Gay Anal Gape Stories

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Anal Sub for an A Ch. 01

by HawaiianShirts on Aug 18, 2017
Gay Male

I'm failing my web design course at one of the top universities in the Midwest. It's my second year here and I'm actually majoring in web design but I'm more interested in the design aspects of it not so much the programming. If I wanted to code I would've done computer science. This course is called "Video in Web 2.0 Sites" so I figured it would be about de...

Dirty Butt Sex: Anal Threesome

by DirtyButtSex on Sep 4, 2017
Gay Male

I should start out by stating that the following story is true. I'm 28 years old and I've had sexual encounters with both men and women. While I lean in favor of being with women for dating purposes, I enjoy sleeping with men more. But perhaps the term "sleeping with" is not entirely accurate; I enjoy being fucked by men. Butt sex, as they say, is the best....

Connor on Campus Ch. 01

by JasonClearwater on Oct 15, 2017
Gay Male

* * * * * A University student takes another student's anal virginity. This story does not pretend to have any literary merit whatsoever. * * * * * ***** He's twenty years old, but Conner looks a little older than his years, leaning against the wall with a cigarette in his mouth, watching the other students walk past. He's lean and dark-haired, blue-eyed...

Mystery Master Demands More

by Spreadtoyforyou on May 15, 2019
Gay Male

It had been about three weeks since I had found myself in a hotel room, blindfolded and serving a dick for the first time. Whomever it was that face fucked me, took my anal virginity and left my ass filled with cum had not sent any messages or left any hint as to when and if I'd have another chance to be a cock slut. My work days were now filled with looking...

Paul's First Assfucking Pt. 02

by JohnLeslie on Sep 17, 2017
Gay Male

I woke up on the soft rug under the couch where Gary had roughly taken my anal virginity. I was sandwiched between Gary and my girlfriend Michelle. I had a raging hard cock and began caressing Gary's ass. As Gary woke up I turned him around so he was laying on his side with his ass pushed out towards me. I put a little coconut oil on Gary's asshole and rubbe...

Hypnotized Male Temple Prostitute Ch. 02

by TaleTeller4035 on Sep 15, 2017
Gay Male

The second cock spewed its sticky load on my tongue as he pulled almost out of my mouth. The familiar, bitter taste lingered on my tongue as I swallowed -just as a third cock drove past my esophagus' opening and began to face-fuck me; the cock in my ass exploded as he pushed into me as far as he could go. The two guys set me down; my hands went to the man'...

The Path Not Taken Pt. 01

by jcsbiguy90 on Mar 18, 2020
Gay Male

Note: The following begins as a true story of how I lost my virginity (anal and otherwise) to two gay top daddies when I was 19. Now, 10 years later, I look back on this experience and fantasize about what could have been if I had just embraced my inner cock slut...and the result is this story series. The first installment will cover the true events and tran...

Billy

by bdavidson on Mar 18, 2020
Gay Male

This is a story of fiction. Author does not recommend unprotected anal sex. *** The personals section of the well-known Craigslist site provided a wealth of opportunity, especially for gay or bi men, and every week seemed to bring new men to the site. There were some fakes, of course, but most were like me, ordinary guys looking for casual sex. If I was tr...

Little Jimmy Grows Up

by timmywells on Sep 14, 2017
Gay Male

In the interest of full disclosure I would like to mention that this story involves the following topics; rough, reluctant but consensual sex, anal sex, and both very dominant and completely submissive characters. This story takes place during the Summer of 1970 and involves a very shy, meek and socially awkward guy whose life is forever changed one day in...

Punishment or Pleasure

by Ewriter111 on Dec 10, 2018
Gay Male

I walked out of the county jail where I was in a holding cell for two and a half days very slowly and slightly bow legged. I had just turned 18 and made the mistake of mouthing off to a police officer during a traffic stop. It was early Friday evening and I didn't have a court hearing until Monday morning. I was put in a remote holding cell with three older,...