Gay Sissy Piss Stories

4,102 results
Orientation
Length
Source
Infinite Scroll

Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...

Drunk Friend to Sissy Slut

by olybiguy27 on Sep 14, 2017
Gay Male

What follows is the completely true story of the weekend that changed my life. This really happened to me and took place in the summer of 2008 just after graduating from high school. My name is Andrew and I was a major stoner in school. I had a lot of friends, mostly due to the fact I always had really great weed that I would get from my rich old neighbor...

The Hanky Code Pt. 15

by His_fag_wife on Sep 14, 2017
Gay Male

Mistress Caprice stood in front of me and looked deep into my glazed eyes, as I rocked up and down on my rubber cock. "I had to pay a pretty penny for you bitch, after so many people had watched some of your more extreme videos. A lot of very depraved people could see just how much use you might be." "But I wanted you before your inevitable trip to the far...

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...

Daddy's Girl

by oskarwild on Sep 25, 2017
Gay Male

The Hitchhiker It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver. "Thanks a lot mister. I...

Little Sex Toy Ch. 05

by keptsissy on Sep 26, 2017
Gay Male

I'm squatting in the middle of his cold cement basement floor, just over the drain in his laundry room, sitting back on my high heels. The 4" spike heels he insists I wear now around the house, wobble in them and get whipped for it, walking or squatting. He says a 'lady-like' little bitch should know how to wear high heel shoes. Leather, padded restraints...

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...

Sorted at the Funhouse Ch. 02

by thick1191 on Aug 30, 2017
Gay Male

This story can stand alone but will be much more enjoyable if you have read the first part; "Sorted out at the Fun House" found at my Authors site (dodge1191) on Litererotica. * I think anyone interested in reading this story realizes that I would return many times to the Fun House. It was just so erotic. About two or three times a week I would go there,...

The Service Station

by thick1191 on Sep 15, 2017
Gay Male

All rights reserved. Other than downloading one copy for personal enjoyment, no part of this story may be reproduced or transmitted by any means, except for reviews, without the written permission of the author. Comments on the story are appreciated and may be addressed to the author, Dave. Any suggestions, comments etc. are welcome. This story contains de...

How I Became a Sissy Pt. 01

by Yngwhiteboi on Jan 14, 2019
Gay Male

As a young man growing up I knew that I liked both men and women, but never had much success with either due to lack of confidence. Being only 5 foot tall and very small I had never been a hit sexually. To top it all off my shoe size was 5 in the UK. I was a rocker as well, which put off most people, shoulder length brown hair always in a pony tail, ripped j...