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Sometimes when business was brisk he would call me up and say, “Hi, Scotty. I see you’ve got a lot of cars pulling in there tonight. Room three’s empty if you want it. It’ll be five bucks.” Or he’d say, “You can have room seven tonight. Six bucks.” I could always send people over there for a half hour. When they were finished he would change the sheets, freshen up the room, call me up, and say, “Three’s ready again if you need it.”

And so, soon enough, I had quite a slick operation going. I’d always had an entrepreneurial spirit, I guess—I suppose that’s what comes from growing up in a household without a lot of money.

A
s I reached my teens in Chicago I had become quite a little businessman. My shoe-shine service and newspaper beat were doing well. I had built up a large, steady clientele and people were recommending me to their friends. But admittedly it was not all about shining shoes and selling newspapers. I often went into bars and pool parlors with other objectives in mind. In some of the fancier places a guy would have me buff his shoes until they were gleaming, toss me a two-bit gratuity, and then invite me to come back to his place with him. I never refused and, of course, I always knew that the sole purpose of those little excursions was sex—which meant money. To use the slang term for it, I had begun “turning tricks.” The word had many definitions. It could refer to a prearranged sexual encounter, or it might simply imply a casual sexual acquaintance. It could also be used to refer to the person you were having sex with, especially when there was no emotional or romantic bond involved. The word could even be used as a verb, as in a sentence like, “Are you tricking that guy?” or as a noun, as in, “She’s my trick tonight.” I was learning fast.

Exposure to the effects of alcohol and the heavy drinking of some of the guys in the bars where I plied my trade induced in me a profound distaste for alcoholic drinks. That’s when I became an avowed teetotaler.

Momma remarried in 1935. Her new husband was a good-natured Welshman by the name of John Davies. At first he worked in a soybean processing plant owned by the Spencer Kellogg Company, but he subsequently became a truck driver. He was a nice guy and we kids all got along fine with him. However, his income wasn’t nearly enough to support us all, so the tips I was making from tricks served our family well. We had already moved twice by this time and after our new stepdad entered the picture we settled in a little apartment at 3801 Ellis Avenue in the South Side. While many people in our neighborhood were struggling during the long years of the Depression our stepdad, Momma, Don, Phyllis, and I always had enough to eat. Our kitchen shelves were fully stocked. In fact, all of our basic needs were met. Momma was able to stop working as hard as she had when we first arrived in the city and, under the difficult circumstances of the prevailing economic climate, things were really not all that bad for us. Amazingly, despite the late nights and other distractions, I never once missed a day of school and I still managed to get pretty good grades. I kid you not. I’ve always been diligent about everything I do. Sex, science, and shoe-shining all received equal attention!

By 1936 I started taking my shoe-shine box and my pile of newspapers deep into the North Side and the Loop areas of the city. This meant taking streetcars or the “El,” the nickname for the extensive elevated railroad rapid-transit system that served downtown Chicago and many of the suburbs.

Many a time a guy would take me home and invite a few friends over to join in the fun. I didn’t mind that at all. It was good for business. I would remain in the bedroom and the men would come in to see me one at a time. The sex consisted of a variety of activities. Most of the guys would get their rocks off by thrusting their penis between my lubed-up legs; others would jack off on me, while others would simply want oral sex. On a few occasions when I was invited to someone’s home I would see as many as fifteen people in the space of two or three hours. As each of them finished, got dressed, and filed out of the bedroom they would leave me a few coins or as much as a dollar bill. By the time the evening was finished I was substantially better off than when I arrived.

In some dive bars in these parts of town there were poker games going on, usually in a smoke-filled back room. The players were usually fat, middle-aged men, who smoked imported cigars and cussed incessantly. Just about every single one of them wore a wedding ring. When I walked into the room with my newspapers and my shoe-shine box I was always amazed at how quickly the ambience changed. The atmosphere and mood softened. The cussing stopped. The joke that someone was telling suddenly hung suspended in midair.

“Ah, here’s Scotty,” one would say, and then they would turn to look at me. There would be a nod here, a wink there, a little wave over there. After I had crawled around underneath the table to give each of them a shoe-shine one of them would invariably leave the game by mumbling, “Deal me out, Joe,” then get up, lead me into a small anteroom next door, sit down, open his arms, and, still fully dressed, invite me to cuddle up against his hot, sweaty body. With his armpits dank and odorous and the smell of liquor and cigar smoke heavy on his breath he would just sit there and clutch me tightly, either stroking my hair or gently caressing my cheek. He just wanted to hold me close for a few minutes. Then, after a while, with not a word being spoken, he would begin to rub his crotch against me. As his excitement mounted he would unbutton his fly and eventually erupt in an orgasm that made every inch of his fat, flabby frame quiver. I would remain locked up tightly against him as his heart pounded and his breathing slowly returned to normal. Then he would gently maneuver me away from him, look me up and down, force a smile across his stubbly face, and hand me a dollar. Not a word would be said. On a couple of occasions I could detect moisture welling up in the guy’s eyes as he looked at me and I can swear that once a tiny tear ran down one of their cheeks.

Sometimes, when a man left the room, another would come in and go through the same motions with me. If not, I would quietly leave, passing the players at their poker game without any of them so much as looking at me. I felt truly sorry for some of those men. I’m certain that despite their loud, gregarious, and aggressive behavior they were extremely lonely. They must have led frustrating, unhappy family lives. Even though they clearly had wives at home, they no doubt all saw hookers regularly for sex, but I guess I brought something else, something indefinable—perhaps a reminder of their own youth—back into their lives. The Depression was like that. It exposed the best and the worst in people, but it also had the effect of tearing out the deepest and most secret recesses of the soul, bringing them out for all to see.

I was totally open-minded and happy to participate in gay sex but I most welcomed those occasions when a guy arranged a ménage à trois with a wife or a girlfriend he wanted me to service or share. Although most of the men I saw were gay, many were bisexual or straight, and quite a few were married. Some of them derived pleasure by simply watching me have sex with their wives. They would sit in a chair in a shadowed corner of the bedroom quietly smoking or sipping a beer, eagerly watching the performance. It was during one of these heterosexual encounters with a man’s wife that I experienced my very first vaginal ejaculation. Although I still give credit to Frank Risnick for my first orgasm I suppose that the first occasion that I came inside a woman’s vagina was technically and clinically the real moment that I lost my virginity. I sure wish I could remember the lady’s name. But I don’t. In fact, I’m sad to say that I can’t even recollect what she looked like. Nevertheless, it was a life-altering experience; from that moment on I knew what my preference was. I had nothing against gay sex. Far from it. I had no compunction about doing whatever a guy paid me to do, but for me, sex with a woman was always more satisfying.

Even though I was blessed with a very healthy libido and sex drive, and despite all my sexual activity, if the truth be told I had not yet reached full physical maturity. I was still in my midteens. My package was still growing and if my natural equipment was not yet sufficient to satisfy the ladies I would resort to other methods to please them. I was already quite proficient at cunnilingus or, to dispense with cold clinical terminology, “sucking pussy.” There were married women who would arrange for me to come over to their homes when their husbands weren’t around to perform oral sex on them. They were never hesitant to tell me that the men in their lives nearly always demanded oral sex but seldom reciprocated. So my services in that department were increasingly in demand. In the more fashionable and well-to-do parts of town these ladies would often favor me with generous gratuities far in excess of those handed over by their spouses and gentleman counterparts.

It had long become obvious to me that sex played an enormous role in human affairs. Speaking for myself, I wasn’t infatuated with it simply because of money or raging hormones. This wasn’t just some passing physical phase that I was going through. To some extent
everyone
had sex on their minds a great deal of the time. It was blatantly clear that it was an integral and essential part of human nature. Sex defines much of who we are and what we do. It exerts immeasurable force on our thoughts and actions. I always wondered why the conventional attitude toward sex was so ridiculously uptight and conservative. I know the Victorians had a lot to do with it, but the ancient Hindus, Greeks, and Romans had dispensed with sexual taboos thousands of years ago. Why couldn’t we take a lesson from them? The rigid contemporary attitude toward sex made no sense to me at all. All it did was stifle people’s natural drives, causing untold suffering and unnecessary guilt.

D
URING THESE YEARS
a roaring prostitution trade was under way on the South Side of the city. There were areas where four or five whorehouses jostled alongside one another on a single block. In each of them there were about two dozen pretty, scantily clad young girls with peroxide-dyed hair, wearing little more than lacy, see-through robes. They sat around in groups in the front parlor, their legs either crossed or splayed wide apart as they lounged on enormous couches and padded armchairs. The furniture was piled high with garish plush pillows and the windows were always covered with faded velvet drapes. Most of these alluring ladies would be smoking, painting their toenails, or checking their overdone makeup in the tiny mirrors of their cheap little compacts as they giggled and whispered to one another. The average age of these prostitutes was somewhere between sixteen and twenty. Many were barely out of school. And they all charged a dollar for their services. A portion of that fee went to the madams or owners of the bordellos. But that was the standard price. It was a buck for a fuck. Or for a blow job. You could take your pick.

Streetwalkers, on the other hand, were in a better position to bargain with their clients. Few of them had pimps. The starting price was always a dollar but you could easily talk that down to as low as fifty or thirty-five cents. These ladies of the night were so desperate to earn something that a guy could often get a blow job for as little as a quarter. Sex was a major industry during those lean and troubled years. It not only provided a welcome relief from the harsh reality of everyday life but was also a lifesaver for many young people who simply could not find legitimate work elsewhere.

I wasn’t the only kid in town turning tricks. Other guys did it, and so did girls. And many of them tricked women—at first I was surprised to learn about it but it didn’t take the brains of a rocket scientist to realize that it was perfectly normal. Some guys liked guys. Some women preferred only women. That’s how things were. End of story. I met quite a few lesbians as I moved around the city, and if any of the men I saw wanted a young girl for their gay wives, girlfriends, or sisters, I could always connect them with someone I knew.

O
NE OF THE FEMALE TEACHERS
at the Oakenwald school that Don, Phyllis, and I attended had a brother who everyone knew was gay. I don’t remember their names but they lived together, not too far away from the school campus. I had met him at one of the gay group-sex sessions at someone’s apartment on the South Side. He was a pleasant enough sort of guy, probably in his early twenties, and quite good-looking. He had taken a shine to me and so I saw him privately now and again, always when his sister wasn’t at home, though I suspected that she secretly knew about our little get-togethers. One day while I was over there he was giving me a blow job and she walked in on us. He didn’t seem to mind but I was a little uncomfortable about it. After all, this was a teacher at my school. I pulled on my trousers and got ready to make my getaway but as I went through the tiny living room she stopped me at the front door, put her hand on my shoulder, smiled, and calmly invited me to sit down. When I saw her brother sitting cross-legged in one of the chairs, still stark naked and nonchalantly smoking a cigarette, I eased up a bit. He threw me a friendly and reassuring smile. She went on to tell me that it wasn’t only her brother who liked people of the same sex, and that she had similar inclinations. In fact, as she offered me a plate of cookies, she confided in me about how she liked young girls.

“Next time you come over, Scotty,” she cooed, “do you think you can bring someone for me, too?”

I shrugged and searched for words but before I could say anything she went on.

“Just don’t say anything to anyone, okay? Especially at school.”

No problem,
I thought. I totally got the message.

There was a very pretty, good-natured young girl with long brown hair in my class who I knew came from a very poor family. I heard that her father had been unemployed for years. While he was out looking for work, her mother stood in breadlines, collecting whatever she could to take home to feed her three children. They could certainly do with some extra cash I thought, so, as discreetly as I could, I asked her whether she would be interested in seeing the teacher. I made it very clear that physical intimacy would be involved and that she would receive a monetary reward for it. I held my breath as she took it all in, expecting to be walloped over my head at any moment. She looked away for a couple of minutes and then turned to me and nodded. How could she refuse? She knew the money would come in handy. I hugged her. We now shared a secret, a special thing, and the next time I went over to the teacher’s house to see her brother the girl came along, too.