Gay First Anal Stories

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First Anal, with a MAN Pt. 02

by DougsLair on Nov 5, 2018
Gay Male

As I was driving home from Fred's, I was already wanting a next encounter. I'm lucky I made it home without having a major accident, my mind was hardly on my driving, or other cars and trucks on the road. Dangerous, I know. I made home safely, pulled into the driveway, and got out of the car. I noticed two things, right away. First, how incredibly pleasant...

My First Anal Experience

by cuminmyasss on Sep 16, 2017
Gay Male

This is my 2nd submission of my true experiences. My first story is how I experienced my first Contact with men, giving and receiving blowjobs through a gloryhole. Months had passed since my first experience but that first experience had a great effect on me. I started going every Friday night for some quick action before I headed home from the clubs. I al...

My First Anal!

by MrJimJim on Aug 18, 2017
Gay Male

Once I had finished giving my first blowjob, I knew it wouldn't be my last. In fact, I stopped counting! One of the guys I sucked on often was nice. Latin, firm, long slender cock just perfect for being naughty with. We had been together enough times we were comfortable in each others homes. We would fool around at his house or outside in the rain. I would...

Surprise First Anal Experience

by BottomBoyUK on Jul 9, 2019
Gay Male

I was 21 and had just finished at university. I knew I was into cock and had sucked one before but had been too nervous to take one in the ass. To me it felt like crossing a threshold into being gay that I wasn't sure about. I had been chatting to a man called David online, who lived in my town for months by this point, and he made me feel comfortable enoug...

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...

Anal Sex for the First Time

by niplock on Sep 14, 2017
Gay Male

I have been a bi-curious male for some time. I tried going to gay bathhouses, nude beaches and even steam rooms at a local gym to explore my gay feelings. Up to this point, the only gay sex that I had experienced was sucking on a few cocks here and there. The most erotic experience was being naked in a porn movie room at The Club with a naked man sucking my...

Seth's First Anal

by MYSTERIOUSMALE on Sep 1, 2017
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. * There we were sitting in the dark theater. We've decided two things tonight. That we would watch the new Adam Sandler film, and that tonight would be the night we would make love for the first time. My name is Seth. I'm 19 about 5' 6" slim build with brown hair and blue eyes. M...

Blowing Max, Then My First Anal

by Headgiver444 on Sep 14, 2017
Gay Male

This is my fifth story and second in my series on Max, a man I met on line (See my previous Max story for the background). This is a story of extreme gay submission. Not everyone's thing but if it's yours, I think you'll enjoy. On my first night with Max, I had passed my blowjob "audition" with flying colors. "Be here next Saturday night at eight", he comman...

First Bi-Blow Job with an Older Man

by loves2stroke on Sep 4, 2017
Gay Male

*** This is an absolutely true story about how I became addicted to pleasuring older men and the event that led to me sucking my first cock. This is my first attempt at writing and I will try to recreate the event as accurately as I can remember. I am not a professional writer just a guy wanting to share his first blow job experience. (Male/Male, exhibition...

First Time at a Gay Bath House

by niplock on Sep 14, 2017
Gay Male

I have always been a heterosexual male that was married and then divorced. I have had several relationships with women after my divorce, but for the most part ended up disappointed with the relationships. I have been exploring my gay feelings by going to nude gay beaches, chatting with gay men online and watching a lot of gay videos. Now I had decided that i...