Assless chaps?

The philosophy of leather


In the name of my been-there-and-done-everything bragging rights, I am going to my first leather event. No big deal you say. Well perhaps, but I’ve spent a better part of my life playing it pretty vanilla with only the craziest of generalizations built in my mind about those who dress in leather.

The decision came with an abundance of issues primarily, what to wear? As comfortable as I am in my own skin, the idea of leathering shaping or clinging to anything on my body left me skeptical.

When in doubt I call my dear friend Randy, who is both kinky enough to actually know a thing or two and unemployed enough to have time to care. “Well, it all comes down to your body, and what you feel comfortable in,” he advises.

Randy, whose gift of fagdom blessed him with knowledge about everything, doesn’t hold back as he lays it all down. “It’s best to pick your strongest feature and build with that. The leather’s gonna demand the most attention so you might as well bring it to the right place” Ahh, the wisdom. Both Randy and I agree that my posterior is by far the highlight of my physique. “I’ve just the thing,” he says handing me a pair of leather chaps, hand-me-downs from an adventure that Randy swears was innocent.

Due to budgetary constraints and a fierce belief that with a little work and the right purse any outfit can look good, I take the chaps without complaint for my leather début at the Resurrection party at Fly nightclub held last March.

Fearful of possible faux pas, I feel some explanation is still required. Who better to call for the skinny on leather fun, than Mr Leatherman Toronto 2002, Bill Dearsley. Bill says the bear, leather and military communities all go hand in hand. He feels that these parts of the gay community are free of the stigmas of snobbery and divas. “We’re more conversational,” says Dearsley. “Not judging on body or clothing.”

People may fear the leather bars, due to years of persecution in lippy fag gossip chains, but functions such as the Resurrection party more like circuit events with leather themes, safe and harmless leather dances opening the community to the curious bystander.

While we got down to business learning important details such as the scientific relationship between leather arm bands and sexual positions, Dearsley shares the philosophies of leather that shape his life. “Leather is” Dearsley repeats, “Leather is whatever I want it to be. Leather is a part of your life at all times; like religion, you don’t always have to be in church to practice.”

“Leather is” I say it like a mantra, as I snap the chaps around my waist and zip the leather tight around my thighs. Looking at myself in the mirror I consider going assless for about 30 seconds before ripping open the closet to plan the supporting cast of my wardrobe choices. I do triple duty at the gym and deal with all the necessary primping. I’m going to knock ’em dead.

 

* Stay tuned: In the next issue of Xtra, learn about Mackenzie’s culture shock while attending his first leather party. Look for Mr Leatherman Toronto Bill Dearsley welcoming partiers to the Sat, Jun 29 Leather Pride Ball and other MLT events.

Read More About:
Love & Sex, Toronto, Fetish & Kink

Keep Reading

Collage with the numbers 2025, an eggplant, half a peach and a full peach, and a shirtless torso

The horniest stories of 2025

The stories that got you not just talking about sex, baby, but thinking big too
An illustration of three shirtless people with short hair holding each other with their eyes closed. There are hearts in the background.

I had a threesome with my monogamous partner, and it couldn’t have been better

There’s more than one route into opening a relationship—waiting for the perfect moment is a good way to start
Collage of photos including a bucket, ladle and brush on a sauna bench; feet resting against the leg of a person in a bikini who is sitting on a bench; and one person whispering into another's ear

The queer community still needs places for public sex

Sex party promoters, kink community leaders and educators refuse to shy away from the more explicit aspects of the queer experience
Illustration of an older person with their eyes closed, reaching toward a younger person with their eyes open and arms outstretched; both are floating against a golden background, surrounded by birds

What my trans son taught me about freedom

I thought I had to fight every day just to exist. Then my son showed me that sometimes freedom is quiet