Gay Chubby Briefs Stories

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Orientation
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Infinite Scroll

Gym Jerk Off

by wred222000 on Aug 30, 2017
Gay Male

It was any other normal day at the gym. I was determined to get a good workout as I pulled my gym shorts over my grey boxer briefs. I concluded that a good swim after my lifts would suffice. I set off on my usual sets of leg presses, military presses, and other lifts. Compared to everyone else I'm much smaller only about 5'8 and mostly lean muscle. Being o...

Bobby's First Suit

by timmywells on Aug 18, 2017
Gay Male

"I thought it would be a good idea to buy Bobby a suit," Gladys Bradley told the little Italian tailor whose shop was down the road from their apartment. "Not only for the dance, but with Bobby going to college in a couple of months he'll probably need a suit for other things." "A college boy now huh?" Tony Caruso asked as he rubbed the dense 5 o'clock shad...

Barber Shop Fun

by manalive250 on Aug 18, 2017
Gay Male

After the enormous feedback from readers on my earlier experience with the watchman next door, I knew I had to write about another experience I had many years ago. This one too gets me very hot and horny whenever I think about it. * * * * * Like the previous incident, this one happened many years ago. It had been a long and tiring day. I had a lot of work...

Secret Life of Chub Ch. 02

by BBB771 on Sep 15, 2017
Gay Male

"Talking It Over But Attraction Wins" On a humid summer night, Ben awoke with a wet feeling all over him. He thought he pissed in the bed, so he lifted the sheets and placed his fingers down his red briefs. He lifted his wet fingers to his nostrils and smelled. The odor was salty, and he realized he had a wet dream moments ago. Then he licked his fingers, t...

Caught with a Wedgie

by marriedhubbi on Oct 8, 2019
Gay Male

I never knew that my straight-laced life could take such a turn. Until that day I thought my hidden life of masturbation would remain undiscovered forever. You see, I have an unusual way of masturbating. When my wife and kids are out of the house, I often head to the bedroom and strip to my underwear. I prop up a couple of pillows in the middle of the bed,...

Buddies Reunite Ch. 02

by joeyo43 on Sep 15, 2017
Gay Male

"Roll over," he said. "I'll do the fronts." By that point, I was no longer thinking clearly. I knew only that nothing I had experienced had ever felt this good. In its own right, that was amazing. Here I was, a college freshmen who had never been kissed, never touched a girl. However, I had experienced physical pleasure, even if it only was at my own hand...

A Plan goes Awry

by HerLittlePiggy on May 29, 2018
Gay Male

I sat beside my wife in the loud, crowded bar. I'd been drinking for most of the day and I had a buzz but I was purposely acting much drunker than I was. My wife giggled nervously beside me as she talked to a young man she had met less than an hour before. He had an athletic build and an attractive face with dark ebony skin and a bright mischievous smile....

Piggy's Corn Hole

by bi3inchpig on Jun 9, 2020
Gay Male

Harry had never had a massage. How could he even consider putting some poor masseur through the torture of massaging his fat body? A guy he chatted with online assured him, "They are professionals; they work with all body types. Your fears are irrational. Just book it and let it happen. You'll be glad you did." His back was killing him. He had put on a bit...

College Guy's Experiment

by wrestlerboner on Aug 18, 2017
Gay Male

*Note* This is a true story with certain details and the names of the characters altered for their protection. Everyone in this story is of age. Enjoy. I had been curious about my sexuality for a couple of months, but never had the courage to act on it and try it out. Sure I'd visit to a video store every once in a while, and sometimes let a guy suck me o...

Sugar Cube Ch. 02

by JimBob44 on Sep 16, 2017
Gay Male

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. This is just a flash story. Not to be taken too seriously. ***** Murphy Margot walked the nine blocks from Northside High School, to the small home he and his mother and step-father were renting. The eighteen year old felt the springtime pollen attackin...