In high school, Paul McKerrow was the starting quarterback and valedictorian. His classmates voted him best looking and most likely to succeed, but today, some may not recognize Helena High's golden boy.
After many years of struggling with his gender identity, Paul decided to become a woman. The transition into Kimberly Reed, a lesbian filmmaker, began in San Francisco just a few years after Paul learned to throw the perfect spiral on Helena High's football field. Kim documents her journey to womanhood in her film Prodigal Sons.
Before her transition, Kim was one of three sons in her family. When her parents, Lorne and Carol, thought they were unable to have children, they adopted a baby boy named Marc. Soon after, they were surprised to learn they were expecting. "The day they picked him up was probably the day they conceived me," Kim says.
A year later, along came another surprise...Paul and Marc's younger brother, Todd. "It looks like a fairytale childhood," she says. "But appearances can be deceiving."
Kim started to question her gender identity at a young age. When she was in kindergarten or first grade, a time when parents and teachers begin to distinguish boys from girls, Kim says she realized something was off. "There was just this friction," she says. "I wasn't even quite sure what it was then."
Over time, Kim says she began to wish she was a girl, but she hid her desire from everyone in her life. Sometimes, in secret, Kim explored her feminine side by dressing in girls' clothes. "In fifth [or] sixth grade, I used to have a paper route. I would get up really early in the morning when nobody else was awake and hope no one would see me," she says. "I'd dress like a girl and go do my paper route."
In the '70s, transgender wasn't a term you heard often, so Kim says she didn't know what felt right until later in life. "I was just kind of magnetically drawn toward it," she says. "I was even trying to avoid it. I didn't want to be weird. I didn't want to be different. I wanted to fit in."
In high school, Kim fit in perfectly because, she says, she did everything a teenage boy was expected to do. "I was this perfect guy in some ways, but I was just trying to overcompensate to be successful at this male thing," she says. "I thought it would fix me. I thought it would make this other crazy idea go away."
Paul even dated women and took a girl to the prom. "I think it was a pretty innocent relationship," Kim says. "A lot of times, I wanted to be one of the girls more than to really have a girlfriend." During her high school years, Kim says she felt like she was carrying on a secret life she would take to her grave.
Then, after graduation, Kim enrolled at University of California, Berkeley, which is just across the bay from San Francisco, a city known for its liberal attitude toward homosexual and transgender individuals.
Far away from Montana, Kim slowly became more of herself. She moved to San Francisco after college and began experimenting with her gender by dressing as a woman. Kim says she also wondered if she was a gay man, so she dated both men and women...but that didn't feel right either.
After years of living a double life, Kim took her transition to the next level and started taking female hormones. "[I was] just feeling like, for the first time, my body just felt right," she says.
Then, when Kim was in her late 20s, she said goodbye to Paul for good. She decided to undergo full sexual reassignment surgery.
"They fashion, out of your genitalia, a vagina, and I had a little help with my breasts," she says. "I changed my name. I changed my driver's license and social security and passport and everything."
If she could go back, Kim says she would have made the transition much earlier, but she is glad she was raised as a boy for one reason. "I think that just [by] being a boy, it's okay for you to be bold and independent and do whatever you want to do. Sometimes, I see girls who are growing up where they reach that age where they really start to doubt themselves and question and kind of withdraw like 11, 12, 13," Kim says. "I'm glad that I was kind of given this license to [have] this boldness."
Once the transition was complete, Kim had the difficult task of telling friends and family she was no longer Paul. To confuse matters further, Kim's surgery didn't change who she was most attracted to—women.
When it came time for her 20th high school reunion, Kim and her longtime girlfriend, Claire, traveled back to Kim's hometown to see former classmates face-to-face. The last time most of these people saw her, she was Paul, the popular athlete. "Twenty years ago, they'd voted me most likely to succeed," she says. "Now, I was just hoping they wouldn't laugh at me."
Kim says her greatest fear was not being accepted. "[I was afraid] that who I used to be would just be erased, and that I would become nothing," she says. "That they wouldn't see that I was really the same person."
When Tim, Kim's former teammate and best friend since childhood, first heard about Kim's transition, he says it was a little bit weird. But, after having a few beers with Kim and Claire, Tim says he realized not much had changed. "I'm so happy and proud of her," he says.
Not everyone has handled Kim's transition well. In her film, Kim talks about the deteriorating relationship she has with her older brother, Marc.
Since they were children, Kim says she and Marc have had an intense sibling rivalry. "Marc was adopted, so Marc kind of, you know, understandably felt a bit like he was the outsider. He was held back in school, so we were always in the same grade," Kim says. "I think it really kind of increased some of the competition that he felt for me."
Marc spent most of his childhood living in the shadow of his highly accomplished brother. Then, at age 21, he crashed his car and suffered a traumatic brain injury. Even with serious medication, Marc began to have mood swings and short-term memory loss.
"He started clinging to the past more than ever," Kim says. "It felt like Marc would have given anything to be the man I'd have given anything not to be. We were both haunted by the same ghost."
One Christmas Eve, Marc expressed frustration with Kim's decision to change genders. When things got heated, someone called 911. Marc was taken to jail.
Through it all, Kim's mom, Carol, has been supportive of her decision.
Carol says she never saw any hint or sign when Kim was younger that she might be struggling with gender identity. "I think I hid it well," Kim says. "I think I was trying to hide it from myself."
Now, Kim regrets not telling her mother earlier in the transition and wishes she hadn't asked her mom to keep it a secret from their extended family for as long as she did. "I put her through a lot," Kim says. "I wish I hadn't done that."
While some people believe homosexuality and gender reassignment are sinful, Carol says she never questioned Kim. "With me, it was never a question of, 'Do I believe in the Bible?' I believed in my child," she says. "I believed that this child was thoughtful, intelligent. ... I just knew that this was a decision that was painfully arrived at."
With her mom and girlfriend by her side, Kim says she's ready to move forward with her life. "It feels like the first part of my life, I was trying to deny the fact that I was really a girl. The second part of my life, after I transitioned, I was kind of trying to deny the fact that I had ever been a boy," Kim says. "Now I kind of feel like I'm in this stage where I'm just trying to make peace with both sides and kind of make peace with my past."
Printed from Oprah.com on Friday, December 13, 2013