Gay Sissies Stories

124 results
Orientation
Length
Source
Infinite Scroll

A Night at the Movie turned me Gay

by jamtby on Oct 6, 2020
Gay Male

During my senior year in college I was a busy, serious student. I had a girl friend and we enjoyed time together and an active sex life. All in all I was a typical 20 year old male. Then an unexpected movie changed everything. My girl was out of town on a field trip for a psychology course she was taking. It was Friday night and I was horny. I made the dec...

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...

Scott Chadwick, Summer Associate Ch. 01

by Victor C. Anderson on Aug 30, 2017
Gay Male

This is a prequel to "Hell Hath No Fury Like A Drag Queen's Wife." Saturday, July 1st "Are you staying here, Quint?" asked Scott. "Yeah," replied Quentin Daniels, one of Scott's two roommates. "With you and Tompkins gone, it'll be like a vacation just staying here." Scott Chadwick, Quentin Daniels, and Melvin Tompkins shared a three-bedroom townhouse own...

Nephew's Readjustment Pt. 08

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. ***** Once her nephew had left, Cynthia got to work. She skimmed through the pictures and video she had o...

The Hanky Code Pt. 12

by His_fag_wife on Sep 14, 2017
Gay Male

I had no comprehension of the time this abuse lasted. I didn't even try to take it or manage it, or do anything, I just lay there. My two mechanical Masters reamed my throat and pussy simultaneously so that both the ends of the two cocks wouldn't have been more than a few inches apart at the end of their in stroke. If I'd been aware of the situation I woul...

Sal's Dilemma Pt. 01

by sj_53 on Aug 31, 2017
Gay Male

[Authors note: This is an edit to correct a cut and paste error that occurred just prior to first publishing the story. My thanks to Literotica member "Fleshmaster100", some of the characters and scenarios in this story are based on his fantasies. When someone feeds the ideas, it makes fleshing out the story much easier. Thanks "Fleshmaster100". ] *********...

Rick Needed a Beer, Gets Much More Pt. 12

by Iwanttwo on Sep 23, 2019
Gay Male

I was awakened by the rough landing and was surprised I had slept through the entire flight. I was glad I had all my gear in one carryon bag and headed straight to the rental car desk after getting off the plane. I rented an average rental as I wanted to have a low profile and keep to myself this week. After checking in, I looked around the hotel. It had a n...

From Alex to Lexi Ch. 03

by oskarwild on Sep 14, 2017
Gay Male

Awakening Lexi lay in bed with the morning sunlight streaming across his naked body. He was in the fetal position and he could see Max, his new Daddy, lying on his back next to him, sound asleep. Daddy's arm was over his head and Lexi could smell the pungent odor of Max's underarm. They had worked up quite a sweat last night before finally falling asleep....

Swimming Pool Eyes

by kicky1000 on Aug 17, 2017
Gay Male

It was late at night and I was walking the streets down near the docks. Because that's where they hang out. Down near the docks. Yeah. They were here all right. All around me. I could practically smell them. The smell of 'gay.' There was one standing in a doorway. There was one on the corner, looking across the avenue at the dark river. They were all so ca...

Power Trip Ch. 05

by Wally_West on Sep 26, 2017
Gay Male

Colin stood in front of the toilet relieving himself through the opening at the tip of his chastity cage. He was growing used to its weight and presence, finding less discomfort from the device every day. He was happy it was Saturday and he didn't have to go to school; Colin wondered what his step-mother had in store for him, as their sexual activities were...