Gay First Anal Stories

20,737 results
Orientation
Length
Source
Infinite Scroll

Black Hawk Down

by Dazman on Sep 21, 2020
Gay Male

Black Hawke Down The winter of 2005 was a barren time, sexually, for me. The endless summer of that year was punctuated by an exciting and sexually adventurous bisexual threesome between work friends that died away with the demise of the company we worked for. Thomas was still around for wonderfully filthy transactional gay sex. When I say transactional, I...

Spanked and Buttfucked Asian Male

by asianspankee on Aug 30, 2017
Gay Male

I'm an Asian male, with slim and very smooth naturally hairless body, and average height. The story happened when I was in my twenties. I hope you enjoy reading it... Ever since a teenager I've always had a very strong, repressed desire to get fucked by another man. I think one reason is because my body is quite slender, and extremely smooth devoid of any b...

Tricked into Gay Sex

by beatoffboy on Aug 30, 2017
Gay Male

This is the story of how I was tricked into having gay sex. I had been dating a woman named Jean for several months. Jean had long dark hair, perfect thirty-six C breasts and long legs leading up to a nice tight behind. Although we were dating regularly, we had not yet had sex. My only attempts to lure her into bed had ended with me getting a quick feel of h...

Failure to Fuck

by assxible on Aug 18, 2017
Gay Male

About halfway on my journey into anal play, I started fantasizing about getting a live cock in my ass. I embarked on a quest to stretch myself to accommodate the size and girth of the cocks in my daydreams. Anal masturbation is pleasurable, but it's a solitary pursuit. Sex is always better with a partner. So when I was able to take a large dildo easily, I be...

Lubrication in the Tool Shed

by Cumfusion on Sep 14, 2017
Gay Male

It brought it all back to me but I never guessed anything like this would happen. Anyway you may have read Carl's first hand account of being caught with his pants down. Yea and that's an understatement. Anyway it was two years since I went on that biking holiday with Bobby and I had almost given up ever being able to fulfil what began that evening in the y...

Reunited - 44 Years Later: The Move Home

by fadedgiant on Sep 14, 2017
Gay Male

This is the fourth installment in my fantasy story about Robert and Patrick. In the first installment I explained that elements of the fantasy are true. What the reader should do is read the earlier segments to understand how and why each installment builds. The author retains all copyrights associated with this writing and those that preceded this. * Par...

Curious Guy Becomes Bi-curious Pt. 02

by walterio on Sep 14, 2017
Gay Male

Author's note: This story was requested by a young man who shared his experience with me and asked me to write about it. I chose not to post any more stories under the title Honoring Reader Requests. All characters in this story are at least 18 years old. I decided to break the story up in to chapters since it started to get a little too long. Chapter Two –...

Paul's First Assfucking Pt. 01

by JohnLeslie on Sep 17, 2017
Gay Male

My name is Paul, I am 40, tall, athletic, handsome and masculine. My girlfriend Michelle, is a cute 21 year old college senior with long black hair, a slightly curvy body and big boobs with sand dollar like nipples. We have an amazing sex life and often fantasize about threesomes and foursomes. Usually, I am very dominant sexually with her and the other wome...

Mr. Right Now Ch. 08: Brad

by KenJames on Oct 6, 2020
Gay Male

I'm lying in a queen-sized bed in an old basement, naked under the covers, beside another naked 18-year-old boy. I'm wide awake. He's pretending to be asleep. My painfully hard cock jerks and my body stiffens when his hand brushes my thigh. * * * It's early summer and I've just graduated from high school. Dad and I have spent the last week at Grandma's ran...

Gym Shower Fun

by kinkydesire888 on Aug 31, 2017
Gay Male

I loved my shower time after my work out at my gym. Every other night at 9 pm I would be down with my work out and striping down at my locker ready to hit the showers. I kept my schedule that way for one particular reason. Every time I hit the gym at that time there would be a 50 some year old man that was showering with his curtain wide open. Being a bit...