It was July of 1975, and I was a horny twenty-five-year-old twink on my very first trip to Chicago.
I'd spent a few days doing the whole touristy, sight-seeing thing. I'd done Michigan Avenue and State Street, Marshall Fields, the Chicago River, the Field Museum, the Art Institute, all this and more. But visiting museums and galleries and gawking at the city's sights and spectacular architecture wasn't enough to satisfy me.
After all, my friends back in Toronto had promised that the Windy City was the gay capital of the American mid-west. I'd seen plenty of well-built, corn-fed, manly men to be seen wandering its streets, but hadn't managed to connect with a single one of them so far.
By Friday night, with just a few days left of my holidays and badly in need of a change of luck, I thought about what one of my friends back in Toronto had told me; no self-respecting leather man should leave Chicago without having visited the "Gold Coast", the hottest bar in the Midwest.
Hoping the place would live up to its reputation, I spent time getting ready. I cleaned myself out with a drug store enema and pulled on my tightest black t-shirt, jockstrap, some well-worn 501 jeans and black boots, and put a leather arm band around my right bicep.
Eager to get to there but wary of arriving too early, I waited impatiently for midnight to arrive before striding out of my downtown hotel and grabbing a cab uptown. Twenty minutes later I found myself nervously following a pair of hot-looking men dressed in full leathers through the front door of the Holy Grail of leather bars; a place of dark corners, erotic wall murals, studly bartenders and sexy leather-clad customers.
Chicago was suffering through one of its insufferable July heat waves, turning the air in the place heavy, hot and sticky and almost overcoming the overworked air conditioning system. Like everyone around me, I started sweating like a pig and seeing that most of the guys were shirtless, I took mine off, hoping my skinny chest didn't look too bad in comparison to all the big pectorals on display.
Looking around, there weren't many other single guys like myself, since the crowd at what was still an early hour consisted mostly of couples or groups of friends gossiping with each other. Feeling that I stood out like a sore thumb, I bought a beer from a bare-chested barman and slunk into a corner to stare at the passing parade.
My friend in Toronto had been absolutely right about the place; there were guys in jockstraps and collars standing submissively at the side of their masters, other men ignoring the heat to wear full leathers and knee length boots, cocksuckers kneeling in dark corners, men submitting eagerly to tit torture; with the scent of poppers and the haze of cigar and cigarette smoke permeating the entire building.
I was certainly no stranger to leather bars, but this was a place of splendour. As I stared around, checking for the guys showing keys or hankies on their left hips, a friendly guy my own age, came over to talk and, as he freely admitted, to check out the competition!
Which made sense since we looked so alike; both of us tall, dark and slim, twenty-something, blue-eyed white boys. My new friend, who told me his name was Eddy, said I had an advantage over him; I was the new guy in town, the new shiny object, the "fresh meat"; unlike Eddy who claimed to have been picked over by half the bar's regulars!
I might have been "fresh meat", but I was far from the hottest guy around. In contrast to all the big chested blondes of Scandinavian descent with their pumped-up biceps and pecs and leather-clothed thighs, I weighed in at 160 pounds on a skinny six-foot frame, with wide shoulders tapering down to a thin waist and a plump little bum. The Freddie Mercury-style mustache and dark brown hair on my head, cropped short even in those long-haired days, was the only hair on my body, other than the treasure trail around my groin.
Once Eddy and I started to talk, it was obvious we weren't rivals; while I was looking out for older, mature, leather men, he was searching for guys close to our own age. Once that was sorted out, he suggested we go find a better corner to stand so he could point out some of his one-night tricks and give me the low-down.
Concentrating on listening to his gossip as we made our way over to an empty corner I didn't look where I was going and somehow managed to barge into a hot older man. Overcome with embarrassment, I mumbled my apologies, only for him to tell me it was nothing and say hello to Eddy before he walked away.
I felt even more stupid about the encounter when Eddy told me the guy was a leather top who loved having boys suck his cock. I tried to put the guy out of my mind and to concentrate on listening to Eddy's stories, and as time ticked by, there were more and more mid-western hunks being added to the bar's delightful mixture, many in full leathers while others were in shorts or jocks, jeans and bare chests, or harnesses and collars.
It was a mostly white crowd, but there was a smattering of super-sexy black guys hanging around, especially in one group standing near Eddy and I. Aware of far better-looking white boys than me in the room, I was very surprised when the youngest and hottest guy in the group seemed to be returning my admiring gaze and began edging towards me through the crowd.
However, once this totally hot guy came close, I realised it was Eddy he was interested in, not me. Understandably, my new friend stopped gossiping with me and turned his sole attention to the handsome stud! And not wanting to get in his star-struck way, I quietly edged away and began a serious search for a special older man of my own for the night.
It had been some older men who'd brought me out at college as both gay and as a BDSM submissive. Partly as a result of that history I'd remained more interested in older guys than younger, however butch and dominating the latter were. I was always careful to see if any older guys were showing any interest in me, which had usually served me well in the years since. Checking out this crowd, I noted quite a few sexy-looking, mature guys, most of whom seemed, sadly, to be coupled up with studs their own age or with boys even younger than me.
Still, with quite a few unattached attractive men in leather or denim hanging around, I cruised around, hoping to catch someone's eye. And as I did so, there was the same forty-something guy that I'd almost knocked to the floor a few minutes before. Peering through the thick haze of cigarette and cigar smoke, I tried to check him out more thoroughly.
I liked his sexy mouth, his deep-set eyes and prominent nose. He stood about six feet tall, with a big barrel chest and comfortably thick waist, plus a thick mat of black chest hair half hidden by a black leather bar vest. He wore blue jeans under leather chaps and engineer boots; all in all, just my type!
Even though I figured I'd blown my chances with him by my clumsiness, I found him so attractive that I kept staring in his direction while he chatted with some friends. That was, I kept looking until, all of a sudden, he stared right back at me. Having just made the same mistake with Eddy's hot stud, I glanced behind me, sure he was eyeing someone else. But there was no one else in his line of sight, and when I turned back, his eyes were still locked on mine and he was grinning broadly.
That made me blush at being caught out, and greatly relieved to see him turn his attention back to his friends. He had me frazzled and uncertain; was he interested or was he just playing with me? I went to get another beer and by the time I returned to where I'd been standing before, he'd moved away from his friends and was chatting to a sexy young man in a leather chest harness and bare-assed chaps.
Thinking how stupid I'd been to get my hopes up, I cruised around the bar for a few minutes and ended up squeezing into a spot against the wall, in between a couple of guys already leaning there. Which turned out to be a mistake, since one of them apparently thought I was interested and was making a move on him. Without saying a word, he turned towards me and started feeling me up, rubbing a hand up and down my naked chest, twisting my nipples and fondling my bum.
I was no shrinking violet and I'd let more than my fair share of overbearing bastards take advantage of me over the years, but there was something about this guy that put my back up straight away. I should have liked him; after all he was a well-built guy in his forties, and not bad looking, but still, he somehow managed to piss me off.
So, when, without asking, he popped the buttons on my 501's and shoved his hand down the back of my jeans to finger my crack, I told him to fuck off and walked away. I walked around for a few minutes to calm down, hoping to find a better alternative, and was surprised to run into the older man I'd just been mooning over. There was the same knowing grin on his face when he spoke.
