The Chicago Theatre isn’t the kind of place you’d expect to see a man on a leash sucking cock. Sipping a martini, maybe. Socializing with Chicago’s upper crust, sure. But not sucking cock. Yet on the last Sunday in May, in the men’s room outside of section 3L, that’s exactly what theatergoers might witness. Memorial Day Weekend in Chicago means one thing for fetishists worldwide: The International Mr. Leather pageant.

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A lavish movie palace when it opened in 1921, The Chicago Theatre regularly hosts the world’s top live performers. But in late spring, the theatre welcomes a different kind of performer – the kind who likes kinky sex – by hosting the annual International Mr. Leather (IML) pageant.

IML is a beauty pageant for men who love the naughty side of cowhide. One guy in the crowd of mostly gay men gathered in the auditorium wears black leather chaps – the assless kind – as he lowers his bare cheeks onto the theatre’s elegant red velvet seats. Another amuses himself by swishing the ends of a cat o’ nine tails over his companion’s back. Several rows back, a man chews on his neighbor’s nipples – a salty, pre-show snack.

The men competing at IML aren’t Miss America hopefuls. They wear combat boots, not pumps. They wear studded jockstraps, not swimsuits. And their prize isn’t a tiara; it’s a thick, leather sash and, if they’re lucky, a bare-ass spanking from their fellow contestants.

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International Mr Leather contest, 31 May 2008
International Mr Leather 2008 Gary Iriza
with International Ms Leather 2008 Hobbit Joost 

These guys aren’t pretty, either. Handsome, sure, but not pretty. Their leather tradition dates back to the 1970s, when gay men rebelled against their sissy image with facial hair, torn jeans and no-holds-barred butt sex that took place more frequently in back alleys than in bedrooms. Far from metrosexual, these men prefer the scent of sweat to eau de toilette, body hair to bare chests and a face full of ejaculate to a handful of beauty cream.

For Chuck Renslow, IML is a 29 year-long love affair. He founded the competition in 1979 at his bar, the Gold Coast – Chicago’s first gay, leather watering hole. The annual “Mr. Gold Coast” contest eventually grew too big for its britches.

“It got…so huge that we couldn’t fit the people in the bar anymore,” Renslow says. Worried about complaints from neighbors, he renamed the contest “International Mr. Leather” and moved it, first to the nearby Radisson Hotel and later, to The Chicago Theatre.

Today, the competition hosts more than 50 contestants and attracts several thousand spectators – most of whom are gay. Its companion leather convention includes citywide dance parties, S&M orgies and a variety of sex toy vendors, and attracts between ten and fifteen thousand attendees every year.

“We represent something like $12 million to the city of Chicago in tourism,” says Renslow, now 77 years old and still IML’s executive producer. “We’re the third largest convention in the city.”

It might mean dollars for the city, but leather means more than money to the men of IML.

“It’s a symbol,” Renslow says. “It represents power…and freedom.”

Leather also represents sex. Rough, raw, kinky sex. Bryan Parker, Mr. Detroit Leather 2007, recalls being turned on by leather while watching Billy Idol on MTV. He likes nothing more than to tie up a shy, submissive young man, blindfold him and thrust his dick balls-deep into his ass. Leather, he explains, is a celebration of kink and confidence.

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“There is something about putting on leather that makes you feel stronger, sexier and in control,” Parker says. “Leather sex is all about saying, ‘fuck you’ to traditional ideas of what sex should be.”

Of course, there’s nothing traditional about sex at IML. Organizers take over an entire hotel during Memorial Day weekend to ensure that. This year’s hotel is the Palmer House Hilton, a stately place where, according to Parker, maids are happy to wipe down your fisting bench. The hotel provides an uncensored place where people can explore their favorite fetish.

“From human urinals to stumbling upon orgies…while walking down the hall,” Parker adds, “Crazy and unusual are commonplace at IML.”

When it’s not about sex, leather’s about community. “It symbolizes solidarity,” says IML contestant Mikel Gerle, Mr. Los Angeles Leather 2007. “I may be different from the world at large, but I am part of a community that is bigger than me and I am willing to stand by its members.”

Leathermen like to think of themselves as wolves, roaming the sheets and streets as a pack. Their camaraderie is the result of a shared history of rejection, according to Renslow, not by straight society looking down on gay men but by gay society looking down on leather. “[Leathermen] had to band together and did,” he says.

In addition to Parker and Gerle, this year’s hopefuls include Brian Mincey, Mr. Mid States Leather 2006, a computer consultant with a tight, firm ass that he proudly spanks for the audience; Bill Howard, Mr. Kentucky Leather 2007, who makes his living as a horse trainer; and Brian “Captain” McCoy, Mr. Pittsburgh Eagle Leather 2006, a disabled veteran and an adoptive father of two.

All 52 contestants of this year’s IML have won either a bar, local, state or regional Mr. Leather contest. (IML competitors who haven’t won a previous Mr. Leather contest must be sponsored by a fetish-centric bar or business).

IML has two rounds of judging; only 20 out of 52 survive the first set that takes place prior to the formal competition. It includes a private interview and a “Pecs and Personality” event during which contestants must eloquently answer judges’ questions while posing in leather gear that shows off their favorite assets. For most Leathermen, that means either their furry chest or their furrier ass.

The second round includes a physique competition: Contestants wear only a leather codpiece (an athletic cup, only kinkier), a harness and boots. There’s also an opportunity for Leathermen to give 90-second speeches on their charitable platforms.

The contestants’ physiques are as different as their platforms – tall, short, stocky and slim, they support everything from HIV education to gay marriage rights. But according to Renslow, contestants aren’t judged merely on looks and speaking ability. “Keep in mind what you are judging is not necessarily the handsomest face or the most muscular body,” he tells judges every year, “but the man who best typifies the ideal Leatherman – a man whose command, presence and sense of self communicates that special quality we celebrate as leather.”

After two hours of watching contestants strut, sweat and bend over in pursuit of the IML title, the judges determine the winner and Renslow reveals the victor. “International Mr. Leather 2007,” he says, “is Mikel Gerle, Mr. Los Angeles Leather.” The theatre erupts with the sound of skin on skin as the audience claps, high-fives and spanks in celebration.

“Why me? I can only guess,” Gerle says. “I like to think that the leather gods have a plan for me.” The champion’s advice for would-be leather kings: “Be yourself.” Oh, and fuck however you like to fuck – with your fantasies on your sleeve.