How I Learned to Grift

They hitchhiked from New York to San Francisco, stopping at high-end hustler bars Michael thought looked promising. While Michael waited outside, Lenny went in to choose an older guy who seemed loaded with booze and money. Lenny would figure out if the older guy, the mark, had a car and make sure he was really drunk before suggesting they go back to his place.

In the parking lot, Lenny maneuvered his date up against his car for a soulful kiss. Michael would throw a potato sack over the man, push him over, grab his wallet, and the two would take off. The next day Michael would phone the guy to say he’d found his wallet in a trashcan on Main Street and ask about a reward.

When they reached San Francisco at the end of their cross-country grift, Lenny stopped participating in Michael’s grifts. I loved Lenny and Lenny loved me. I was young and new to San Francisco and wanted to keep Lenny in my bed forever. Big, manly Lenny had a tiny, handheld sewing machine he brought from London. With it, he constructed leather belts, bags, patches and skirts made in a graphic hippy style. He made good money and was always generous and sweet.

When I met Michael, he was doing sex work and finding clients via a “massage” advertisement in the counter-culture weekly paper, The Berkeley Barb. A Royal Academy of Dramatic Art dropout, Michael trained his whole life to be an actor but could only believably play minor parts in minor productions. When he put on a dress, however, he became brilliant, inspired, and hysterically funny. When he played Lady Sneerwell in Sheridan’s School for Scandal and Lady Bracknell in Oscar Wilde’s The Importance of Being Earnest, Michael had the audience rolling in the aisles.

Michael wasn’t handsome but his Svengali-like persona ensured that, no matter the con, he always had followers enlisted in his scams. He had two expensive-looking Savile Row suits bought thrift-store cheap that he wore with a tie. They made him look irreproachable while running shady deals. A resounding British accent added respectability to his performance.

In the midst of his many ongoing cons, Michael dangled the notion of traveling to Europe for my twentieth birthday that July.

“Michael, I don’t have the money!” I protested.

“You can make money working my massage ad.”

“But I don’t know anything about massage,” I said.

“You give them sex, silly. That’s really what they want,” he said. “You got it, so you sell it. You still got it, so you sell it again and again and again.”

I was a dark, curly-haired kid, with sexy, Italian-looking features. I’m not Italian but Michael instructed me how to embody the fantasy. He showed me how to work Market Street and the Union Square street corner by the St. Francis Hotel. He said to tell the johns I wasn’t gay, that I didn’t kiss, give blow jobs or bottom, feeding their straight-boy fantasies. In a month I’d made $2,000.

Michael also had me help with his infamous coats-and-bags maneuver. We’d crash parties; I would be the lookout by the door while he went through coats and handbags the guests stashed in a bedroom. Michael took the drugs he found and kept most of the cash, but I was going to Amsterdam, so I did whatever he wanted me to do.

Michael’s plan was to go to LA, work the rent-boy streets, and hustle across America to New York. His actress friend, Holly Woodlawn, would put us up when we got there. Then, we’d continue on to England, Holland, and the beaches of Greece. At the time Amsterdam was the hippy, hashish-dream destination. I would do anything Michael told me to just to see Amsterdam.

We flew to LA on youth-fare tickets, but the city was dead. We retraced Michael and Lenny’s moves, hitchhiking our way to New York City. After hitting our first call-boy bar on the outskirts of Vegas, I told Michael straight up I did not like rolling drunk old men. “I won’t do it.” Finally, we went to the Trailways station and bought two tickets to New York for $56 each.

When we arrived in New York, we linked up with Holly Woodlawn, the first drag queen I’d ever met. I’d seen drag queens, but never actually talked to one. As soon as we were inside her Hell’s Kitchen railroad flat, Holly asked me to help paint her face with this goopy mixture, careful not to get it in her eyes. She kind of scared me. Holly stirred the wax and plastic in a small, chipped, enamel pot she kept on low on the stove; its fumes stank and made me dizzy. But the slop dried quickly on her face and the smell went away.

“Okay, darling,” she smiled, trying to put me at ease. “I want you to grab it and pull it off my face, honey. Pull it hard. Pull it quick.”

I looked at Michael. “She wants you to pull out all the hairs on her face so her skin feels soft and smooth,” he said.

“Why don’t you just shave? It’d be easier,” I said.

“No baby, this is the way, it feels so nice when you touch it.” Holly crooned.

So, I pulled the shit off her face in short staccato tugs with Holly letting out little screams with every pull. It was kind of disgusting, but I did what I was told.

Checking her hand mirror, she nodded approvingly, “Muy bien, darling. You make this Puerto Rican bitch look beautiful and you’re so good at it, too.” She went to kiss me but I turned my face so her lips landed on my check. Michael laughed. Holly laughed and I don’t know why, but I laughed, too.

If Michael was a grifter, Holly Woodlawn was even worse, haunting the subways looking for wealthy, well-dressed, forty-something women she could pull off in drag. Throwing the unlucky lady down on the platform, Holly ran off with her purse. Michael would help Holly dress and do make-up and we would go to New York’s best restaurants on the woman’s credit cards. The next morning, Holly would buy glamorous outfits before the cards got reported, and always got away with it.

Holly went on to star in 1970’s Trash and became a big Andy Warhol film star. Michael ended up in a cold-water trailer and died of pneumonia. Me? I found a new love – directing movies – and became the only fellow of the American Film Institute ever inducted into the Gay Porn Hall of Fame.