Whip Smart: A Memoir (27 page)

He smiled down at me and reached into his pants’ hole, fishing around for a second before retrieving a knotted white string, about six inches long. He reached down for my hand and pressed the string into my palm. Closing his fist around mine, he jerked it toward me. His penis jiggled against the leg of his jeans, and I could see that the string was tied around its base.

“Is Mommy going to make me take money out of the money machine for her? Mommy knows how she controls the Baby.”

Not meeting his eyes, I tugged stiffly on the string (something I had done hundreds of times in the dungeon). “Oooooooh, Mommy, look what you do to me!” I tugged more violently. “Look-whatyoudotomelookwhatyoudotomelookwhatyoudotomelookwhatyoudotome!”

“Now put your little card into that little hole,” I said.

“Yes, Mommy.”

After he punched his code I pushed his hand aside and selected “Withdrawal from checking.” I withdrew $500 from his account and folded it into my coat pocket.

“Now let’s go,” I said, dropping the string so that he could tuck himself back into his pants, or at least zip his coat back up.

He did neither. Instead, he lifted the string toward me again and cooed, “But Baby doesn’t know where Mommy is taking him. Doesn’t Mommy want to lead the Baby there like a good little doggy?”

How could he not have known how little I wanted to do such a thing? My eyes said as much, I know. His eyes reminded me of the money in my pocket. We stared at each other for a long breath before I picked up the string and pushed the glass door open.

I was petrified the whole way that I would see someone I knew, that we would see anyone at all. I felt like a dog pulling on a leash, pretending that I didn’t get my dinner from the other end of it. “Why so fast, Mommy?” he whined. At one point, a couple passed by us on the other side of the street. My heartbeat matched the hurried click of the woman’s heels against the street as they neared. Wrenching on the string, I pulled him up beside me, between the building’s façade and my body, hoping to hide him in shadow. They looked at us as Tony took advantage of the close range and reached for my face, prompting me to dodge him awkwardly. I doubt they saw anything lewd, but my whole body burned with humiliation anyway.

We made it to the block of the hotel without further incident. I stopped at the corner, from which we could see people smoking outside the lobby doors.

“Close it up,” I said, and he did.

It being Friday, there was a wait for a room. This might have been the worst part. We sat silently together on cheaply upholstered chairs by the checkout desk, which was protected by a bulletproof glass window, like those in taxis. After a drunk man with an overly made-up woman in a wig tossed his key through the
opening in the desk window, I paid for an hour. The clerk avoided my eyes and only looked directly at me for a brief moment, but in that moment I knew he saw a prostitute. Maybe he noted that I was more sober or cleaner than most, but maybe he didn’t see anything beyond an image of me having sex with the big bald man behind me for money. I wanted to protest that image but was helpless. I felt trespassed, the clerk’s glance a subjugation much worse than any client’s appraisal. I elected to be seen as a sex object at the dungeon; the clients
paid
to see me this way. I had an absurd urge to show the assuming concierge my college diploma, to use vocabulary that he wouldn’t understand, to explain that I was
a dominatrix
, not a whore. He wouldn’t have cared. He wasn’t even smug; there was no spite in his assessment of me, only casual certainty and dismissal.

The room was hideous, with a mirrored ceiling and bony mattress. I turned the sound up on the television and did my best to avoid the mirrors. It was the usual exercise in withstanding. Afterward, I sent Tony away and took a shower in the yellowed stall, scrubbing my body with a tiny bar of soap. I sat on the closed toilet seat wrapped in a nubbly towel and waited to stop feeling like a whore, waited for the swell of accomplishment. It came, albeit slowly, and not quite until I emerged from those lobby doors, the shame seeping away like soft steam from the cracks in that room.

THERE WERE A FEW MORE
sessions in that hotel and then never again. From then on I stuck to Miss K’s place: a small loft on the line between SoHo and the West Village. She had a massive industrial loft out in Brooklyn and maintained this one just for work. There was a tiny kitchen and lofted bed, both of which she had outfitted with black curtains that could be pulled to hide them, leaving only the main area, about twenty square feet. Its theme was hot pink, with lots of black and Lucite accents, mostly made by her. Along the walls she had installed rows of silver hooks for paddles, floggers, crops, and every thickness of rope. The opposite wall shelved an impressive (and mostly pink) dildo collection. There were drawers of gloves, condoms, clamps, needles, cotton balls, alcohol wipes, and lube, whose use was included in her hourly rental rate of $75. She made me my own set of keys, and I started sessioning there weekly with a select group of regulars.

There was Tony, whom I hated but whose session was usually short and the money good. After his sessions, I would tell myself that it was the last time, and so it was, until I needed money or
wanted to call in sick to Mistress X’s. Then I’d give in and schedule him again. Thirty minutes of hell with him often seemed easier than a whole day in the windowless dungeon. Our ATM charade became a miserable routine.

There was Albert, the Englishman who lived in France and worked in fashion. Albert was a round, scruffy beaver of a man, with ruddy cheeks, a man purse, and a full-length fur coat. He had the body of a stodgy British businessman and the fashion sense of a Parisian fag. He liked switch sessions, and when I saw him he dommed me for an hour, then I him. We went out for dinners beforehand, and he always brought me a bottle of perfume.

There was Billy, the blue-eyed stockbroker, dubbed Hairless Billy at the dungeon, as he shaved everything but his legs and armpits with a razor. Occasionally shaving would be incorporated into his sessions. Once I got over the fear of accidentally slicing his balls open, it was something I looked forward to, a session consisting of mindless grooming and chitchat. But mostly he wanted his extraordinarily small penis tied up with string and pulled on while I laughed at him. At the dungeon a few times, we played jump rope this way. Being filthy rich and dumb as wood, Billy scheduled a lot of sessions and never tired of the same scene, the same lines. Sometimes I would blindfold him just so that I didn’t have to make all the facial expressions. Once in a while, he would let me mummify him with latex ribbon or put him in a body bag, but he wasn’t into sensory deprivation, so those parts never lasted long.

And then there was Jacob. Jacob was different. We sessioned once at a Holiday Inn in Queens and every time after that at his apartment. I had seen him for a couple of years at the dungeon, but he was Autumn’s client first. We all passed clients between us, after we got sick of them or they got sick of us. Jacob was a kind of ideal client, at least to me. First, he was young. Usually sessions with younger men, men my own age, or even within ten years of my age, were uncomfortable. The likelihood of our social spheres overlapping was too great. I don’t mean that we might have friends in
common (though that did happen once), but that we might be able to put each other into a realistic context.

But it wasn’t awkward with Jacob. It was
fun
. With other young men, they were too close but also too different and our sessions felt like trying to fit two slightly mismatched puzzle pieces together. I was always afraid of what they’d glimpse, how they would interpret me, what they would assume. With old men, I was a chess pawn and they were a checker; I just played their game and they never knew the difference. Jacob and I were alike enough to escape un-ease. We actually fit. His session didn’t turn me on sexually, but it was wildly fun. Sometimes we used a specific fantasy; schoolyard bully was a favorite. I would taunt him, imitate the lisp that he actually had as a child, and there was always a lot of spitting and face slapping. I didn’t know why those were my favorite things; I’m not sure he did, either. They were the pinnacle not of pain but of humiliation. Even now, I can think of few things more offensive than spitting in someone’s face. You have to look into their eyes to do it.

Jacob was short, clean, cute in a blue-eyed bashful way, and funny. Sessions were always so dead serious; that was part of what made them exhausting; there was no room for the actual absurdity of what happened in them, only a manufactured mocking. That’s why I loved doing sessions with other mistresses, Autumn especially. A witness lessened the pressure, allowed for the humor in the ridiculous. Jacob did this, too. I often laughed genuinely in his sessions. He could allow his own objectivity to slip in and consciously self-deprecate, acknowledging that he could see the humor as well. These were the least lonely sessions I ever had. In order to enjoy sessions, I had to enter the world of my client’s fantasy. But, until Jacob, I always had to bear the truth alone, to carry the full weight of objectivity.

Jacob had a girlfriend and a studio apartment in Astoria, a sweet residential neighborhood in Queens. He would drive his Saab to Williamsburg to pick me up and take me back to his place
to session. I loved getting into his car in jeans and a T-shirt, no lipstick. With him, the overlap of the “real” me and Justine didn’t feel awkward or false; it felt like a kind of freedom. I knew that I was a fantasy to him beyond our sessions and that he was a little bit in love with me from the very beginning.

RICK WAS A REGULAR
of mine. He was a nice, clean, single guy who made good money tutoring rich Westchester brats for the SAT and ran the marathon every year, and it took him years to work up the courage to walk through the door of Mistress X’s. I was the first domme he had ever seen, and after his inaugural session he came back every second Thursday for a year straight. Occasionally we did a stock medical scene, but usually I impersonated his tutoring clients, donning my schoolgirl outfit and pigtails. I had begun wanting to apply to graduate school around this time and considered offering to trade sessions with him for GRE tutoring but never did. I had the books to make our sessions authentic, at least. It was a switch session that began with him making lecherous advances on me, his student, lifting my pleated skirt to spank me when I didn’t finish my practice tests. This part I always tried to prolong.

“But Mr. MacDonnell! I didn’t study my vocabulary, either! Are you going to have to punish me for that, too?”

“Of course I am, you naughty little girl! You are going to get a
spanking for every word you didn’t learn!” Then he would pause, rubbing my lower back as I waited, bent over the desk. “What’s that I hear?” he’d ask, and I would sigh, resting my cheek against the open Kaplan book beneath me. “Could your mother be home early?” Then I would have to run out of the room and change into my Mean Mommy business suit.

I wasn’t proud of the clichéd route my own fantasies sometimes took, but on some level I had accepted them. The fact that I was ideologically opposed to my own misogynistic, youth-fetishizing turn-ons actually made them more exciting. Succumbing to my submissive impulses reminded me of discovering drugs as an adolescent; a door had opened into something big, something that made me feel both empowered and captive to it. It was that feeling of something awakening in me that I didn’t quite know and couldn’t quite control.

I was so weary of Mean Mommy. Rick had a startlingly high-pitched and nasal submissive voice, and I loathed the second half of our session doubly for the fun that preceded it. But he paid well and his sessions were easy to hurry. I could depend on his $300 for thirty minutes of work every other week, and when I started moving clients out of the dungeon he was one of the first I took.

Most of my clients were lonely, and their sessions demanded a certain amount of pretending that you cared about them and their problems. After my first year at the dungeon I no longer took clients who wanted sessions that were half domination, half therapy; they were more work in most cases. Still, when Rick called me one Sunday in November and invited me to go to the New York Marathon Expo at the Javits Center in Midtown, I agreed. I had made a lot of money from him and figured it was a shrewd investment, something I wouldn’t have to do more than once a year, like a company picnic. If he wanted to pretend for an hour that we were friends, I could stand it. I guessed there was a chance I could finagle a new pair of running sneakers out of it, too. My feelings about my job were complex, but sometimes I could be just that shrewd and shallow.