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Chicago Sex Tour

Chicago sex worker Serpent Libertine leads tours to some of her favorite places.

By Jake Malooley
Published: October 19, 2011

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    Everleigh Social Club (939 W Randolph St, everleighsocialclub.com)
    “People will never be able to experience the actual Everleigh Club, but burlesque starlet Michelle L’amour and her husband, Franky Vivid, were highly influenced by the Everleigh sisters’ brothel in starting this members-only club. They do have some open-to-the public events, though, including Naked Girls Reading [coming up on October 28] and Speakeasy night every Sunday with live jazz and burlesque.”

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    Early to Bed (5232 N Sheridan Rd, 773-271-1219)
    “Early to Bed deserves praise, not just because it was the first female-owned sex-toy shop in Chicago. It was also the first store in the city that put out display models of all its toys, so you could see how a vibrator operated before you brought it home and took it out of the box. A woman knows what a woman needs.”

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    Bijou Theater (1349 N Wells St, 312-943-5397)
    “Steven Toushin has run this place since 1970, the oldest gay porn theater in the country. There’s always a movie going, so when we take the tour through, there are guys sitting in the seats watching. We go upstairs, too, which is more for cruising, and there are glory holes and stuff.”

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    Leather Archives & Museum (6418 N Greenview Ave, 773-761-9200)
    “Chuck Renslow, the cofounder and president of the LA&M, is a legend in the leather scene. In 1958, he started managing a bar downtown called the Gold Coast and turned it into Chicago’s first leather bar. He also founded Man’s Country and the International Mr. Leather contest. There are all kinds of floggers, harnesses and other sex devices in the museum, but the highlight for me is the re-creation of a leather bar in the basement, with old posters and T-shirts on display, and a mannequin dressed in full leather seated at the bar.”

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    The Levee District
    “Not much of anything is left of Chicago’s old red-light district in the South Loop. As Karen Abbott wrote in Sin in the Second City, aldermen, judges and police officers used to frequent prostitutes here. Sadly, the infamous Everleigh Club, at 2131–33 South Dearborn Street, is now a high-rise apartment building.”

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Everleigh Social Club (939 W Randolph St, everleighsocialclub.com)
“People will never be able to experience the actual Everleigh Club, but burlesque starlet Michelle L’amour and her husband, Franky Vivid, were highly influenced by the Everleigh sisters’ brothel in starting this members-only club. They do have some open-to-the public events, though, including Naked Girls Reading [coming up on October 28] and Speakeasy night every Sunday with live jazz and burlesque.”

Photo: Andrew Nawrocki

Serpent Libertine has worked as an erotic masseuse, escort, dominatrix and porn director and producer. Now the 35-year-old Pilsenite can add “tour guide” to her extensive résumé. As the new host of Discovery Center’s Chicago Sex Tour, she leads groups to the naughtiest, most depraved spots in the city—and we don’t mean City Hall. On her first five-hour jaunt in July, Libertine showed some wide-eyed novices around an S&M dungeon in the Loop; a couple of dominatrices even put on a little leather-and-whips show. Though she wouldn’t reveal the dungeon’s address, the sex-industry vet did discuss some of her favorite prurient places, which might pop up on her next tour itinerary.

The Chicago Sex Tour departs from Discovery Center (2940 N Lincoln Ave, 773-348-8120) November 6 at noon. $49.

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