On Tax Evasion

Plus my Hasidic Heartbreaker

It’s tax season and this time of year has taken on new meaning since joining the industry. When I started, I was dead set on evading taxes. How would the IRS know? I was paid predominantly in cash and Cash app/Venmo was still unsupervised to some degree. I thought about the people who I had known to deal drugs and used exclusively Venmo and Cashapp for business. They didn't seem too concerned about the government coming down on them. I also saw not paying taxes as a way to condemn the government, especially TN which is the state I started working in. I didn’t want my hard earned money to go to cops or any policy that was actively trying to fuck over marginalized people. Plus, wouldn’t reporting my income out me? One of the few resources I had in TN was a badass swer in her 40’s who had started in the industry a few years before I did. We met up in person one time, and I paid her for her labor as she generously gave away crucial lessons she had learned as a worker.  

“Girl, the IRS doesn’t care if you’re a hoe. They care that you pay your taxes,” she told me as we sat and ate papa johns at my kitchen table.

But I wasn’t convinced. And after she told me she paid $1200 every 4 months or so in taxes, I made up my mind that I would not be doing such a thing. I was also vastly ignorant of tax preparation and wanted to stay in the dark about it as much as I could. Though I was paranoid the IRS would come after me due to the many nondescript payments via Cashapp, I rationalized it. 

After moving to NY, I was stuck with an ethical dilemma. I was made aware of the numerous social services that the state and city could provide for its people. Public transportation, health insurance, other services that indicated that NY cared more about its people than TN did. And don’t think I’m not aware of the complaints and the real and violent ways the NY government fucks over people all the time- especially the homeless. Not to mention the military force that is the NYPD where unimaginable amounts of tax dollars go. But relatively speaking, it was better than TN in many ways. And the right thing would be to pay for my share as well, right? 

One of the first relationships I had in NY was with a former Hasidic man and let me tell you- this man was a heartbreaker. Even sidelocks triggered me for weeks after our breakup. It was hard for me to go to Bushwick and parts of Crown Heights for a while. But before breaking my heart, he taught me all about tax evasion. I am now convinced he was a part of some sort of Hasidic mafia. Putting together what I know about the dwindling Italian mafia via Sopranos and a mob boss I had as a previous client, looking back, there was something shady going on. 

Let’s call him Sam. Sam and I connected online and agreed to meet for a spa day in NJ. Keep in mind that I didn’t really know what a real spa was before coming to NY. He purchased a car for me too and I met him at the exquisite spa which had five different levels of saunas, heated pools and waterfalls. I was highly impressed. I even got butterflies when I saw him for the first time. He was beautiful, young, and held himself confidently. He was too good to be true. I thought he was Icelandic when he started to speak. I couldn’t place his accent but he had bright blue eyes and white-blonde hair. Scandinavian I thought. I asked him where his accent was from, but he ended up revealing to me he was from a way of life I knew little about.

 Sam was born into the Spring Valley “cult”- his word not mine- which is a dense Hasidic community in upstate New York. He told me about the poor education system in his hometown. He said, “if you want to know how to do something archaic like purchase and take care of ram, the education is absolutely valuable. But besides that, we had no real education outside of religious texts.” During his childhood, he defiantly read books, learned English and became acquainted with the outside world which culminated in his exit after he was married to a woman at the age of nineteen. After his departure, he even garnered public support and went after Hasid men who threatened their wives with violence when they tried to leave their abusive marriages. He told me that the Hasidic community was a cult because anyone who tried to leave or defy the principles were condemned. 

So why did he still do business with them I wondered. One evening as we met before a Broadway show at his office at the Brooklyn Navy Yards, he filed out with other Hasid men into the parking lot. Though he lacked a long black coat and top hat, a kippah sat on his head. At my confused expression, he promptly pulled it off and threw it in the backseat as we got into his car. “Forgot I had that on,” he said passively. I did not know what to say so I said nothing.

As we dripped sweat at one of the many saunas we visited, he taught me about tax evasion. “You must get an LLC,” he advised, “it’s easy to apply, you just have to pay a small fee. I have LLC’s that pay for my LLC’s,” he bragged. I asked him if he feared the IRS coming after him and he assured me that I was in a great position as I had never paid taxes before. 

“Think of it like this, if you never get into the pool, the IRS doesn’t know you exist, but once you get into the pool, they’ll know you.” So essentially he was saying- don’t pay taxes. Amazing. That was my plan exactly and now I had the research to back it up. 

I started falling for him that first day we met at the spa. We had not met through an escort-exclusive platform but it was still sex work adjacent. A place where sugar babies could find a daddy-essentially. And though he flaunted his sex positively- his familiarity with non monogamy and play party scenes- I had a gut feeling he did not want to date a hooker so I didn’t tell him at first.

My primary partner and I ended our relationship shortly after Sam and I met. He was not exactly the reason as we had an open relationship but my romantic feelings did not help. My ex was the first person I ever loved fully, but we couldn’t be together anymore. It was traumatic so I put all my hopes in Sam to cope. I even imagined what it would be like visiting for weekends on his huge estate in Jersey. He had a four year old whom he shared with a previous partner. Was I ready to get domestic and ditch my big city dreams so soon? I considered it. So when we laid on a hotel bed in SoHo, I told Sam what I really did. I told him I was the hourly type, not just a curious girl who was interested in spa dates every few weeks. He scooted away from me and considered this new information. 

This really let him down. He thought I was a good girl, as he had called me many times before. But no longer. He told me he couldn’t date someone like me. “I was looking for a second girlfriend but I’m not interested in dating a woman that is so sexually active. The girl I date in Jersey is very inexperienced and reserved and I like that a lot.” Essentially, I was too dirty for him. Can you imagine? A man who grew up in the Hasidic community thinking a girl was dirty for having sex? My chest grew heavy and tight. I wanted to sob and beg him to reconsider. But we had an appointment for a couples massage in Korea Town in thirty minutes and goddamnit, I deserved a massage after this devastating interaction. I held in tears as we drove to the spa. After receiving our massages, an attendant gave us an entire room that consisted of at least 10 shower heads. It was insinuated that it was ours for thirty minutes or so. We were still seen as a couple after all. And though I was dirty, it didn’t stop Sam from receiving head from me for the last time. As he later called my Uber, I knew it would be the last time I would see him so I tried to hustle him out of two $500 pit tickets for a show at the Barclays for my trouble. He didn’t oblige. Oh well, at least I tried.

I was crushed about the break up and bawled to my friend on the phone. For weeks I missed him. Now, more than a year later, I hope his tax evasion catches up with him. Going into this tax season, I am paying someone else to do my taxes. Avoiding the “pool” is no longer something I am comfortable doing. Recently, I went to a tax seminar for swers which was run by an escort who had a CPA license. She echoed what my friend in TN said about the IRS just wanting our tax money. Plus, she taught us about how we could legally deduct lingerie, travel, phone bills, sex toys and condoms on TurboTax. I was sold. But I still had an overwhelming amount of W-2s and I99’s from another job that I work on the books. So she recommended me to a place in Texas who was sex worker friendly- for a high price. Whatever. I paid it. I am no longer willing to put up with the paranoia that I will be forced to pay tons of back taxes in the future. 

Tax evasion? Never. Underreporting? Maybe.