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Black Boots and Big Booties at the International Ms. Leather and International Ms. Bootblack Contest

For four days, nearly 600 people from all over the world took over the Doubletree Hotel in San Jose to wear leather and get laid in dungeons, cramped hotel rooms, and public bathrooms.

Photos by the author

Think about your favorite pair of leather boots. Do you love them? Like, REALLY love them? Love them to the point where you’re sexually obsessed with them, and feel the need to connect with a community of people who love to fuck while wearing leather?

This, and many other things, is what leather means to the queers and heteros who attended the 28th Annual International Ms. Leather and International Ms. Bootblack Contest (IMsL/IMsbb) at the end of April.

For four days, nearly 600 people took over the Doubletree Hotel in San Jose, about 50 miles south of San Francisco. The weekend served as a chance for pervs from around the globe to gather and get laid in meticulously designed temporary dungeons, cramped hotel rooms, and public bathrooms.

According to rumors I read online, the event moved from San Francisco’s SOMA neighborhood to San Jose this year partially because the raunchy sex bothered San Francisco’s squares. For years, IMsL/IMsbb took place in SOMA—which after Stonewall was known for being filled with bars where you could receive a mouthful of piss and a fist in your ass—but the neighborhood has become so gentrified it’s now unrecognizable.

Although I have been involved in various kinky communities for nearly ten years, I had never attended IMsL/IMsbb before. Based on past participants' stories, I imagined the event was like a beauty pageant where contestants wore fetish gear instead of sequin-covered gowns. In April, I decided to throw my bar vest and reporter cap in a suitcase and see what a leather weekend was really like. 

Like a doughnut, the Doubletree lobby circles around an enormous pool courtyard, so to get from my bedroom suite to the dungeon, bootblack stand, ballrooms, classrooms, and café, I had to past the civilians in the lobby. IMsL/IMsbb didn’t book the entire hotel, so I saw several vacationing families eating sushi next to women in full-body, latex catsuits. I also walked past people who crawled on the ground and wore collars and special hoods to make them look like dogs. 

The official contest took place Saturday night, and the schedule for the rest of the weekend was packed. The Alameda County Leather Corp hosted a cigar party with human ashtrays. Vendors turned one ballroom into a kinky shopping mall, where they sold everything from handmade chain mail to enormous dildos. Workshops with names like “Advanced cock confidence” included explicit live demos. During Bawdy storytelling, which is like an X-rated version of The Moth, I heard the tale of a man sticking a thermometer in his urethra in front of noted science fiction legend Sam Delaney.

The bootblack salon consisted of three chairs with metal stirrups on raised wooden platforms. Sitting for a kinky bootblack was like receiving a shoeshine in Grand Central Station, except it was acceptable for me to sexually objectify my bootblack Allison. (She gave me a view of her magnificent cleavage while she rubbed leather up and down my calf like a masseuse.) After the shoeshine, my boots looked brand new and I felt “shiny on the inside,” as International Ms. Bootblack 2011 described the feeling. 

On Saturday afternoon, I took a walk through the 24-hour dungeon, which was actually a hotel ballroom furnished with donated furniture. Spanking benches, wooden ladders, and a gynecological table stood next to sterile prep surfaces. Curtains distinguished a few men’s sections and women’s sections, but anyone could play in most of the dungeon.

The event encouraged voyeurs to watch as long as we behaved respectably. On Saturday, I saw a young woman wearing gym shorts hold an older man in a chokehold on a wrestling mat.  Elsewhere in the room, someone bent over a chair to receive welt-raising punishment from a long rattan cane, and an elderly woman sat in a chair while another woman performed fellatio on her cherry red silicon strap-on cock. It was 2 PM, and the room was relatively quiet compared to the previous evening, when people filled the room with the sounds of 90s sex music, screams, orgasmic moans, and the thwap, thwap, thwap of different objects colliding with flesh. As I eavesdropped on kinky sex enthusiasts setting up “dates” and “scenes,” I thought their negotiations sounded similar to comic nerds' conversations about their favorite characters.

At Saturday night’s contest, a panel of judges chose the people to represent the titles of International Ms. Leather and International Ms. Bootblack for the following year. Anyone from any gender could compete as long as they identified with the women’s leather community.

This year’s International Ms. Leather, Patty, won for her achievements in community service and education (it’s like a Rotary Club community service award, except the community service involves pledges to “cruise, fist, and fuck” across the globe), and International Ms. Bootblack, Dara, earned his title because he possessed the best technical skills to take care of his kinky gear. 

During the most entertaining part of the contest, a talent show called the Fantasy Scenes, contestants created a performance illustrating their unique desires and personalities. Narine sucked Rock em Sock em robots' lightsaber-like cocks; SubMissAnn performed human-pony choreography; and Patty starred in an elaborate rock star scene involving a human drum kit.

No matter how much you really know about kinky sex, leather is probably one of the first things that comes to your mind. Tom of Finland-style daddies in caps and chaps. Rihanna or Madonna in dominatrix drag. These archetypes and many more wandered around the Doubletree during IMsL/IMsbb. Some opted for rubber, or vinyl, while others wore ordinary dykey jeans and flannels.

Despite the different kinds of outfits, there was a unified passion for what leather clothing represents. For the people who congregate around leather events, that material is symbolic of their proud deviancy. 

After sitting for a sexy bootblack, reeking of the smoky smell of Huberd’s shoe grease, and watching the contest, I realized I would never look at my leather boots the same way again.

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