The Aging Sex Lives of Samuel Steward 

Design by Grace O'Grady

In 1979, seventy-year-old Samuel Steward went to an Oktoberfest house party thrown by a coterie of middle-aged queens—his gay male friends in San Francisco—who drank, ate pot brownies, and lounged on leather sofas. They gabbed about sex, astrology, decrepit twenty-somethings, masturbation, and liberation. Steward did not initially want to go. “I don’t like being stone cold sober amidst a group of euphoric drunks who think they’re being witty,” he recalled saying to his friend, Don, who chauffeured him to the party. 

“Eat some brownies,” Don, a big-muscled hunk, offered in response. 

By this time, Steward had long withdrawn from the San Francisco gay scene. He had moved to the Bay Area in 1964, fleeing his home in Chicago after a series of disappointments with his sexual and social life. He installed himself in a bungalow in the Berkeley flatlands, far from the Castro, the Tenderloin, or the South of Market—hotspots of Bay Area gay life where Steward, in his earlier years, would have gorged himself on the cornucopia of attractive young men. But he was fifty-five, and he believed that his older age had rendered him totally undesirable to the younger men he wanted. 

Among the crowd at the Oktoberfest party was J. Brian, legendary for his gay escort agency named Golden Boys and his filmography of gay porn. Tagging along with him was Scott Anderson, a twenty-five-year-old with the beauty of a Grecian catamite. “Dreamstuff of soft cornflower violet came from his eyes,” Steward wrote. For all his defenses, Steward couldn’t resist his charms. An affair burst forth, first in small gifts and regular visits, then a full-throated consummation. 

One of those first offerings was a color photograph of Anderson, nude, emerging from lush, green foliage. His body was hairless, save for the wispy blonde on his arms and the bush gesturing towards his genitals. He stood in contrapposto with a crown of golden hair, lips parted just enough to reveal his tooth gap. On the back he had written, in large, looping script, “Sammy, I always enjoy your company. Hope to have more visits in the future. I hope to be as charming and witty when I get past 30!”

***

I am twenty-two now, soon to be twenty-three. That’s two years out from twenty-five, the age that marks “twink death,” whereby a young gay man, skinny, smooth, and hairless, becomes a crone overnight. Suddenly, he believes that everyone can see the microscopic loosening of skin on his face; he can feel his ass start to sag. 

This, to say the least, is bad. I am 5’4” and ninety pounds. My shoes are size seven and my waist is between twenty-three to twenty-five inches. Men’s underwear doesn’t fit me, so I have to shop in the kid’s section. For better or worse, this is the body with which I started my sexual exploration, and it has not changed—for now, anyway. As it turns out, there are many men out there for whom a young, previously anorexic, skin-and-bones frame is peak attractiveness. 

But don’t let me tell you. Here are some of the texts I’ve received from enterprising older men trying to get in my pants: 

I love how tiny you are 

I love your tiny waist and long hair

Love rimming a sexy smooth boy

Love slim and smooth and super fem

U must be the skinniest twink in town

Fuckkk love that slim body

How’s that smooth Asian pussy

I love skinny bottom

I can’t wait to run my hands over your beautiful thin body

Get you completely naked and play with your skinny boy body

Fold you in half and pound your smooth pussy

Bony little fucker

Stay skinny, sweet and sexy baby

I’m not going to sit here and pretend that many of these didn’t work on me, or that I wasn’t pleased by the attention, or that my casual relationships with these men weren’t sexually, socially, and emotionally fulfilling. They were; I don’t regret any of them; I remain friends with several. However, I have to wonder whether I would have had the same experience if there was a little more meat on my bones, or if my retinoids couldn’t chase away the incoming smile lines. 

“Just wait till you’re older. Your metabolism will slow down,” is a refrain I hear often, especially from older folks, who append that aphorism with a gesture to their apparently-bloated bellies, as if to say, your looks won’t last forever. This—aged, dilapidated, thirty-five-year-old me—is what awaits you. “That’s ageist!” I want to say. I believe in life after twenty-five! Except I sort of don’t, at least not while there’s a man crooning in my ear about how sexy he finds my little body, or how hot he finds our size difference. Again––not complaining. They’re good guys, and honestly, it is kind of hot. I just can’t shake the feeling that I’m living on borrowed time. 

***

Born in 1909 in Woodsfield, Ohio, Samuel Steward grew up an academically and sexually precocious child. While he loved literature, once he discovered that his sexual attraction unquestionably laid in the direction of the same sex, he would suck off, at age fourteen, many of the boys in his town. 

Steward is mostly famous for his proximity to other famous people, including Gertrude Stein and her partner, Alice Toklas. He had limerances with Thornton Wilder, Lord Alfred Douglas (the lover of Oscar Wilde), and even the silent film heartthrob, Rudolph Valentino. Steward had literary ambitions, but he never surpassed the modest critical attention of his 1936 novel, Angels on the Bough. His fiction over the next few decades would largely consist of gay erotica under the pseudonym Phil Andros. He was a professor of English in universities across Ohio, Washington, and Chicago, where he eventually got disillusioned with academia and quit his job to become a tattoo artist. 

Many things changed in his life, but the one through-line was sex. He had a lot of it. He had it with his students. He had it with men he cruised at the Embarcadero YMCA. He was noting it all down in what he called the Stud File, a dark green file box where he logged, in small white cards, all the sexual encounters he had had from 1925 to the 1980s..One such card reads, “Another one of those goddamned cocksuckers who don’t suck cocks. What a frost!” 

According to his biographer, Justin Spring, the flavor of his libertinage took a different turn when he reached mid-age. Suddenly, men who used to yield to his touch started rejecting his advances. As he aged, Steward increasingly took to paid sex, since it seemed that no one was in the market for men in their mid-forties. In 1958, he met Chuck Renslow, the owner of multiple businesses, including a gym and a mail order business specializing in softcore gay porn. Renslow shot bodybuilders and would set up the most sexually willing ones with other men willing to pay. For the rest of his years in Chicago, Steward would become reliant on Renslow’s network of hustlers for his sexual needs. 

Steward also became obsessed with the idea of being beaten and used during sex. “There is not so much masochism in me […] as there is the slave complex,” he contemplated. Most of all, he wanted to be abused by Renslow, now a consummate sadist with whom Steward had developed an obsession. But Renslow, twenty years younger than Steward and surrounded by gorgeous muscle men, didn’t want to; the few times Renslow did have S&M sex with Steward, it was to quell Steward’s cajoling. 

For Spring, it was Steward’s “advancing age, diminishing libido, and rapidly deteriorating self-esteem” that fueled his desire to be used and abused. Unfortunately for him, few of Steward’s other masochistic encounters ended up being sexually fulfilling, and he would only receive from Renslow a resolute rejection—one that completed his transformation at age fifty, Spring writes, into a “sexually undesirable older man.” 

The same year he met Renslow, Steward had published an essay for the Swiss gay magazine Der Kreis called “Detachment: A Way of Life,” a manifesto for older gay men to deal with the disappointments of age. “With detachment,” he writes, “it may be granted that we will grow old as easily as possible, as good men should, knowing the virtue of giving up at the psychological moment, the right time, le moment juste.” This Stoicist orientation became more important to Steward as paid sex came to dominate his sex life. In detaching himself from expectation and desire, he could protect himself from the rejection of the men who once came calling. 

Smarting from Renslow’s rejection, and attracted to the Bay Area to take over a friend’s lease, Steward moved to Berkeley in 1964. Steward refused to go out into the gay scene and invested in an Accu-jac, a device in which “the best of masturbation, oral sex, and copulation are combined” through the use of air-powered attachments that massage penises “without hand manipulation.” He still had a hustler come by every now and then, but no longer did he rely on other people for his sexual gratification. As he told his friend Witold Pick, with the Accu-jac, “I don’t worry about sex anymore.”

***

You can see Steward’s Accu-jac at Beinecke Rare Book & Manuscript Library. It looks like a rather innocuous mustard-yellow toolbox with two latches. One of these latches has a sticker reading, “SEALED UNIT DO NOT OPEN,” and the other is missing. The only indication that this box might have even come near a penis is the accompanying nine-inch dick sleeve made of yellowed rubber—firm enough to hold its shape but pliable enough to squeeze—attached to a transparent plastic tube, which is supposed to connect to a node at the back of the device. The sleeve is kept inside a clear plastic bag which, when brought out of the archival box, reflects the overhead lights of the reading room and creates the effect of looking at something through a condom. 

When I went to see it, the box unlatched with a groan like a shuddering ship hull. There hung a musty, stale air like old cardboard and glue. I didn’t quite know what I was seeing inside. There was a grey motor attached to a contraption of bolts, bars and hinges, which were screwed to a flat wooden plank flush against the back. Black and red wires connected to the sides of the box at places where I assumed gears used to be. However, my attention was fixated on the bottom of the box, which was littered with what could have been dust bunnies, insect casings, popcorn kernels, or  facial debris.  One thing was for sure: there was definitely human hair in there. It was black. Some strands were loose and scattered, others clustered and stuck to each other. Steward had dark hair—could they be his? 

I turned the box around. Shoved in the gap between the wooden plank and the back of the box was a wadded-up paper towel. It was crisp in places. Discolored, too. I was sure there was a warning somewhere about keeping tissues far away from a masturbation device, but I didn’t listen. I plied open the hardened folds and took a whiff. It smelled as if recycled toilet paper fibers had been soaked in acid and left to dry. When I looked back down, a strand of hair, ever so wiry, had made its way onto my thumb. I stuffed the paper towel back.

The Accu-jac was heavy, but it could be carried around easily. Looking at it alongside the sleeve’s plastic tube, I was reminded of a portable oxygen tank—just like the one Steward had been using when chronic pulmonary emphysema had rendered him, by age seventy-three, unable to breathe without assistance. Over the years, he had dealt with a stomach tumor, a varicose vein, and erectile dysfunction. His barbiturate addiction, which had started in Chicago, also started interfering with his medications.

It’s tempting to read the Accu-jac as a late-life implement, the completion of Steward’s isolation. He died on December 31, 1993; the emphysema had stopped his heart. Michael Williams, a friend who became his executor, described the clutter of Steward’s home in his twilight years: “books, magazines, old mail, dog paraphernalia, artworks, dismantled clocks, ashtrays, and anything else that had happened to settle nearby.” Red velvet draperies blocked off sunlight. I imagined the Accu-jac, stashed somewhere in the mess; I imagined an older Steward, accompanied only by his ephemera, feeding his penis to electric-powered air pressure and suction, leaving his imprint on plastic and rubber. In a nearly empty reading room at the Beinecke Library, I felt that imprint settle over me, emanating from the hair, the pump, and the paper towel before settling in my psyche, as if to say, your looks won’t last forever. This is what awaits you. Was that my fate?  

***

Between the ages of forty-two and forty-seven, Steward picked up a Polaroid camera and photographed sex. He was still living in Chicago, where he would invite friends, lovers, and hustlers back to his apartment. Though some of these Polaroids depict other people having sex, many more of them feature Steward, sometimes with one partner, sometimes with many, sucking dick, sucking two dicks, eating ass, getting fucked, standing up, lying down, on his knees, in 69. His aquiline features, his pencil-thin mustache, and his short hair are striking. His chest is muscular and taut, as are his abs, guiding eyes down to a white, Speedo-shaped tanline on an otherwise bronzed body. He is remarkably attractive. 

In another picture, presumably taken in his seventies and eighties in San Francisco, Steward is sitting at the alfresco dining area of a café. He is looking straight into the camera, unquestionably aged; he wears gold-rimmed glasses and a three-piece suit, and his hair, once dark, is lighter and thinner. But he has not lost the pencil-thin mustache, nor his sharp features, nor his piercing gaze. He is still remarkably attractive. 

Steward may have been right that fewer men wanted to sleep with him as he got older. However, as wild and experimental as he was in the bedroom, he was arguably blind to the panoply of sexual possibility; who is to say he wouldn’t have found someone who would have desired him, fucked him, even cared for him? 

Steward refused to find out. He had gay friends, of course, but he disliked many homosexuals, which precluded him from the gay scene. In his essay for Der Kreis, he writes, “We are never satisfied with our partner,” claiming that gay men always have their eyes set on the “impossible and unattainable ideal.” Like the butterfly, “we hover at one flower for a moment, extract its sweetness, and flit ever-hungry to the next.” To Steward, there was no possibility of long-term homosexual connection. He also hated effeminate men, and often made fun of them in his writing. By refusing to engage with the gay community in all its shades, he remained convinced of his undesirability as an older man. 

It doesn’t help that Steward’s legacy is defined by a narrative of aging decline. For all the love and care that Spring, his biographer, invested in telling Steward’s story, he makes his subject seem destined for loneliness and isolation. “His body was aging and his potency was diminishing; he was no longer the relatively carefree, attractive, and resilient young man he had once been,” Spring writes of the time when Steward was forty-five. At this age, he was still taking his sex Polaroids; in these pictures, he is supposed to have crossed the Rubicon of “middle age.” 

In his final, frail years, Steward was surrounded by people who loved him. His calendar was packed till the end. Ike Barnes, the S&M “slave” of an old friend, visited every week to do errands before he died of AIDS. Michael Williams, who was a fan of his pornographic Phil Andros novels, became his caretaker and executor after his death. He was responsible for sorting out all of Steward’s belongings for donations to archives, a Herculean task which necessitated a leave of absence from his engineering job. And yet, he still found the time to label, on the back of every photograph taken at Steward’s memorial in April 1994, the full names of everyone who appeared in each frame. 

Steward was surrounded by so many models of queer sociality, kinship, and care, but he still couldn’t imagine a world where he would be loved beyond a youthful appearance. It’s a pity; Steward was sexually candid and risqué when homosexuality was persecuted. His sexual record-keeping was ahead of his time, furnishing an alternative history of homosexuals in the longue durée of twentieth-century gay history. That he could only locate his value in an ageist body economy is the real tragedy—not the fact that he grew old. 

***

I met a guy. He’s funny, smart, and deeply thoughtful. The first time we met, we talked for six hours about literature, philosophy, gastronomy, dating, love, and sex. We’re physically attracted to each other, obviously, but he sees past my body. We understand each other. I think I could let him into the parts of myself I don’t show anyone. 

He is forty. He is whimsical, spontaneous, generous, sexy, and full of life. 

I probably won’t like it when the number on the scale begins to go up, or when my body starts to change, or my face, or my hairline. Maybe all of that won’t happen and I’ll look better than before. Maybe I’ll look the same. Or maybe it doesn’t actually matter if I look better or worse or the same because there will be people around me who won’t give a fuck if I’m 5’4”, ninety pounds, or a shoe size seven, or that I’m twenty-two going on twenty-three and on and on and on. 

I do, in fact, believe in life after twenty-five.

Ethan Kan
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