Transfeminine: Cowboy Edition

We sometimes long for the old days. Where men were men and gals were slaves to the needs of the man. Well, fuck that, honey. However, I will admit that I love a corset and a big flowing dress, tight around the bosom. Ugh, to have a bosom!

Column by Jacklyn Henry
Art by Jesse Davis Karshner

Transfeminine: Cowboy Edition

As a young…person … I grew up near Los Angeles, not quite the epicenter of the Old West, that would be San Francisco, but close enough. The Wild Wild West so to speak, and it’s still wild, honey, just a sexier way. Los Angeles, specifically, and California as a whole, share a long, long history of being wild and lawless and a bit out of control, just like the Old West.

Currently, I don’t have to be reminded of those old tyme days as I live in ranch country now, or ranchero. Still California but a little more remote, a little more rural, out in the desert. There are still cowboys. Real cowboys not urban cowboys or the yee-haw boys that drive the big pick-em-up trucks with the flags waving and wearing cowboy hats purchased at Boot Barn. No, I am talking about riding horses, roping calves, wrassling up stray cows from the herd, and bull riding, or whatever, at the Ro-dee-oh!!

My God! Cowboys. Real fucking cowboys made of pure muscle. Girls you know what I am talking about, right? Tight jeans, tight butts, boots, that big aw-shucks grin, the big belt buckle, the big bulge, strong arms, broad hairy chest…oh dear lord!!

I’ll be right back; I’m overheating with illicit thoughts.



Where was I? Does it matter?

The Southwest is still a vast playground for cowboys and cowgirls, real and otherwise. We watch Yellowstone and its many spinoffs, or other Hollywood make believe, and sometimes long for the old days. Where men were men and gals were slaves to the needs of the man. Well, fuck that, honey. However, I will admit that I love a corset and a big flowing dress, tight around the bosom. Ugh, to have a bosom!

And the thought of being homosexual or, gasp, trans, in those days? Forget. About. It.

It should be noted that some scholars suggest that acts of homosexuality may have been more frequent than conservative alt-right Amerika wants to admit, but the identity of homosexual may not have fully developed out on the range. Think of Billy Zane’s character in Tombstone, a great film if only for all the sexy male actors and the divine Dana Delany. Mr. Fabian is an actor and Josephine Marcus’ sidekick. He certainly appears homosexual at least I picture him that way, but the fellas in those times would consider him as effeminate, not quite gay, but not quite a man. And that would be, potentially, a normal association. 

Think about the Old West and a couple of fellas traveling together alone with just each other for company, depending on each other in the dangers of the prairie. Doing everything together, no women around, cold at night, wrapped together to stay warm. Needs arise. A couple of fellas could knock boots and no one would be the wiser. Platonic intimacies can lead to physical relations. Doesn’t mean you are homosexual, just means your human. 

And one might conclude that trans folkx did not exist in them olden days, and one might be wrong.

An article I found online, when I took a break from gay porn, puts it best:

It’s difficult to think of a world with clearer gender roles than the Old West, or at least the Old West as we know it from movies, television shows, and genre novels. But when historian Peter Boag studied the real nineteenth-century American West, a different narrative emerged. For one thing, hundreds of people lived as the opposite gender from the one they were assigned at birth—and that’s just counting the people whose stories were reported in newspapers.

As a transfeminine person I cannot picture someone of my size (remember I am a 6’5” gal) running around in a prairie dress and living on a farm or ranch, but I can picture a woman dressing as a man to survive. Or a smaller man living as a woman. 

While we are considering Cowboys, we must also touch upon Native Americans, who led the way in gender affirmation.

Given the Wild West was built on the bones of indigenous tribal lands, its more relaxed approach to gender wasn’t surprising. Tribes like the Navajo and Cherokee were never moved by Christian colonizers’ binary dog-and-pony show, recognizing anywhere from four to six “genders” on average. Their tradition of accepting “two-spirits”—transgender, gender fluid, and/or non-binary tribe members—as treasured community members bled subtly into the culture of the West, creating cracks of space for other queer people to experiment. Infamously lawless, the burgeoning area was too busy dealing with murders and dysentery to make Puritanical “masquerading laws” a priority, removing the legal leverage well-established cities used to subjugate queer bodies for offenses like wearing a dress while male.


Cowboys are sexy, without question. Especially tall, handsome Mexican vaqueros. Ay dios mio!

Quick story, mostly true.

A few years back, while spending time with friends down in the Imperial Valley of California, near the Mexican border and hot as balls, I met a cowboy, a vaquero. Friendly, kind, handsome, and unassumingly gay. My friend that introduced me to Eduardo felt we’d hit it off. And we did.

Eduardo, who spoke little English, and dear Jacklyn who spoke zero Spanish, spent a few days wandering around the farmland in an old pick-up truck, stopping at homes and ranches where Eduardo did random Cowboy things. He would help round up strays, fix various things, check on horses, and, at a last stop one sunny afternoon, castrate bulls. Yup. Eduardo assisted in the removal of the testicles of two bulls. Why? I didn’t want to ask. He explained as he went in his beautiful Spanish baritone, but I removed myself from the area and sat on the porch drinking lemonade with Marisela, the wife of the bull owner, and her three darling children. I pondered the idea of not having my own testicles, a thought I have oft considered, but in that moment, on the farm, I found myself momentarily comforted that they still were in place. One day maybe, and that ugly penis would have to go as well.

Later that evening, being the last night I would be in Imperial Valley, with my friends, Eduardo saddled up two horses and led me to a somewhat remote spot out amongst the stars and coyotes and bugs. He spread out a blanket and we made love under the semi-luminescent light of the moon. And yes, dear friends, I rode a cowboy. Three times.


When I think of the Wild West I think of opportunity and a certain acceptance of gender identities, and Eduardo. That acceptance still exists in the West, well…West Coast. Arizona and Nevada are getting there. Openness came from the sheer size of the range, the tradition of Native Americans, and the need to connect physically.

I’d like to think if I lived in the Old West, in my prairie dress, on a farm, I would find an Eduardo, or maybe just a lonely Ed, and live happily ever after. And I could ride a cowboy into the sunset.

About The Columnist

jacklyn henry is a transfeminine genderqueer old bitch based on the fringe of insanity, Los Angeles. finally accepted their feminine self, jacklyn has been published here and there, and has a penchant for writing colorful tales of sex and sexuality. she also edits 1870 magazine, a sex positive online hideout.

About the Artist

Jesse Davis Karshner is a California artist and a member of The Cream Scene Team, working in the Art Department.

One response to “Transfeminine: Cowboy Edition”

  1. […] columnists put western spins to their usual columns – Jacklyn Henry’s Transfeminine: Cowboy Edition took us to the desert on a moonlit night and Audio Astrology (Sept. 2023) left us […]

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