Gay First Time Anal Stories

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Bathhouse Heaven Ch. 35

by glory_first on Nov 20, 2018
Gay Male

I had been expertly seduced into cumming into and around his waiting hot hole, seduced by how good it felt to fuck a man without a condom. He had perfectly exploited two advantages - my sluttiness and his. It has been over a month since my last sauna visit, a much longer interval than usual over the last years of having sex with other men here. And it had on...

Massage Clinic for Men Pt. 02

by mastertosub on Sep 14, 2017
Gay Male

John turned partially on his side when Eric introduced himself. When he looked up at Eric he realized that the picture on Eric's website didn't really do the man complete justice. Eric was dressed in a form fitting t-shirt and a pair of silk Japanese pants similar in style to those worn by martial artists. Outlined in the thin material of Eric's pants John c...

My Teammate

by Deeplust on Dec 24, 2017
Gay Male

I wrote from a story that was told to me. I asked him about his first time and he gave me vivid details about what happened. I did not send it to an editor as I have given up on Literotica editors. So please skip this story if you need a perfectly edited story. ***** I have always kept myself in shape and prided myself on my appearance. I am not as physica...

Adventures of Wiley Coyote Ch. 21

by wiley4377 on Sep 14, 2017
Gay Male

NOTE: I received several emails wanting more of Wiley's gay action—so here's the final and last story. I was fucking Debbie and her girl friend but it was not as powerful an orgasm as when Jeff plowed my ass. I was missing a hard cock in my ass to stimulate my prostate and I realized that I liked pussy but needed a hard cock too. I called Jeff on Sunday wh...

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...

Teenage Jerry Stays in the Closet

by walterio on Sep 14, 2017
Gay Male

PRELUDE Jerry Barnes was sitting on the front porch of his parent's house reading the morning paper and listening to the patter of rain. It was forecast to rain all day so he knew he would be staying at home. He normally went to the community pool to hang out with his friends but not that day. He finished reading the newspaper, refreshed his coffee and got...

Rear Windows

by KenJames on Jun 4, 2019
Gay Male

Dave Burke scanned through his notes, then pushed the laptop aside and looked out the window over his desk, trying to think of an opening sentence. It was Wednesday afternoon and Dr. Hillier, his Freshman English instructor, had assigned a 500 word essay for Friday. He was renting one of the units in a two-story duplex. The bedrooms were on the second floor...

Blow and Go Ch. 03

by Jay142 on Aug 12, 2019
Gay Male

It had been more than a month when my colleague Peter and I became suck buddies at a conference while we shared a hotel room. Our cheap company brought us together and the rest is history. Not only did I find another dick to suck but Peter also returned the favor and he found out he enjoyed sucking a dick as much as I do. Our schedules didn't allow us to ho...

A Birthday Femboy's Night Out (Now Public)

by meris on Nov 4, 2016
Gay

My name is Samantha. I wake up in the morning feeling very excited, today is my Birthday and I have very special plans for celebration. I step out of bed and take a look in the mirror, my dark brown hair gone frizzy from yesterday’s antics. I can still feel that guy’s hand gripping a big handful of my hair as he railed me. I giggle musically to myself at the...

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Steve and Kyle

by JASONSHOMOEROTICA on Sep 5, 2018
Gay Male

CHAPTER 1 Kyle Sinclair, the main character -- let us call him the hero -- of this story, is a Chicagoan; active, young, muscular, sexually superbly equipped and totally gay. Kyle comes from a working class family living in the western suburbs of the city and has never paid much attention to learning anything at school, which, when he was eighteen he left r...