Shakina Nayfack takes a selfie in Thailand before surgery.

So I became super butch. I drove a big, black truck with the Virgin Mary on the back. I wore wife beaters and True Religion jeans and white kicks. I had a shaved head. All my friends knew what was up. I was slowly killing myself.

I came to New York in 2010 for my first professional theater job and things began to change. I said, I’m going to wear a sundress in Central Park. I’m going to see Broadway shows in sundresses. And I did. I went to like seven shows that season, including “Hair.” An actress took my hands at one moment and I felt 30 years of emotions rise. It was so cathartic.

I made the decision to transition medically on July 4, 2012. I started hormones in January of 2013. I was taking testosterone blockers and synthetic estrogen. It’s really, really difficult — and expensive — to transition medically. I’m very grateful to the Callen-Lorde clinic downtown. They have a trans-care program that made it financially possible for me to have hormone replacement therapy.

I tweeted, “This is so expensive, I should just crowd-fund my surgery.” And then it was like, Why not? I launched Kickstart Her in November of 2013. I raised $22,787, which covered the surgery and travel totally. Originally I was trying raise $48,000, which included the cost of facial feminization and gender confirmation, but then decided against the former. I was too scared to damage my voice.

I’m now in “Manuel vs. the Statue of Liberty” at the New York Musical Theatre Festival. I’m a white trans woman playing the Statue of Liberty in a show about illegal immigration. It’s really meaningful for me. I’m representing a struggle to cross borders that I identify with politically, spiritually and socially. There’s a lot of delicate dancing around what gender confirmation is. Even the term “transgender” sort of has usurped the politically incorrect and somewhat offensive term “transsexual.” But I like the term “transsexual” because it is for me about sex. It’s not only about sex, but I feel like sex gets erased from the conversation a lot of times. I don’t mean sex like the thing between your legs – although that’s important. But I mean the act of actually being a sexual being.

I did my surgery in Thailand, because there’s a doctor there who does it completely different from everyone else in the world. He’s pioneered a very unique way of doing the surgery. The traditionally accepted method of the surgery is called penile inversion, which explains itself in the title. Dr. Suporn is much more complicated, but I feel much more sound and, for lack of a better word, organic, the way that it repurposes tissue. The results are better, I think, in terms of sensation and functionality, and appearance.

Shakina Nayfack grew up as Jared Alan Nayfack.
Shakina Nayfack grew up as Jared Alan Nayfack.

My surgery was on Sept. 22, 2014. I was in Thailand. Alone. I’d been in bed for a week, bandaged. The day they took the bandages off and handed me a mirror, it was like meeting myself.

I walked to the shower, supported myself, took my time shaving my face, my head and my body. When it was time to wash my body, I was scared.

Then I slowly reached down and I felt my vagina. It was like mapping new territory. It was like a discovery.

Before the surgery, I’d been on hormones and things had filled out — my hips and my breasts. The more that my body became more feminine, the less sense my genitals made. There was this separation, and now I was looking at a complete picture.

The nurse put a towel around me, and I started to weep. She said, “You feel pain?” And I said, “No, I feel good.” I had a lot of difficult things happen in the recovery. It was not an easy road. I’ve blogged extensively about it and I’m working on a new show just about the surgery. The working title is “Post-Op.”

The surgery itself was the most painful experience you could ever imagine. I was alone in another country for a month. The recovery is really brutal. I was in pain for seven months following. A lot of the celebrities have transitions in secret. They appear on the scene as these finished products.

Shakina Nayfack calls this portrait one of her favorites from her former life, a “deepy ironic” shoot just before her 30th birthday.

When I came back from Thailand, I wanted a way to tell the world that something had changed, but I couldn’t go around showing everyone my private parts. I’d had a shaved head for 15 years. So when I reentered New York, I was Shakina with hair. It’s a weave. It’s a huge part of identity now. It carries a lot of emotional weight.

I used my process and was very public with my process because I wanted to demystify what it meant to transition for my friends, my family, my community.

The theater company the Civilians invited me to a part of a concert at 54 Below, and I was just a little more than two months post-op. I went up and sang a song I always wanted to sing, it was Nina Simone’s “I Want a Little Sugar in My Bowl.” It’s one of those really wonderful, bluesy songs about sex. I got up there. To be up there that soon after post-recovery, still in pain, and to be singing that song. That was huge being back on stage again.

I’m single. I didn’t go through all of this not to put it to good use, but also, how many people get the chance to reclaim their virginity? And I’m not going to give it up easy.

Nayfack, artistic director of Musical Theatre Factory, begins performances of “Manuel vs. the Statue of Liberty” July 21. For more information, go to nymf.org