Becoming a (Feminine) Man, Happily

In 1957, I vowed never to dress in women’s clothing again and knew I desired boys. In 2015, a friend’s daughter announced she was now a boy named Bobby. We were both four years old at the time of our respective decisions. Regardless of social pressures, we began defining our feminine and masculine identities on the journey to become the man, woman, or shade of the rainbow we were born to be. Everyone seeks comfort in his or her skin.

At four, I was comfortable wearing Dad’s size 11 clodhoppers or Mom’s high heels — preferring neither — for fun and giggles. One summer day, I donned a sister’s dress, Mom’s heels and veiled velvet hat, and click-clopped to fellow kindergartener Suzie’s front door to share my pride and glee. I loved her and thought, Won’t she be surprised! Suzie’s shock, then hysterical laughter boiled me in hot humiliation. My joy crushed, I turned on my heels (literally) and tearfully click-clopped home.

Though ignorant of the gender conceit, I decided my drag days were done. I learned the behavior was repulsive — from a four year old! — a lesson repeated many times for many other behaviors. Like boys don’t cry. Vulnerability betrays masculine normalcy, and shame is the penalty. So I decided never to cry and always to fight my desires for boys.

Artsy, brainy, noncompetitive, slight of build, homely, clumsy, sensitive — in 1950s Colorado I was a bad example of a typical boy, compounded by my feminine traits. Which was confusingly contradictory because men dominated the arts and sciences. And though I loved girls (much more relatable), I desired boys, my puerile awareness excluding an adult’s language of sex, comprehension, or expression. Understanding that my church and society damned my desire came later.

Movies and TV of the time paraded men dressed as women for laughs. The film Some Like It Hot (1959) made drag artistically and commercially successful, but the feminine caricatures of Tony Curtis and Jack Lemmon never seemed to lose their masculinity entirely to avoid audience discomfort. Search “Milton Berle in drag” on YouTube to watch the funniest and ugliest drag depiction on I Love Lucy. Early twentieth-century feminist Mae West provided a drag prototype for decades.

Mentors, friends, reading, movies, plays, bars, music, and Jim Palmer underwear ads opened my mind to the world of homosexuality. The underground fraternity made my natural state of vulnerability more comfortable, but it too had its objects of shame. Nellies (feminine gay men) and bottoms (the receiving position in gay, male sex) suffered ridicule from masculine gays who reduced their self-loathing by claiming a butch exterior and the top position (the giving position in gay male sex) as proof of their superiority in the pecking order of prejudice. Even within my own tribe, I had to seek comfort in my skin.

My heart opened from my church’s philosophy, Science of Mind; Paul Monette’s memoir Becoming a Man: Half a Life Story; and the personal growth workshop, The Experience, founded by Robert Eichberg, also co-founder of National Coming Out Day. Ralph Waldo Emerson’s essay Success revealed that a “successful” man had nothing to do with weeping or how far I could throw a ball, and everything to do with living as a compassionate human being.

Like drag queens.

During the plague years, I learned to appreciate their courage, creativity, and community service. Also, that to survive the plague years, tears were essential.

Some childhood decisions prove we are wise beyond our years. Some we spend years unraveling. Almost six decades later, my trek to Suzie’s remains my only dip into drag, but I wonder if her laughter expressed delight, if I leaped to shame on my own, because I don’t recall any subsequent torment. I’m comfortable crying. I still desire, well, now men.

And I still find women more relatable. They’ve always felt safe sharing intimate details to the point where I’ve had to declare, “TMI!” We bond over battles fought in a straight man’s world; women’s are worse. Is my sympathetic ear masculine or feminine? Is sympathy gender specific? I don’t know, but I do know if women ruled the world, a little blue pill would cure breast cancer, not just a limp dick.

In Seinfeld’s “Shrinkage” episode Elaine says, “I don’t know how you guys walk around with those things,” meaning the tripod of male anatomy. I’m glad I do. I’m comfortable in my masculine skin, happily becoming the feminine man I was born to be. I doubt it takes as long for the daughter of my friend, that courageous whippersnapper who announced she was a he.