Escort Stories: What Life Is Really Like As A Chicago Call Girl

Before one paid me $2,000 — to stop.

By Hannah Sward — Written on Jul 05, 2021

Photo: Pixel-Shot / Shutterstock

The first time I became a call girl I was in Chicago.

I was nineteen and living with a girlfriend on State Street near the Water Towers. She was filming a movie. The movie paid for her 23rd story apartment with its white carpet, crystal chandelier, hotel beige lamps, beige curtains, and the sunken living room that I slept in.

We ate Cobb salads five nights a week in a diner with brown vinyl booths below the high rise. The other two nights we ate Chicago burgers and drank laxative Lacie Le Beau tea. We’d wake up with stomachaches in the night and swore no more burgers or Lacie.

We rented movies and went to our first peep show next to the video store, across the street from Mickey’s Blues.

Blow up dolls in the window with blonde hair and checkered mini skirts in knee-highs. Brunettes with cherry red lips and black vinyl thigh-high boots. We walked by these blow-up girls every night that we rented a movie. Us staring at them. Them staring at us, waiting to be bought. The dolls made us feel fat and sad.

I got a job at 24 Hour Fitness — the 5:00 am shift checking people in. I stood there in the uniform of a white nylon shirt and shiny blue spandex leggings. That lasted four days.

On the last day, I went home at lunch, made a tuna sandwich, and never went back.

I spread "The Chicago Tribune" out on the table and turned to the classified job section.

Hostess at a pizzeria. Typist at a law firm. Caregiver.

I opened another can of Bumble Bee tuna and thought of my first job. I was nine years old, cleaning houses on the island I lived on.

My neighbor sat in his navy blue Hanes underwear on the floor as I was folding them and putting them in his drawer. Cleaning his sink and toilet with Ajax. Finding quarters and putting them in my pockets.

I sit down on the couch with the paper and turn to the Adult Classifieds. "Earn three hundred dollars an hour."

I get up. Open another can of tuna. Sit back down. Read about more three hundred dollar an hour jobs. I throw the can of tuna out and pick up the phone.

That Saturday I take the L train to the South Side to meet a man at a deep-dish pizza diner.

“The girls call me Mr. Sam,” he says. “Order whatever you like, but I’ll tell you they have a mean garlic bread.”

“Coffee would be good,” I say.

The waitress walks over.

“Coffee for the little lady,” he says. “And bring us a basket of that fine garlic bread.”

I didn’t know what to say and Mr. Sam, he just kind of talked like he had known me a while.

“No need to explain nothing,” he said. “And I ain’t gonna ask you a trail of questions. I got the feeling you need to make a little money and you got not a thing to worry over.”

After coffee and garlic bread, we walked across the street to his office/apartment. There was a velour zebra on the wall, and three girls sat on a jungle-green fake leather couch underneath the zebra with their legs crossed, eating baloney sandwiches. Another one sits cross-legged on the floor filing her nails. They don’t acknowledge us as we walk in.

I follow Mr. Sam to the back office.

“All I need is an ID and for you to undress,” he said.

My hair is long, dyed henna red. I am pale and nervous. I undress. Stand there. Mr. Sam leans back in his swivel chair behind his desk. Motions for me to turn around.

“Looking good,” he says. “No visible scars. No tats. I think I can do something with you.”

Two nights later I’m sitting on the jungle couch with the other girls eating baloney sandwiches on whole wheat with yellow mustard.

All I can remember about man number one was his penis.

It smelled of baby powder and the driver waiting outside didn’t say a word — before or after. I wondered if he had read a book while he waited for me.

Man number two was at a fancy hotel. “Act like you’ve been at this a while,” Mr. Sam said. “He wants a redhead who knows what she’s doing.”

In the man’s room, I just stood next to the bed in my black mini dress and heels. Kind of frozen-like.

“You’re new aren’t you?” he asked.

I undressed. We had sex. I left. He never called for me again. Baby powder man didn’t either.

That first night I went home and ate air popcorn, spraying “I Can’t Believe It’s Not Butter” on the kernels in the dark.

The next night I took the L train to work and told myself I could do it. I’d do better than the first night.

I didn’t do better.

A man wanted me to talk dirty. I couldn’t get the words out so we ate cinnamon twists together and he told me I should go with a more high-class service.

“You have the looks,” he said. “Even if you can’t talk dirty.” He gave me money without having sex and a donut for the driver on the way home.

The next guy was young and thin with curly brown hair pulled back in a ponytail. He had an apartment full of hardback books and sketches of ballerinas framed in chipped windowpanes without the glass.

He seemed sad. He was different.

If we didn’t meet the way we did, maybe ... I don’t know. He said he liked me, and I liked him and his books on the stairs leading up to his bedroom. Bukowski, and Leaves of Grass with Whitman on the cover under a tree.

“Why can’t I just meet a girl like you?” he asked.

During the day I walked a mile down State Street to Fitness World. Took an aerobic class in a room full of magenta and hot pink spandex. Walked back down State Street past the billboards for United Colors of Benetton, wedding dress shops, and boutiques then returned home to an iceberg salad with no-oil tuna and low-fat ranch dressing.

At night, I walked down the steps into the subway station. A man with a rainbow knitted hat played the flute — eyes closed, his whole body moving, real smooth-like. Coins and dollars lined his open flute case.

"Tonight," I tell myself, "I just know I’ll make some good money."

Flute man’s got these black work boots on with the laces untied; his feet look too big for his body. I wonder what he does during the day with those feet that don’t match his graceful body.

The subway reminds me of being a kid in Toronto. The winter cold. Walking down into the subway. Croissants baked at this one-stop: Eglington. Those doors would open and that warm smell would come in with the wind. I had my toe shoes and pink ballet tights in my knapsack. My hair was in a bun, all knotted up with bobby pins. Off to ballet class, I would go. Five nights a week.

And here I am ten years later, dressed in a black tube top dress with teased hair and red ninety-nine-cent Wet N’ Wild painted lips, on my way to sit with other girls on a fake leather couch under a velvet framed picture.

All of us waiting for a man to call. Hoping — and not hoping — we will fit the description.

We wait and eat more baloney sandwiches. Tonight, no sandwich. I must lose five pounds. Instead, I’ll chew a wad of double bubble gum.

Four hours later I am eating pizza with an Indian man at The Ramada Inn.

He has a red dot in the middle of his forehead. We sit crossed-legged on the brown carpet with navy blue paisleys on it that I can’t stop staring at. I’m picking off the warm pineapple pieces from my slice.

“You’re beautiful,” he says.

Later we have sex.

“I would very much like to have the pizza with you again next Friday,” he says.