Photo by rachel libeskind, a few months after my “date”

Sugar Baby, Don’t Cry

The summer before my senior year of college, I decided to take a semester off, which involved moving to Chicago, buying two kittens from an animal hoarder, and regularly smoking gigantic quantities of marijuana. The part-time retail job I secured using a fabricated resume was harder than I had anticipated. At one point I tried to sell a confused-looking woman a pencil skirt that was actually an upside-down cowl neck sweater. “You are whack,” she told me, and promptly left.

The clothing store paid four dollars an hour plus commission, which I rarely received. I was quickly running out of the money I had squirreled away; I could no longer even afford the brand of hot dogs I preferred, which made me very sad (they had cheese in them). So when someone at a party said I had a nice ass and suggested I find myself a sugar daddy, I cocked my head and did some verbal nodding.

“If worse comes to worst,” I said. Then I went home, smoked a bowl with the kittens, and posted a naked photo of myself on a site for connecting sugar daddies with sugar babies.

I don’t actually remember the name of the man I eventually found. He was tan, tall, maybe sixty years old, and had large bleached teeth, like rows of Chiclets.

“I’m going to send you some materials — pamphlets and things with my face on them,” he explained over the phone. “I don’t want you to be scared that I’m not who I say I am.” He cleared his throat. “I’m trying to help you feel safe because I expect a certain amount of discretion. Do you understand?”

“Sure,” I blurted, not knowing what else to say. When the pamphlets came I stashed the package in a corner and stuck a note to it that read, “This is the guy who killed me,” just in case.

I found all of this very funny. It didn’t occur to me that I might be bad at being a sugar baby, like I was at selling clothes. I figured I had the requisite skills: a predilection for casual sex, a body without any missing parts. Sure, I’d never had an affair with an older man. But I told myself it couldn’t be too awful. There would be some part of him that was still nice to look at, and I would train my eyes on that.

On the limo ride over to the hotel bar where we had agreed to meet, my driver bemoaned the plunging temperatures, saying that whenever it got cold the crime in Chicago quickly escalated.

“People are hungry,” he declared, and our eyes locked in his rearview mirror. The look on his face was sympathetic — and I wondered briefly how many prostitutes he had ferried to this very hotel, in this very manner. I wondered whether he could tell that I was new at this. It was my first sober evening in months — and being clearheaded had the effect of making me temporarily introspective. Could the driver tell I’d grown up in the suburbs with supportive parents, and attended a liberal arts college, and was only doing this lazily, as a lark?

“There’s bubbly back there,” he told me. I smiled gratefully at him, immediately changing my mind about the need for sobriety. Maybe he didn’t know anything.

Standing in the lobby, I found myself remembering Cotillion classes, and I walked across the marble tiles pretending there was a string attached to my head that pulled it up to the ceiling, straightening my spine. Back at college, I had gone up to any boy I liked, or thought I might like, and said something along the lines of, “Would you like to have sex with me?” My seduction strategy revolved around the following principles: locate easy prey, be explicit, and get what you came for.

I had decided to go for a more toned-down, “sophisticated” version of myself that evening. “Where exactly is the bar?” I asked the man at the front desk, flipping my hair. The cheap champagne sloshed in my stomach, making me feel a little bloated, but mostly confident.

The hotel employee pointed me past the ornamental rock garden and toward the escalators, which zigged and zagged four stories overhead. On the way up, I smoothed my cheap, red satin dress against my stomach, and saw my sugar daddy the moment I shuffled off the last mechanized step. I knew it was him because of the pictures he’d sent, but also because, aside from the bartender, he was the only person there.

“Hi,” I said, swinging one leg over the barstool adjacent to his as if I were mounting a horse. Sometimes, guys at college responded to my propositions by slitting their eyes to indicate both suspicion and fear. But more often they would cooperate, following me back to my room to compete in the Sex Blooper Olympics, which is not actually a thing, though if it were, I would be the winner, because I am excitable, graceless, and lack all basic spatial reasoning skills. I cannot tell you how many times I have hit my head, bitten my partner, or fallen out of bed while making sweet love because I cannot count how many times.

“And you’re…” I had already forgotten his name. “Cute!” I kicked my feet happily. He drained his drink in one gulp. We sat there for a minute, not talking.

“Do you have any brothers and sisters?” I mumbled.

“What?” He sounded bewildered. The bartender brought him another blue cocktail, and slid a matching one toward me on a paper napkin.

“Sorry,” I said. It was quiet for a minute. I stared at his thinning, white hair and realized that if he did have any brothers and sisters they were probably already dead from natural causes. “I’m really sorry.”

“I’ve never actually done this before,” he told me.

“Me neither.” I reached for my drink.

“The thing is.” He sucked on his lips. “I… I actually had an accident two years ago that…well, I was in a wheelchair for a while. Some of my friends signed me up on the website. I’ve only been walking on my own again for the last six months.”

“Uh huh.” I assumed this was part of the same protest — that whole discourse of, I never do this sort of thing — only with more bells and whistles attached.

“What do you mean, ‘Uh huh’?”

I shrugged. “It’s fine.”

“It was my female friends, actually. They convinced me to join the site.” He smiled stiffly at me. His two front teeth were tinted blue from his drink.

Let’s get this over with, I told myself, and slapped a hand on his leg.

“Um,” he said, looking at his lap. I decided to interpret this as positive reinforcement, and gave his thigh a firm squeeze.

“I guess…” he stuttered. “Shall we—”

“Yeah,” I said.

He signaled for the check. I couldn’t tell if we were on our way to his room to do sex things, or to sit silently on the bed while watching some game show. His body language was inconclusive. So on the elevator ride up I took a deep breath and threw myself at him with my tongue already out of my mouth. He swooped back, pried my fingers from his ears, and held me at arm’s length. I wilted in his hands, picturing a sophisticated actress fainting in an old black-and-white movie.

“This is way too much for me,” he said.

The elevator door dinged open. When I tried to follow him into the hallway, he held up an admonitory hand.

I took a step back. “Are you okay?”

“You honestly don’t seem to care.” The door started to close and he reached to stop it, digging in his pocket with his free hand. “I told you, I’ve been sick — rehabilitating for an entire year — and here you are, you’re…” He held out a twenty-dollar bill. “There, for a cab.” He shook it at me. “You’re a very aggressive person.”

I stood there as he walked off. Then the elevator started to move. The doors dinged open, and another lady got in. She reached past me to press the lobby button. I wanted to speak to her, to ask her something, anything — whatever people talk about, when they’re being honest. But I averted my eyes for the rest of the descent, as if growing up were just a thing that happened so long as time kept passing.

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