Gay Sissy Gangbang Stories

908 results
Orientation
Length
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Infinite Scroll

Avery's Desire Pt. 20

by Chancem77 on Dec 24, 2018
Gay Male

Kass stared at the door, eyes wide, in total disbelief. Sean and Zach stopped the music when they realized that Kass wasn't playing along. They caught his gaze and their eyes veered towards the door. "Unbelievable." Sean hissed under his breath, his eyes narrowing into two thin slits. "Hello Boys." Mickey gave a sort of playful salute as he descended the s...

New Frontier

by NRMathis on Dec 23, 2019
Gay Male

Author's note: I tried my best to be accurate (scientifically, biologically, and otherwise) when writing this story, but there might be some mistakes. +++++ "Hey, Grant!" I hadn't seen him in months, but I would have recognized his face anywhere. It had been a while and he reached out, asking if we could catch up over lunch. He jumped a little like...

She Found Out

by nada_doing on Sep 14, 2020
Gay Male

Ryan sighed as he pulled into the driveway. When did things get so hard? He shifted into park and laid his forehead heavily against the steering wheel. It hadn't always been like this; he used to be excited to get home to his wife, to open the door and engage in the ritual of a hug and a kiss and a "how was your day?" Something had changed, lately. He could...

The Porn Star and the Prostitute

by ladyroxanne21 on Oct 12, 2020
Gay Male

Chapter One Dylan "Alright my lovelies! You know how much I hate to disappoint all my cherished viewers, but I haven't had a weekend off in months! So after I finish up here, you're just going to have to satisfy yourselves with watching my videos until I come back online. Sorry! I'll miss you all as much as you miss me, I promise!" The comments that poppe...

Lake Cascade Ch. 01

by TheCandyManCan13 on Sep 16, 2017
Gay Male

My name is Dave Burnell and I live in Portland, Oregon. This story is about my introduction to the greatest sex of my life. I was 24 and going to Portland State University, studying Engineering. I had a beautiful half-asian girlfriend with big ol' titties named Catherine who I would fuck as often as I could and we often got into some kinky shit. But this sto...

Curious No More Ch. 10

by bicurve on Sep 25, 2017
Gay Male

Thank you for your patience! I really appreciate all your emails and support. But enough about me; let's get to the stuff you men want. * "Are you looking forward to getting your ass used and filled?" I pushed my crotch into him, my hard cock apparent. "Does that answer your question?" "Let's get dressed and get some food. Alex and Cory are going to call...

Sporting Chance

by perihelion on Aug 30, 2017
Gay Male

Two hours after the school board hired me, I sat with my new principal in his office. "Jeremy, I'm glad you decided to call me. I just wish you'd done it sooner so we could talk." "It's like I said, no point in bothering you until I completed the courses I needed to teach in Georgia. I still don't understand why I had to take those extra classes if I didn'...

Rest Stop Management Pt. 03

by rimaday on Dec 24, 2018
Gay Male

I awoke around 4:45 on my belly, my red panties a little twisted and crusted with dried cum. I could feel Big Daddy's deposit oozing down my taint and hardening in the panties. I could not believe, this was not some kind of twisted dream but my stretched leaking asshole took away all doubt. Twelve hours ago, I was kissing my beautiful wife and leaving for an...

Max's Chance

by robcub32 on Sep 26, 2017
Gay Male

(Note: This story features characters from "A Clean Start". You don't have to read that story first, but I recommended it.) "Hi, Max!" the familiar voice called out. As I walked out of the locker room, I looked and saw Pete's smiling face standing next to the weight rack. Pete was my best friend Tank's boyfriend or partner or whatever you want to call it....

Master and Slave - The Road Trip

by Harry_Ballsack on Aug 18, 2017
Gay Male

Day 1: The sub sat in his room with butterflies in his stomach and his heart pounding in his chest. After over a year of chatting and trading emails with Master he was going to finally meet him. Two times in the past they had made plans to meet for a session when Master was going to be traveling in the area where Slave lived but situations came up that forc...