Gay Anal Stretching Stories

6,645 results
Orientation
Length
Source
Infinite Scroll

Being A Gay, Flash Back From Past

by fox-for-fun on Aug 18, 2017
Gay Male

I have been very curious about my anus and have been playing with it since child hood. But once I turned eighteen I became a bottom. As a bottom my favorite pass time activity was to bend over before dressing table mirror and open my hips and shove lipstick or hair brush in my anus and then move it in and out of my ass for hours, of course I always applied s...

Bill's Christmas Gift

by alexcarr on Aug 18, 2017
Gay Male

I can feel it in my hand. Bill asked me to touch him as he was leaving, he stood at the bottom of the banisters and the Christmas party was ending. We were all tired and ready for bed and all of the others had all departed, most by taxi because they wanted to let themselves go and take advantage on the drink on offer. Bill was the last. I knew him through t...

Black Cock Party Ch. 09

by MarkLazer on Sep 14, 2017
Gay Male

After that fraternity house hookup, I went home for Christmas and returned back to campus on the 28th. Most everyone was off campus, even the athletes. The football team was playing in one of those lesser bowl games on that same day. Vinny, our starting linebacker who was black, built like a muscular god with the biggest cock I have ever had, called me that...

Bottoming with My Mentor Pt. 02

by shadoblivion on May 22, 2019
Gay Male

Once again, this story is entirely fictional. Names are changed. ***** It had been over a decade since I last saw Fred because of a falling out due to a miscommunication. Not long after our intimate experience together, he had tried to contact me to hang out casually but I was indisposed and couldn't meet up. He took this as a slight, like I was blowing...

A Pig's Tale Ch. 02

by Best709 on Sep 14, 2017
Gay Male

Part Two: Maintenance “Oh, yeah; he’s a total Pig,” my Master said. And yes, he knew what Pigs liked. . . . Within a few minutes the man began to cum in the ass before me, moaning, groaning and violently slamming into the ass until he pulled out. He dangled before my face his long, thick cock --and as I guided its smeary, slippery, dripping head into my mo...

Mike and Me Forever

by alexcarr on Aug 18, 2017
Gay Male

I'd never been frigged in a shop doorway before and neither did I like it. Okay it was after dark but there were still people about, but Mick was adamant he couldn't hang on. It was nice of course it was having this young guy eating you, but there was a time and a place: "If you could hang on and I will take you to my place" I suggested but it was like he w...

Pegging Peter Ch. 06

by KenJames on May 23, 2018
Gay Male

Peter kept thinking about his first time during the drive to Mark's apartment. He and Janna had been dating for two years, gradually progressing from tongue kissing to mutual masturbation. The last time, in the back seat of his dad's Suburban, he'd pulled her panties down, then eaten and fingered her to orgasm. She'd given him a great blow job. After he'd c...

Questions and Answers

by Robert_Furlong on Aug 18, 2017
Gay Male

QUESTIONS AND ANSWERS Part of the 'Butt Monkey' series of stories by Robert Furlong === I arrived at my office the next day to find an envelope on my desk with my name written on it in neat, if rather florid, handwriting. It read "Robert" which was slightly odd because everyone at work calls me Rob. My ex-wife used to call me Robert, although it was inva...

Dick Dancers Ch. 02

by KenJames on Jul 31, 2019
Gay Male

"Me." A hairy-chested man with short dark blond hair, a heavy mustache, and beard stubble stepped out of the crowd. He was wearing black work boots, black leather chaps, and a black leather cock ring with chrome snaps. His stiff cock thrust out from his closely-trimmed crotch. The guests cheered. "Go get 'em, Carl," one man shouted. Carl grinned and extend...

Nympho Discovery, Love of Cocks

by Alluring_Crimson_Shifter on Aug 31, 2017
Gay Male

Ricky was getting ready for his first sales convention with his new job. He hoped he would make a lot of valuable contacts. Looking in the mirror he straightened his tie, and practiced a charismatic smile. For a 19 year old he was confident and knew he would be successful in his new sales career. He had opted to postpone college and try making a successful c...