Hales Skelton knew early on that he wasn’t the girl his body said he was. At age 6, he’d lather his face and “shave” with his dad’s razor. After puberty started, he avoided tops that accented his chest and was self-conscious about his voice.

But revealing the boy inside was out of the question.

“I grew up in a white, suburban, middle-class household, fairly conservative,” Skelton, 27, says of his upbringing in Keizer. “I just couldn’t do it then.”

Skelton continued living as a woman after leaving home. In August 2016, he began dating Ashley Brown, an emergency room social worker and single mom with three young kids.

“I’ve always been a boy, pretty androgynous, but publicly identified as a female,” says Skelton, who lives in Northeast Portland and works for a human resources company. “We were seen as a lesbian couple.”

But his urge to transition — to stop living a lie — grew stronger. He knew it was time to let those closest to him know the truth. “I didn’t want to hide anymore,” he says.

25 years of feelings pour out

Skelton told Brown within weeks after they started dating that he would eventually transition. “I knew wholeheartedly that Ashley loved and supported me, and that she was the person I wanted to make this transition with,” he says.

When he called her, 25 years of feelings came pouring out. “She was so excited for me and said that we would make this change together. She also made it known that she saw me as the man I am, and that I was always a boy to her.”

Things were different with his parents. When he was growing up, his mom sometimes asked him if he “wanted to be a boy” and why he “dressed so masculine,” he says. But he always said no, fearing she would disown him.

Then, after a few glasses of wine at his parents’ home on Christmas Eve 2016, he blurted it out.

“I was tired of lying to my mom and to myself,” he says. “I wanted to be out and proud as a trans person, and I also wanted to get the legal process started due to concerns of the [Trump] administration rolling protections back.”

Their reaction, he says simply, was “not supportive.”

Skelton decided to begin his medical transition anyway, excited about finally having “my outside match my inside.” He started testosterone therapy through OHSU’s Transgender Health Program in January 2017. That began a new journey, with more rough times ahead.

Managing a new emotional landscape

Skelton projects an easy confidence as he talks about his transition. Dark stubble sprouts across his face. He wears a stylish bamboo-and-leather wristwatch and a slate-gray crewneck sweater on his compact frame.

“When you first start transitioning, you think it’s just physical, but it’s emotional, too,” Skelton says. “Hormones change how you react to things. It can be very difficult, and I didn’t expect it.”

For example, he says, he used to be emotional bordering on impulsive, and cried often. “I’ve cried like twice since my transition.”

He’s also been surprised at how quickly he becomes irritated by even small things, such as forgetting to pick up dog food. He goes to counseling every two weeks, in part to adjust to being a man.

It hasn’t been easy on Brown, either. She went to all his appointments as Skelton progressed from hormone therapy to chest masculinization surgery to a hysterectomy at OHSU. She offered emotional support. But it wasn’t — and isn’t — easy, even with her training as a social worker.

“There’s been a dramatic change in his emotional capacity and communication styles and skills that I’ve had to adjust to,” Brown says. “We never had a fight before he went on testosterone. Since then, we’ve gotten into (verbal) altercations, and it took me awhile to realize why and that we need to adjust.”

They had many awkward moments at a family wedding near Seattle, for example. Brown thought they should take some quiet time back at their hotel after the ceremony. But Skelton, feeling a family obligation, insisted on going out for drinks with male relatives.

“He wasn’t understanding where I was coming from, and he wasn’t understanding his own emotional situation. It was a disconnect from his body, from his partner,” Brown says. They argued, and “it was not a pretty scene.”

Skelton says he’s paying more attention to Brown’s feedback about his behavior. Helping raise his stepkids has sharpened his focus, too. “I want to be emotionally talented and emotionally aware,” he says.

At the same time, Brown calls Skelton’s physical changes “delightfully surprising.” Skelton now has a fanatical drive to do something physically intense every day: go to the gym, go for a run, mow the lawn.

“Before testosterone, he enjoyed it, but now it’s a requirement,” Brown says. “If he doesn’t do it, he gets cranky.”

Overall, though, supporting him — and herself — is hard work. 

“There’s this person who is finally ready to be who they are, who they were born to be. But it’s frightening, and our culture isn’t as accepting as it should be,” she says. “You watch this person go through emotional turmoil, physical changes, and it takes a profound amount of patience and unconditional love and acceptance.”

At times, she also misses the person she fell in love with. “All of a sudden, it’s the same person but a huge shift. Obviously, I’m very supportive, but sometimes I mourn the loss of this other person.”

Using his experience to help others

Skelton has plans mapped out. He and Brown became engaged. He has finished pre-med studies and plans to apply to medical school. He wants to be a plastic surgeon who serves transgender patients. He also wants a phalloplasty within a few years, whenever he can take time off for the months-long process.

“Dysphoria is always present for me,” Skelton says. “It’s morphed throughout my journey. Before top surgery, I worried if people could see my sports bra. Once I had top surgery, more focus was on my bottom surgery. You worry if you go into a public restroom, will a stall be available? At the gym, will people know if I’m trans? You have to cope with it. No matter your medical transition, it’s hard to be trans out in the world.”

In the meantime, he’s helping others. He joined Transgender Health Program volunteers, who support patients and their allies, run training sessions and help people access care. And he’s part of a group helping Dr. Jens Berli, an OHSU plastic surgeon, study ways to improve access to transgender care.

“I’m so privileged to have my experience that I want to use it to help others — and to educate,” he says.

He is also enjoying victories big and small. He gets to shave for real — “what little facial hair I have, anyway,” he says — and mow the lawn with his shirt off. He gets to be “one of the guys” at the gym. “I love that people physically see me as a dude,” he says.

The biggest victory? His relationship with his parents is improving.

“My mom has come around, and my dad is trying,” he says. “My mom called me her son about a year ago, and that made my world. My parents were a big part of why I didn’t transition sooner, and to have that acceptance, ‘I love you,’ it’s the best feeling.”

— By Pete Lesage, a Tigard writer and editor who previously worked as a reporter, editor and director at The Oregonian.