Gay Sissy Gangbang Stories

810 results
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Infinite Scroll

Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...

Ron Sets Up my Gangbang

by sunny77777 on Dec 24, 2017
Gay Male

Ron had been teaching me the Bi Life since we met about a year earlier. Ron, his wife Carla and my girlfriend Sue and I had had spent almost every weekend together and the four of us had sex in every configuration possible. Ron and I also spent a good bit of time alone where we enjoyed each other and Ron had even invited a well hung friend Denny to join us o...

The Exploits of Cockslut Kelly 05

by CSK on Aug 29, 2017
Gay Male

WARNING!! THIS IS A GAY MALE STORY, BUT IT IS ALSO AN EXTREME BDSM STORY AS WELL. THIS STORY COULD EASILY BE PLACED INTO ANY OF THE FOLLOWING CATEGORIES DUE TO THE CONTENT: GAY MALE, BDSM or FETISH. I HAVE REQUESTED THIS FOR THE GAY MALE SECTION, BUT IT MAY END UP IN THE BDSM SECTION OR ANY OF THE OTHERS IF THE EDITORS OF LITEROTICA DECIDE TO RE-CATEGO...

Cock Sucker App

by silkstockingslover on Sep 25, 2017
Gay Male

Summary: Straight guy discovers a sex app that changes his life. Note: This is a NUDE DAY 2017 CONTEST STORY... so please vote... the focus of the story the glorious nudity and visuals of COCK. Thanks to: Tex Beethoven, Robert and Wayne for editing this. * As I sucked my father-in-law's big, thick cock while he was watching football, and my wife and moth...

Becoming a Cocksucker: A Journey

by silkstockingslover on Sep 25, 2017
Gay Male

Becoming a Cocksucker: A Journey Summary: Man's journey from straight & married to loving cock sucking Note 1: Although unorthodox, this is a 2017 Valentine's Day Contest. No it's not a love story between a man and a woman, a woman and a woman or even a man and a man... it's a love story of a man and the discovery of his love for cock. No hearts and fl...

Remember Yahoo Chat? I Sure Do

by FinallyOpeningUp on May 22, 2019
Gay Male

The news was unexpected. I can't say it was devastating. In fact, it elicited no truly emotional response from me whatsoever. But just a few months ago I was scrolling through my Twitter feed and a headline jumped out: "Yahoo Chat to shut down permanently." I paused for a moment when I read that headline. Yahoo Chat. It had been probably ten years since I,...

The BBC with Benefits Thing

by silkstockingslover on Mar 9, 2020
Gay Male

Summary: White friend discovers the joy of BBC while hanging out. Note: Thanks, as always to Tex Beethoven and Robert for editing this story. It was after a couple hours of shooting hoops on a Sunday afternoon that my sexual awakening began. Ben said, "Let's go back to my place and play some NBA2K." "I need to shower first," I demurred, dripping with...

Curiosity Fucked the Straight Guy

by silkstockingslover on Sep 25, 2017
Gay Male

Editor's Note: this story contains incest content. NOTE 1: A special thank you to Estragon and Goamz86 for editing this lengthy multi-chaptered journey. Curiosity: Fucked the Straight Guy I can't explain for the life of me when I suddenly became curious. I mean I am 44 and have never found any man remotely attractive. Oh sure, I can tell when a man is goo...

Nephew's Readjustment Pt. 16

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** That evening Nicholas took a very long shower. He was finally unlocked again, and the soreness of his anus made it difficult to clean. Despite being free,...

Nephew's Readjustment Pt. 15

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas was able to refrain from masturbating that night and the next morning, but only because of the tenderness of his ass. Without access to his genita...