Gay Sissy Toilet Stories

3,030 results
Orientation
Length
Source
Infinite Scroll

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...

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...

Transforming Tim

by oskarwild on Sep 25, 2017
Gay Male

The Elevator Rafe could hardly wait for his lunch hour to come. But he wasn't hungry for food. He was hungry for the new elevator boy. The new boy was just the type Rafe lusted after. He was short and slim; probably five-six and maybe a hundred twenty pounds at the most. And he was young. All of the elevator boys the building employed were high school seni...

From Brother to Bitch Ch. 02

by Mixedwritings1993 on Aug 29, 2017
Gay Male

James was sleeping soundly, around 8 o'clock still sucking his thumb like a baby. At that time, the alarm went off, waking him up instantly. The sleep wasn't such a deep one because he woke up too many times while finding himself in the middle of various nightmares. He sat up on the bed, rubbing his eyes. His entire face was wet from the baby like drooling...

"You Go First," Samantha Said

by donaldelliott11 on Jan 21, 2020
Gay Male

[Most authors love feedback. Please let me know how I did.] This is the third story in this series. You will want to have read the other two. https://www.literotica.com/s/you-go-first-01-jake-said https://www.literotica.com/s/you-go-first-02-john-said + + + + + + + + Jake phoned me Tuesday morning and told me to come visit him that afternoon. His paren...

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...

Nephew's Readjustment Pt. 03

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed, and remind me to keep writing! *** She set everything in motion over the next two days. Her excuse about...

The Moment of Choice

by WatchingAndWaiting on Aug 31, 2017
Gay Male

I had been fantasising about dick for a long time. On and off, I had spent most of my adult life masturbating to thoughts of cock and of getting fucked. Very rare was the orgasm achieved from aroused thoughts of women, though I was always looking at them with lust. But if you had asked me, I would have said I was straight; *maybe* bi if push came to shove. I...

Turning Myself Gay Pt. 02

by bart_allen on May 29, 2018
Gay Male

It had been an exciting experience. I jerked off two more times once I got home that night, focusing more on the thought that I had taken such a large step in turning myself gay. I certainly didn't feel any different, I just did what gay guys do, suck cock. Of a random guy they solicited off Craigslist, chiding myself for the thought. But it was one of many...

My New Master

by jasoninsjca on Aug 18, 2017
Gay Male

Finding a new place to live is always a drag and I was spending Saturday morning looking through the online classifieds for someone to share a house or apartment with. There were plenty of ads that looked just fine but one jumped out at me and raised my curiosity. It was an ad from a 50ish guy looking for a guy to share his four bedroom house. That in itself...