Federal judge gives probation sentence to woman who ran West Side fetish business

When Jessica Nesbitt — who eventually pleaded guilty to prostitution conspiracy — was first charged in summer 2019, her attorneys insisted her business was legal and that she paid her taxes, saying, “Fetish-based eroticism is not unlawful.”

SHARE Federal judge gives probation sentence to woman who ran West Side fetish business
Jessica Nesbitt Kink Extraordinaires

Jessica Nesbitt had pleaded guilty to prostitution conspiracy centered on her former West Side business, Kink Extraordinaires.

Sun-Times file photo

A woman who ran a successful high-end fetish business known as Chicago’s “premier dungeon” was sentenced to probation by a federal judge as her long-running prostitution case came to a close Tuesday.

U.S. District Judge Matthew Kennelly told Jessica Nesbitt she would have to serve nine months of her two-year probation sentence in home confinement. While handing down the sentence, Kennelly said that “it’s difficult to look upon this as a crime that had identifiable victims who suffered significant harm.”

Kennelly also told Nesbitt, who has a teenage son with special needs, that her crime should bother her because she put her son “at risk.” But the judge said he didn’t want to visit “any greater degree of harm on him” by sending Nesbitt to prison.

Before learning her sentence, Nesbitt told the judge she accepted “full responsibility” for her crime, and she explained that she got involved in “an alternative lifestyle at a very young age.” She said it turned into her primary method of making a living.

Nesbitt also said she’d “become well-versed in the potential harmful effects of prostitution” in the last few years.

“Whatever sentence you impose, I will comply,” Nesbitt told Kennelly.

Nesbitt pleaded guilty in February to a conspiracy that centered on her West Side business based in the 2400 block of West Augusta Boulevard. When she was first charged in summer 2019, her attorneys insisted the business was legal and that she paid her taxes.

“Fetish-based eroticism is not unlawful,” defense attorney Barry Sheppard told the Chicago Sun-Times.

Still, in pleading guilty, Nesbitt admitted arranging for prostitution appointments with clients — and performing acts of prostitution herself — while charging rates of $300 to $1,000 per hour “depending upon the services provided.”

Her attorneys have said her business, Kink Extraordinaires, boasted 9,000 clients, including people holding “positions of prestige in the community, including in law enforcement and government.”

Barry Sheppard and co-counsel Adam Sheppard told the judge that a veteran Chicago firefighter who attended Tuesday’s hearing served as a so-called “house slave” in Nesbitt’s building, performing “ministerial” tasks on the premises.

In a memo seeking a 30-month prison sentence for Nesbitt, Assistant U.S. Attorney Erika Csicsila denied that the case amounted to a “no harm, no foul” offense. She argued that Nesbitt employed women “who worked in an illegal, unregulated business that provided an inherent danger” and that her employees had “no protection.”

“While the women who worked for [Nesbitt] were not trafficked, many of the women were harmed during their employment, including when their own personal and stated sexual limits were exceeded by clients,” Csicsila wrote. “For example … one woman suffered anal bleeding, bruising and a broken toe because a client disregard[ed] that woman’s sexual limits.”

But Adam Sheppard wrote in his own memo that Nesbitt conducted background checks on her employees and required them to present clean health screenings and avoid substance abuse. She compensated them “at the highest level in the industry” and “treated them with dignity and respect.”

Adam Sheppard wrote that there’s no evidence that Nesbitt “tolerated” or “facilitated any violence.” She chastised the customer who harmed the employee cited by Csicsila, he wrote, and forbade him from meeting with the woman outside Nesbitt’s building in Chicago.

One woman referenced in Nesbitt’s indictment wrote a letter on Nesbitt’s behalf. She described it as a “declaration of amicability” and added, “I do not feel wronged.”

“I found my personal experience while employed by [Nesbitt] to be pleasant, fair, and to honor my personal boundaries and limitations,” she wrote. “I personally did not experience [Nesbitt] to ever push me beyond my areas of comfort. I became employed in my mid 30s — clearly an adult and treated as such.”

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