Sissy Gay Stories

27,439 results
Orientation
Length
Source
Infinite Scroll

Lisa: A Tale

by sparkle8 on Sep 14, 2017
Group Sex

Chapter 1 My name is Lisa. I work as a secretary in a large downtown insurance company (if I tell you the name, I will have to kill you). My friends and co-workers tell me I'm hot. I look in the mirror, and I can sort of see what they mean, but I'm not particularly confident of my ability to attract the opposite sex. So I often find myself alone on a Friday...

Directions

by patricia51 on Sep 16, 2017
Letters & Transcripts

Dear Sonya, I suppose I did sound a little incoherent last night. Okay, very incoherent. But I just had quite a shock and I don't have any idea what is going to happen, or even what I want to happen. You have always been a wonderful sister. You were the one that stood by me after my marriage to Adam collapsed. When I finally realized that I was gay you hel...

Set-up Wife Turns The Tables

by subFLmale on Sep 12, 2017
Loving Wives

I had worked for several weeks to see my plan come together. I had always had a fantasy to see my wife get used by several men while I watched. I had spoke to her about it over the years and each time she would get mad and call me a kinky pervert and that would be the end of our conversation. My wife and I liked to visit the forums on Literotica.com and to...

Womans Vanitie

by NoJo on Sep 1, 2017
Humor & Satire

The following story was translated from the Italian in 1607 by the English Poet William Grebe. Grebe claimed the original version was Boccaccio's, but Historians generally agree that it is much more likely that he just downloaded it from some web site or other. The full title given by Grebe goes on for eight pages, but in later editions it was abbreviated t...

How to Write Romance

by MarshAlien on Sep 1, 2017
How To

My name is Marsh Alien, and I am a Romance writer, and I have a problem. "Hello, Marsh Alien." Yeah, yeah. Anyway, in "How to Break the Literotica Toplist, an entry in Literotica's How-To Contest, Tink4Fairy debuted with a work describing the best ways to reach the top-rated lists in each of the site's categories. The Romance category included the followi...

French Lesson

by J G Parkes on Sep 12, 2017
First Time

In today's moral climate when young girls barely into puberty are given sex advice, condoms and pregnancy tests and their parents don't even have the right to know about it, the sexual mores of the past are quite unbelievable. No, I'm not talking about the long ago past, but only fifty years. I was an only child and spent my early years in the shadow of war...

Gay Like Girls

by ThomX on Sep 16, 2017
Transsexuals & Crossdressers

I won't bother you with the specifics of what happened. Hell, I'm not even exactly sure of how everything had happened! It all started one day when I was at my friend Randolph's house, and me and him were just casually watching the ball game on his big-screen TV that he'd just purchased at the local Wal-Mart chugging a beer and having a gay old time (if you'...

Kitten: A Pantyboy Story

by pantyboy4mistress on Sep 13, 2017
Transsexuals & Crossdressers

It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first few seconds we met. Or so she likes to remind me. She didn't n...

The Perfect Scene

by sublocked on Sep 15, 2017
BDSM

In my roamings on the WWW I came across a few self bondage sites and I found it amazing what people would risk in order to achieve fantasies of helplessness. Some do die in such scenes. One does have to be careful. Here is a story of one man who took all the care required in order to survive, but was it enough? Jason had dabbled in self bondage for many yea...

MissileToe Mania

by vegina on Sep 15, 2017
Toys & Masturbation

Margaret Sanderson, Vice President and director of marketing for PLEEZE ME Products had been reprimanded for her apparent deficiency in developing innovative new merchandize. The CEO, Stephen Miller, indicated he would give the young, ambitious and beautiful MBA one last chance. “Either do it, Margaret, or I will have no choice but to ask for your resigna...