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Video blogger shares his transgender journey

Mass. man’s videos touch many

On the first day, Skylar Kergil turned on the webcam and gazed into it, seeing a familiar digital reflection — the smooth cheeks, a crest of brown hair eclipsing one eye.

“It’s January 21st,” Kergil said, smiling at the camera. “It’s, like, noon. This morning I went to the endocrinologist in Boston.”

The doctor had shown Kergil, 17, how to inject testosterone — the first step in changing the female body he was born with to male. The hormone had been in his system for only an hour, but Kergil’s voice was full of wonder.

“So today’s my first day being born, I guess,” he said.

Kergil was recording himself, especially the depth of his voice, hoping to document his physical progression. It was 2009, and he uploaded his videos to YouTube when he ran out of computer memory. He didn’t expect anyone to watch what would become his video blog.


But soon viewers of all identities and orientations discovered Kergil’s journey.

Now, nearly six years later, Kergil lives in Cambridge and has more than 61,000 YouTube subscribers. His 191 videos have been watched nearly 6 million times. Thousands of people from around the world have written to cheer him on, and seek advice.

Earlier this month, he flew to Los Angeles, where the Trevor Project, a national group that works to prevent suicide among gay, lesbian, bisexual, transgender, and other young people, awarded Kergil its prestigious Youth Innovator Award.

But back on Jan. 21, 2009, Kergil was just a high school senior, sitting in his Acton bedroom, a Red Hot Chili Peppers poster and his guitar behind him. He spoke with the voice of a teenage girl. He had persuaded his parents to let him start taking testosterone before he began college.

“It’s nice,” Kergil said, “to finally feel that maybe my body is trying to adapt to me instead of me trying to adapt to my body, like I was for 17½ years.”

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Skylar Kergil, playing the guitar in 2005 at home in Acton, began his transgender journey in January 2009.Amy Piermarini

Kergil, named Katherine Elizabeth at birth, was 3 years old when his grandfather took him to a hardware store. Eager to introduce himself, Kergil, wearing a yellow sundress — a rare sartorial victory for his mother — held out his hand and announced, “You can call me Mike!”


He answered only to “Mike” all summer. No one suspected anything other than a cute phase. Now, looking back, Kergil believes it was the beginning — “my most raw moment of explaining my gender identity.”

As Kergil got older, he remained a tomboy, loved sports, and secretly was elated when he was mistaken for a boy.

Kergil expected, without knowing why, that his own body would eventually change the same way his older brother’s had during puberty. So when his breasts began to grow and his period started, Kergil felt despondent. He had never heard the word “transgender.”

In eighth and ninth grades, he tried to fit in with girls. He wore tighter shirts, grew his hair longer, and dated boys. “I realized about halfway through freshman year that I felt so fake, and I felt so uncomfortable,” he said.

So he stopped. He began dating a woman. Hanging out with the school’s lesbian crowd helped — he saw another path for women, one that was less stereotypically feminine. He cut his hair short and began wearing baggy clothes. But he didn’t fit in there, either.

“The world was perceiving us as this lesbian relationship,” Kergil said. “But I was perceiving myself as this boy loving this girl.”

Everything changed when he was 15, a sophomore. At a concert in Worcester, he began talking with a man in the crowd. The man told Kergil that he was born female. He was transgender, six months on hormones.


“I saw him as my reflection,” Kergil said. “It opened up this world for me.”

It was the briefest of conversations, but it was all Kergil needed to make sense of his inner dissonance. He knew immediately that transgender described him. Even better, he saw a way to align his body with his mind.

He approached his family gently, telling them he was questioning his gender and asked to visit a gender therapist. His parents, who were divorced, agreed. In the summer before his junior year of high school, he decided to change his name to gender-neutral “Skye,” and asked others to describe him with male pronouns.

He remembers that his mother cried. He knows now that she was grieving the loss of a daughter and also that she worried about him. But 16-year-old Skye felt like she wasn’t supporting him.

His mother, Stephanie Tyler, told her son she would love him no matter what, but she knew so little about being transgender. Still, she began to glimpse his unhappiness.

“He told me that I didn’t understand waking up every morning and hating the body I was in,” she said. “That really hit me.”

Tyler balked at first at the idea of testosterone injections, wanting her son to be older before he physically altered his body. But Kergil convinced her that he wanted to begin Skidmore College as a man.


That year, 2009, Tyler announced in the annual Christmas letter that she now had two sons.

* * *

Kergil’s videos documented his body’s second puberty: His voice deepened and hair sprouted on his chest and stomach. His muscles bulked up. His Adam’s apple thickened.

Some people who followed his YouTube channel wrote nasty messages, others cheered him on.

“Your videos were the first thing to make me realize I wasn’t the only one,” someone wrote recently.

One of the most common questions from transgender teenagers was: My parents aren’t supportive. How can I get them on my side? After Kergil made a video Q&A with his mother, she agreed to e-mail transgender children and their parents to talk about her experience. She got hundreds of requests.

Logan Brooke-Smith, a transgender man from South Africa, was one of Kergil’s early followers. Brooke-Smith wrote: “His videos always motivated me and showed me that I could get to where he is one day.”

In the early days, Kergil never gave his full name or told viewers where he lived.

Kergil, now 23 and in Cambridge, works as a bank teller, plays guitar, and sings. He has recorded one album, with a five-song EP on the way. (When he learned about the Trevor Project award, his boss at the bank took him shopping at Macy’s to buy his first suit.)

Kergil gets requests to speak at colleges and high schools about being transgender, sometimes playing his music or reading his poems. In “I Will Mean Everything,” a poem he read on YouTube this summer, he calls himself, “a recycled man in a repurposed body.”

When Kergil went to LA to accept his Trevor Project award, he took his mother with him as his plus-one.


Some transgender people say they see themselves as two beings: the person they were born, and the person they became. Kergil said he felt that way for a while, as if he had murdered his twin sister. Now he feels like one person who changed along the way. Yet, he knows he is still evolving.

On his 18th birthday, he got his forearms inked with Michelangelo’s alleged last words: “Ancora imparo.”

Translation: “I’m still learning.”


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Kathleen Burge can be reached at Follow her on Twitter @KathleenBurge.