I Failed At Getting Paid For Sex

I had 99 problems and my Sallie Mae student loan balance was one. Two years out of law school and dealing with my own unanticipated legal expenses from a DUI arrest, I was faced with unpalatable prospect of asking my parents for money for my attorney, or the truly unthinkable — having to make actual changes to my lifestyle and spending habits — I decided to start thinking outside the box. More accurately, with my box. The information super-highway led me to exactly what I was looking for: SeekingArrangement.com. God bless America.

One night, I had a fairly routine hotel tryst with a sales-executive “Charles.” Everything about the encounter was uneventful. Like most of my dates, when an amount wasn’t explicitly presented, I was wary of bringing up a specific “allowance.” I never did quite shake those nagging, if far-fetched “FBI sting operation” fears. So, I endeavored to always stay firmly on the correct side of the largely arbitrary legal line separating sugar daddy dating from actual prostitution. Charles simply said he’d “love to help me out with my monthly bills” in exchange a date that evening. Since he seemed to have all in ducks in a row otherwise, I thought it sounded like reasonably good dip into the sugar daddy grab-bag.

After we had sex, he started dressing and thumbed through his wallet. “Hang tight, gorgeous, I’m going to go hit the ATM.”

As soon as the door slammed I knew what had happened. I am a fucking idiot. No bags in the room and nothing left behind. Like the “dine and dash” restaurant patron, he had simply skipped out on the bill. Mother fucking shit, I thought, I just got 69ed and dashed! In disbelief, I called his phone, needing to hear it go to voicemail to confirm what I knew was obviously true.

To my surprise, Charles answered on the first ring, “Hey, sweetie.”

“Uh, hey, what happened to you?”

He sighed deeply. “Sweetheart, I’m sorry, I’ve had second thoughts about entering into an arrangement like this. I think deep down I’m still looking for love.” It was so much worse than I thought. “Uh, that’s fine, no hard feelings. We don’t have to see each other again. Did you find the ATM?”

“You want me to pay you?”

I laughed. “Yes, I want you to pay me.”

“Hey now, you wanted to hook up. If you want me to pay you now you are a prostitute.”

I blinked, fanning the flame rising inside me. Hell hath no fury like a cheated sex worker trying to argue with a misogynist. “Are you fucking kidding me? You changed your mind on the way to the ATM. Call me whatever you want, but you met me on Seeking Arrangement, not OKCupid. You are a monstrous human being for tricking me like that.” “That is untrue. I never tricked to you. What you did was your choice. I was sincere in what I thought I wanted. We were both looking for something, and it just didn’t work out.”

“It didn’t work out? I think it worked out pretty well for you. You busted a nut and I’m just a hooker without a pimp to beat you down. What, did you run out roofies tonight and Seeking Arrangement was your backup plan? How would you feel if a predator date-raped your daughter?”

“I am not a predator. What, so every guy who has a one night stand is a rapist? Get real! You were awfully quick to take your clothes off. You degraded yourself. As for my daughter, she would never put herself in that position.”

“Good luck sleeping tonight.” I hissed. I’m sure my lame threat sounded even more pathetic on the other end of the line.

“Thank you, I sleep well every night.”

I threw my phone on the bed and began to ponder how one goes about the process of hiring a hit man. I walked into the bathroom and puked my guts out. It would be one thing if he had just ran away like a coward into the night. Instead, the sociopath had actually rationalized the situation and believed every word he said. He didn’t think what he did was wrong. I was just a slut who wanted to get fucked. There was absolutely nothing I could do. I had never felt dirtier. I guess I finally answered the age old question–if you stiff a prostitute is it rape or theft? It feels like both. And it sucks.

I guess I could have brushed off the incident as just an isolated liability of the job, but after that experience I knew I was done. When you play with fire you’ll eventually get burned. I had discovered the fatal flaw of the Old Balls, Inc. business model–payment on the honor system. My misadventures in sugar daddy dating had come to an end. I’ll definitely be in therapy until the end of days deconstructing the layers of daddy issues that led me to voluntarily take up selling myself as viable part-time gig, but I can honestly say that I have limited regrets. I learned something from each of my sugar sweeties, and from a place of compassion and understanding I can see each of them as human beings with their own demons leading our paths to cross. Some were nice, some not so much, but at the end of the day my experiences with each of them were invaluable in their own illuminating ways. All of them, that is, except that one. Thought Catalog Logo Mark

image –Hillary Boles

More From Thought Catalog