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Photograph: carlsweetsModel: Magdalena/Elite. Location: Hotel Sax, 333 N Dearborn St

Erogenous zones

Three sex workers expose what makes Chicagoans good in bed.


We know what kind of sex we have with our regular partners, or that one-night stand from the corner bar. But what kinds of sex do Chicagoans pay to get? We spoke with three local sex workers to find out: Ginger, 23, who has been in the business for four years; Mistress Heather, 31, who has provided bondage and domination services for seven years; and Darren, 25, who has worked as a male escort/prostitute for three years.

All three get asked to do the occasional golden shower (pee on your client)—perhaps the Mistress more often than the others—for an extra price.  But aside from the occasional kinky stuff like that, they describe their clients as everyday people—they just pay for sex.

Like most sex workers report, most of their clients are men and many—whether they are looking for sex with a man or woman—are married. “Some guys are just out looking for young, hard cock,” Darren says. “Others want a quick release on the way home from work.” Unlike Ginger and Darren, Mistress Heather sees several straight couples who want to learn how to safely and seductively whip, flog or powerfully tease each other. Less often, she’ll get a couple who pays to be tortured together.

So these ordinary clients are looking for relatively ordinary sex. Or is it so basic? When you think about paid-for sex, many people conjure Richard Gere–Julia Roberts sex in Pretty Woman—she goes down on him (basic), he puts his penis in her vagina (yawn) and then they have sex in the bathtub after singing Prince songs (doesn’t everybody do that?).

While all that ordinary stuff might happen (except the Prince), during the course of a $300-per-hour session with Ginger, she also gets frequent requests from men to go down on her. They often tell Ginger about partners who won’t let them go down—and they miss seeing the vajayjay up close. Mistress Heather gets a ton of cunnilingus requests, too, only she makes her clients beg from within her in-office dungeon to go down on her. If clients plead enough, she says, they’ll get a lick. If they’re very well behaved, she may grant them a full minute of worship.

Darren, too, gets tons of men who pay to go down on him, especially the married guys. “New guys have lots of questions; they worry what will happen if I run into them when they’re out with their wives,” he says. “And I have some regulars who call me on the way home from work and I’ll meet them on the El or at a stop and go somewhere to suck them off or jerk them off.”

Considering all three have worked in other cities (Ginger in San Francisco, Mistress Heather and Darren in NYC), we had to ask: How are Chicagoans different?

“More guys in New York City wanted me to wear a cock ring or fuck their wives,” Darren says. Mistress Heather said she’s doing more “financial domination” since moving to Chicago. “I have a few guys who call me and want me to be very stern with them and tell them that they should give me their money, pay for my rent or my car.” They don’t want to be physically dominated, rather it’s a psychological game—with her clients paying about $5 to $10 per minute of phone time or per text message to be financially dominated.

And Ginger? In San Fran she had several unpleasant run-ins with self-described “hobbyists”—men who like to sample a range of sex workers and post online reviews about them—and she loves that Chicago men have resisted this particular West Coast trend. Coming soon: We jest, of course.

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