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  He ordered me drink after drink, insisting that we were “celebrating,” but kept refusing to say what exactly this celebration was for. I thought it was slightly odd that he seemed so intent on getting wasted—it was barely noon, after all—but an alcoholic loves an enabler, and so I chose to ignore what in hindsight was clearly a red flag.

  By the time we got back to the St. Regis, where he was staying, I was more than tipsy. I made my best effort to remain upright as I stumbled through the lobby and into the elevator. Soon we were on his bed making out—sort of. We’d kiss for like five seconds, but then he’d find some ADD reason to get up and do something on the other side of the room—change the music, turn off the lights, close the curtain, turn the lights back on again. Eventually I got up and dragged him back to the bed by the arm, but then he just started awkwardly rubbing his face back and forth across my boobs, over my dress, with a blank expression on his face, as if he was meditating with his eyes open. It felt like that awkward scene in Big where Tom Hanks, who’s secretly a thirteen-year-old boy in a man’s body, is attempting to have sex with a woman while hiding the fact that he clearly has no idea what sex is. I suddenly felt like I was babysitting, and not in a hot way. I wanted to move things along, so I went for his zipper, but he dodged me and jumped up onto the bed. “This isn’t right,” he said. “It’s the wrong moment. Let’s go down to the bar and get another drink.” And so I begrudgingly put on my heels as he dragged me by my wrist down to the bar.

  The King Cole Bar at the St. Regis, with its opulent velvet armchairs and thirty-foot golden mural, is the sort of place you imagine Salvador Dalí sipping cocktails next to chic old ladies in Chanel. It’s less the sort of place you go to take a drunken afternoon nap. But there I was, laid out on the velvet couch, my Zara dress riding up over my butt. App Guy was looking over the whiskey list. Their most expensive glass was $300. “Do you have anything better?” he asked the waiter, whose forced smile conveyed a quiet rage. “I only drink whiskey that’s older than me. And I’m forty-two.”

  I put my hand on his inner thigh and slurred something along the lines of “Let’s go back upstairs.”

  “I have a better idea,” he said. “We should call up one of your friends. Don’t you have any hot friends who would come hang out with us?” Predictable, I thought. As a Millennial woman, I’ve grown to accept that first-date conversations tend to go something like this: Question 1: “Where are you from?” Question 2: “What do you do?” Question 3: “Do you have any hot friends who you might want to suck my dick with?” Sorry, but when did threesomes go from being a dessert to an appetizer?

  I suggested Madeline, but he wasn’t interested in her. “I don’t want a professional,” he said. “We need fresh blood.” I told him that, unfortunately, I didn’t have any friends who would be available to fuck a stranger at a moment’s notice at 3 p.m. on a Wednesday, and that even if I did, I didn’t know how I would explain this situation to them. He frowned and slumped back into the couch, letting out a long sigh of disappointment at the epic unfairness of life. I felt like a failed hooker.

  And then I remembered my fan.

  See, around this time I had this internet stalker fan-girl type person who’d been sending me near-daily Facebook messages with too many exclamation points. Ya know, like: “Hiiiii! I’m a student from Denmark!! I’m in New York for the summer on an internship!!!!! We should totally hang out because I’ve always felt like we could totally be best friends lolll!!!” Obviously, I never responded. But suddenly, Danish intern seemed newly appealing. “Well…” I said to App Guy, “I do have this one internet stalker who seems pretty desperate. She might be down.”

  He nodded excitedly. “She’s perfect.”

  My Facebook message read: “Hi! Sorry I somehow missed your last 5 messages. But OMG I would totally love to hang! Actually do you want to come meet me and my boyfriend right now?” Followed by the sly-face emoji and the salsa-dancing-lady emoji. I had to type it with one eye closed, like a cartoon drunk person. She responded within two minutes. Overeager. She could be at the hotel in an hour. App Guy was thrilled. I was dizzy.

  You know how’s there’s that tipping point when you’re drinking, when you’re trying to hold on to just enough sobriety to appear somewhat normal? And then there’s that other tipping point when you’re just straight-up trying to stay conscious? I was there. And then…I failed.

  The next thing I remember, I was waking up with a dull headache in a dark, empty hotel room. Scary-ish, but also, realistically, not super foreign to me. The sky outside was dark, and since it was summer and the sun didn’t set until around 8 p.m., I knew it had been at least five hours since my last memory. Wait…was I just low-key raped? I wondered while scraping dried drool off my face. I still had all my clothes on, so it seemed kosher. But my confusion quickly turned to anger: Why the fuck did App Guy abandon me here? And more importantly, is he partying with my stalker without me?

  Quickly, without thinking, I got up and marched out of the room and down the hallway. I hadn’t thought about where exactly I was going, but I was eager to get there. But about halfway down the hall I realized: Oh shit, I’m not wearing any shoes. And I don’t have my bag or my phone, which I guess are back in the hotel room? And I don’t have a key to the room. And actually, now that I’ve walked down the hall, I don’t even remember what room number I came out of. Fuck. I guess I could go to the front desk and ask for help…looking like a crazy shoeless lost hooker. But actually, I don’t even know App Guy’s last name. Uggghhh.

  For some reason—drunken rage logic—I decided to pound my fist repeatedly on the door directly in front of me. I think I wanted to use the phone? To call the front desk? Honestly, I’m not entirely sure. But I was definitely feeling confrontational and ready to yell at someone. And then the door opened, and there stood a shirtless, very sexy, and very confused-looking British man.

  “…Hi?” said the shirtless man, who was roughly thirty and had a nose that looked like it had been broken many times over, but in a good way. He stared at me, waiting for me to say something, but I just stood there with my mouth open.

  Him: “What’s going on…?”

  Me: “Oh, not much. What are you doing?”

  Him: “Not much…”

  Me: “Well, so, I’m staying at this hotel, and I happened to misplace my key. Uh. And my shoes. And my phone. Could I use yours?”

  Once I was in his room I realized I really didn’t want to make that phone call, especially in front of the shirtless hot British stranger. I was stalling. “So, what are you doing in New York? What kind of business? Oh, really? I find finance so interesting.”

  He offered me some sparkling wine from the minibar. And then we started fucking, because I’m a slut (if you haven’t figured that out already).

  I’m sure the sex was fine, although not exceptional enough for me to remember the details. You could tell he worked out, though. Anyway, sometime after (or during?) the sex I fell asleep, and the next thing I knew I was being woken up by the British guy, far too politely. “Excuse me, miss, miss. Uh, I hate to wake you, but I was just thinking that you probably don’t want to wake up here tomorrow without any of your things. Do you have somewhere to be?” He looked simultaneously scared for me and scared of me.

  I looked at the clock: 11:30 p.m. Fuck. I grabbed the phone and called the front desk. “Um, hi, so, this is awkward, but I’m staying at this hotel with a friend and I seem to be lost. I think his name is—” The person on the other end interrupted me with a long, resentful sigh. “Yes,” said the voice, “we’ve all been looking for you. Room 501.” Whoops?

  By the time I got my clothes back, the guys at the front desk had clearly informed App Guy of my whereabouts, because when I opened the door into the hallway there he was, staring at me, looking sort of amused but mainly like an angry schoolteacher.

  “What were you doing in that room?”

  “Oh, just…taking a nap.”

  He laughed a slow, man
iacal laugh and placed his hand firmly on my lower back, leading me to his room. And there on his hotel bed was my fan, naked and touching herself. She was thin with tight brown curls and the bland, rectangular brown-framed glasses of a cartoon librarian. “So nice to finally meet you,” I said, smiling awkwardly. She dropped her vibrator and ran over to hug me.

  “I hope this is okay…” she said nervously.

  “Hope what’s okay?”

  “Ya know, sleeping with your boyfriend. He said you wouldn’t mind.”

  “Oh, he’s not my…” And then I saw App Guy behind her, miming slitting his throat with his finger. I shut my mouth. “Anyway, sorry to arrive late to the party! So, where were we?” And here we go again, I thought.

  We threesomed, which was fun and technically good but not necessarily what I was in the mood for at that precise moment. Throughout the whole thing, App Guy was repeatedly telling my fan how hot she was. “God, baby, you’re gorgeous…fuck, it’s so hot when you do that…” was the constant soundtrack. I kept arching my back, trying to get attention. At some point, she got up to go to the bathroom.

  “I love fucking normal girls,” App Guy whispered, swigging more whiskey. “They just want it so badly. We should do this more often—find really unspectacular girls and coax them back to our room.” I was confused about whether I, too, was one of these unspectacular girls, but I figured that either way, this sounded like a better gig than being a noodle slave.

  When it was finally over, App Guy pulled out a duffel bag from the closet and unzipped it to reveal a ton of cash: impressive at first, until you looked closer and realized that it was mainly fives and ones. He started grabbing huge handfuls of bills and shoving them into our handbags without counting them. My fan looked confused.

  “He’s not exactly my boyfriend,” I said, yawning aggressively. “Oh, and you’re a prostitute now.” I felt oddly proud of myself, like I was becoming Madeline. My fan seemed weirdly unfazed. Maybe because she’s European? In a cab back to Brooklyn, she and I counted our money: it was $2,480, so $1,240 apiece. Not what I was promised, but I couldn’t really complain, given that I fell unconscious and then left to fuck someone else for free in the middle of my shift. I’ve never been a very loyal employee.

  This disaster threesome was the beginning of, well…I wouldn’t necessarily call it a love affair, but it was definitely an affair that I loved. As I’ve said many times, I love myself a sex maniac. Or really, anyone who the majority of society would classify as having a “problematic sexuality.” The problematic nature of his or her sexuality tends to be the variable, whether they’re hypersexual to the point of self-destruction, or they’re autistic and find sex awkward or annoying, or they’re caught up in a sex scandal, or they’re just kinda creepy in a way that would put most women off but for some reason makes me wet.

  App Guy was all of the above. In moments when most of my other sexual partners would have told me no—“No, Karley, the cabdriver doesn’t want to give you a back massage, go home, you’re drunk”—App Guy always said yes, and then he’d egg me on even further. We’d get together a couple of times a month, usually in a hotel bar, and our goal generally became to see if we could pick up another girl on the fly. It always proved to be a fun challenge. We almost always failed, but the fun was mostly in seeing the reactions of the women, and the more repulsed they were by us, the funnier we found it. Who knew being turned down could be such a turn-on? App Guy was definitely sort of a weird sadist, and would often point out all the reasons that the girl at the other end of the bar was “unremarkable” and therefore sexually appealing. I suppose that sounds mean and potentially sexist (hence the “problematic” element), but App Guy’s fault was more that he was an insecure idiot rather than a bad person, and he would never insult someone to their face. Admittedly, I’m not super proud of these moments—at least we were annoying, at most we were creepy, but we were always ultimately harmless. But still.

  And then one day, App Guy ghosted. After five months of seeing each other. I was pretty hurt, honestly. Although, I’d sort of expected it would happen. Madeline had warned me about this. Part of the appeal of these sites is that you don’t really owe anyone anything. The money acts as a barrier between you—no matter how much fun you have together or how many times you’ve fucked, the fact that you’re on the payroll creates an undeniable, and often intentional, distance in the relationship. And when one person decides it’s over, there’s rarely a formal goodbye.

  Over the next two years, SeekingArrangement changed my life pretty drastically. During that time I “dated” a handful of rich guys—five, to be exact. Some wonderful, some sad and lonely, some hot, some totally insane, all worth it. During this time I became un-poor, and the money I made allowed me the freedom to be a full-time writer. It felt like a huge weight had been lifted off my shoulders. I was financially comfortable for the first time in my life, which drastically reduced my levels of stress and anxiety. I felt more confident. And on a superficial level, the money meant that I could finally afford a good colorist so that my hair didn’t look green in certain lights, and I was able to start wearing some (somewhat) nice clothes, which I’m pretty sure are both factors in why Vogue decided to hire me to write a column. Real talk.

  I also genuinely liked the guys I met through the site. It made me feel stupid for having once bought into the all-too-common notion that all men who pay for sexual interactions must be creepy, ugly, exploitative, lonely trolls. There are many valid reasons why a man might hire a sex worker: because he is not looking for a relationship; because he wants the sex to stay casual; because he has a fetish that he feels comfortable opening up about only to someone he’s paying; because he is turned on by the exchange of money; or, simply, because he’s busy and getting an escort is just easier. Sometimes you’re too lazy to go to a restaurant. Sometimes you’re just in the mood for Seamless.

  I’m not claiming that my experience as a sex worker reflects everyone’s. But I think it’s valid to say that on SA I never felt exploited—or at least, not in a way that I couldn’t handle. In fact, I felt far less exploited on SA than I did working for Vice or at other culture magazines, where my labor was clearly underappreciated and I was drastically underpaid. Don’t get me wrong, there were definitely annoying things about SA. I went on some awful dates over the years, and I encountered a number of douchey guys through the site. But there are douches everywhere, and I’ve certainly gone on my share of awful Tinder dates. Sure, sometimes I’d be hungover in bed looking at memes, and the last thing on earth I’d want to do was go to the Upper West fucking Side and stroke some millionaire’s ego and then have really performative sex—the last thing on earth. But in the end, I always felt like it was worth it, and ultimately more interesting than handing drunk people dumplings.

  One time, while I interviewed the porn star Stoya, we were talking about how when you’re a sex worker, people either victimize you or overpoliticize your work, but they often neglect to acknowledge the practical element of the job. Stoya told me, “People love to say ‘We love that you’re making a political statement with your body!’ Or ‘We love how money-motivated you are!’ But I’m like…Um, I do porn because it sounded like fun, and like a great way to pay rent. And when it’s not fun it’s stuff I can deal with—aka how I would evaluate any other job.” Solidarity.

  The Whorearchy

  So why am I telling you all of this? And why now? As someone who regularly spills my guts on the internet as a profession, being on SA was notably a part of my life that I chose not to write about before this book.

  One reason I’ve kept this a secret for so long is because, like most people, I have parents. Specifically, Catholic parents. And no matter how many times I say, “Mom and Dad, I promise, it was fun, I made good money, and I don’t regret it,” they will still not be thrilled to hear this news. I didn’t write about it because I didn’t want to submit myself to people’s unwanted pity. I didn’t want to feel like somehow, this informat
ion would taint my success as a writer—that people who thought I was successful enough to support myself from my writing alone would suddenly think less of me.

  I ultimately decided to go there for a few reasons. For one, I had a feeling that my fear around this subject was somehow confirmation that it was exactly what I should be writing about. Also, I know that, when dealing with sexuality—or any other sensitive topic—it helps to hear the stories of people with experiences similar to our own, because it allows us to better understand our own experiences and our own bodies. It helps us to not feel so alone, basically. As I got deeper into the sugaring, and as I began to meet and interview other women in that world, I was shocked to learn how many women I already knew in New York, with ostensibly good jobs in creative industries, who were selling sex. Basically: New York rent prices + student debt + female sexual liberation = sex work. Maybe I should have been less surprised by this discovery, but it really shocked me—in a “Wow, that’s badass” way, but also in a “It sucks that you can’t make a decent living wage as a creative person in New York anymore” kind of way. In the seven years that I’ve lived in this city, most of the women I know who were able to sustain creative careers were those with rich parents and those who did sex work on the side, whether that be stripping, sugaring, domming, selling their underwear online, or letting a random man from craigslist smell their armpits (I know a girl who did that, FYI).