It's a sleepy Saturday afternoon in Downey, California, a dull suburb of Los Angeles, where I grew up. I'm 10. The sun rains a shower of light through the window in my parents' bathroom. I'm sitting on the cold toilet seat after a hot bath, examining, in horror, the burgeoning mound of flesh on my chest. My mom is golfing at the Rio Hondo Golf Course, and my dad, a computer engineer, is invariably hunkered over his workstation. My brother, 13, is probably biking around Cord Street, on which our house sits. I'm certain that all the potential witnesses to the devious act I'm contemplating are out of sight so I proceed to the medicine cabinet and pull out my dad's Barbasol shaving cream.

After slathering it like frosting all over my face, I take the bristly end of my toothbrush in the palm of my hand and start "fake-shaving," mimicking my dad's brusque hand strokes. It's exhilarating and satisfies me on a level too deep for words, but halfway through, my brother appears out of nowhere. "What are you doing?" he asks. He looks shocked—like he's just seen a monkey-manned vehicle drive by. "Just messing around," I say, trying my best to make it seem like innocent fun. A smirk of contempt spreads across his face and he snort-laughs. "Dude, you're weird," he says before sauntering off. I pray he doesn't tell our parents. I can't quite lift the feeling of his disdain off of me. It lingers as I wash off my face, retreat to my bedroom, and realize that I'm only a boy in my mind.

***

Courtesy of Stephanie Fairyington

Over the past few years, transgender issues have garnered bursts of positive attention in the media: In 2011, Chaz Bono, Cher's trans son, boogied his heart out in front of a cheering crowd on Dancing With the Stars; In early 2012, Glee portrayed its first transgender character; a year later, Netflix premiered its original series Orange is the New Black, featuring trans actress Laverne Cox. But nothing rivals Facebook's radical comment on the limitations of our binary gender system: In February, the social network added more than 50 gender options for how users can self-identify.

Related: Trans Translated: 'Boys Don't Cry' Director Kimberly Peirce On 20 Years of Queer Culture

And yet, despite these inklings of progress, the discourse around transgenderism remains far more complicated than these milestones suggest.

Nothing seems to challenge people—destabilize them, really—as much as the idea that someone can reject his or her assigned sex and defy the limits of biology by transitioning from one to another. Take, for instance, Piers Morgan's blundering interview with trans author Janet Mock or Katie Couric's insensitive questions of trans actress Laverne Cox (about which Mock penned an impassioned essay for this very publication). By blurring the neat line between male and female, trans people force us to occupy the middle ground between two polarized extremes, and demand us to re-conceive our gendered assumptions.

The lively debates that ensued after Morgan and Couric's missteps showed what a vital cultural force trans people are. The unsteadying questions they evoke—Is that a man or a woman? How can you tell? What makes one a man or a woman? Who gets to decide? And so on—help us think with broader complexity and imagination.

But I admit, it took me a while to "get it."

Courtesy of Stephanie Fairyington

Even though I'm a self-avowed lesbian feminist who appreciates all shades of queerness, I took the long road to trans acceptance, largely because of my own youthful gender ambiguities. From the moment my body began to defy my wish to "grow up to be a boy," I fruitlessly challenged my unwanted maturation by peeing standing up (I'd literally straddle the toilet bowl between my legs), opting for Little League baseball with the guys over softball with the girls, and avoiding skirts and dresses with fierce resolve. But when I grew up to be a lesbian instead, I found myself expressing a disdain—similar to the one I witnessed in my brother's eyes when he caught me "shaving"—toward trans men.

Because there often seems to be so much crossover between the behaviors of lesbian tomboys and trans guys, my past, at first, clouded my ability to differentiate myself from them. Was I really trans after all? I wondered. Or were they really lesbians? I couldn't quite wrap my head around the idea that I might be trans, so I began to see their desire to morph into men as a manifestation of homophobia (an attempt to disavow their lesbianism) and sexism (a violent rejection of their femaleness). Changing their bodies in order to express the full range of masculinity went against everything I'd been taught as a feminist. Wouldn't real social progress aim to untether gender expression from sex? Why do you have to inhabit a male body in order to express maleness?

Related: A Closer Look at Women Who Leave Their Husband for Other Women

Courtesy of Stephanie Fairyington

It was a conversation with New York magazine's Jesse Green, who wrote a brilliant cover story on the topic, that helped me to understand the difference between my gender nonconforming young self and trans kids. "Trans youths experience an early onset identification with the opposite sex," Green explained, "an unwavering persistence in feeling that they're in the wrongly sexed body and torment at the approach of adolescence."

I realized that I had never felt tormented about my body (only disappointed) and that it didn't persist beyond my early teens.

The more trans people I meet, the more I realize how diverse and idiosyncratic each person's iteration of transness is. Some, like transwoman Janet Mock, contest the very notion that they ever belonged to the sex they were assigned at birth. Others pride themselves on the physical markings that show their journey from female-to-male or male-to-female and celebrate their queerness. And, obviously, plenty of trans men are gay and effeminate, which shows how limited my longstanding questions and beliefs were.

Looking back, I think my desire to be a boy stemmed from the belief that it would allow me the privileges my older brother enjoyed—and from the (incorrect) assumption that in order to love women romantically, which I did, I must be male. Once I grew out of these misperceptions, I was ready to accept the body into which I was born. Boobs and all.

Photos: Courtesy of Stephanie Fairyington

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