IT’S WEIRD LOOKING at your new boss’s online dating profile. It’s weirder when the website in question is collarme.com, which boasts the largest S&M community on the planet. I soon knew more than Bill’s height, hobbies and hometown—I knew the size of his junk.

It was my fault really. After two weeks of answering Craigslist part-time job advertisements—which led to three headshot scams, one generous Nigerian prince down on his luck and a very short-lived stint as a flower and vegetable seed seller by Union Square—this posting seemed a godsend. Cash, stability, cash, easy sales, cash…it was easy to overlook the first sentence, the one that called for a “submissive salesperson” to obey a “very bossy boss.” It was a little harder to ignore it after Googling his email address and finding the X-rated dating profile, but the promise of making money in my expensive new hometown was irresistible.

It was simple: I was hard up for cash and selling sunglasses at street fairs seemed innocuous, even if the bossman was into nipple tor ture and gang bangs. I imagined a bright, sunny day—the laughter of children, colorful scarves and hand-painted pottery, maybe even a juggler or a minstrel.

This was the beginning of one of the most terrible weekends of my life.There was something I had never realized in my happy bubble of consumerism: Street fairs are brutal and miserable places where the best of humanity goes to die.

Bill was a short, round, middle-aged man with beady eyes and a salt-and-pepper beard. As we shook hands at 7 a.m., more of his online stats flashed in my head—body hair (hairy), circumcised (yes). We set up the stand, joked around as if I didn’t know his detailed sexual preferences. It added another layer to our interaction though—when he laughed about me submitting myself to torture by working the whole weekend, I winced and thought of leather and whips.

I knew Saturday morning that Bill was dominant in the bedroom, but by Sunday’s end, I also discovered he was a fussy, foul-tempered, demanding boss. He refused to tell me the prices of the sunglasses but he would leave me in charge of the stand for 20 minutes at a time to go enjoy some chicken wings. Even if he were there, he demanded I say, “Price check!” or he wouldn’t answer me.

“Hey, Bill? How much is this pair?” He turned his head away as if he hadn’t heard me. “…Bill? This one here…this lady would like to know the cost.”

Finally he whipped his head around and glared at me. “I didn’t quite catch that…”

“Oh right—price check?” I sighed.

“$45!” he sang out.

Sometimes Bill would drop a pair of sunglasses and look at me expectantly. “You need to pick this up, dear,” he’d say in a condescending tone. So I’d stop painstakingly labeling the different boxes and walk over to grab whatever fell at his feet.

To give Bill some credit, he was an equalopportunity asshole. He stopped smiling around 10 a.m. He snapped at customers who tried to bargain or, God forbid, asked the same question twice. He pointed at anyone who lingered and stage-whispered to me, “Watch them.Watch them carefully.” I’m sure I was not the only person who daydreamed about smacking him with one of our faux felt display stands.

The first day, it rained. Sideways. The whole afternoon. Sellers, their faces glum and despairing, sat behind their tables watching their wares get soaked as people hurried past under umbrellas.

The negativity didn’t end when the sun came out the next day. A gleaming white Mercedes was blocking part of Bill’s space.Within 20 minutes, the tow truck had been called. People gathered to watch, viciously gleeful, as the car screechingly lurched sideways into the street.

Soon after, Bill and the poster seller next to him started a passive-aggressive conflict to see who could push his canopy further into the street. Every 10 minutes for about an hour, we would get behind the heavy tables and heave them forward, even as pairs of glasses tumbled off their racks.

“I’m not a confrontational guy,” Bill snarled as he and his competitor glared across the small gap between their stands. “But if he wants to start something, I’ll answer it. I’m not going to let him get away with that.”

On our other side, a rug-seller shrilly screamed at her two beaten down Mexican underlings.They stood there, heads bowed, as she abused them for their failure to keep everything organized.Then they trudged back to the truck to pick up another load of troublesome rugs.

Everywhere I turned at the street fair I saw unhappy, sullen faces—a sharp contrast to the friendly, lingering customers, the delicious smell of crepes and the brightly colored handbags of my fantasies.Two months ago, my eye would have been on those purses, but no longer. Now I can see the sneers of hatred between competing vendors, the condescending scowls at shoppers and the profound looks of relief at day’s end.When I walked away Sunday evening, never to return, I was $200 richer. But it also felt like I had gone a round in Bill’s dungeon—complete with discipline, humiliation and role play. I suppose I feel lucky to have avoided the collar and bullwhip.

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