Gender Roles Stories

14,399 results
Orientation
Length
Source
Infinite Scroll

Breaking In a New Dress

by mysecretwithu on Sep 14, 2017
Erotic Couplings

"I bought a new dress today." She said over the phone as I lay in bed thinking of her and she doing the same with me. "Really?" I asked... "What's it like?" Gigi is very adventurous in what she wears in public... and what she does not wear under these things. We once had sex at an outdoor restaurant that she had waitressed at a year earlier before they ope...

Black Widow Chronicles Ch. 01

by Treylot on Sep 14, 2017
Transsexuals & Crossdressers

A puff of smoke, exhaled from my lungs, drifts onto the snowy city below me. Standing in my penthouse, I am a woman on top of the world. In one hand alone, I have held the lives of countless men, and with the other, brought ruin to them all. A black widow. I don't think there's a better term to describe a woman like me, though the men in my life might pref...

Pretty Chris-tine Ch. 02

by jealouscuck on Sep 26, 2017
Fetish

My wife, Sharon, and I were lifelong friends. We eventually began dating and then got married. The idea that eventually shaped part of our sex life was her grandmother remarking that I was too "pretty" to be a boy. She thought that my complexion and clean looking face was attractive. One time as a lark, Sharon asked me to let her put makeup on me. I initiall...

'Jenny' & 'Mike': Date Night

by hfernandez1983 on Sep 25, 2017
Transsexuals & Crossdressers

Hi guys, I hope that you enjoy this story that deals with Pegging and Gender Role Reversal. The idea of pegging has always been a hot topic for me. I have tried it in my personal life, though not in the same way as the characters in this story, and have found it to be a highly erotic experience. I have wanted to write this story for a while but have been put...

Ginger's Makeup Ch. 02

by MadQuill on Sep 16, 2017
Transsexuals & Crossdressers

Please remember this is a copyrighted work and all legal disclaimers apply. The story covers a history of changes that Charlie experienced with Ginger after that first night. MadQuill ***** Three weeks later I was heading out to shop with Thelma at the nearby Mall. She had suggested that the day would be spent looking at and possibly buying some new shoes...

Victoria Giang of Vietnam

by Samuelx on Jan 23, 2019
Transgender & Crossdressers

Victoria Giang is a young Asian-Canadian woman of Vietnamese descent living in the City of Ottawa, Ontario. A native of the City of Da Nang, Central Vietnam, Victoria moved to the Capital region of Canada with her parents, Joseph and Nina Giang a long time ago. Unique, brilliant and fearless, Victoria set out to make her mark on the world any which way she c...

The Dummy's Mind for Females

by cashcrunch on Sep 12, 2017
Reviews & Essays

I recently posted the Male Mind for Dummies. If you haven't read it, it was a rant, intended to be ironic and sarcastic, about a generalized male perspective. I did not intend for it to be considered a universal declaration of the male perspective of the entire human species. I got into a discussion with some colleagues at a Christmas party about these relat...

She Makes Him into a Better Lover

by manyquestions on Sep 16, 2017
Transsexuals & Crossdressers

The orgasm rippled through Jenny's sensuous body as she tried to muffle her moan. As usual, she was masturbating on their living room couch after she and Eric made love. As usual, their lovemaking left her unfulfilled. As usual, she was forced to finger herself until she was satisfied. Tonight she brought herself off twice because Eric was particularly clums...

gigi Ch. 01: The Auction

by natcameron on Sep 14, 2017
BDSM

The world has changed. In many countries, large areas have been designated as adult only regions and in these states and provinces, human slaves are legally bought and sold. In government operated facilities, designer clones are cared for and educated until they reach the age of eighteen, at which time they are sent to other institutions where they spend two...

Black Soldier Defeats Nazi Woman

by Samuelx on Sep 16, 2017
Interracial Love

In times of war, men and women are called upon to do terrible things. War is useless, wasteful and devastating. Yet it's a constant part of human existence. Often it's a large scale conflict involving powerful nations. Other times, it can be a war between households, businesses, neighbors, friends and family members. War cannot be avoided. I think it's part...