Erotic Crossdressing Stories And Captions Stories

369,179 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Crossdresser Evolution Ch. 03

by pantyhigh on Jun 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties, though there was still a feeling of shame surrounding it. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

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....

Fan Fiction Captions

by pornsleuth6 on Apr 29, 2025

I have been making a lot of captions lately, so I thought it made sense to split the captions off from my short story collection (https://chyoa.com/story/Short-Fanfics.46075). They are similar things of course but different enough that I don't want to disappoint people looking for one and finding the other, update to update. The grouping on these will be fai...

Open in Reader

Farewell from Randydaughter

by randydaughterreborn on May 15, 2018
Reviews & Essays

I've been writing my erotic stories on and off for almost 10 years now, and I think my well of creativity may finally be running empty. I might post the occasional story here if the muse strikes me with a good enough story, but I think overall I might be done with actively writing erotica. Before I go, I thought I might write a kind of farewell letter to my...

Tales from the Oedipal Zone

by crazydorian on Mar 24, 2019
Fetish

The Oedipal Zone idea is a creation of Squelchapron, from his old “freeusecaptions” Tumblr. The original captioned stories (Field Observations and Paragon Magazine) have been used here with his permission. An Oedipal Zone is an area within a more general free use world. The normal free use tropes apply in most parts of the world: society functions more or le...

Open in Reader

2020 - WIC

by Rekki on May 10, 2020
Miscellaneous

WIC, short for „Weekly Image Captions“, is a project I started this year to post an image caption each week. The characters, scenes and kinks are often different from piece to piece but there are some reoccurring themes like Timestop and Mind-Control, since these are my own favorite kinks. Since March, it‘s possible to choose the character for an upcoming we...

Open in Reader

Image Captions 2021

by Rekki on Jan 19, 2021
Miscellaneous

Another year, another collection of smutty writing! Thank you for your continuous support! To assure quality over quantity, I won't be doing these on any regular basis for this year, though I can say that I won't be stopping at all and you'll see one when I feel like it's finished. I hope my work is worth your time by then! Other than that, have fun reading...

Open in Reader

Short Fanfics

by pornsleuth6 on Apr 29, 2025

Each chapter will be a different short story. Most of these at least initially will be from my work over on the Image Inspiration thread, which is a great post but is unwieldly for new cummers. I will also post completely new ones, including a new Kate Upton story to kick things off. Several of these will be more of the ****/**** variety, so I will go ahead...

Open in Reader

Crossdresser Evolution Ch. 06

by pantyhigh on Aug 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's panties. Recap - Crossdresser Evolution - Ch 02 - Getting my wi...