Sex Workers Explain the Struggles of Running an Illegal Business

When Dane* gets into a car with a client, the first thing he does is ask the guy to pull out his dick.

It's a measure he developed after nearly getting arrested for having an escort ad on Craigslist. "I met up with the person, and we drive around the block, and he starts talking," said Dane, a Seattle-based escort. "The way he was talking was weird, and you could tell he didn't know anything about gay sex. After a while, I told him to stop." That's when the cop pulled out a badge, terrifying Dane before letting him off with a lecture.

Since then, Dane does what he can to ensure that his clients are honest about their intentions. He previously used Rentboy.com, but federal regulators seized the site over a year ago, and its legal status today remains unclear. Once the most visible site for male escorts, Rentboy allowed them to check client reputations and block minors, providing a peek at what a regulated escorting marketplace might look like.

Because their work is illegal, escorts face a near-total lack of access to the protections and professional services that other entrepreneurs take for granted, from marketing to legal advice to insurance and beyond. As a result, sex workers who already face physical risks and financial volatility endure a unique form of economic isolation.

"Hiring drivers, security, people who assist in the screening process, money management, or utilizing a friend for a ride or as a safety call—all come [with] the risk of those people being charged with sex trafficking crimes," Maxine Holloway, a Bay Area sex worker, pornographer, and activist told me in an email. "I personally have employed drivers and screening services. Though hiring someone does keep me safer or make my job easier, involving someone else in the legal and safety risk I am taking always weighs heavy on me."

"I had a client stiff me once," said Ben*, a San Francisco–based escort. "He was like, 'Oh, I don't have the cash on me, and I'll just pay you with a check.' Being young and not knowing much about the financials of banking and checks, I was like, 'OK, sure.'" The account turned out to have been closed.

"There wasn't anything I could do," Ben said. He couldn't call the police or go to small claims court. "I just took the loss."

Ben takes his taxes to H&R Block, but only reports income from his retail day job. He tracks escorting income via his phone's text messages; when I asked if it would affect his insurance if he was caught driving his car for business, he seemed surprised. "I've not thought of that. That's a good point," he said. "I dunno. I have no idea. Could I write off my car?"

Those questions are nearly impossible for most escorts to answer, since most financial advisors avoid helping clients break the law. If they're lucky, a sex worker might find a sympathetic friend or unofficial mentor; Dane takes his taxes to a client who mentioned that he did financial counseling. The two men pay each other out-of-pocket whenever they avail themselves of each other's services.

But such arrangements are rare, especially when it comes to health and safety. "Public health research shows that sex workers experience higher rates of occupational harassment, violence, and murder," Holloway wrote. "In the Bay Area, we're lucky to have the St. James Infirmary and Red Light Legal," organizations that provide medical and legal care to sex workers. But on the whole, she wrote, sex worker-focused organizations "have difficulty functioning outside these pockets of self-run wellness services."

"There's very little help available," said Dallas Steele, who left his career as a TV news anchor to become an escort and adult performer in 2014. "You're pretty much on your own. The help I get is from other porn performers who have been around doing porn and escorting for a lot longer than I have, who can pass along experience."

Dustin*, an IT professional based in Portland, charges an escorting rate exactly three times his computer consulting rate. "Every escort hour I record on paper gets recorded as three computer hours," he said. "Money from the computer business goes in the bank, money from the escorting stays in my wallet. That cuts down how much travels through the bank in the first place."

In contrast, porn performers, whose work is legal, may have a wide array of services at their disposal. Steele works with TitanMen, one of the world's largest gay porn producers. "They're very much on top of it," he said. "They have all of the forms in place and are always good about getting you 1099s back, and they always provided good advice in terms of money."

In fact, the porn industry provides a model for how prostitution could be legally regulated. Mainstream studios have employed extensive STI testing programs for decades, overseen by organizations like Performer Availability Screening Services.

Currently, Nevada is the only state where prostitution is legal, with strict licensing requirements that include STI testing. A widespread licensing program for escorts could follow similar guidelines, and most escorts I spoke to were eager to operate legally. As it is, Dustin estimates he loses hundreds of dollars each month due to his inability to accept credit cards.

Violet Blue, a writer specializing in online censorship and security, noted the financial industry's refusal to process payments that could be even remotely related to sex, a practice that she says disproportionately impacts women.

"All women deserve business opportunities facilitated by Chase, Paypal, and Square," Violet wrote, "not just those who live in what these companies consider the 'right neighborhoods' on the internet."

Decriminalization could eliminate many of these obstacles, and is supported by a wide range of medical and civil rights organizations.

Cut off from legal protections, unable to access financial services, harassed by police—why do escorts pursue such challenging work in the first place?

"It's gratifying," said Dane. Though he acknowledged, "This isn't for everyone. If you're going to escort, you should have a backup job, because it's not stable."

But he does love the work. "Not because of the money, but because I helped someone else. I've had several clients who have cerebral palsy, people who shake, or people who are bigger. It gives me a good feeling that I got someone off."

Recently, an older client hired Dane just to cuddle. "All he wanted was an overnight and 'boyfriend experience,'" said Dane. "I was weirded out because usually I'm like, 'Let's just fuck.' But I got to lie down and talk about his whole life and stay up till the morning." Dane says that, the next morning, the client cried as he told him it was the most intimacy he'd experienced since his husband passed away. "It was so good to have someone in his bed again. He didn't want sex, he wanted to be loved. I think that's what everyone's trying to go for."

*Names have been changed to protect the anonymity of some interviewees.

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