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.
DURING 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 t
he 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.
ONE 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.
In 1938, at the age of fifteen, I started high school at Tilden Technical School at the corner of Union and Forty-seventh streets, not too far away from the notorious Chicago stockyards. Things would remain much the same for me for the next three and a half years. The Depression continued its throttling hold on society. I pursued my double life at night, accumulating experiences, perspectives, and cash. Within a year war came to Europe and my newspaper sales skyrocketed. Don finally found himself a girlfriend. In time, he, Phyllis, and I gave Momma a secondhand radio that I had bought for a few dollars at a pawnshop downtown for her birthday. With it she listened to all her favorite music, especially the big bands and shows like The Shadow, The Burns and Allen Show, and the Mercury Theater on the Air, including the famous 1938 Halloween broadcast of Orson Welles’s production of “The War of the Worlds.” Life went on, and few of us could foresee what was coming.
8
Boot Camp
The Japanese attack on Pearl Harbor gave America an enormous jolt. The only positive thing that came out of the unexpected offensive was the fact that the country was grabbed by the scruff of its neck and forcibly yanked out of its long Depression. We hardly knew what hit us but employment shot up overnight as industry speedily swung into action to create the machinery of war. When we kids gathered around Momma’s radio to listen to a scratchy broadcast of President Roosevelt talking about the bombing of the U.S. Pacific Fleet we were not sure what to do. But clearly everyone was being swept into the conflict. Just a couple of weeks after hostilities began I rushed over to my best buddy Bill Nall’s house.
Bill was as straight as an arrow. He was a red-blooded, all-American male, but to help him make ends meet I occasionally fixed him up with gay or straight tricks. Like all of us, he needed extra cash. Both of us became caught up in the pervasive spirit of patriotism, eager to join in the fray against the enemy. So one day we headed for the nearest recruiting station and, despite Momma’s tearful objections, we signed up. In January 1942 I waved good-bye to my family and a handful of friends who slowly diminished in size as they stood on the platform while my train chugged out of Union Station. I was eighteen years of age, bound for boot camp in San Diego, California.
What really appealed to Bill and me was the potential excitement of frontline action. We were anxious to fight so we had joined the branch of the service that would best fulfill our ambitions, the Marine Corps. Marine recruits were paid $50 a month for serving, but I didn’t find this figure very enticing. After all, I was already earning close to that kind of money during my ventures around town. So I opted for something that paid more. I decided to become a Marine Paratrooper. Jumping out of aircraft was deemed such a difficult, dangerous, and demanding occupation that we were paid an extra $50 a month. I didn’t care about the dangers. I just wanted that extra fifty bucks. As the train rumbled across the Great Plains and the prairies toward the west my excitement grew. I was leaving the state of Illinois for the first time in my life and a great adventure lay ahead. With mounting eagerness I looked forward to my twelve weeks of military training.
The Paratroopers were a brand-new, highly specialized unit of the United States Marine Corps. They were being honed for a crucial task. As I understood it, their primary purpose was to be dropped from the air to what was known as the Burma Road, a strategically important seven-hundred-mile stretch of roadway cut through the mountainous jungle linking Burma and China. It had fallen into Japanese hands after they invaded the Burmese mainland. In support of troops from the United Kingdom, Australia, and New Zealand, the objective of the Paratroopers was to wrest the road from Japanese control and to reopen critical Allied supply lines.
When boot camp got underway I was so enamored with the handsome pose I struck in uniform that I had a picture taken of myself and sent it to Momma. I think she kept that photo on her dresser for the rest of her life. As an ex–farm boy I had a good, lean, hard body. I felt very comfortable in my own skin. I had brown hair and blue eyes, I stood about five feet ten, and was happy with my physique. A lot of my sexual partners, both male and female, praised my looks but inwardly I didn’t feel anything special about myself. As far as I was concerned I was just a regular, clean-cut, all-American boy.
Training was tough and made me fitter than I had ever been. A few weeks elapsed before we were ready to be sent to sea to engage in combat. The Pacific War was raging. All we knew was that our first objective would be to attack a number of Japanese-occupied islands. Needless to say, like most of the other guys, I was nervous about what was coming. How on earth were we Paratroopers going to jump onto those fortified islands that we were hoping to take from the Japanese? Because there weren’t any airfields near the islands, we would have to be put ashore by landing craft. Once we got onto the islands how were we going to get off them? A million questions haunted me but I guess, like all the other three thousand young men who had become Marine Paratroopers, I tried to dismiss such thoughts from my mind. What was the point of thinking about it? What was the sense in contemplating fa
ilure or capture or death? So, for the time being, we resolved to play as hard as we could before we went into battle. With few exceptions, we had one primary objective in mind: to screw ourselves silly.
As we had some time before being shipped out, a group of us got a weekend pass and decided to take a trip up the coast to visit Los Angeles. After all, the City of Angels was home to Hollywood, the film industry, and all those glamorous movie stars I had admired as a kid. In addition to looking for a little carnal action the prospect of catching even the briefest glimpse of one of those sexy actresses was enough of a reason for me to make the pilgrimage. The only way for us to get there was to hitchhike. Dozens of guys were always standing on the side of the road thumbing rides. Fortunately, folks were only too happy to help out. You never had to wait long to be offered a ride, especially if you were in uniform. The vistas of the glimmering Pacific Ocean were breathtaking as we made our way northward. Halfway up the coast we passed the Del Mar Racetrack, a famous venue renowned for its high stakes horse racing. Back in those days the road between San Diego and Los Angeles hugged the coast all the way, unlike today when traffic speeds along the 405 freeway slightly inland. As we drove by the grandstands, parking lot, and wide, sweeping racetrack I noticed that the place seemed desolate. And then we passed a big hand-painted sign that announced OWNED & OPERATED BY BING CROSBY & PAT O’BRIEN. SORRY, WE ARE CLOSED DURING THE WAR. WE WILL REOPEN WHEN HOSTILITIES ARE OVER.
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