I Was a Call Girl in Trump Tower
“I think women are incredible," Derek told me on the phone before we met. “What women are capable of sexually—it's just incredible.” His voice was deep, with the hearty, peremptory inflections of a businessman.
"Well, the Kamasutra says that a woman's desire is eight times as great as a man's," I recited. On my sugar dating profile, I had described myself as smart.
It was the summer of 2014 and I was living in Chicago. A month ago, finding myself single for the first time in four years, I had created an OKCupid profile. It was scary at first, but I quickly got used to the online self-presentation, the sifting through messages, the meetups and hookups with strangers. From there it was a fairly straight shot to Seeking Arrangement.
I was drawn partly by the thrill of the taboo: the idea of “selling my body” excited me. Then there was the example of my literary idols such as Mary Gaitskill, and the vague conviction that the experience would be good for a short story or two. Perhaps most important, I was unemployed, and the profile was easier to fill out than a job application. I thought I should at least give it a try.
Derek was the first person I talked to from the site. I understood that our conversation on the phone was an interview, his way of screening sugar baby candidates. Apparently I passed. He asked me to come over to his place the next evening: 401 North Wabash Avenue, a.k.a. Trump Tower.
Derek's profile was even more minimal than mine. It listed only these essential details: He was a consultant with a net worth in the millions. He was 38. He was divorced. He could “help you meet your financial goals.” There was no photo, but he described his looks as “above average.”
When I saw him in the Trump Tower lobby the next evening, my first thought was that I had been lied to. He had a big, round gut on a frame slightly shorter than mine. As for his face, its features seemed united by a theme of piggishness. After we had exchanged greetings, I worried that my reaction had betrayed my sense of betrayal. Then I thought that if it did he must have been used to it by now.
We caught the door of a crowded elevator. I watched him punch the button for the 46th floor.
He had asked me to meet him on the hotel rather than the residential side of the lobby for the sake of discretion—he didn't want people to “talk.” I wondered, with some pleasure, whether anyone on the elevator suspected that I was a whore. Part of my pleasure came from feeling that Derek was nervous.
Once we got off, it was a short walk down the hall to his door. I thought: this is the part where the whim becomes a very bad decision. But I followed him inside. If something went wrong, I told myself, I could always text my friend.
The place was rather small. Opposite us was the living room, furnished with a white leather sofa and a glass-topped coffee table. To our right was a kitchenette with stainless steel appliances and dark marble surfaces whose scattering of papers and mugs, combined with a general shininess, made it look seldom used. The far wall was made of a window.
Derek offered me a drink, and I accepted water. While he opened the fridge I went to get a look at the view. My sandals sunk into the plush pile of the rug as I gazed down at the city lights far below. Derek might have lied about being a good-looking man, but at least he was a rich one. I was determined to soak up the opulence like a tourist imbibing the local flavor. Yes, I observed, from up here everyone on the street looks like a peon.
Derek handed me a cold bottle of Ice Mountain.
“You have a nice view,” I said.
“You like it, huh?” He was pleased. He motioned to the sofa. “Have a seat, make yourself comfortable.”
I smoothed my short flouncy dress against my butt and sat down.
“You look amazing, April.” He sat down right next to me and wrapped his arm around my shoulders. I jerked away.
“Just—hold on. Can we just talk for a minute first.” I hadn't yet forgiven him for being so ugly.
“Okay, okay, sure, whatever you want.” He seemed bemused, and spoke indulgently. “What do you want to talk about?”
The wall opposite us was almost completely covered by an enormous flat-screen TV, which was cycling through a Chromecast screensaver consisting of close-ups of dew-laden flowers. This was what I looked at while replying to Derek's questions about myself. I didn't hold back, but answered honestly, and I enjoyed our conversation. I was conscious of performing a feminine charm. It came naturally, being a mode in which I was well trained, and which inflected many of my interactions with older men, with men in positions of authority, and with my dad. When I think of this flirtatious manner I am reminded of a line from a novel: “Most people, he had discovered, won't go out of their way to punish a clown.” I had discovered that most men won't go out of their way to punish a pretty woman who flatters them with her attention. In fact, they will reward her.
But punishment and the avoidance of it—being, perhaps, the original currency—are the more intuitive terms in which to think of it. For me, anyway. Because I had always been afraid of my father. And it was out of fear that I learned the charm, the flattery, and the dissimulation that made me, that night, such a good prostitute.
“I don't get along with him very well,” I told Derek. “He has anger problems. And he won't accept that I'm an adult who can make her own decisions. Like, he's always telling me to go to law school.”
“And you don't want to do that?”
“No. I'm living my life the way I want to.”
I marvel now at the self-righteousness with which I spoke.
We talked for thirty minutes, maybe an hour. I got up to pee. When I came back to the living room, I sat down close to him. We began to make out.
He was wearing a strong cologne with I appreciated for its impersonality. I thought, “He's a good kisser.”
While we talked I had been preparing myself to let this man put his tongue in my mouth, and now I was preparing to let him fuck me. It was the usual process, only encouraged and accelerated by the circumstances. As on every date with a new person, I had to move from an initial standoffishness and distrust of the foreign to a position of openness and sympathy which, in adopting the person into the circle of what was mine and related to me, readied me to take him into my body.
And there was another part I'd been learning for even longer: how to let my self go limp and quiet so that I could be carried along by the man's loud, brash, insistent, demanding desire. This was an important skill for a sugar baby. To judge Derek unattractive, too fat and ugly for me, was too willful. It was my own plan to fuck him, but, paradoxically, its fulfillment required my surrender. Some may question this tactic, and so have I; but I would be lying if I said it didn't feel good.
We decided to move to the bedroom, which was around the corner behind the sofa. This room mirrored the setup of the other with the bed against the south wall, and, on the north, a twin giant TV screen. We climbed onto the bed and began to kiss again. Leaning back, I sat on something hard that clinked. I twisted to see what it was: a spoon, half tumbled out of an empty bowl. Derek apologized and moved the objects to the nightstand.
The deliberate motion of my mind was to ignore and forget that bowl and spoon. I was well on my way to being turned on and I couldn't let this, of all things, distract me. But as soon as I saw what it was I knew what it meant. I saw Derek lying in the bed propped up on pillows, eating a late-night bowl of ice cream while watching TV on the massive screen (so clearly a medium for porn). And with this unwelcome image, the luxury of the condo—with its furnishings out of a magazine, its superfluous kitchen, its signifying name—suddenly these lost the substance of their glamour and appeared as mere consolation: a lonely man's tacky idea of what winning looked like.
I pitied him. I would never fuck this guy if he weren't paying me. But pity was a useful emotion in reconciling myself to the task ahead of me—a warm emotion. I tried to use it to ward away the coolness of my judgment.
I put the bowl of ice cream out of my mind and let Derek take off my clothes.
To my surprise, this capitalist bastard gave amazing head. It helped that I was free of my usual compunctions about the comfort of the giver: I didn't give a fuck if he got a cramp in his neck. Even more than that, my very revulsion toward Derek enhanced my pleasure. There was something about having his piggish face buried in my pussy that made me want to squirm, but also made me come hard.
Had I gone home after that, it would have been a perfectly pleasant evening. But Derek had lots of other plans for me. He wanted me to go down on him. “That's it,” he directed me, “concentrate on my cock and balls.” I felt fortunate that his penis was small. He fucked me from behind and told me, repeatedly, “This is what you were made for, baby.” In fact what I remember most vividly about the sex, apart from its uncomfortably long duration, was the sexy-baby-talk voice he used throughout.
In what turned out to be the finale, we lay side by side while he masturbated me and narrated a long and bizarre fantasy in which he and I went to a bar, we met another guy, and Derek invited the man to “share” me. “We'll both use your pussy until it's raw and pink. It's gonna be so, so pink. I love to see a pussy that's pink like that.”
“Would you really like to have a threesome with me and another guy?” I interrupted.
“No, that's not really my thing. I just thought you might like the idea of that.”
And so I discovered that this fantasy scenario was recounted for my benefit.
“You know, I don't think I'm going to come again.”
He stopped touching me. We lay in bed for another hour. Now he talked more than I did. He spoke with derision of his ex-wife (“I don't see anything in her now, as a woman”) and with admiration of his daughter. “You can tell that my son is my ex-wife's favorite; she's always going on about how smart and talented he is. But I think my daughter has a lot to offer too.”
I had exhausted my pity for Derek. All the wetness on my body had dried up, leaving me sticky and chilled. But I still felt sorry for his daughter. It was terrible to be the daughter of a man who had given up on having relationships with women on the basis of equals.
“Well, April, what exactly are you looking for?” Derek asked at one point, then immediately added, “Let's not be transactional about it, please. I hate being transactional.”
He said he considered his last long-term relationship, with a college student whose tuition and other bills he had paid every month, “close to ideal.” We discussed my expenses and he said he could cover them. “I'll give you some cash for tonight, too.” I said OK. I did not name a price.
By that point I was so tired I hadn't the heart to negotiate. I was ready to punch out, get home, take a shower, and reconvene with myself.
I turned down Derek's offer to let me spend the night. We got dressed, and Derek went into another room to get some cash. As we walked out the door into the hallway he stuffed a handful of crumpled bills into the purse I held on my shoulder.
He called an Uber for me while we rode the elevator down. “I never take cabs anymore,” he said. “I Uber everywhere. It's great. Some of the drivers, though, I don't know where they find these people. I got into the car with this one guy, I thought I was going to get robbed. He looked like he was straight out of the ghetto. I gave him zero stars.”
“Wow,” I said, attempting to inject the word with feeling without revealing what my feelings were.
Downstairs, we stood waiting for the car next to the revolving door of the hotel lobby. “Where the fuck is this guy,” Derek grumbled after ten minutes had passed. His phone rang.
“It's the Trump Tower! The big building that says 'Trump' on it, right on the river!”
I flinched without moving. It was the quick anger of a man who was used to getting his way. I knew I was not going to come back and see Derek again.
He hung up. “What a fucking idiot. Who doesn't know where the Trump Tower is?”
“Why don't I just get a cab?” I gazed longingly at the yellow vehicles lined up along the curb.
“No, no, don't waste money. Save that money I gave you.”
Finally a car arrived, and I bid Derek goodbye. In the backseat I took the twenty-dollar bills out of my purse and counted them. $240. I would've made more money tutoring for the ACT.
I should have named a price.
Though I was bad at asking for things, I was okay with being transactional. I thought the “non-transactional” relationship that Derek envisioned would be like working for a nonprofit, the kind that expects its workers to put in extra unpaid hours for love of the cause. I suspected that he wanted the transactional side obscured both so he could feel more loved and desired, and so he could have me at his beck and call.
But this, I now realized, was exactly the opposite of what appealed to me about sex work. I didn't want an overbearing boyfriend or, worse yet, “mentor” (as some sugar daddies like to fashion themselves). No, I wanted to instrumentalize my body for my own purposes. If that form of use symbolically dispossessed my father of the body he sought to control, so much the better. But more important was to deny the meaning entirely: to deny the sanctity that others attributed to my body. I would fuck for money, and I would do it like any other job.
I counted the money a second time. Still only $240. I felt indignant. I let him put his finger in my butt! And I was young and I was beautiful—I was worth more. Derek had gotten a deal.
I had done it like any other job. But like with any other job, I had gotten screwed over.
Though I continued to do sex work for the next three months, I never saw Derek again. A year later, when I had a job in the Loop doing data entry for $14 an hour, my route from L stop to office building took me within sight of Trump Tower. I would look across the river at that proud, obnoxious phallic monument and think with contempt of Derek and his ice cream and his larger-than-life porn. Is he still living up there, looking down on all the Uber drivers, the administrative assistants, the sex workers? Probably. Is he any less lonely? I doubt it.
I no longer have that righteous sense of “living my life the way I want to” that I had at 25. At that time I said to myself: “Let them use my body for their pleasure, but they won't get me—they won't hurt me—they won't win.” A little more contact with a bleak necessity showed me that the body is vulnerable, is easily subject to their harm; and forced me to revise my terms. Now I thought, of the Dereks, the Trumps, and the bosses: “So long as they don't kill me, or make me want to die, I'll be okay—they won't win.” And here I still am today.