Gay Jockstrap Stories

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The Red Jockstrap

by Coxswain on Sep 14, 2017
Gay Male

This is a true story, as told to me by an Army buddy. The names, places, etc. have been changed. "Just keep your underwear on, son. Don't take off any more than that, and you'll stay out of trouble." My father told me that when I was seven or eight, when he caught my cousin and me "playing with each other." Never forgot that. Even in the years when I didn'...

Inside Mark's Jockstrap

by cutandhorny on Aug 18, 2017
Gay Male

I hadn't seen my pal Mark since graduating from high school five years ago. I figured we could reconnect at our 5th year reunion. He practically had to be there, having been the student body president for our senior year. I spotted Mark across the room when I walked in. We both continued circulating, and while our eyes met once in a while, it almost seemed...

Green Berets & Jockstraps

by Coxswain on Aug 18, 2017
Gay Male

GREEN BERETS AND JOCKSTRAPS PART ONE I had a bad feeling. Something was wrong. My Special Forces team stood ready and eager in the plane, about to parachute out the big cargo door over Pukudu Deme. But something is wrong! The moment they opened the C-130's big rear door, and I got my first view of the Pacific island, when the air rushed in with the heat...

Horny Teachers Ch. 02

by Coxswain on Sep 19, 2017
Gay Male

The Mark of the Jockstrap I was part of the Bohemian scene in Los Angeles in the '50s. My roommate turned me out: after discovering the great turn-on of his cock, I was eager to spread my legs for just about any horny friend. Didn't have much trouble finding guys to top me while I was a student. My first teaching job, though, was at a small-town school, Th...

Chase Becomes Chaste Ch. 03

by growing_interest on Aug 22, 2017
Gay Male

Chapter synopsis: Our narrator expands Chase's hell beyond his home, Chase's new wardrobe beyond the one jockstrap, and Chase's virgin asshole beyond its normal size. ********* "I'm not going out like this!" How long was it going to take Chase to figure out that he didn't have a choice? I wasn't "asking" him to do anything. I was telling him. "Come on, m...

Turned Out on a Bet Ch. 02

by Coxswain on Sep 19, 2017
Gay Male

Too much of a good thing? After kissing First Sergeant Kovachek--a very crotchy, locker-room tasting smooch since he'd been sucking his own jockstrap while I fucked him--I rolled over, all fucked out. I pulled the dripping-wet sheet over us both and we fell asleep. I planned to wake up after a short nap for more fucking--but both of us were more exhausted t...

My Asian Master: Tested Twice

by Bootlick on Aug 30, 2017
Gay Male

Master was not ready to take me as his slave. He subjected me to two tests. The first was my ability to obey. I knelt. He handed me a black jockstrap, a white handkerchief and a blue cloth napkin. All three were stiff with semen stains. I learned that these items were prepared from the Master's cum by his previous sub. My orders, for the next three days, wer...

Pushing My Limits

by assman244 on Aug 30, 2017
Gay Male

So I got there at 7:00. We made small talk, then he told me to get upstairs, strip and wait for him on my knees. When he arrived, his jockstrap was full. He pulled his stiff cock out and I took it all in my mouth. He pulled a belt over my head and used it to jam my head onto his rod until I choked. I sucked and choked for several minutes, until he got bore...

Hairy Assed Homo Honchos

by danielblue on Aug 18, 2017
Gay Male

Billy realized that he was a long way from Keokuk, Iowa when he stepped into a bar in San Francisco and found himself surrounded by men wearing nothing but boots and jockstraps. His virgin cock lurched in his underpants as his eyes devoured the hunky hairy assed dudes prowling the floor. His heart pounded in his ribcage and his mouth went dry. His head was...

Dad's Dirty Underwear Ch. 03

by thebearwriter on May 29, 2018
Gay Male

As with the others this is a story about incest. ***** The Sun had started to rise and I was already awake holding Dad's jockstrap, still starstruck by what happened yesterday, and by how quickly he opened up to me. It shouldn't have been too surprising considering the incest entries in his browser history, but one can never guess how someone will react wh...