I have a good job, a house, and a girlfriend. Our sex life is good. None of that has stopped me from paying for sex, something I’ve been doing for more than thirty years. There isn’t a missing piece in my relationship that explains it away.
It started in Chicago in the early ’90s. I was eighteen, finishing a coffee after eating at a Golden Nugget, when a middle-aged woman approached me. She chatted, complimented me, and eventually offered sex for twenty dollars. I told her I had ten. She agreed, and we went to her house.
I saw her many times over the next year. Looking back, I don’t think she was a professional sex worker. My impression now is that she was a woman who needed money. At the time, what stayed with me was how quickly an ordinary coffee could become something secret.
Eventually, I started driving through areas where sex workers walked. There was a familiar routine: eye contact, pulling over, introductions with names neither of us necessarily believed. Some women had their own improvised checks for undercover police. I couldn’t tell you whether those checks proved anything. They were simply part of the exchange.
The draw was the immediacy and the variety. I wasn’t having trouble meeting women, and I usually had a girlfriend. Still, I kept going back. If someone began recognizing my car and expecting me to stop, I sometimes changed areas. Familiarity wasn’t what I was looking for.
One encounter pushed the boundaries further than the others. After a roughly forty-five-minute drive, I stopped to relieve myself. A woman I’d met before approached, asked whether I was offering a tip, and proposed an unusual encounter involving that bodily function. I accepted. It was over in minutes, but the taboo made it stick in my memory.
Across those decades, I’ve never knowingly contracted an infection, been robbed, been stopped by police, or had a girlfriend discover the secret. I call that luck. I know what continuing says about me, and I still enjoy it.
Then the internet arrived—Craigslist, Backpage, and the rest—and finding someone became easier. That’s where the next part of the story starts.
