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Beyond the Gender Box: 'ALIVE' co-founder lives authentically as transgender man

Kelly Hamilton
2013 File Photo | St. Louis Beacon

This article first appeared in the St. Louis Beacon, Feb. 11, 2009 - When Kelly Hamilton was 5, he stole his little brother’s tighty whities. He hid his bathing suit top, swearing it was lost when it was really stuffed in a drawer.

Once, in their shared bed, he was surprised to hear his older sister say, “You know the doctors can turn you into a boy now.”

Hamilton, a transgender man, doesn’t ever remember telling his sister he wanted to be a boy. Sometimes family just knows. But in 1980s Dallas, Texas, parents weren’t exactly embracing gender variance.

“You’re a girl and you will wear girls’ underwear!” Hamilton remembers his mother insisting.

Looking back over his life, Hamilton sees a trail of puzzle pieces. Four years ago, when he was 31, they began to fit together to form an idea, then a path.

Every transgender journey is marked by dissonance between one’s physical gender characteristics and the gender with which he or she identifies. But Gender Dysphoria — as the new Diagnostic and Statistical Manual will call it — is no one-size-fits-all diagnosis.

Hamilton knows first-hand that the pilgrimage of each transgender person is unique. In contrast to popular notion, Hamilton never hated the way he looked, or regretted his past.

Kelly at age 5
Credit Provided by Mr. Hamilton
Kelly at age 5

“I never felt trapped in the wrong body,” Hamilton says.“It was just never aligned with my sense of self.”

Wardrobe wars

At 14, Hamilton fell hard for a female classmate. “I wanted to be her boyfriend,” Hamilton remembers. For months, he prayed every night, to “wake up a boy with a boy body and a boy life.”

“But every day, I’d wake up and think, ‘Argh, it didn’t happen,’” Hamilton recalls.

Now, he understands his prayers were a kind of magical thinking, a method for dealing with female puberty.

In his junior year of high school, he discovered a word for his attraction to girls: lesbian.

“I thought ‘Oh! That’s what I am,’ and was happy to have discovered I wasn’t alone,” 
Hamilton says.

The label seemed to fit. But clothes were a problem. He came out publicly at 18 but constantly struggled with what to wear, particularly for special occasions.

“I felt mortified every time I had to wear a dress, and refused most of the time,” Hamilton remembers. “But I rejected ties because they felt too daring and overtly masculine to me.”

You don’t have to be trans or even gay or lesbian to understand his dilemma. Almost all straight people experiment with expressing their gender, especially in their 20s. For young women, it might be: Makeup or a natural look? Stilletos or Uggs? Cleavage or not?

Or, “A man, gay or straight, might play with a ‘hipster’ look one year — skinny jeans, thin build, beard — and then decide he wants to be a hyper-masculine muscle guy the next,” Hamilton points out.

Many changes of clothing later, Hamilton moved to St. Louis for a master's program in German at Washington University, after earning a bachelor's in psychology and German at Austin College near Dallas. Looking back over this period, he sees more clues.

“My master's exam addressed masculinity themes in German literature. I was in the Women’s Studies program, thinking, ‘Where are the men’s studies courses?’” he says.

‘I had to pay attention’

Successful in college, early relationships and work, Hamilton mostly felt happy. By 2002, the health and fitness newsletter he’d launched with friends Attilio D'Agostino and Elizabeth Tucker had become the promising “ALIVE” magazine, which now has a circulation of 35,000.

Elizabeth Tucker and Kelly Hamilton
Credit Provided by Mr. Hamilton
Elizabeth Tucker and Kelly Hamilton

Hamilton was also becoming more and more involved in the St. Louis LGBT scene. He launched monthly “Girl Friday” happy hours, and in 2008, became involved with PROMO, Missouri’s LGBT equality advocacy organization

Still, the concept of transgender wasn’t on his radar. He didn’t even know any trans men. But in the summer of 2009, a serendipitous collusion of relationships, the internet and books became touchstones.

A then-girlfriend encouraged Hamilton to experiment with traditionally male clothing. A desire to bulk up led him to Google information about building muscle, and search results included videos about using testosterone to transition from female to male.

“It wasn’t like I said, ‘Oh my God, this is the answer to my prayers’ — I wasn’t there yet,” Hamilton says. “But I knew immediately it was something I had to pay attention to.”

Memoirs by trans authors including Jamison Green, helped bring clarity and certainty. Hamilton compares his sojourn to a fall into an “Alice in Wonderland” world. The rabbit hole dropped him into a year-long research period of figuring out what it all meant.

“Since I’d come out as gay 15 years before, I felt pretty confident I knew who I was. I was an out and proud, active in the community,” Hamilton says. “It was certainly unsettling as the lights started coming on.”

Working with a therapist, he embraced the change as something beautiful, and carved out time to begin the actual transition. Along the way, Chaz Bono came out as a trans man, pushing the topic further into the American consciousness.

Kelly Hamilton and Sarah Bruno
Credit Provided by Mr. Hamilton
Kelly Hamilton and Sarah Bruno

In spring 2011, Hamilton took a big step: taking testosterone, under a doctor’s supervision. “From that moment on, I felt more balanced,” he says. Coincidentally, just a few weeks later, he began a romantic relationship with marketing professional Sarah Bruno, with whom he’d been friends for six years.

“He kept saying things like, ‘I really want you to know me,’” Bruno says. “And I’m thinking, ‘Well, yeah, of course we want to get to know each other,’ but I could tell there was definitely something he wanted to tell me.”

While Bruno was surprised to hear about Hamilton’s transition, she also surprised herself with her own response. “This wasn’t something that would deter me from continuing the relationship,” she says.

‘Show up for your own story’

Just before beginning male hormone treatment, Hamilton wrote letters to his parents, brother and sister in Texas. All replied with loving acceptance.

“My dad wrote back, ‘Life is short. Be who you are,’ and ‘Your brother always wanted a brother,’” Hamilton says. “And my brother said, ‘Whatever, bro. It’s all good.’”

Kelly Hamilton before transition with David Freese at an Alive photo shoot.
Credit Provided by Mr. Hamilton
Kelly Hamilton before transition with David Freese at an Alive photo shoot.

Hamilton had already told best friend and “ALIVE” business partner Elizabeth Tucker.

“I said to him, ‘You’re my best friend, no matter what,’” Tucker says. “But I really respected his concerns because they are legitimate. The biggest concern anybody has is that they’re going to lose the relationships in their life.”

As the friends walked and talked through Tower Grove Park, Tucker inspired a new mantra that would help Hamilton worry less about external reaction and embrace his journey: “You have to show up for your own story.”

Over coffee and in other one-on-one settings, Hamilton told more “ALIVE” employees and friends, asking them to “share the good news” with their wider circles. Everyone quickly came on board but they weren’t always sure how to respond.

“I started getting messages and calls and they would say, ‘Congratulations,’ and then, ‘Is it OK to say congratulations?’ and I’d say, ‘Yes,’” Hamilton says.

Within three months, Hamilton’s voice began to change. His sex drive increased and he was constantly hungry. Over the course of a year, he gained 30 pounds of mostly muscle. He also gained a newfound sense of vitality and joyousness.

“More than anything, what contributed to my joy was the feeling I was living authentically,” Hamilton says.

Hamilton, after hormone treatments, talks about interacting with people as a man.

Hamilton’s exuberance is in line with what local Licensed Professional Counselor Jan Beckert sees with her transgender clients. The feeling of authenticity outweighs any number of possible negatives a transgender person may be facing.

“Family rejection, past abuse, poverty — no matter what else they’re dealing with, the transition is the most important thing,” Beckert notes. “It makes them feel like they are themselves.”

In late fall 2011, Hamilton made his male gender Facebook official. The next step: “top surgery.” Removal of breast tissue came in February 2012. Insurance doesn’t typically cover the procedure. Hamilton paid $6,000 out of pocket, having the surgery near Dallas, recovering in the home of his sister.

Strangers already correctly perceived him as male. Now, the task of getting people who already knew him to say “he” and “his” became a priority.

“Once I had chest surgery, it felt more imperative to me that people used the correct pronoun,” Hamilton says.

Sorting through stereotypes

With no present plans for what’s called “bottom surgery,” Hamilton’s physical transition is complete. But his journey continues.

On the practical side, he changed his middle name but decided to keep the more androgynous Kelly as his first. His driver’s license says he’s male. So does his passport. But he’s still working on getting the court order that will change the gender marker on his birth certificate.

Figuring out what kind of man he is — and how to be male in a new world of machismo and misogynist jokes — are ongoing personal quests.

For others, there's the question of sexual orientation. Is he now straight? What about his girlfriend?

Kelly Hamilton and Sarah Bruno
Credit Tim Schinsky | Alive
Kelly Hamilton and Sarah Bruno

Both feel the word “queer” better describes and honors their experiences. “Transitioning doesn’t mean my sexuality shifts to heterosexual because I date women,” Hamilton says.

Hamilton and Bruno‘s unique situation upends gender stereotypes. Both have only been in lesbian relationships before, so there have been no “his” and “her” household tasks. Both are feminists. But with Hamilton being male, Bruno occasionally catches herself contemplating chores along traditional gender lines.

“I’ll think, ‘Are you going to take out the trash? Or carry this heavy thing?’” Bruno laughs. “Then, I’ll remind myself to pay attention to why I’m thinking like that.”

As the couple sorts out the small stuff, Hamilton feels fortunate, in his mid-30s, to have already had such a full and varied existence.

“I never thought my life was a big mistake,” Hamilton says. “I think it’s a very special experience to have lived as both male and female adults in one lifetime.”

(This article originally appeared in the St. Louis Beacon.)

Transgender Resources and Information

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Vice President Joe Biden: Transgender Discrimination is "Civil Rights Issue of Our Time"

Huffington Post explores transgender issues

LGBT Center of St. Louis

"The New York Times": "College Health Plans Respond as Transgender Students Gain Visibility"

Follow Nancy Fowler on Twitter: @NancyFowlerSTL

Nancy is a veteran journalist whose career spans television, radio, print and online media. Her passions include the arts and social justice, and she particularly delights in the stories of people living and working in that intersection.