Crossdressing Cuckold Stories

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How Nathan became Natalie Ch. 01

by saintlycd on Nov 22, 2017
Transsexuals & Crossdressers

My name is Natalie but that was not the name I was born with; rather it's the name my wife gave me when she made me her "sister" and her cuckold sissy not long after we were married. My real name is Nathan but that's a name I would prefer never to use again because I enjoy being Natalie much more than I ever enjoyed being Nathan. This is a story of how my wi...

College Adventure

by thashyw on Apr 22, 2025

Hello, you are 19 years old. You have long blonde hair. You are skinny feminine built with a girly bubble butt. You are 5.6ft and weighed around 110 pounds. You were never good at sports and always shy and submissive. You have a girlfriend. Her name is Ashley and she also 19 years old. She is 5.7ft and weighed around 120 pounds. She has long blonde hair with...

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A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Life's Changes Ch. 02

by eagle166 on Jun 19, 2018
Transsexuals & Crossdressers

If you haven't read chapter one, please read first. Please enjoy and vote. *** Hello my name is Donnie Baker, after reaching our agreement with Kurt, I've put my Daughter to bed in her crib, My sexy blonde wife Lisa is at the end of the hall probably sucking on the biggest cock we've ever seen. How can I be this calm about it? Well really I'm not so calm...

Girlfriend Problems

by colleenslittletoy on Sep 13, 2017
BDSM

This story is about a woman humiliating a man. It includes crossdressing and cuckolding. After a heartbreaking divorce I wasted a a few years in mourning, reflecting on all the things that had gone wrong in the relationship. What had started as an equal-sided affair turned into a female dominated one. Basically, her pussy ruled. Finally pulling myself...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Story Tags

by Literotica on Sep 18, 2017
How To

You've written your story, edited it within an inch of its life, and are all ready to show it to the world. You open a submission page and – what's this? Story Tags? What the bleep is a Story Tag? The larger any archive grows, the more important organization becomes. Separating stories into our current categories helps connect readers with stories they'll e...

Stephanie's Toy Ch. 03

by cuckoldwishes on Sep 25, 2017
Transsexuals & Crossdressers

THIS STORY CONTAINS THEMES OF FEMINIZATION, CROSSDRESSING AND FEMDOM. IF YOU DO NOT LIKE THESE TOPICS THEN PLEASE DO NOT READ THIS STORY. I APPRECIATE ALL CONSTRUCTIVE CRITICISM BUT RUDE COMMENTS WILL BE DELETED. THANK YOU AND ENJOY ;) I stared at myself in the mirror. Over the past few months my body had changed a lot. I had never been fat but I did have...

A Cuckold Earns His Horns Pt. 01

by lapraline70 on Sep 16, 2017
Loving Wives

Dozens of replies. Dozens. I did it on a whim without Her permission; I was horny and thought it would be fun, never expecting anything to come of it, really. I've never been good at fortune telling, though, as the results attested. Hotwife/Cuckold-to-be seeks Bull to seal deal - mw4m my Wife is a pro Domme and has instructed me to place this ad for U/us....

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...