By Jesse Marx
By Chris Parker
By Jake Rossen
By Jesse Marx
By Michelle LeBow
By Alleen Brown
By Maggie LaMaack
By CP Staff
On paper, Will is fully male—he's changed his driver's license and birth certificate. By all outward appearances, he seems like somebody born a man. He works in a macho field, and he says his co-workers have no clue. His goatee and bright green eyes and snowboarder style make him hot enough that girls—straight girls, the kind he likes—regularly hit on him. But dating has been kind of fraught. "I can't just meet a girl at a bar and bring her home," he says, grimacing as he imagines how he'd break the news. "P.S.—By the way, I don't have a penis?"
On the eve of his 23rd birthday, Will and a buddy went to Liquor Lyle's to get wasted. A girl named Kara noticed his Burton hat and recognized him as a fellow snowboarder. She sidled up next to him in his booth and started to flirt. The drinks and conversation flowed. They shut down the bar, and Kara and a girlfriend invited the guys back to their place. When Kara kissed him, Will panicked.
"I've got to go home," he said.
She called him wanting to get together. He made excuses. But within a few days, he caved. He wanted to see her. One evening when they started kissing, he stopped her.
"I've got to tell you something," he said, his heart pounding. "I'm trans."
"Okay," Kara said, confused. "What does that mean? You're a drag queen?"
"No, I'm transgender," he said. "I was born female."
KARA DIDN'T KNOW what to say. She'd grown up in a small town in a religious family and been taught that being gay was wrong. She'd never met anyone transgender. She'd had a lot of boyfriends but had never been attracted to women. She didn't know what to think.
"Do you want me to take you home?" Will asked.
He dropped her off and she hugged him goodbye. Then she went for a long run, wanting to clear her head. Her mind was a blur all week. Was she lesbian? Did this make her bisexual? She called Will, then went over to his house to talk. She told him she was attracted to him and liked being with him, but she just couldn't date him. On the way out he kissed her—and she kissed back.
A week later, she called Will. She'd changed her mind—she wanted to date him, she just needed to take it slow.
Will was elated—so proud that a straight girl wanted to be with him. Kara began to read everything she could find about being transgender. Her research led her to decide that people are born gay, and she reasoned that being transgender must also be innate. "There's no way these people want to be like this," she says. "For most people, they have really sad stories to tell about it."
Kara and Will spent time with each of their families. They went camping and snowboarding. Slowly, she began to tell her friends that her boyfriend was transgender. They went to a Jack Johnson concert at the Apple River in Wisconsin, and intertubed down the river. Will was the only guy who didn't take his shirt off. By the end of the trip, he was weary of not being able to pee at a tree like the other guys.
Somewhere along the way, Will fell in love. When he started talking about their future together, Kara panicked. She felt too young to think about that, and she knew that her parents would never approve. They really liked Will, but she knew they wouldn't once they found out he was transgender. And she was thinking about kids. She wanted to have them naturally, and with Will, she never could.
They broke up after a year. "I would like to be in a relationship with him, but I don't want to make him think there's a possibility" of a future together, Kara says.
"He told me the other day, 'Straight girls, they don't end up with trans guys.'"
But Kara thinks there could be a way. She knows a trans guy who is dating a straight woman who used to be married and has two kids. Will, too, could find a woman like that. It's just that she's not that woman.
STEVEN TRANSFERRED to a new high school where fewer kids knew about his past. Always, he tried to go unnoticed. Girls called him at home, invited him to Sadie Hawkins dances. He developed crushes but never acted on them, scared of what might happen if it went too far. When his friends got drunk at parties, Steven stayed sober and drove. He worried about losing control and blabbing his secret.
He always worked hard at school, sports, everything. "I had to be as good as I possibly could because I needed to compensate for something, you know?" he says. "It's not logical, but I need to prove to myself that I'm worthy to be here, on the Earth."
When it came time to choose colleges, Steven chatted at school with his friends: I hope I get in, I hope my roommate's cool. But at home, he was talking with his parents about bigger worries: which schools would be safe.