I was unpacking boxes I had finally pulled out of storage. It had been sealed. Very little dust and everything looked intact. Magazines, books - most Gay and pornographic. Then under a pile of International Leatherman and Advocate magazines I found a jockstrap.
The tag is faded but you can still see “Young Mans Size L.” It was yellowed from age but the elastic was still intact, amazingly enough. Soon as I held it in my hands I remembered.
I wore it the first trip to a leather bar.
I wore the jock the first time I sucked off a stranger in a bathroom.
1987. My then partner, Don, and I were spending Labor Day weekend in Chicago. I wore the jock to my first trip to a Leather bar. I don’t remember the name, but there was a back area with a doorman; the Oil Pit. Dress code was enforced. I had to take off my shirt since I wasn’t in leather. Selfconcious at 6ft and 150lbs, I generally didn’t take my shirt off in public. But my partner handed me a drink and told me to relax.
We were on the dance floor. Sweaty bodies all around us. High humidity. Don reached around me and slipped his hand in the back of my jeans. He tugged on the jockstrap band, pulling it up to expose it over the waistband of the denim. Leaning into me he shouted over the music, “Pays to advertise.” I laughed and left it, just reaching down to adjust the small pouch around my cock and balls.
Pounding music, heat, humid air redolent of men and poppers. I was feeling light headed. Both me and my partner had a sheen of sweat - some of it from others in the crowd. He held me close and I gyrated against his body, laughing. He turned me around and gyrated against my ass, pushing me down so I bent over like he was fucking me in the midst of the crowd. I lost track of time, lost in the movement and sound.
Finally we took a break and moved on to the bar. A tall, burly dark-haired man with a full beard grinned at me and nodded at my partner. I smiled back and turned to order. I felt the dark haired man move up behind me, pressing against me, as he spoke to Don. With the music I couldn’t make out what they were saying. Both men had their bodies pressed up against me as I half lay over the edge of the bar. Getting the drinks, I dug in my pocket for the cash when a large hand reached past me with a bill.
“Allow me, sweetboy” came the bass rumble in my ear. I turned, pressed against the bar, to nod my thanks. Don was smiling at me, looking like he was up to something. We toasted our new friend. The man continued to grin at me and shouted his order at the bartender. A few minutes later an icy bottle of beer, condensation dripping, passed by my bare skin. We clinked bottles and he leaned down to talk in Don’s ear. I looked around the room at the mass of men. All ages, all sizes. Some in leather. Some in very little. My body swayed to the music as I looked around.
The large hand clapped down on my bare shoulder. The mouth by my ear; “Gotta go to the head. Come with me, your buddy says it’s ok.”
I looked at Don, puzzled, as the large man pulled me away from the bar. Don nodded, smirking, and made a thumbs up with his free hand. The hand on my shoulder pulled me along as we pressed through the crowd. He led me through a doorway and the music was not quite as loud. I looked at the long trough along the wall and the men standing around. Some were pissing, some watching. I looked at the man, eyebrows raised.
Another toothy smile from the dark beard. He nodded his head towards the stalls. A door opened and someone stumbled out. The large hand now around my bare bicep pulled me along.
The click of the door lock. The smell of the closed in little booth. Grubby toilet, empty roll holder. Market graffiti on the walls. Suddenly the large body was up against me. My nose was full of old cigar smoke, sweat, spilled beer. I was backed against the door as he tilted my head. My face was covered by his wiry beard. At six foot I was used to being at least as tall if not taller than most of the guys around me. This man was several inches taller, and considerably heavier.
His tongue filled my mouth as I awkwardly put my arms around him. His arms were moving as he suctioned my tongue with his mouth. I heard the clank of keys and a belt hitting the floor. He pulled off my mouth, a bit of spit connecting us. He grinned again/
“Sweet boy.” he whispered in a low tone. I was conscious of the sounds in the restroom outside our stall. Both large hands clamped down on my bare shoulders and he half pushed me to my knees. I saw a bush of dark hair and a thick cock standing out at attention. One of the hands pulled my head forward and I quickly opened my mouth. His cock jabbed the back of my mouth as I coughed. The smell of old smoke and the musky scent of his balls. I choked a bit as i tried to free myself of his hand, and grasped the thick rod in my hands. I closed my lips around it and he relaxed as I started to suck on him.
I worked this big dick forever. I was aware anyone outside the stall could see the two sets of legs. Me on my knees. As I did my best to tongue and deepthroat his thick cock he leaned down over me, reaching to slide his hand down the back of my jeans. He tugged on the jock. His belly pushed down on my head.
“Got a sweet ass. Next time I’ll fuck you.” came the low rumble. I heard laughter outside the stall. Wondered if someone heard him. I redoubled my efforts and tried to remember all the tricks my older partner had taught me. Soon he was holding my head still as he moaned loudly. My hands wrapped around his jeans half hanging off his legs, I kept my mouth clamped shut as I felt his cock start to throb. I somehow knew better than to try to pull back. His large hands clamped around my skull as, kneeling on the filthy floor, I swallowed and swallowed as he flooded my mouth.
The rest of the evening passed in a blur. Being led out of the stall, a smattering of applause from the guys standing around the trough. Being pushed ahead of the man through the crowd until we found Don by the wall chatting to two leather daddies. A pat on my butt and a high-five with my partner and the tall man disappeared into the crowd.
Don pulled me over to him and leaned up for a kiss. His mouth met mine and his tongue worked mine. He pulled back with a laugh. “I can taste him.” He said with a smirk. I gawked at him, “What the fuck was that all about?” I said over the loud music.
He leaned up to my ear, “I wanted to give you an adventure. And the dude liked the look of you. You’re a cute guy.” He said with a wink.
I wore the jock the first time Don and I had a three- way with one of his buddies.
Late dinner, walked back to the house. More drinks for them, water for me. We collapsed on the couch in a pile. Me in the middle, the two older men on either side. Hands moving, fingers stroking. Lips and tongues licking. Jeans pulled down and t-shirt pulled off. Fingers slide along the straps of the jockstrap.
I remember being bent in half on the couch as one pushed his tongue deep in my ass while the other unwrapped the condom. There was no discussion, just two men getting ready to fuck me. Cocks in my mouth and ass simultaneously. The discomfort from the angle and trying to readjust while one was pushing his body into my backside and the other was pushing his cock into my mouth.
Don’s blond body at one end, then his buddy - what was his name? Kevin? Roy? - at the other. Then they swapped places and I had a cock that tasted like latex in my mouth and the faint taste of cum.
I was wearing the jock when two strangers fucked me. I wore the jock the first time I got fucked for money.
A year later, when we were on vacation in LA. Another leather bar. Don struck up a conversation as we were waiting for our drinks with another couple. Two older bears. One heavy, bald with a brown beard and furry bare chest. His jeans were covered by worn pair of chaps. The other taller, thinner, salt and pepper crewcut. His bare chest was covered in a harness. His legs encased in leather as well.
The bar was getting crowded. The lights seemed to dim as the night went on. The music louder. Soon I saw guys on the dancefloor, amid the mob, in jockstraps and thongs. Bare buttocks glistened with sweat amid the leather clad dancers.
Our new friends - Rob? Mike? - were crowded in with us against a table on one side. Don pulled my shirt off and I stood with my bottle of water, feeling cool as the air hit my sweaty skin. One of the guys - the one with the crewcut - was running his hand over my back and over my butt.
“Damn, nice ass.” I heard, as fingers slipped into my jeans. I almost jerked away in surprise. I felt the hand move around.
“Jockstrap. Nice.”
Don’s voice nearby, “He walks everywhere. Incredible ass.”
I felt myself blush and I looked at him. He grinned and waved his beer bottle.
An hour or so later. A small house in the burbs. Nondescript. Our rental car in the driveway behind the other guys’s jeep. More drinks passed around. Firm, muscled arm around my shoulder and a beard pressing against my neck. It tickles and I move slightly but he holds me steady.
Now in the bedroom. Clothes on the floor. Large prints of naked men in leather on the walls. My shirt is pulled off again and then I’m on the bed, my legs raised as my tight jeans are pulled off my legs.
I hear Don in the other room with the beard guy. Crewcut guy is still in his leather pants and harness. I’m stripped down to the jockstrap. I go to pull it off but he stops me. His tongue is in my mouth, tasting of beer. His breath heavy and hot in my ear, “Leave it on. Frames that ass so nice.”
A yelp from my mouth as that same tongue works its way up my channel. Slobbering spit covers my hole as firm hands grasp my legs.
A voice from the other room, through the half closed door. “Don’t forget the condoms.”
A grunt from the body wrapped around my form, my face pressed into his chest and the leather straps of his harness. I feel an arm reach and hear a drawer open.
The initial push into me is slow but soon as he breached me, the cock started pistoning faster and deeper. I tried my best to clench tight as he pushed in and out, his hands gripping my hips, my feet on his shoulders. Suddenly he stop, panting. I look up at his eyes and he’s staring at me. Then with a smile he pushes my legs down.
“On all fours boy.”
When the other guy takes his turn my jock is sodden with sweat and, I realize, precum. Neither man has touched my dick. I hear Don in the other room. Wondered when he’d join us and realized the first guy was in there with him. His husband had me on my side. He balanced on his knees and slid fingers along my buttcrack. I reach back to help guide him in and my eyes widen as I felt his cock. Thicker than I had ever felt. Long. I start to protest but before I can get the words out he’s thrusting in to me.
Thank god his other half had opened me up already. Even still it hurts as he drives in and out until my body starts to adjust. I’m still sore but able to handle it better. He grunts wordlessly as he continues to fuck me. I have my hands gripping his broad hips. His furry belly is bouncing against my ass cheeks. He spits and I feel saliva hit my butt. He pulls out and wipes the condom clad rod across my skin then reinserts. I see the magnum wrapper on the floor where he tossed it.
An hour later there’s three condom wrappers on the floor. Don never came in the room though I think I saw him looking through the door. When we finally finish both men are on the bed with me, taking turns pumping my hole. Occasionally the heavy set guy grabs the cotton pouch of my jock and gives me a squeeze. I reach down to stroke myself but the crewcut guy pulls my hand away.
“Uh uh,” he says, his body thrusting, “Don’t touch, boy. You’re here to be fucked.”
I’m walking awkwardly, my legs cramped when we finally leave. I could use a shower and feel dirty from sweat - mine and the two guys. My ass feels like I’m gaping but when I reach back it’s greasy from lube but feels ok. My pouch is soaking wet and I feel the seat of my jeans starting to dampen from the sweat and lube leaking from my butt. Probably some cum from where they pulled out and pulled off the rubbers. Both men had given me a deep kiss and hug as Don helped me to the car. I’m sitting back on the seat as my partner navigates his way back to the hotel. I’m glad he’s from the area; I’d be lost at this point. He has the classical station on. I tune out the orchestral music.
My body is sore. I feel like I've been put through a wringer. My mouth and tongue are sore. I have a taste in the back of my mouth that isn't stale beer.
I shift in my seat, remembering to buckle the seatbelt and feel something by my hip. I push my hand down and feel around. I find something pushed into the strap of the jock. I pull it out.
Two fifty dollar bills.
I stare at the bills. Don notices and focuses on what’s in my hand.
He pats me on the leg.
“You got a bonus, baby.”
I look at him.
“What? Where did this come from?”
He looks at me sideways, cocked eyebrow.
“I told them sixty. Guess they really liked you.”
My mouth is open as I stare at him. I remember the two guys giving me a hug. Hands moving over my waist, fingers touching me.
“Motherfucker.”
1991 I have my own house now. in South City, just off Grand. Don and I split a while ago. He never pimped me out again. At least for money, but did initiate a few gang bangs with his buddies from one of the computer bulletin boards. I wasn’t the only one getting banged then, which was a change.
I pull the jock out of the drawer and slip it on. I’m gaining weight, working out t the gym. The pouch is getting a bit tight when my cock is hard but I still wear it to the gym. Tonight though I’m wearing it for luck.
The Riverfront Times is sitting on the edge of the bed. It’s folded open to the classified ads. One ad, just a few lines, in simple black type.
“Bodywork” is the title. My height, weight, race and cock size is spelled out. My first official client is due in an hour. I’ve showered and cleaned myself out. Brushed my teeth twice. Checked my hair. I debate between two pair of jeans then decide to go with sweatpants. Easier to pull off. Then have to decide between t-shirts. Finally a plain one.
I wore the jock when I officially started sex for pay.
There were plenty of other jockstraps. A favorite in black. Now worn and faded. A few white classic models. Nobody ever thought they’d stop making them. A large red one from a customer that was too big for me but I still wore it when he pounded me on the bed. Then the first one, the faded slightly stained white one, got misplaced. In the bag with the bondage stuff. Or fallen behind the bed after a busy night. Eventually I lost track of it until one day I opened a box of magazines and books and found memories of sweaty nights.
