“Feel like making $200 the easy way?”
Sally, like me, was an artist and a pervert. The difference between us was that, at this point, I had yet to monetize my perversions. She, on the other hand, was a comparative mogul of filth. A successful dominatrix with a sterling reputation and a frankly bewildering arsenal of gear and clothing, she’d come into my life when I very unexpectedly attended the Black and Blue Ball. A friend’s friend had to drop out, which left an open ticket. I attended, but only after being fussed over by a couple of dommes, trussed up in fishnets and rope and heels. I looked, I thought, like a particularly chic lesbian. Sally used me as a footrest for a while and we escaped to her place in Queens. I woke up, realized my non-rope-heels-and-fishnet clothing was locked in my fellow partygoer’s apartment, and had to make the long trip back into the city looking, after an evening’s revelry, like a disheveled streetwalker.
But that’s not really what this story is about.
This story is about when Sally asked me if I’d like to make $200 the easy way.
At this point, we’d been lovers and play partners and friends, and I had a pretty solid idea of what she did for money. Hell, I’d had a pretty solid idea before I met her, having attended several houses of domination as a young man (if not for sex workers, I’d never have had any idea how to process my more gonzo desires). But all of my experience with sex work was on the client side. Sally wanted to know if I was ready to hop the fence.
“So he loves having me come over and make fun of his penis. And he loves it when I bring friends who humiliate him about it,” she explained.
“So it’s, what, small?”
“No. I mean, it IS, but he doesn’t like being humiliated about that.”
“Well, what the hell am I supposed to make fun of if the size is off the table?”
She smirked. “I don’t think you’ll have trouble.”
Slightly baffled, I agreed, and the next night I was on a train heading out onto Long Island. Excitement and a certain terror were building within me. Yes, this was an adventure, but was I crossing a line here? What did it mean that I was about to accept money for getting someone off? Was I going to be hauled off to some special prison for man-whores? WHAT IF HE WAS THE PO-PO?
But then I remembered that I was about to be paid $200 to make fun of some rich guy’s penis, so, you know, good deal. It was a fallow period for me as a performer. I’d begun to do burlesque, but not with any regularity, and my legit acting career was stalled. Not particularly thrilled about the idea of going back to the old days of eating 2 McChickens and walking both ways over the Brooklyn Bridge because I couldn’t afford subway fare, this sounded quite reasonable. Let’s be honest, I wasn’t about to perform urethral sounding or flesh suspension. The terror was decidedly short-lived.
(I was told years later by a brilliant woman, Jo Weldon, that when laypeople talk about “sex work,” they always focus on the first word. The second word, however, is the key.)
We were greeted at the station by a little fellow who resembled a sausage casing fresh out of the tanning bed. One of those pudgy, stocky, muscular men who’s always a bit red in the face and looks as if he simply hasn’t got enough skin to hold it all in. Bleached hair, if I’m remembering correctly. Crew cut. Thin layer of Long Island sweat at all times. We hopped into his sleek, silver automobile and away we were whisked.
Perhaps the most unnerving thing about him (and let’s call him James) was that he seemed to want to go out of his way to impress us. The ride over was a series of boasts about the size of his mansion and the number of cars he owned, but, I mean, not really a big thing because that’s not what he cared about, man. Not really his deal. I mean, sure, it’s nice to own them, because there are so many of them and they’re so shiny and nice, but his concerns tended more toward the environmental. Man.
The conversation about what really mattered to James continued as we strolled through the enormous front doors of his enormous house. The ceiling was as high as any I’d ever seen, and there were a plethora of chandeliers. The dinner table was perfectly set and all of the decor had an odd uniformity. I realized: this was a pre-fab residence. A McMansion. While most of the place had an undisturbed sterility, the things that screamed of James and his tastes stuck out like a sore thumb. A mess of unopened mail on the kitchen counter, a pile of DVDs, a surprising number of toys scattered around, and, most eyebrow-raisingly, a cardboard cut-out of Angelina Jolie as Lara Croft from a theater standee.
My god, I thought. I’m about to engage in professional kink with a 12 year-old boy.
“Most of my work is with my environmental charity. I mean, like I said, that’s my passion. That’s what drives me. It’s what pays for all, you know, THIS,” he said, shaking his head and chuckling with a garish sort of humility.
Sally and I nodded sagely. I commended him on his dedication to the Right Things.
James shrugged and grinned. “Well, we do what we can, you know? Anyway, shall we head upstairs?”
And up we went. The terror never returned, though my heart beat a bit faster as we hastened to the moment of truth. Suddenly I remembered the mystery that had been tickling my mind since I agreed to the job: what on earth was the deal with his penis? Why, apart from size, was this penis so eminently mockable? What had Sally smirked about?
Once in James’s bedroom (the door to which was guarded, gargoyle-like, by another Jolie/Croft cut-out), things got underway with surprising haste. Sally undressed to a fetching, if fairly unfancy, lingerie set, and James stripped down to nothing. And once his underwear came off, I understood. His penis was small, but that wasn’t what caught the eye.
His penis was curved.
It was curved to the left.
Not like a little curved, but curved in a way that if you’d put a red circle and bar over it, it’d look like a U-turn warning.
My memory may be playing tricks on me, but I’m fairly certain it had a curvature unlike any I’d ever imagined or seen. And it began to erect instantly. Maybe, I thought, it’ll straighten out as it fills with blood. Like a garden hose. But no, it began to leap to life and the curvature was more or less perfectly preserved.
Sally directed James to lie down and secured his hands to the bed. I was still speechless, staring in astonishment at the most eccentric cock I’d ever encountered. I imagined what it must be like to get fucked by that cock, and how perhaps if you did it with both bodies perpendicular, it might hit a woman’s g-spot well enough. But…I mean, how did one even masturbate with it? Did all of his tugs have to whip off to the left like an artist’s brush strokes?
Sally, being a professional, launched in with some very convincing and sensuous talk about how RIDICULOUS his cock was. How pathetic and WEIRD. James was in total ecstasy his eyes rolling back and his prick jumping up and down.
Sally looked over at me. “What do you think? Isn’t it silly?”
I paused for a moment. And then replied, “Yeah. It’s fucking ABSURD. I mean, is it even a cock? It’s shaped like a girl scout cookie. Did you sleep on it weird when you were a kid?”
Pulse, pulse, throb, jump. Oh holy FUCK, I was turning him on. So I continued, voicing all of those odd questions I’d nursed on first sight with what I hoped would come off as a studied aloofness.
And so it went for a good long while. I like to think I held my own, but watching Sally was an education. Much of the time I was reduced to awed laughter at how she worked him, cajoling and teasing with a virtuosic fluidity and grace. He was a puppet jangling at the end of expertly deployed strings. I, meanwhile, felt like a heckler at the world’s strangest comedy club.
Eventually, of course, James would have to cum. Sally snapped on a pair of surgical gloves and asked, “Are you ready for me to drain all of your power?”
“Yes, Mistress, please, drain all of my POWER…”
For this I had not prepared. I’d assumed Sally would just have him jack off or maybe help him along, but what she did was fascinating: she placed the tip of her gloved finger on the underside of his glans and barely moved it at all.
“Can you feel it? Can you feel me draining all of your power away?”
James writhed and groaned, helpless to whatever bizarre spell Sally was casting. His cock jolted and leaked precum, which pooled amidst his pubic hair. Sally turned to me and cocked her head. An invitation. She looked at the box of surgical gloves and then back at me. It struck me that, considering I’d come all the way here and what had transpired, it would be genuinely weird of me to turn prude at the idea. I pulled the glove onto my hand and, to see if it would make a difference, let it snap. James twitched and moaned. Oh, theater.
So I tickled his penis for a little while. My only disappointment was that, while Sally seemed to have an almost supernaturally minimalist command, I was clearly a rank amateur. After a few minutes, and a few more insults, I thought it best to let Sally finish him off.
I looked at the clock. It was almost exactly an hour since we’d entered the bedroom when James’s cock erupted and spewed several thick globules of semen. His orgasm was obviously a very intense experience for him, but I was at a certain remove. I wondered how it must be to regularly work a job where the client’s fetishes may or (more likely on average) may not align with your own. Sally seemed keen, engaged, nurturing. After so many years did it ever become difficult to muster the enthusiasm, or even the appearance of it? I’ve always felt it tasteless to ask.
As James dressed, he babbled a bit more in his signature humblebrag, but he did say something so ludicrous that I’ll never forget it.
“You know, I really envy you two.”
We looked back at him, unsure how to respond.
“I mean, you’re artists. You don’t make much money. That’s so much easier. You don’t have all the responsibility that comes with…THIS.” Again, he gestured around at his kingdom. “You know, I was walking along the beach by my house in the Hamptons the other day, and I looked out at the ocean.” His face became wistful, lost. “It was just so huge and endless. And the waves crashed on the shore. And I thought…I’d give anything to live like you guys do. No money. No responsibilities. Just free. I envy you.”
After a moment, he returned to us and smiled beamingly. “Anyway…let’s get the money out of the way.”
What do you say to that?
You don’t say anything. You smile and take your $200. And if you walk away, as I did, not feeling particularly compromised by the experience, well, you made it the easy way.