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The First Time I Was Paid for Sex

"I was motivated by a nagging curiosity, a voice in my head I couldn't tune out."

by Kaytlin Bailey
Jul 6 2018, 3:11pm

Photo of the author by Mindy Tucker

When I decided to get into sex work, I did my homework. For years, I read about famous courtesans, real and fictional whores, tragic victims, and heroic femme fatales. But when I decided I wanted to find out for myself what crossing that line was like, I started by googling "Escort Raleigh, NC." I found a few websites, studied the ads, reviews, and chat boards and was relieved to find a FAQ. I reverse engineered the information from the frequently asked questions directed at prospective clients.

I was motivated by a nagging curiosity, a voice in my head I couldn’t tune out. And of course, like all teenagers (and people) I was attracted to the forbidden. Even though I was young—just 17—I wasn’t in a hurry. I spent weeks online, studying.

I chose to do sex work, and choose to write about it, from a place of privilege. My story is not everyone’s but it is not especially unique. I used my privilege, in addition to online platforms and the culture of consent they created to keep myself physically and psychologically safe. Not all sex workers have had access to those tools. And after the passage of SESTA/FOSTA now none of us do.

From the message boards, I learned how background and reference checks worked, and that a fair amount of scrutiny was expected from “reputable” escorts. I learned ID checks and condoms were universal. I learned giving a client a warm washcloth after sex was a professional courtesy. I felt empowered knowing what the rules and expectations were. I insisted on things, confident hundreds of other women were enforcing the same boundaries. No client ever suggested that I was being too careful or too uptight. They seemed relieved by my dogmatism. They knew they could trust me because I was consistent and uncompromising. I never felt this way when negotiating with men in the hookup culture.

When I was ready to post my first ad, I looked at what the other ladies were charging and added $50. I wasn't interested in volume, I had no urgent bills to pay. If anyone tried to negotiate rates with me, I deleted their email and moved on to the next 50 prospective clients. I was looking for reasons not to see people.

I specified "outcall only" since I was too young to legally reserve my own hotel room. My 18th birthday was a few months away, but I presented myself as a 20-year-old college student. I could still tell clients I was too young to drink. Physically, I didn't look "barely legal." I developed early. I listed my stats, which seemed normal. Hair and eye color, bust, waist, hips.

Once I posted the ad, I was committed. I made a decision and everything that happened after was simply what happened next. It never occurred to me to break an appointment, or not go through with it. In my own mind, I became an escort after I posted my first ad, not after my first appointment, which was simply the next step.

I was overwhelmed with the response. In between class, homework, debate, rehearsal, and eating with my parents, I checked prospective clients’ references. I always asked for two. These were other working women that this guy had seen, and presumably had not robbed or upset. I didn't have to get in touch with both references, only one. Both had to be searchable on the message board I had come to rely on for information. I started to recognize the names. If someone had never seen an escort before, they couldn’t book an appointment with me. Too risky.

Nothing in particular stood out about my first client. I don't remember his email specifically. He was simply the first man who passed my screening process. I don't remember his name, job, or much about him physically. He was white, “middle aged” in that generous way old men use the phrase. He was kind and soft spoken. I didn’t tell him it was my first appointment. I don’t believe we ever saw each other again.

I remember how I felt—nervous and jittery. I wanted to be good at my job. I wanted to make a good impression.

I showed up to the hotel he’d booked ten minutes early. Because I was taking theater so seriously in school I thought I needed to change into my "costume" and "get into character.” I checked his ID at the door, pulled out my cell phone and called my best friend. I said "I'm here with So-and-So, I’ll call you in about an hour." That way Mr. So-and-So knew someone knew where I was, who I was with and what time to expect to hear from me. After the formalities were done, I went to the washroom to get ready.

I came out in my junior prom dress. It made me feel sexy and classy in a dress up way. In retrospect, this makes me blush with embarrassment and laugh at my own naïveté. Back then, I really believed “fancy women” wore something resembling a prom dress all the time.

He was still dressed but had put porn on TV. I took my dress off and got onto the bed. I asked him to join me, he did. I let him touch me. He seemed deferential, almost reverent, something I’d come to learn was true of most clients. I put a condom on him before I put it in my mouth. I hated the taste of latex, but it was a barrier, both physical and psychological. I wanted to reduce risk and contact.

The sex itself was perfunctory and short. When it was over, he turned the porn off while I got him a hot washcloth. I started to ask him about himself. Before that moment I was so focused on staying in my sexy character that I forgot. Later, I learned to make clients more comfortable with small talk earlier in the session, but there was a learning curve.

He seemed hesitant, suddenly uncomfortable. I told him we had plenty of time, which was true. Escorts are paid for their time, not for individual sex acts. I had only been in the room for 20 minutes. He told me I didn’t have to stay the whole time if I didn’t want to. We did an awkward dance. I tried to suss out his “real” feelings. Was he asking me to go? Asking me to demonstrate that I wanted to stay? I got better at this over time, but I didn’t quite know what to do at that first appointment. I decided to get dressed and leave. I almost forgot the envelope with the cash on my way out the door.

When I got in my car I drove like a maniac, blasting Garth Brooks’ “Standing Outside the Fire.” I had four crisp $100 bills. I pulled into a smokey pool hall, walked up to the bartender and ordered a Diet Coke with lemon. I asked her if she could break a hundred—she could. I sat there for an hour, vibrating with adrenaline, trying to calm down. I got into the habit of drinking Diet Coke at bars after appointments. Even though I wasn’t ordering alcohol I knew I wasn’t supposed to be there, but no one ever carded me when I was still “in character.” The money excited me in a way a client never could. I felt alive and excited. I was hooked.

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Tagged:
Sex
sex work
kink
service industry
fosta/sesta