Gay Gay Anal Stories

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First Gay Anal - Surprises

by dkmywife on Sep 4, 2017
Gay Male

Surprises In the months following my first meeting with Archer, Charles and I fell into our old routine, only with snow on the ground there was no lawn to mow and I started my new job of shoveling snow and deicing his sidewalk and those of his neighbors. Being that this was not a weekly event our private excursions into his hot tub, bedroom or garage were l...

My First Gay Anal

by dkmywife on Sep 25, 2017
Gay Male

My first full penetration gay sex experience was with my FORMER gym teacher the summer after graduation. I was 19 and legal...graduated so he was no longer my teacher. Unlike so many gym teachers he was actually fit with broad shoulders teeny waist and a decent look to him. What none of us knew, at least what I didn't know was that he was gay. The first mont...

My First Gay Anal Ch. 03

by dkmywife on Sep 25, 2017
Gay Male

Autumn Surprise My first threesome After the first month of summer break Charles, for the sake of keeping up appearances had me visit him every other weekend to mow his lawn. The last thing he wanted was for my parents or his neighbors getting suspicious of my frequent visits. Even though I was of legal age the town we lived in was stuck in the 1950's and...

My First Gay Anal Ch. 04: Surprises

by dkmywife on Sep 25, 2017
Gay Male

In the months following my first meeting with Archer, Charles and I fell into our old routine, only with snow on the ground there was no lawn to mow and I started my new job of shoveling snow and deicing his sidewalk and those of his neighbors. Being that this was not a weekly event our private excursions into his hot tub, bedroom or garage were less frequen...

My First Gay Anal Ch. 02: Deepthroat Lesson

by dkmywife on Sep 25, 2017
Gay Male

A Summers Schooling After Charles had left me sprawled out on the tires in my garage I went to my bed with his hot cum still warming my insides. I had spent practically the whole day and a good portion of the evening either sucking his cock or with his cock inside me. Still I was not satisfied. It was an easy bet that had either he or I weakened and called...

First Time Gay Anal and Breeding

by RoughBreedingLover on Sep 25, 2017
Gay Male

I've always wondered what it felt like to receive a creampie, at 24 years old I finally decided to post an ad on Craigslist. The ad was named "wanting first time gay anal with a deep breeding creampie." I wasn't interested in blowjobs and anything I just wanted to be topped really hard, balls deep with the absolute minimum amount of lube so I would really...

Hard Start

by KeithD on Mar 17, 2020
Gay Male

(gay prostitution, age difference, gay interracial, tough times, street rent-boys, car sex, fake cops, gay anal, rough gay sex, historical) [There is no under-18 sex activity in this story.] Jimmy grimaced and let out a gasp as the cock bulb breached his sphincter and the rest of the cock followed it up into his channel. He looked over at the wad of bills—...

First Time Fears Overcome

by JASONSHOMOEROTICA on Aug 18, 2017
Gay Male

A Help for Timid Young Gays A homoerotic tale ***** CHAPTER 1 Serge had been fucking his partner, Chris's arse for several minutes with ever increasing amplitude and force, when he suddenly felt that magic something in his cock which was the intimation that the climactic moment, that incredible sensation when he would reach what had the makings of being...

The Ingram-Lewis Chronicles Pt. 06

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

PART 6 - PATRICK'S FINAL TERM AT RIGBY ***** CHAPTER 1 Patrick Ingram-Lewis, the Head Boy had just returned to Rigby School after the Easter holidays. It was the last time he would be returning to the school at which he had been a pupil since the age of thirteen. At the end of this, his final term, he would be leaving the place for ever to start the next...

The Paint Job Pt. 03

by Robert_Furlong on Nov 27, 2017
Gay Male

"So... onto the first consummation," I suggested, pausing for the two men to reposition themselves and sit alongside each other on the couch. "In this painting, Adam is... er... making love to Stephen. Am I okay to describe it like that?" I'd expected Adam to haughtily inform me that one man doesn't make love 'to' another but rather that their sex is collab...