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My Brief Career As A Waitress Dominatrix

A high-tipping regular was obsessed with getting bossed around. The customer is always right, right?

Posted on June 6, 2015, at 9:30 a.m. ET

Jenny Chang / BuzzFeed

"Swab the deck, err…matey." I said, disguising my stuttering with the growl we've come to accept as a pirate's favorite exclamation. "Arrr... swabbie, and then use the, um-arr, tip o' yer dirty mop t' shine me shoes!"

Did I sound more Irish than pirate, I wondered?

I looked around to see if any of the nearby customers were listening. Just Steve, who seemed quite pleased with my mediocre impersonation.

"Avast ye!" I added, worried I might be overdoing it now.

"I'll be right back, matey," I said to Steve. I rushed away to clear some plates, ask Max the bartender to make another round of drinks for the first date sitting by the bar, and enter into the computer system food for the older couple by the window.

Flatbreads, extra pesto, no pine nuts, I typed in just before the iPad screen froze.

Steve had been coming into the stylish Italian restaurant where I worked on the Upper West Side for about a month and a half. At first he seemed like the kind of guy you encounter often as a waitress: the older man, sitting alone, often divorced, who clearly wants to chat. Lonely, a bit flirtatious, but nothing shocking. Steve told me the night we met that he was in his sixties, divorced three times, no kids. He casually made it known that he had money, at first working it into conversation the way people do when they want to seem like they couldn't care less.

"I'll be going to the house in East Hampton this weekend so I have to finish some errands in the city," he once said. "My Porsche is in the shop, so I have to drive the BMW up there."

Eventually, he decided to just go for it.

"I got an enormous bonus this year."

I waited for more, but that was it, so I said, "That's great, congratulations!"

He wasn't dumb, he just seemed sort of simple in his rich-person hang-ups.

He appeared to fit the usual profile until, toward the end of his meal — which consisted mostly of Glenlivet on the rocks — things took a turn for the unusual.

"Do you want to play a game?" he asked as I cleared his half-eaten shrimp, bruschetta, and mostly untouched arugula salad. It was a meal he'd insisted that I choose for him (this should have been my first clue) and then apparently didn't enjoy.

"What kind of a game?" I asked, smiling, balancing one plate delicately atop another, trying not to get tomato sauce on my sleeve.

"It's called 'Who's the Boss,'" he said, straight-faced. He was serious. "It's simple. Here, let me go first. Who's the boss?" I waited in silence.

"Well?" I asked.

"No, you tell me — who's the boss?"

"Um…." I looked around, wondering if I should just laugh and walk away. Act dumb or make it clear — somehow, in one clean gesture — that I am not to be messed with. But I was curious. "….You are?" I suggested. The customer is always right, right?

"That's not the answer I was hoping for," he said. "I like a powerful woman. Tell me you're the boss."

"I'm the boss?" I said, incredulous. And so it began.

Steve started coming in regularly, once or twice a week. He got drunk while I asked him about the women from other restaurants with whom he played The Game. He, in return, asked me what I was writing and my favorite books — then interrupted to tell me, as many men have, that I just have to read Hunter S. Thompson.

I asked him questions with genuine bemusement and a feeling of superiority.

The Game was that Steve took women to dinner after their shifts (I had an open invitation, he made clear). The woman he'd been taking out for five years, one of the original players, helped him conceive of The Game, which consisted of verbally bossing Steve around — from ordering him to hypothetically wash the dishes to requiring him to actually kneel down and beg forgiveness for some transgression. One player he'd temporarily "housed" (his word) successfully ordered him to pay her clothes, her phone, Prada sunglasses, and Marc Jacobs bags, until Steve's Jungian analyst, Hilda, implied he "had to give her up."

Hilda had some theories about the archetypes that explained Steve's submissive fantasies, though Steve — intentionally, it seemed — didn't share the specifics. To me, Hilda was the most fascinating character of all.

"It's worthy of note, Steven, that you also pay me to talk to you for an hour each week," she'd recently said. Naturally this gave Steve ideas.

Steve paid women in exchange for participation in his game. A kind of escort service incubated, for the most part, in bars and restaurants, with large tips and gifts as reward for verbal stimulation. Some will think I'm naive, but I believe The Game was actually the main event for him.

"Oh, I've scared you," Steve said a couple of times as he told me one anecdote or another.

"No, I'm fine," I replied, truly interested.

I'd often thought waitressing was a performance. Working for tips can mean smiling when you feel like shooting daggers, not laughing in someone's face when it's absolutely warranted, or simply being "on" when you'd rather be reading or taking a bath. Steve came in with unusual specifications to the job description — and additional rewards. He wanted to play at dominance and submission, and I wanted to make as much money as I could without doing anything that I didn't feel good about.

There were limits to what I would agree to, and I set them as I went. After our first conversation, I would not play The Game, per se, but continued to talk to him. I felt in control because we were at my workplace, and I trusted the owner of the restaurant. And while I wanted Steve's tips, I didn't need them; I was making enough money without him.

I felt superior knowing that he was willing to pay me to do something that was as simple for me as talking. How funny, I thought at first, to seek out women whose job it is to serve you and pay them to assert faux power over you. It really was a game! I realized, perhaps belatedly, that paying for it was obviously part of the pleasure for Steven — an integral part of The Game.

I haughtily distinguished myself from those who played The Game — not that I didn't entertain the idea of going to lunch with him (Hilda had advised him to try The Game in the daytime, without alcohol). I thought I occupied some space between Hilda and those who played — an interlocutor, just doing my job, but testing its boundaries and my own.

We talked about psychoanalysis and philosophy, about books and movies, and, most often, about the "women he visited." My curiosity alone earned me 200% gratuities (the most I ever got was a $200 tip for an $80 bill), but that's not to say he stopped trying to get me to play.

"If you're the boss, would you make me clean your apartment?" he asked the first night. Later, "Would you have me kneel down and beg?" And soon, "Would you make me wash your panties?"

It was the word "panties" that pulled the reins on my advancing curiosity. First, it's a word I never use. And second, I was not going to let him talk about panties — not mine, someone else's, or hypothetical — while other customers were in earshot. I needed to keep this job. But I also wanted his tips.

"Oh, now I've scared you," Steve said again.

"I'm fine," I said, annoyed. "If I get uncomfortable, I feel very capable of asking you to leave, or of asking my manager to help you leave. I think maybe you're the one who's scared in this situation." I felt in charge, but then that was exactly what he, grinning, wanted. It took all I had to keep myself from rolling my eyes.

I suggested we use our imaginations to a different conversational end. The compromise we made was this: We would try a different game. A role-play, he suggested. "Nothing overtly explicit," I'd said, eyeing customers a table over.

"So where are we?" Steve asked.

"Hold on," I said, taking orders and walking drinks from the bar while I thought about it. A farm? No, too dirty — could easily be made sexual. A circus? No, too weird — could easily be made sexual.

"A pirate ship," I said when I returned. They didn't even have women on pirate ships. "Panties" would be irrelevant — or at least would be called bloomers. "I'm a rum-trading pirate captain," I continued. He would be, he decided, my faithful servant and swabbie. "As in someone who swabs the deck," he explained. Of course this was still The Game, just in costume.

"Shiver me timbers! Haul up the anchors and let down the, um, sails." I explained the ship's course — we would circumnavigate Cuba, then land in Jamaica, and I told him, again, to swab the deck. I couldn't think of what else a swabbie did. The action defined him.

"Captain, I've brought ye the finest pearl off the coast o' Montego Bay. 'Tis the shiniest gem in all the land!" he said. It seemed genuinely fun for him. Like he might productively harness his interests into an improv class.

"Eh, no thanks," I said, shrugging, "I don't care for it." I turned to greet the couple who had just arrived, turning my back to Steve.

"Hi, welcome, would you two like to sit at the bar or at a table?" I led them to the table across the room, as far from Steve as possible. As they looked over their menus, I ran some drinks, took a few orders, and returned to Steve, dreading the obligation to invent more pirate-speak.

Role-play was more interesting to me in theory than in practice — at least when playing with Steve. I felt like I was back in high school drama class — a combination of performance anxiety and boredom. In Ms. Ray's class, we played games like those on Whose Line Is It Anyway? and my stomach would be in knots when it was my turn to jump in.

So you're in a step aerobics class and all of a sudden you realize your failed blind-date from last week is next to you, but the class has already started. AND YOU HAVE JUST GOTTEN A CRAMP IN YOUR LEFT LEG.

Don't forget, "Yes, and!'"

It made me shudder to remember. Within 10 minutes I was done with the swashbuckling.

Weeks later, 15 minutes late for my last shift before leaving for a monthlong journalism fellowship abroad, Steve was already there when I arrived. And from what I could tell, already pretty drunk.

"Come'ere," he said in a too-loud voice as I passed the bar to go change. I raised my finger to indicate I'd be there when possible. In my all-black uniform, I did my makeup quickly, giddy in the bathroom mirror, imagining that in less than a week I'd be across the ocean.

After checking in with Max and taking a few orders, I got to Steve's table. He was on his way to incomprehensible. We'd only opened an hour before; he must have been drinking somewhere else before he came in.

"C'mere, c'mere," he kept saying.

"I am here," I said sharply, but unintentionally comforting nonetheless. Seeing that I needed help, Johnny, the busser, brought Steve a coffee he hadn't ordered. Steve spilled it.

"I pay you a lot of money, right?" he slurred. "I think that entitles me to a certain amount of…" he trailed off, staring at me emptily and unashamed, and as if he had already finished his sentence.

"Attention?" I offered. Our already cliché arrangement had become painfully straightforward.

He nodded, his watery blue eyes empty.

"I hadn't realized that was the agreement," I said evenly. Of course, I had realized very clearly what he'd wanted. But accepting his tips didn't mean I'd signed on any dotted lines, I thought.

"You're boring me," he said loudly.

So was I — boring myself. It was suddenly unbearably boring, all of this.

"Bring me my fucking check."

He practically yelled it. I felt heads turn. Trying to appear calm, I printed his check at the register by the bar and set it down on his table. He was speaking loudly, but I didn't hear words. "Go in the other room, I'll close him out," Max said, and I waited in the hallway between the bar and the main dining room until he'd gone. He left no tip, didn't even sign the receipt.

Later Johnny joked that I shouldn't have lost their $200 tip that night and I smiled. What part was I playing for him? The sisterly coworker? The woman abused? The dumb girl? The child who'd played with fire?

"Well, you kind of brought it on yourself," Max said, laughing, while we closed up. "You shouldn't let people like that bother you," he'd said earlier. Had I seemed bothered?

"If you hadn't wanted any part of it," my boyfriend later said, "you shouldn't have talked to him." I told him Steve's outburst upset me less than the men around me — Max, Johnny, my boyfriend — telling me what I should or shouldn't do. I was sure it was partly a misguided expression of protectiveness, especially in my boyfriend's case. But they each insisted, in different ways, that I admit to being implicated once things went sour.

I wanted to add that I hadn't been afraid, prove to them all that I wasn't surprised or bothered — not really. Or that I could be all three and still be OK. But I heard my voice, shrill and young. "I guess the thing is that I wasn't sure I didn't want any part," I said. I hadn't known what I wanted, but I had known what I was doing. I'd been the boss.