Gender Role Stories

41,277 results
Orientation
Length
Source
Infinite Scroll

Stranger Fuck

by hfernandez1983 on Sep 13, 2017
Transsexuals & Crossdressers

It's been a while since I have written something. It's mostly because I have felt so uninspired and didn't know what to write. My main fantasies these days revolve around a man crossdressed while he is pegged by a woman who likes to dress as a man. My last story series Jenny & Mike got a decent reception and I wanted to write more. But like I said, I've...

The "Secret" of Attraction

by Selena_Kitt on Nov 18, 2019
How To

This is an official entry into the 2007 Literotica How-To Contest. Please take a moment to make your voice heard and vote at the end of this essay. ----- Lately all anyone can talk about is "The Secret." (If you haven't heard about "The Secret," yet, you've probably been really busy, huh?) But remember back in the 80's, when the big topic was the "Superwom...

Pilot Makes Penelope Pitstop

by MeganOckers on Jun 9, 2020
Humor & Satire

As I've boldly stated in previous works I believe that role play will help you survive lockdown until normal sex lives are resumed. But even during a pandemic I consider that some sexual fantasies should remain just that. So, if I was to mention the word 'Thunderbirds' I'm not advising you to trawl the internet looking for superannuated supermarionation stoc...

Love is Grand

by AnnabelleRaven on Sep 16, 2017
Transsexuals & Crossdressers

PREFACE Retired and independently wealthy, 60 year old Stan Berman discovered he had only 12-18 months to live due to a rare neurological syndrome that would sap his strength and motor skills, but the symptoms would not onset for at least a year. The widower's only family was his devoted son Patrick and grandson Michael. A life-long cross dresser, Stan co...

Ogres and Ogresses Ch. 01

by stubborn_dreamer on Sep 12, 2017
Sci-Fi & Fantasy

Chapter One: Humble Beginnings This is what we were told. In the old world predating the 31st century, women generally lived in patriarchal societies. The people thrived in technological advances and worked hard to improve their society. Robots came in the forms of nurses, teachers, even companions. Cures for what man had previously thought incurable were...

Role Playing with Michelle Ch. 01

by gunhilltrain on Apr 11, 2018
Erotic Couplings

[This story takes place in the some fictional universe as my previous story A College Tryst.] Prologue – Michelle There were thousands of students at the City College of New York, tens of thousands in the City University system as a whole. For the fall semester of 1974 there was one of this multitude named Michelle, a graduate of Bayside High School in Que...

In the Torture Chamber

by Connerandfionuala on Sep 13, 2017
Sci-Fi & Fantasy

Foreword: Before you read this story we think it is important to point out a few things. This story was actually written by two people myself and my friend Helen, and is part of an ongoing role-playing scene. Having logged our scene we decided it would be fun to submit it to Literotica, and so we edited the logs to make them nice and presentable and this is...

Waking up at the Crack of Dawn

by backdoorboogie on Oct 5, 2020
Fetish

Hello, here is my story. If you do not like cheating wife storied please do not read this. Please only write, positive, constructive feedback. I ignore negative or useless comments and suggestions by readers. My name is Madeline, I work in a Designer Clothes shop selling male items. I have worked here for a long time, nearly twenty years. For many early yea...

A Visit to the North Ch. 01

by MadQuill on Sep 15, 2017
Transsexuals & Crossdressers

Preamble The beauty and range of Life, strikes me as unsettled. There are reasons that changes occur to each of us. Things are just imperfect and some choose to revise the conditions. We say we are what we are, but life requires adaptation. Some people "might by force of will, cause their face to approach those of they're ideal. Some imagine that this is...

Art, Part Two Ch. 05

by art4real on Sep 15, 2017
Novels and Novellas

Art, part two. Ch. 05 Art finds out what Dr. Heidi's plans are for him. * I was reliving last night's activities in the shower, which unfortunately, included experiencing a healthy dose of guilt about Suzanne. There's no way I could just claim I was doing Lisa a favor. Well I could, but it would be pure BS. Lisa's a nice lady; I'll have to be damn careful...