Sex worker diaries: I was raided and sent to Chicago’s infamous ‘hooker school’ During my 5yo sex worker career, I have experienced work-related fear twice. This is the story of my raid and sentence.

During my almost five-year career as a sex worker, I have experienced work-related fear exactly twice. The first time was at the very beginning of my adventures in the sex industry, when a client outed me to my mother (I got my revenge — and wrote about it here).

The second time was two weeks ago when I got arrested. After almost five years of whoring in various legal grey–and even black–areas, it finally happened.

The day started like any other; I got to work (our “fetish house”) early, brushed out my pin curls, socialized with the other girls, and was generally having a blast. The day was neither slow nor particularly busy, and everyone seemed to be in good humor. The house slave, Leif, came by and did most of our chores for us. His presence and labor always cheer us up.

Everyone left that evening, leaving myself and another girl, a submissive named “Stephanie.” We both had clients arriving within a half hour of each other, mine was established and hers was new. As I waited for my client to call and ask if it was clear to come up, I met Stephanie’s guy at the door. He was a husky Polish man in his mid-thirties with a thick accent and scruffy hair. He was better-looking than most of our clients, and seemed nervous. Nervousness isn’t uncommon, though. A lot of the younger men who come to see us haven’t experimented with fetish activities very much and have never paid for sexual services. If we were to write off every client who seemed nervous, we’d probably never even break even. Stephanie poured him a shot, which he gulped down gratefully, and led him downstairs.

With fifteen minutes until my client was set to arrive, I went outside to smoke and rub my feet in the dirt so the gentleman would have something to clean off. I was halfway done with my cigarette when Stephanie came outside.

I was immediately concerned, “Don’t you have a session?” I asked.

“Yeah, but he went to get more money.”

“More money?” I asked. This was unheard of. I was pretty sure clients weren’t allowed to leave and come back in, whether or not they intended to return with a greater tribute.

“Yeah,” confirmed Stephanie, “I upsold him to a blowjob.”

Now, some of the girls at my dungeon, mostly the submissives, do perform more overtly sexual services. Extras, all the way up to full service, are built into the price structure, but we’re allowed to set our own limits and decide what we will and will not do. That being said, we have a hard-and-fast rule to avoid upselling new clients, and to never, ever upsell a man who is not both naked and erect. Theoretically, undercover police officers are not allowed to remove their pants while conducting a sting operation, and though it happens, it’s much easier to construct a case for entrapment if the officer is naked and erect.

“Um,” I said, “he was naked and hard, right?”

“Yeah,” Stephanie replied, “and he was fingering me too. He’s cute, right?”

“I guess, but he’s kind of short. Good luck, though”

I was still nervous, but her assurance that her client was not only naked, but also handsy, made me feel better about the situation. I put my shoes back on, threw away my cigarette, and went back inside, just in time to answer my client’s call.

Stephanie’s guy wasn’t back yet when “David” walked up to the door, and I walked him back to the room, wishing I could be there to meet him at the door when he returned. There seemed to be something not totally right about the situation, but I wasn’t sure what.

The feeling of strangeness carried into my session, and I found it very difficult to get into Mistress mode. I ordered David to strip, tied up his genitalia, put a few clothespins on his nipples, and told him to get to work cleaning my feet. He took off my shoes, and got to work sucking my toes and licking the garden dirt off the soles of my feet. When I deemed my feet to be sufficiently clean, I stood up and grabbed a riding crop. David was on all fours, kissing my feet as I smacked him when I heard loud, booted footsteps in the hallway, and shouts of “POLICE, POLICE, THIS IS A RAID!”

At first I didn’t believe it was real. My first thought was that someone was playing a sick, fucked up joke on us, but when the door burst open and four men in boots and vests charged in, it was obvious this was no practical joke. I had time to make eye contact with my client and put my finger to my lips in a gesture of silence before one of the men was yelling at me to drop the “whip.”

“What whip?” I asked, ever the smartass, “I don’t have a whip.”

“The whip you’re holding!” yelled the policeman.

“You mean this riding crop? It’s not a whip, but I can put it down if you like.”

“Drop it, miss. Put your hands up and face the wall.”

I gave the officer my best “you have got to be kidding me” stare, but put down the riding crop and turned to face the wall with my hands on my head.

“I don’t understand why you can’t leave me and this gentleman in peace,” I said as I stared at the wall, listening to the police go through the drawers in the room, most of which were full of dildos of various sizes, “we’re not doing anything illegal. This is ridiculous.”

“There was an offer of prostitution made in this house!” yelled the police officer who had mistaken the riding crop for a whip earlier. He seemed to be the leader, and what’s more he seemed very distressed at the goings on of the establishment. I silently speculated about his lack of sexual prowess.

“Who cares that there was an offer of prostitution?” I asked, “I didn’t make one! I’m just consensually beating this man and we were having a blast until you showed up.”

“This is a house of ill fame now,” replied the officer, “it’s illegal for you to be operating out of here.”

“Ill fame? What is this, the 1900s?! Besides, we aren’t really of any fame. We’re very discreet.”

“That’s it,” snapped the lead officer, “You need to go with this female officer and get your clothes.”

Apparently while I was facing the wall, a female officer had come in. She led me out of the room, where I saw Stephanie standing in the hallway. She looked small and scared.

“Are you mad at me?” she asked.

“No honey,” I replied, “I’m not mad at you. I’m mad at this situation, though.”

The policewoman shepherded us into the main area where our clothes were stashed in cabinets. There were police everywhere. Some of them were rifling through our drawers, others were looking at our call log, and two men were questioning my client, who looked frightened and ashamed.

The policewoman led Stephanie and me into the side bathroom that we all used as a sort of dressing room and watched us dress in our street clothes. I continued to protest about the ridiculousness of the situation as I put on my coat and dress, and when we were brought back out into the main area I began to ask every officer in my vicinity if they had a warrant. They didn’t need a warrant, they told me, a crime had been committed and an officer had witnessed it. When I asked if that gave them license to go through our drawers, they ignored me.

Stephanie asked me if we should call Cecilia, our boss, and I told her no. Overhearing our conversation, the head officer first said there would be no calls made until we got to the station, and then changed his mind.

“Go ahead,” he said, “call Mimi. We’ll arrest her too.”

For the purposes of this column, “Mimi” is my boss’ real name. Perhaps it shouldn’t have been shocking that the police knew who she was, but hearing her actual name come from the lips of this unpleasant man did come as a surprise to me. I tried not to show how discomfited I was by this revelation, but I’m not sure I was successful.

The police were doing their level best to keep my client away from me, as if he might be infected by uncooperative whore cooties. I wanted to apologize to him for the unfortunate circumstances, but didn’t get a chance to. They gave him a ticket and sent him on his way.

I kept asking if I could go home, no one answered me. I asked if I could get my purse, and was told I could. The moment I picked it up, however, a police officer asked me who told me I could move. I pointed out the officer who had told me I could get my purse, and he denied having said any such thing.

“That’s it,” said one of the officers, a huge, heavyset man with glasses, “you’re under arrest.”

I obediently put my hands behind my back, but continued to protest as they put me in handcuffs.

“But officers,” I asked, “what did I DO?”

“You’re present in a house of ill fame,” they said, over and over.

I sat, handcuffed and seething, in one of the chairs at the kitchen island. I watched the police tear apart my place of work, search through the cubbyholes where my friends and I kept our things, and tear apart my boss’ desk. The fact that they were violating my neat, ordered workspace and touching my friends’ and my belongings, was almost as bad as the fact that they were raiding my place of work. I considered crying. That’s what people do in these situations, right?

But I knew tears were not an option. Tears are universal sign language for weakness, and goddammit I was not weak. I would be strong for myself and for Stephanie and defiant for every hooker who had ever gotten arrested for her profession. I watch film noir. I know how to play the hard-boiled, wisecracking dame.

And so, as I sat handcuffed at the kitchen island in the main area of my work, I cracked jokes and acted like I didn’t give a damn what they did.

Finally the police decided we had sat there long enough. They told us it was time to go, and the man who had burst into my room lead me outside. I secretly hoped people were watching. I wanted everyone to see that not all criminals were crack whores and I hoped the billowing red lining of my coat would signal to them that I was a whore. Maybe it would lead them to think new thoughts about criminals and criminalized sex workers! It was stupid, I knew on some level, but hope springs eternal.

The officer opened the car door for me, but didn’t help me to get in. It’s more difficult than you’d think to get into a car with your hands are tied behind your back, but I managed. I waited in the car until another officer brought Stephanie out. No-one helped her into the car either, and she sort of flopped in. The second officer got into the passenger seat, and we drove off to the lockup.

Two cops driving continued to ask us questions, despite the fact that they hadn’t yet read us our Miranda rights.

“Why do you girls have so many dildos?” asked the man who’d arrested me. “What do you need all those dicks for, don’t you see enough as it is?”

“We’re a lesbian sex cult, officer, what do you think we need dildos for?” I asked, “Just because we don’t have cocks of our own doesn’t mean we don’t want to fill our sisters up.” My M.O. at the moment was to avoid every possible question.

“Huh,” said the cop, “right.”

“Right,” I said, “why else do you think I’d be so into beating men?”

After a few other smart-assed answers, the police moved on to obvious scare tactics.

“You know,” said the other officer, the one who’d written my client a ticket, “you girls are done. We’ve got phone taps, computer taps; it’s over for you. We’re going to get Mimi and arrest her. You’re going to have to find something else to do.”

I hoped Stephanie knew this was bullshit. There were no phone taps. There were no computer taps. If there were, the raid would have happened when Mimi was present in the building. They would have arrested her for pimping, and everything would have been over. My beloved dungeon would be on the news for human trafficking.

“Really?” I replied, “You hear that, honey? We’re going to be cracking whips at Cermak and Kedzie in a few days. I hope these officers try to pick us up. They look like a lot of fun.”

The officers were quiet for a moment, seemingly put off by my attitude.

“You know, we’re taking you ladies to the 18^th street lockup, okay? It’s the women’s lockup, it’s nicer. We’re doing you girls a favor here. If either of you have any information about any murders or drugs or anything, we might be nicer to you.”

I hoped this didn’t mean we were in for a beating, or possibly something worse once we got to the department headquarters. Law enforcement does not have a good track record when dealing with sex workers, and I wasn’t sure what to expect. Stephanie was silent and I worried she was thinking the same things I was, worrying about demands for free samples, beatings, or who knows what when we got to the station. It had immediately been clear to me that I was the one responsible for keeping her chin up and that without my jokes and constant insistence that badasses don’t cry, Stephanie would have melted into a puddle of tears and god knows what else.

“Hey,” I replied, “I don’t know about that. I’m a law-abiding citizen. I pay taxes. But you’ve seen my ID; I live in a terrible neighborhood. There are kids selling drugs all down my block. I don’t buy them, but they sure offer. Sometimes, I hear gunshots.”

The police didn’t seem to think this was amusing.

“You pay taxes,” they driver, the man who’d burst into the room, asked, “how?”

“I’m an independent contractor,” I replied, “1099, I probably pay more taxes than you do. Just because I work in a house of ill fame doesn’t mean I’m not an American.”

The cops had nothing to say to that. They stopped asking questions until we got to the station, talking among themselves, discussing some event that night. The driver was trying to convince his partner to attend some event that night, but the partner claimed he was “dressed like a bum” and therefore couldn’t go. After that, there was an awkward silence until we got to the station and the cop who was driving used a keycard to open a garage door. He drove in, opened the door for us, and watched, as first Stephanie and then I flopped ourselves out of the car.

I was released on bond and assigned a court date. My boss provided me with excellent legal representation, and I appeared at court confident that I would have to face the most minimal of consequences, if any.

In Chicago, a first arrest for prostitution or any similar offense is dealt with by assigning a class to the fallen woman. They do their best to make it cute–the class is called “UnHooked” and is paid for mainly by the fines levied on men who are caught patronizing or soliciting sex workers.

I was fairly certain I was never going to experience hooker school. Presence in a house of ill fame is not the same as prostitution and I felt there was a good case for me just being, say, a cleaning lady who wandered about in lingerie and recreationally hit guys with riding crops at my place of work.

When they called my name, my lawyer went to the front of the courtroom, some words I didn’t catch were exchanged, and he motioned for me to follow him out of the courtroom.

“They want you to take a class,” he explained. “We’d be crazy not to take it.”

“Seriously?!” I asked, “I wasn’t even doing anything illegal! This is ridiculous!”

My lawyer explained that it really didn’t matter. My charge was such that there was pretty much no way the city would let me walk away with no consequences. I could accept the class immediately, or try to fight it and end up having to take it anyway. I agreed to take the class.

When they called my name, I walked up to the front of the courtroom with my lawyer, and was given a piece of paper with the name of the program and a number to call.

As soon as I got back from court I lost no time in calling the number. An old-sounding woman answered, asked me when I’d been arrested and when my court date was. She then informed me that I would have to take a class one day before my next scheduled court appearance. This was ridiculous. I managed to talk her into letting me attend the class two months before my next appearance and listened to her speech about how it was a special class and I absolutely had to be there. I told her I’d be there, hung up, and looked up the address she’d given me on Google maps.

Hooker School, it turned out, was at 111th and Vincennes, an address so far away from any part of the city I was familiar with that I wasn’t entirely sure it was even within city limits. I’m from the south side, but this was a side farther south than I had ever been. I was going to have to get up at five in the morning if I was to be there by eight. It was weeks away, but already my anger was mounting.

In the weeks leading up to my class I took a special, sick pride in every single session. “Ha ha,” I would think every time I put a dildo in a guy’s butt or gave a footjob, “they’re going to try to teach me not to do this!” I was expecting a class that mostly consisted of scare stories and speeches about how we dumb whores need to value ourselves, as this can’t possibly be something we’d chosen.

Surprisingly, I wasn’t entirely correct.

It was pouring the day of my class. I got up when it was still dark outside, and dragged myself from Daniel’s house on the north side all the way down to 111th and Vincennes. I intended to record most of the class, and wanted to preserve my phone battery, but couldn’t resist going on a small, espresso-fueled Twitter rampage anyway. Just thinking about how my tax dollars were going to fund the punishment and persecution of myself and my fellow sex workers was too much to bear, and since none of my friends were awake I just ranted into the ether.

My anger increased when I saw the sign on the building where I was supposed to be unhooked: Christian Community Health Center. This did not bode well. I suspected it might double as one of the fake women’s health centers that tricks pregnant ladies in with promises of implied abortion, then feeds them and forces them to get ultrasounds in order to guilt them into believing the potential humans living in their uteruses are, in fact, actual current humans.

There wasn’t any evidence of such a practice inside, but that didn’t help me feel better. I looked around and saw two other girls sitting in chairs, presumably my new classmates. There was a young, pregnant black woman and a Ukrainian girl. They looked at me as if I was an insane person as I went to sit with them.

“Are you here for Unhooked? You don’t even look like you belong here!” the black girl exclaimed.

“No,” the Ukrainian agreed, “she looks like she could work here.”

I laughed, and told them that was exactly what the women at the police station had said when I was brought in. I privately wondered what it says about our society that even other whores have a set idea of what a whore does and does not look like. Neither of the girls waiting for me looked “like whores” they both looked like ordinary girls. The only thing that set me apart from them was the fact that I was dressed like it was the 1950s, as usual.

After chatting about how we got arrested for a while, we were ushered into a room and asked to fill out a survey. It asked for our ages, race, phone number, address, why we were here, and what our definition of prostitution was. I defined prostitution as “a valuable sexual service that ought to be decriminalized” and was prepared to defend that position to the death, if need be.

As we filled out our survey, three other women filtered in. A pretty young redhead, probably about my age, an old toothless woman in sweatpants, and one of the most exquisitely beautiful girls I have ever seen.

We told our arrest stories, and then a heavyset woman came in and told us she was going to play us a film about street prostitution in Chicago. It was poorly made, and mostly featured horror stories from “rescued” sex workers about how they’d been horrifically abused by their pimps and wanted to further rescue other workers. There was no mention of voluntary sex work, and the only part of the film I could really get behind was the related storyline about lobbyists trying to remove the felony charge for third-time prostitution arrests.

We all basically laughed through the film, even after the woman kept coming in to tell us it was serious, and afterwards the black girl, who I’ll call Leia for now, informed us that street work on the West Side wasn’t really even like that anymore. Most girls, she said, used their phones like she did. I asked if she’d ever been a street worker, she had! I was fascinated. I have so many luxuries and privileges as an indoor worker, and I have so many more options and so many fewer safety risks. I resolved that by the end of the class I would ask her for an interview, and hopefully get a yes.

Shortly after the film finished up, the heavyset woman came back.

“I’m here to talk to you guys about domestic violence,” she said, “we’re going to talk about the cycle of abuse and how pimps trick you.”

Great, I thought. Here we go with the “all sex workers are coerced victims, no one would ever choose this life” bullshit.

Surprisingly, this was not the case. What followed was a surprisingly sensitive discussion of actual abuse that barely even touched on the problem of pimping. I was confused. Where was the shaming? Where was the insistence that we couldn’t make choices for ourselves? Why was it that when I said, “I love my job” I was greeted with only the slightest touch of skepticism? I was immediately suspicious. They had to be buttering us up. There was no way the unhooking process would go on being this whore-positive, if only passively so.

After the discussion about abuse, we were given a lunch break, and even served lunch. Fortunately there was a Subway across the street, otherwise I would have been forced to eat the greasy chicken and limp French fries, but I thought it was sweet of them to at least consider our appetites.

As I finished my alternative lunch (Subway cookies because I am a healthy, responsible adult) and the other girls finished off their prison food, the heavyset woman who had showed us the film about Chicago street workers came in and informed us the next speaker would be a former vice detective who would inform us about the consequences of prostitution.

“Aha,” I thought, “this is where it begins.”

I was correct. Lunch was the marker between acceptance, albeit vaguely disapproving acceptance, of our choices and blatant fear mongering. The next few hours would be filled with a message that could be boiled down to “if you decide to be a whore you will get pregnant and you will die of drugs and also murder.”

Sorry for the anticlimactic end.