The Struggle To Properly Pay Taxes When You’re A Gay Male Escort

The Struggle To Properly Pay Taxes When You're A Gay Male Escort

It started like any other Grindr hook-up. Frank was visiting New York City for business and staying at a hotel near my apartment. He invited me up to his room. The chemistry was electric. It was the best kind of sex: He was mentally present, engaged, and listened with his whole body—every move, moan, and breath. He knew where to put his fingers and lips. He looked deep into my eyes as he ran his tongue across my body. I’ve had more Grindr hook-ups than I can count, but this one was different. There was something different about Frank.

We finished and layed in bed together, a sweaty, sticky tangle of limbs. What a shame that he was only visiting.

“So you’re in town for work?” I asked, still recovering from the throws of orgasm.

“Yeah,” he replied.

“What kind of work do you do?”

“Oh, I’m an escort.”

“An escort?” I choked. I don’t think I visibly flinched upon hearing this, but I was certainly taken aback. Now it all made sense. That’s why the sex was so good. He’s a professional and he’s very good at his job. “And you’re in town for, what, an escorting conference?”

“I visit New York every couple of months,” he told me. “I can charge three or four times more here than I can back home.”

I had a million questions bubbling inside me. How long have you been an escort? What are your clients like? How do you protect yourself? Do you ever feel unsafe? How do you find clients? Do your parents know what you do? How much do you charge? Good God, how in the world do you file your income taxes?

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That was the beginning of what has become a very good friendship. Frank has since returned to New York for several more business trips. Each trip, he busts his ass (you’re welcome) working all week and reserves a couple of days to hang with me.

I’ll admit, I was a little apprehensive about befriending an escort. Sex work was unfamiliar terrain for me. I don’t have a problem with it as long as everyone involved is a consenting adult. But it’s more complicated when the sex worker is someone you know and care about. The more time I spent with Frank, the more I grew close to him. He’s unfailingly kind, a great conversationalist, a visual artist, and a musician. I introduced him to several friends and he charmed each one of them. He’s the kind of person who can make you feel seen and heard. He can anticipate what you need before you even know you need it. I had been dealing with the emotional fallout of a recent break-up and Frank must have sensed my need to be nurtured. On his first return to New York, he prepared a lavish dinner and had it waiting for me when I got home from work. It was the nicest thing anyone had done for me in a very long time. His talent is making other people feel special.

On his most recent visit, he seemed a little on edge. Tax season is upon us, after all, and turns out that even escorts are accountable to the IRS.

Filing taxes can be complicated when your main source of income could be interpreted as illegal. While Canada, Mexico, and most of Europe allow the sale of sex, the United States still outlaws it. It’s only legal in a handful of rural counties in Nevada. 2017 was Frank’s first year working and filing taxes as a full-time escort. It would take him some research to figure out how to file while staying in compliance with U.S. tax law.

He sought advice from friends who, for various reasons, were also unable to fully disclose their income sources. They recommended an accountant with experience in handling clients in similar situations. The accountant told Frank that even if you can’t be totally upfront with where you get your income, it’s still best to declare all of it. “Make sure all of your income is accounted for,” he warned. The IRS cares less about where your money comes from than whether or not you are paying your legally determined fair share. As far as the IRS is concerned, Frank’s income comes exclusively from “consulting” work. Makes you think differently about all those McKinsey and BCG boys, doesn’t it?

The accountant also told Frank that, as a sole proprietor, he should’ve been paying estimated taxes, including self-employment taxes like Social Security and Medicare, on a quarterly basis. He might have to pay a penalty for waiting to file on Tax Day. Fortunately, Frank anticipated a large tax burden and throughout the year had been setting aside enough money to cover it.

The accountant instructed Frank to set up an LLC, to shift his revenue from self-employment to business income, expand his allowable deductions, and lower his expected taxes for next year.

“Save your receipts!” the accountant told him. Frank travels frequently for work so almost everything is deductible: airfare, taxis, entertainment, food, and hotel. State taxes would only have to be filed in his home state.

Frank’s tax situation, despite his line of work, is fairly routine. His income is steady and he hasn’t had too many awful experiences with clients. However, the financial security and relative safety he’s enjoyed while escorting may now be in jeopardy.

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On April 11, President Trump signed a new bill into law that may severely complicate sex work. The Fight Online Sex Trafficking Act and the Stop Enabling Sex Traffickers Act (FOSTA-SESTA) makes website publishers responsible if third parties are found to be posting ads for prostitution on their platforms. It could make Craigslist, Facebook, Reddit, Twitter, Google, and any number of other sites legally liable if sex work originates on their platform. The bill passed with rare bipartisan support and has already had a chilling effect on the sex work industry. Craigslist preemptively took down its classified personal ads before the bill was signed. Two weeks ago, the Justice Department seized Backpage.com, one of the largest online marketplaces used by sex workers to advertise their services and screen clients. Dozens of similar online platforms have since changed their terms of service, blocked access from the United States, or shut down completely. Some sites have moved their business operations overseas where its legal, but FOSTA-SESTA enables law enforcement to prosecute individual sex workers in the U.S. if they advertise services on those overseas platforms.

Opponents of the bill argue it threatens to push sex workers underground and onto the streets where their incomes are less stable, they’re unable to screen clients ahead of time, and they have less control over the terms of their service. This bill, they argue, endangers many of the people it aims to protect.

Did President Trump, a man accused of paying for sex, understand the ramifications of this bill when he signed it?

For now, Frank will file his taxes and pay his legally determined fair share. But as the government cracks down on sex work, escorts will have to decide for themselves how best to move forward. Frank is taking a wait-and-see approach.

I have complicated feelings about Frank’s line of work. I’m grateful it provides him financial security and affords him the time to pursue his artistic talents. But I can’t help but worry about the dangers of the business: the unsavory clientele, the health risks, the emotional consequences, and the legal exposure. At the end of the day, I have to come to terms with the fact that how Frank spends his time and earns a living is not my decision to make. Perhaps, it’s time the government understood, that too.

Jasper Sparrow is a pseudonym of a New York-based writer.