Gay Anal Stretching Stories

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A Friendly Wager

by binroe on Aug 18, 2017
Gay Male

I stared blankly at the television. It was a chip shot. A gimme. My favorite football team had just missed a 22 yard field goal that would of won the game. Hell my 14 year old neighbor could of made that kick. What rubbed salt into the mental wound was my girlfriend, who was dancing around the living room with glee. We had made a little wager on the game a...

Homosexual Humiliation

by take the wife on Aug 18, 2017
Gay Male

My name is Subhash kaloo I am 30 years old married for the last 6 years to Nirmala, residing in England. We are from an Indian Hindu background. Our marriage is open and consequently enjoy a wide and varied sex life, but was becoming routine. My story began 5 years ago, Nirmala and I regularly watch pornographic films of all types while we fuck. She never...

Three Firsts: 01

by Lucklove on Sep 2, 2017
Gay Male

Have you ever been caught masturbating? By a guy who's your fiance's grown daughter's boyfriend? Watching gay porn? Awkward. Well there I was, just about to release a pent-up load watching a video of two men fucking not knowing that 22 year-old Paul has snuck up behind me until he asks, "Dude, beating off to guy's fucking? Guys?" I was living with my fiancé...

Back Crack Tag Team

by buttcheeks777 on Feb 6, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. This is a fantasy of a man (me) being forcefully taken by other men and contains some things that not all may want to read about, including spanking, anal sex, pissing, enemas, etc. If you're not into this type of fantasy please don't leave negative feedback. If this turns you on,...

Spun Out Fun Pt. 01

by homewreckingpizzaboy on Oct 6, 2020
Gay Male

Unfortunately, this is still just a fantasy. I truly am an anal virgin so please forgive me if I get some details wrong. I meet up with a guy for a 3 day weekend long pnp session. He gets to the motel room and we sit next to each other on the bed and start smoking. After a couple of hits he gently but, firmly takes me by the back of the head and pulls me i...

Bathhouse Heaven Ch. 40

by glory_first on Jun 5, 2019
Gay Male

When the second man kneeled in front me, I opened the poppers bottle, feeling how he began sharing my cock with the other man already going down on me. It was exquisite surrendering to both men, two mouths worshipping a cock that felt increasingly immense, guiding them over its vast length. Breathing out, lost in heaven, seeing other men have sex around us a...

Jamies Saviour Ch. 02

by alexcarr on Aug 18, 2017
Gay Male

Jamie could hardly sleep being so excited about tomorrow. He felt himself rising like never before, with carnal images in his mind about how it would be, going all the way with Jack. He wondered if it would hurt first time with Jack, he imagined how it would feel with Jack penetrating deeply inside him, he thought about too; that Jack asked for him to suck c...

Trucker Turned Me Out Pt. 01

by homewreckingpizzaboy on May 20, 2019
Gay Male

That night around 7, as I was checking out online dating apps but, not finding much of interest in my area other than the typical one word- "hey" or "looking" conversations. It had been a while since I had been with a guy but, I was not desperate by any means. I was just about to give up when, it refreshed and a new one popped up. The tag line said "Trucker"...

Jack Hammer Ch. 04

by KenJames on Jan 7, 2019
Gay Male

"Gentlemen!" Steve Steel addressed the crowd. "And you guys, too!" There were 107 men gathered around the wrestling mat in the big main room of Steel Steve's Global Health Club. Each had paid $250 to watch this event. Many had paid extra to do more than watch. The proceeds were going to a group of gay organizations. A dozen of the spectators were totally na...

Peter Meets Mr. Johnson

by 1mbibry on Aug 18, 2017
Gay Male

My name is Johnson. I recently posted an ad on craigslist ISO a first time experience with another man. Because I'm not in a social situation that allows me to go out and meet other men I proposed that we first exchange fantasies via email and see where it takes us. I quickly received a response from Peter. He was in a similar situation and like me he was...