I will always remember my first prostitute.
Lori was a sassy little brunette from a small town in western Tennessee. She had a floral tattoo on her hip, and a twang in her voice that wandered between trashy and charming. She wasn't the prettiest hooker I ever met, or the funniest, or the most seductive. She was my first, and so, nearly twenty years later, I still remember her. I'm a middle aged man now, and I understand that just about all of my memories are colored by either nostalgia or regret, but I swear I'll tell you this story as honestly as I can.
I don't mean to give the impression that I made a habit of buying sex from prostitutes. True, I've spent time with plenty of girls over the years, but I've only ever tried to buy sex from a few of them.
Let me back up for a minute. You know I'm a cop right? Or, at least I was when this happened. I just realized I was about to turn this into an elaborate shaggy dog story, only with prostitutes instead of shaggy dogs. Let me clarify: my first experience with a prostitute was also my first experience doing any kind of undercover work.
My encounter with Lori didn't come about because of some clever investigation on my part. It was because a Chicago Police detective called us to let us know an escort service was working in our town. In the motel directly across the street from the police station.
My partner and I got excited, because, you know, prostitutes across the street from the police station! We jumped at the opportunity to work on something that night other than bad check cases. I called the number and found out that a massage cost $80, and the girl would be available for one hour. I gave my name as "Sam" and made an appointment. I had no idea why I used the name "Sam." I mean, really, why not use my real name? At least I managed, in spite of my inexperience, to not ask over the phone how much the sex would cost.
So, I was tasked with the job of posing as a john. How would I do this? I tried to remember every war story I ever heard from every Chicago vice cop I'd ever been drinking with. I knew the prostitute had to be the one to offer sex for money. I was nervous, and so I decided to build on that. I created an elaborate backstory for my encounter. I would be a high school guidance counselor who had never done this kind of thing before. I would have a pregnant wife at home and I would be a perfect square. Or at least the kind of nerdy, sexually creepy square who'd be trying to get off with a prostitute at the Travelodge at eleven o'clock on a Sunday night.
We came up with a plan. I'd leave a cell phone line open so my backup could hear what was going on in the room. Once the girl said the necessary words, I'd exclaim, loudly, "Oh yeah, that's great" and the arrest team would swoop in. I was afraid that the girl would have someone with her and I'd get rolled once the door closed behind me. I was nearly as afraid that she'd take one look at me and say, COP, and that would end it.
Lori answered the door in a sheer lace teddy and a short red silk robe. "High" she said, only it sounded like "hah." "Sam?" "Yeah, I'm Sam!" I walked in and I could feel a bad case of flop sweat forming at my temples, neck and armpits. Without a badge, radio, or gun I suddenly felt more vulnerable in the presence of this petite woman than I'd ever felt.
"Relax baby, you seem nervous." She had no idea.
We made some small talk and confirmed that the price for a massage was $80. Lori asked if I was a cop. No, I said, I'm a guidance counselor, why? Just asking, she said. I asked if there were other services, and Lori said to go on and get undressed. "Ah cain't talk about anything else if you got your pants on baby."
I was wearing a v-neck sweater, a black tee shirt, jeans, and Chuck Taylors. Lori perched on the bed, a little nipple showing through the teddy, feet tucked up under her butt. I started to freak out.
I took off my sweater. Lori sat there, regarding me with a knowing half smile. I took off my Chuck Taylors. I took off my black tee shirt. Lori didn't move. I unbuckled my belt. I opened the button of my jeans, and undid the zipper. I took a breath. I opened my jeans and began to slide them down past my thighs, exposing my underwear.
The instant the waistband of my jeans cleared my junk Lori spoke:
"$140 for a blowjob, $200 for straight sex or anything else."
I found out later those prices were inflated. Lori had made me as an easy mark.
I need to mention underwear here. Not hers, mine. My bride, having a lovely sense of humor, has always enjoyed gifting me with novelty underwear. As luck would have it, that night I was wearing some--a set of silk boxer shorts bearing Dr. Seuss' "Green Eggs and Ham" characters. That's right. I unconsciously chose the undercover name "Sam" because I was wearing Green Eggs and Ham boxer shorts on which a cartoon character proclaimed "I am Sam. Sam I am."
Time to give the bust signal. "Oh, yeah, that's great!" I said. Lori looked at me, smiled, and patted the bed next to her. "Come on baby." "Oh yeah, that's great," I repeated, louder. I paused. Lori stared. "Oh yeah, that's GREAT" I called out. The cell phone had shut off and no one outside could hear a damn thing. My jeans had fallen down below my knees. I had to do something.
"Ok, I have to tell you this, I'm a police officer. You're under arrest." "THE FUCK YOU ARE." Lori bounced up and rolled toward the opposite side of the bed. I waddled after her, trying simultaneously to hitch up my pants while grabbing desperately at the retreating sex worker with my free hand. "I really am a cop" I yelled.
I managed to grab Lori, who was now shrieking for help herself, and pulled her back from the nightstand drawer she'd opened. There was a can of pepper spray inside. Back up officers rushed into the room and handcuffed her. 'Fuck, you are a cop?!" Yes, I told her. Yes I am. Lori took a deep breath and exhaled, like she was deflating. She started to shake.
"I thought you were just some crazy asshole."
We searched the room. We found some lingerie, a pair of high heels, and 36 condoms. I was relieved that she'd left her gun, a little Beretta .22, in the glove box of her car, parked outside. Lori said she carried it for protection while she was on the road, and had forgotten to bring it inside that night.
Once we were back across the street, everyone calmed down and we talked. Lori was kind of a free spirit, and she was chatty. She wasn't too angry at me for arresting her, and I certainly didn't judge her for any choices she'd made either.
Lori had come up to Chicago and was working as an escort after some other "opportunities" didn't work out. Lori got a little of her flirt back, and assured me that she probably wouldn't have shot me--she would've just used the gun to scare me.
I left the booking room for a while, and when I came back Lori looked offended. "Your partner's trying to talk me into working in a titty bar" she said. "I was just saying it might be a little easier and safer than turning tricks in a motel, you know. And she's got the body for it."
"Knock it off" I said. My partner continued, leaning in, conspiratorially. "Come on Lori, be honest. Did Joe get all the way naked? Was he smooth and hairless? I've heard he has piercings..." "Oh, stop" said Lori, grinning now, and I swear she blushed a little.
Lori bonded out. Four months later she pleaded guilty to prostitution and took one year supervision. A couple months after that we arrested another girl from the same escort service. During the investigation the girl described Lori as a coke fiend who'd do just about anything for some blow. I think that girl just said those mean things because she was jealous.
As far as I know Lori never got arrested in Illinois again. Last I heard she was back in Union, Tennessee, and I wish her well.