Gay Master Sissy Stories

3,801 results
Orientation
Length
Source
Infinite Scroll

Research Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

Please read Research part one first. ***** "So in summation I submit that although a certain portion of the male population engages in homosexual acts, they aren't homosexual at all. No, they are under-endowed males who wish they could have heterosexual relationships but whom women shun. Through aggressive parenting, peer pressure, and social activities th...

Converted to Gay

by bart_allen on Sep 14, 2017
Gay Male

This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading. ***** I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes we...

The Pet Ch. 02

by Gman26 on Aug 18, 2017
Gay Male

Leave real feedback or don't comment at all. Indecent comments will be flagged for the webmaster. ***** I found myself in master's basement with two chairs sitting in front of me. Voices upstairs are definitely my parents. Mom sounds like she's crying. "This isn't how I wanted it to happen!... My baby boy." She doesn't seem to want to come down. Dad sound...

House Rules Ch. 07

by EROTICbearscribe on Aug 7, 2019
Gay Male

WALKING THE WALK "We're going to have a visitor today," Daddy announced during breakfast one morning. He was wearing a suit because he had a business meeting. He looked very sharp. My daddy was so handsome. I was such a lucky sissy. When I asked him who was coming, he told me it was Miss Marguerite. "Miss Marguerite from The Beauty Mark?" I asked. L...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

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...

Ozark Bitch Pt. 02

by oskarwild on Sep 14, 2017
Gay Male

Caged It was a long night for Patti. He wasn't used to sleeping with someone and Zeke stayed snuggled against him all night with his arms wrapped possessively around his new slave. Zeke snored and he mumbled in his sleep. Patti couldn't make out what he was mumbling, but occasionally "Patti" came through. Zeke dry-humped him a couple of times that night an...

What Being a Sissy Wife Means to Me

by SissyWife on Aug 18, 2017
Gay Male

I am a sissy wife. I hate clichés as much as the next girl, but sometimes they make for the most apt of descriptions. I have a job, friends, and a life. I go out, I go out for movies and drinks. I enjoy long walks and drives, and I love travelling to new places and locations. And yet, there was something missing. There was something that was needed. I found...

Runner's Story Pt. 03

by booshakey on Aug 17, 2017
Gay Male

I woke up the next day and headed on to work. The image of Black Daaa, I mean, Terrence's dick sliding in and out of my mouth still haunted my memory. More disturbing was the fact I was getting an erection from it. I mean, I wasn't gay, not that Terrence cared, but after the past two visits I was definitely questioning it. Worked dragged on mainly because I...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...