By Kenneth Kann

I’m a 69 year old straight, married man, in a glittering red dress, on a bicycle, pedaling 42 miles through conservative California ranching country. I am with 2,000 other cyclists, similarly attired.

It’s Red Dress Day on the California AIDS Lifecycle Ride. Climbing the golden hills out of the Santa Maria agricultural valley, streaming past Vandenberg Air Force Base, and winding through the small town streets of Lompoc, the other bikers and I form a living red ribbon, a symbol of the fight against AIDS.

Photo courtesy
Kenneth Kann feeling fine and pondering gender roles in his red dress on the AIDS Lifecycle Ride. Photo courtesy of author

We wheel along, a rolling extravaganza of red dresses, pajamas, kimonos, bustiers, boas, and ballerina tutus. We are a carnival display of red couture and faux cleavage.

Men in full-length red satin gowns and parasols dressed as Southern belles. Husky Dolly Parton lookalikes. Bearded middle-aged men in red poodle skirts. Male Wonder Women and female Supermen. A co-ed synchronized swim team flaunting women’s one-piece red polka dot swimsuits. Muscled studs in skimpy red party frocks powering forward aboard high-end Italian racing bikes.

Laughing pedestrians and honking drivers cheer us on. “It is fabulous!” exclaims an excited participant from the People’s Republic of China, a young gay man wearing a demure red shift.

It is indeed fabulous. And for me, revelatory.

The Ride is an annual fundraising event. Cyclists pedal for seven days from San Francisco to Los Angeles, raising millions of dollars for AIDS support services through the San Francisco AIDS Foundation and the Los Angeles LGBT Center. This was my seventh Ride, but my first in a red dress.

I first rode in 1999, after my friend David had told me, “You should do the AIDS Ride. It will be good for you.” David is gay and HIV positive. He described the Ride as an experience of profound life affirmation, an event that galvanized people to fight AIDS — the disease and the stigma — through cycling.

David knew I was a hardworking attorney, decades removed from my last social justice movements in the 1960s and ’70s. Beyond my wife, daughter, and friends, my life focused on a demanding litigation practice. He thought I needed more.

I was curious about this very gay event, but I worried about how I’d fit in. Indeed, from my first Ride on, I felt keenly aware of myself as a straight man. I was an outsider, a sidekick to gay outrageousness, a sympathetic witness to gay sorrow and struggles, an appreciative observer of gay humor, creativity, and accomplishments. I was the straight man, and as such I helped to define this bubbling gay world on wheels.

The Ride is more than a demanding athletic event. It’s a week-long parade, a traveling public AIDS seminar, and an unapologetic public demonstration of gay presence. The Ride blasts through California communities as an outsized happening, with thousands of cyclists and volunteer supporters on the roads, dozens of trucks and cars and motorcycles, cheering onlookers, and kids high-fiving passing riders. Cyclists wear colorful costumes, decorate their bikes, and discuss the spectacle with pedestrians and local media.

In my early years on the Ride, particularly on Red Dress Day, the unspoken public message of the riders sometimes struck me as defiant: “We’re queer… we’re here… get used to it.” Or, often, a jubilant “Here we are again!” Either way, I had to stifle an uncomfortable impulse to inform spectators, “this is not me. I’m not gay.”

On my first Ride in 1999, I was startled by the pervasive ethos of grief. Almost all participants have partners, parents, siblings, children or friends who have died of AIDS or been infected by HIV. The Ride begins with the solemn walkout of a “riderless bike” at opening ceremonies. Each day, riders write moving messages of memories of loved ones lost to AIDS in a tent built for the purpose. On the road between San Francisco and Los Angeles, many riders have pictures on their bikes of loved ones who died from AIDS. On the final night of the Ride there is a silent candlelight vigil on the beach in Ventura, where flickering candle flames are held by 3,000 people. One hears only the waves lapping against the shore, and I always can feel the vastness of the AIDS calamity.

I too had lost a friend; I had been stunned to learn she had AIDS, shocked by how her body was ravaged by the disease, and I grieved her loss. For many years I had followed the spread of the plague in the papers and discussed it with friends, as an interested outsider. It was different experiencing the epidemic through the intensity of this gay event. On the Ride I was among a community that had been deluged by AIDS deaths. Many riders are infected with HIV and others, young gay men, are at high risk for infection. When I struck up a conversation with other riders and listened to the speakers at the Ride’s evening programs, I heard stories about AIDS, about suffering and redemption, about the Ride as a spiritual and political journey.

On the third day of the 2014 Ride, as I wheeled up to rest stop No. 4, I was directed into bicycle parking by a lovely young man in a bold maroon and black dress, stiletto heels, Marilyn Monroe wig, come-hither lipstick and cheeks rosy with blush. On each Ride I am delighted, and sometimes scandalized, by the extravagant themed rest stops. This was the most entertaining display, on the grounds of Mission San Miguel between King City and Paso Robles. Rest Stop 4 crew, including the winsome Marilyn look-like, played drag queen models. They performed salacious songs and dances, sauntered about displaying their wares, and snapped pictures with riders in naughty poses.

I’ve wondered about the propriety of this bawdy merrymaking on the sacred grounds. But year after year the mission’s robed Franciscan Friars chat comfortably with cross–dressed rest stop crew and costumed riders. I’ve decided that the Catholic Church must regard the Ride as blessed work.

David was my guide to this fantastic bash. Over the years in our tent in the evenings, prompted by my questions, we’ve held a continuing conversation about the significance of the Ride; what makes it gay, the role of straights, the rest stop performances, and the meaning of Red Dress Day. I was trying to understand the Ride and why I joined it a second time, a third, and again and again. As our voices floated outside the tent, neighbors sometimes shushed our frank exchanges about the Ride and sexual orientation.

In recent years, we discussed whether I should wear a red dress. The pros: in a red dress I would be part of the symbolic red ribbon, and the thought of transgressing this gender taboo was daring. The cons: it’s so flamboyant and so not me. I never had worn a dress. Over the years I had become comfortable as an AIDS rider. But this might make me look like a woman. Or worse, a man dressing as a woman, a transvestite. Outside, where people would see me. I could not picture it, even as I debated it.

Other riders frequently assumed David and I were partners. When it first happened I felt misperceived, weird, and compelled to explain that I was straight and married to a woman. Several gay friends claim to have “gaydar,” the ability to intuit whether another person is gay, and I always expected to appear as a straight blip on the gaydar screens of other riders. I’m shy and quiet and serious, unstylish in dress, wooden in bodily movements; I’m not a bit touchy-feely, and, by my reckoning, not perceptibly gay by any stereotype. None of this seemed to matter. Over my years on the Ride, I accepted being seen as a gay partner and left the clarifications to David.

No man has made a pass at me on the Ride, but I did feel uneasy about showering. Showers are available in sex-segregated shower trucks with partitioned shower stalls and a common changing area. The insides of the trucks are hot and steamy with naked men showering, drying, and dressing in close proximity. I cannot tell who is gay and who is straight in the shower trucks.

Male bodily beauty is celebrated on the Ride — you see many handsome faces and buff male bodies, you hear many jokes and much innuendo about male beauty. I was self-conscious over how my exposed uncultivated aging physique would withstand scrutiny. In reality, there was no scrutiny in the shower trucks, and little talk or eye contact either. But every year I ride, approaching the showers in our Santa Cruz campsite at the end of Day 1, I wonder if I will shape up compared to the hard bodies.

On my third Ride in 2005, a young woman rider flirted with me. She was in her late twenties, slim, blond, and pretty. She struck up a conversation as we walked our bikes out of a rest stop, and she continued throughout that day’s ride. I realized I was being hit on, I enjoyed it, and then, after that day, I never saw her again. I liked the attention of this attractive young woman. Youth, like beauty, is prized on the Ride, and I was flattered.

But as I pondered our encounter over the following days, some anomalies crept in — she was the only woman riding in a group of young men, her body was straight rather than curvy, and her voice was several registers low. Finally, it dawned on me that I had been cruised by a transwoman. Or, I thought the next day, was she a transman? Or somebody else? All possibilities left me confused — she was feminine and attractive as I recalled her, and now she seemed exotic too. I had strayed. I had been attracted to someone somehow queer, and it was forbidden, fun, and strange.

My life has been entirely in the straight world, at home with family, in traditional schools and legal workplaces, in social movements of the ’60s and ’70s, and in social settings with friends, gay friends included. When I grew up in a Chicago suburb in the ’50s and ’60s, calling a boy a “homo” was a charged insult, one I’d much rather deliver than receive. Living in the Bay Area in the ’70s and ’80s, with the public emergence of a San Francisco homosexual world and a gay rights movement, I had reservations about these developments. I believed in heterosexuality, marriage between sexual opposites, and heterosexual procreation as an affirmation of the future.

My views changed only gradually, through friendships with gay men and women. I came to recognize the legitimacy of gay alternatives as I saw people I liked in committed relationships, finding meaning in gay community life, and advocating for gay rights. And then came the Ride.

On the Ride, I adapted to a world of gay political and health preoccupations, public displays of same-sex sexuality, varied forms of sexuality and gender, outlandish gay antics, inside gay humor, obscure gay slang, and gay bravado. As a straight outsider, I variously felt apprehensive and cautious, intrigued and dazzled, sympathetic and moved, surprised, puzzled, overshadowed, and outwitted. I felt colorless and humorless. I felt stiff and asexual. I felt very straight.

During my years on the Ride, I observed this gay culture permeating the straight world, from politics and civil rights issues to literature and fashion and television sitcoms. It was all around me — homosexual cowboy romance, metrosexual guys, lesbian comediennes, gay marriages, and then Caitlyn Jenner, national cover girl. I heard a gay friend speak with alarm about the loss of gay specialness with this cultural integration. And, having lived as a minority misfit on the Ride, I wondered about my place as a straight older man in this emerging new mainstream society with its galloping gayness, sexual orientation mysteries, and disintegrating gender rules. I foresaw more straight strangeness, that is, feeling out of sync as a straight man, even in my own straight world outside the Ride.

But there was more to it. “First you commit yourself; then you know.” I gradually realized that I was not just a sympathetic straight outsider at an AIDS fundraising event; I was a participant in one of the great civil rights struggles of my time. In 1999, when David said it would be good for me to do the Ride, I did not understand that I was signing up for life membership in the battle against AIDS and the campaign for gay equal rights. Through my Rides, I discovered I had become a valued straight partner in the gay civil rights movement. And this was my kind of movement — for social justice, for public health, smart, serious, funny, and dedicated to a long-term crusade. I was in it, and I was surprised, and I was proud.

When I first did the Ride, wearing a red dress was unthinkable. But over the years growing numbers did it, celebrating all day, and they were puzzled by my straight riding clothes. Feeling left out, I wondered, “Can I do that?” For three decades I had worn only dark suits to work. Now I wanted to join the dress-up party. I never had defied any gender convention, but in solidarity with the Ride, I thought I should be part of this public show of gay presence.

And so in 2014 I took another step — I decided to ride in a red dress. I took off my usual riding regalia and joined the gender-bending exhibition of cyclists on Red Dress Day.

I could not do full drag. No red pantyhose, padded bra, blond wig, ruby heels, or bold lipstick. I did wear a red flapper dress, with shining red sequins and shimmying red fringe, made by my amused wife. I wore it over my black Lycra riding tights and jersey, with bright red bead necklaces.

And I was surprised. Riding in public in a red dress was big fun. I liked being part of the spectacle of two thousand red-dressed riders in a red ribbon on the road. I liked being looked at, laughed at, honked at, and, yes, admired. At a Lompoc restaurant two teenage girls spotted me in my red dress, asked if I was on the Ride, and praised me.

I decided I looked pretty good in a red dress. And I felt, well, attractive, with that shimmering red fabric clinging to my body. It made me wonder: what would it be like to wear soft, silky, colorful, feminine clothing every day? If clothes make the man, was I a different man in my red dress?

I received many compliments from other riders on Red Dress Day, and, at the lunchtime rest stop I was invited to perform in a red dress show organized by the irrepressible crew of Rest Stop 4. I was flattered, I felt happy, kind of giddy actually. After all, I was in a Lompoc public park, in a flaming demonstration of gay civil rights, in my sparkling red dress. Someone could have called me “homo,” and I didn’t care. But I was not ready to appear on stage, vamping in drag before a boisterous gay audience.

Not yet. Maybe this year.

This year’s AIDS Lifecycle Ride takes place June 5-11. More info on how to participate or support here.