In place of this week’s usual Harlotry essay, Cate files a frank Q&A with a former “street walker.”

“Leia” is a 24 year old Chicago sex worker. I met her at the UnHooked program we had both been assigned to by the court, and she agreed to give me an interview.
I was pretty nervous, going into it, as I’ve never interviewed anyone before. I met her at her house in West Lawndale, and asked her a few questions. Leia is not her name, and but it’s what I’ve been referring to her as up until a couple of days ago when she told me she would like to be known as “Miss Cash Money.”

Probably the scariest thing about interviewing her was the possibility that I wouldn’t be able to remain sensitive to her humanity. I have a tendency to sort of study people even at the best of times, and I was worried my studying would take on the kind of freakshow patron creepiness other people often have when they discover what I do.

Miss Cash Money and I may both be whores, but the worlds in which we ply are trades are completely and utterly different. I work out of a beautiful condo and meet my clients through emails or phone calls; Miss Cash met hers on street corners and in cars. I’ve always been curious about the world of outdoor work (never curious enough to overcome my fear of trying it, but certainly very curious) and I went into the interview hoping to learn something… but also hoping I wouldn’t make her feel like she was under a microscope, or worse, the roof of a sideshow tent.

I opened with some basic questions, “How old are you?” “Is it cool if I record this?” “What would you like me to call you?” “Sex work is your primary form of employment, right?” and then got to the important stuff.

“How and when did you start working, and why?” I asked. I knew enough to know most street workers started at least somewhat voluntarily, but I wasn’t really sure how it worked. Did you just walk down to known strolls, or was there some kind of initiation? It turns out it was a lot simpler than that.

“I was 21,” Miss Cash said, “I wasn’t working and I couldn’t find a job that was stable so instead, I was walking down Cicero one day, I was actually walking to Cicero and sixteenth so I could walk down 16th and go home, and one guy who I actually still roll with right now today, he stopped me and we got to talking and one thing led to another and we were at a hotel and that’s where it started.”

“How do you feel about your work now?”

I’m so familiar with The Happy Hooker Experience. I’m a very happy hooker, but I also know very well that it’s the party line. Our main defense against antis is that all sex workers love what they do, especially women. I’m not so naïve as to think this is true in every case, sex work is a job like any other: some people love it, some people are ambivalent about it, and others hate it, but love (or need) the money. I was interested to know what Miss Cash, this completely unpoliticized whore, would have to say.

“It’s not street work anymore, but I’m confident about it. I’m comfortable with it, I like it, I like the lifestyle. You know, it’s not like I’m on the streets, walking back and forth, it’s like, I’m a call girl, you know? If I was still working a nine to five this would still be an option because it’s not like it’s an all-day, every day thing, it’s when you get calls in.”

I wasn’t too surprised by this. After all, I think most of us whores are content with our choices. It’s hard not to be, considering the money that can be made. The one real downside seemed to be that since Miss Cash started on the street, the risks involved with her work had been much greater, at least at the beginning. This led to my next question.

(Photo via Shutterstock)

“As a street worker, what kinds of procedures did you use to protect yourself from police or predators?”

“I never really was worried about the police, because I was just a normal person, like they wouldn’t know to look at me twice, until the one day when I wasn’t even working. But I never had worries about the police, or predators for that matter. I kept a little .22, a little silver piece that I just had. That’s what I used to use just in case, but nothing ever happened to me.”

“So I’m assuming this means you never felt the police took advantage of you while you were a street worker?”


This breaks a common narrative of street work. My impression of the streets has always been that they were full of cops who would lure girls into their cars, get what they could, and then arrest them if they weren’t pleased with the quality of the free sample or just if they had a quota to fill. I know perfectly well that one woman’s experience is not representative of every woman’s experience, but the fact that Miss Cash hadn’t had even one unfortunate run-in with the police until she was entrapped into being arrested was a pleasant surprise. I had to know more.

“That sort of leads to the next question, since there’s this narrative of corrupt police always taking advantage of outdoor workers in media. Do you feel outdoor workers are fairly and accurately represented in film and television?”

“Yeah! Because, it’s like, especially Pretty Woman, the first part, that’s a good example, right there. Like that’s exactly how it goes.”

I was surprised at her choice of Pretty Woman as the go-to sex worker film. In my circle of pro-whore, politicized happy hookers, saying you expect life to be like Pretty Woman is akin to playing Slayer in the middle of a Westboro Baptist Church service. If you were to say your life actually was like Pretty Woman, you’d get a lecture about how Richard Gere’s character was originally a sociopath, and it shows through in a bunch of places in the movie. Whoever you’re talking to will ask you if you’re doing okay and if there’s anything they can do to help. But, as Miss Cash says later on, different strokes for different folks. I was there to interview, not rant about the damage of the hooker-with-a-heart-or-gold (and other savior myths) do to sex workers.

“So even in like, SVU-type shows where all street workers, and even some indoor workers are portrayed as drug addicts? You think that’s fair?”

“Well, no, that’s not accurate. I mean some are, like in this area right here down by my house, all the little workers around here are all addicted to drugs. But not all of them.”

“Do you think the stigma against sex workers is stronger against outdoor workers, or that since they are so often seen as victims and objects of pity, they get more of a pass?”

“Well, it’s worse, because street workers are known to be nasty, because you’re jumping in and out of cars, different cars with different guys, not washing in between. You don’t know if they aren’t using protection, you don’t know if they are. It’s different rules. Different strokes for different folks.”

This made sense. Not everyone is as conscientious about cleanliness as they ought to be, and heads are easily turned by extra money, especially in a world where many kids’ sexual educations consist of “if you have sex you will get pregnant and you will die.” I could have talked to Miss Cash about this all day, but there were other questions.

“Have you ever had any really unexpected clients? Either someone famous, or just outside the usual type?”

“Santa Claus.”

“Santa Claus?”

“It was this man, his name was Santa Claus, because he had the big white beard, the long white hair, and this big ol’ body with a red truck.”

“Sounds like Santa Claus, yeah. So what happened?”

“That was my worst experience, because it’s like, he’s big as hell, you had to lift up his stomach [to find his penis] and then, it’s like, it was so little and he wouldn’t get hard, it was just terrible.”

I know the pain of a client who can’t get it up. The first time it happened it was terrifying. Now I’m older, I’m higher end, meaning my clients tend to be older, and I understand that the older a man gets, the more common episodes of ED are, but even now it’s jarring. I hoped this didn’t mean she’d lost money.

“You were doing outdoor work about three years ago, so maybe this is a bit outdated, but how did the market work then? Were the rates fixed, were they by activity, by time, did they vary from customer to customer?”

“They were by time, it was hourly, and like, I don’t do oral, so I would try to do anal.”


“Yeah, a lot of my customers are, like, pencil small, and they come so fast, it’s just easier that way.”

“Do you think the market has changed at all since you were doing street work?”

“Yeah, they give more now, but it’s not really me, it’s them. There were certain times when we were together I used to tell them I needed more money for this or that, and now rather than having to tell them they just give it to me.”

“So it sounds like you’ve kept some of of your street clientele, even though you work from your phone now, is that right?”

“All of them, yeah.”

I was impressed at her client retention. That’s one of the most difficult things in this business. Girls get possessive, they expect men to see only them, just to keep getting a steady paycheck, the men get bored, and they move on. Was Miss Cash possibly also doing light fetish work? I knew many midrange escorts would charge extra for fetish activities, and it seemed like a smart way to get a bit more out of guys with relatively mild kinks, and I decided to ask.

“What’s the fetish market like on the street?” I asked.

“What do you mean?” she replied.

“You know, people who do the weird stuff. How is that viewed by the workers?” As Miss Cash wrinkled her nose in disgust, I already had my answer, but she elaborated.

Miss Cash wrinkled her nose even further. “Nasty, like, guys want us to do all kinds of stuff. I was against it. I’m not doing all that extra stuff.”

“So what was the most common request?” I expected toe-sucking or possibly golden showers, but I laughed at her answer. Apparently, her idea of fetish was guys asking girls to play with their balls while the girl was in top.

“That’s not fetish!” I exclaimed, “That’s so vanilla. I mean, like, guys who want to suck on your toes or something.”

“EW!” Miss Cash exclaimed, “Suck on your toes?! No! Hell no! No golden showers, none of that. I don’t do that shit you do.” She seemed distressed at the very idea, so I decided to move on to the next few questions.

“When you were growing up, what kind of messages do you feel like you got about sex work that may have informed your attitude towards it?”

“Growing up, I didn’t have nothing. Nobody told me anything, and I just fell into it meeting that one guy. After that, I started seeing stuff, but before then I didn’t really hear anything.”

“What about positive messages? Do you think outdoor workers are well enough represented and have their voices heard enough in the sex workers’ rights movement?”

“Wait, there’s a movement?”

I wasn’t completely shocked, but I was a little surprised at her surprise. I sort of assumed every non-trafficked sex worker at least knew that organizations like the Sex Workers Outreach Project existed, whether or not they were involved in them. I wasn’t expecting Miss Cash to be any kind of expert on the whore revolution, but I did think she’d at least be aware that there were a bunch of sex workers who had her back, at least on principle. Fortunately I’d come prepared. I brought a little PROS Network brochure, and handed it to her.

“There’s a sex workers’ rights movement!” I exclaimed, “It’s a real thing and you should get involved! Here is a list of sex work friendly organizations, including SWOP.”

“How long has this been?” asked Miss Cash incredulously.

“Like, ten years!” I exclaimed, “There are meetings, and it’s all run by current or former sex workers and allies of sex workers. The next time there’s a monthly meeting, you should come with me!”

Miss Cash agreed enthusiastically, and we parted ways. I was happy, not only had I made a new friend, but I’d furthered in some small way, the cause of sex worker rights. It had been a good day.