Sexy Crossdressing Stories Stories

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Infinite Scroll

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Marion's reTurn Ch. 02

by jomar on Sep 13, 2017
Fetish

If crossdressing and male-male sex isn't to your taste, please back out and try one of my other stories. Also, the action here is not safe sex, but this is fiction, after all -- pretend. ********** I stopped at the door and ran my hands down my sexy little black dress, pressing the wrinkles out. I felt the tug of my ebony earrings as I looked down and saw...

Tony and Alicia Celebrate Halloween

by Ice_Tease on Sep 16, 2017
Fetish

Author's note: The Tony and Alicia stories are more about experimentation between a loving couple than hard core stories in a certain category. If you are looking for a hard core crossdressing story this is not the one for you. If you want a story of a guy who will do anything for his girl to include dressing as a hooker and strapon sex then please enjoy it!...

Caught Out at Work

by alexis19901 on May 12, 2020
Fetish

For those of you who have read the stories that I've already put on, you will already know a bit of my back story, but for those of you who are reading a story of mine for the first time, I will give a bit of background in the intro. WARNING - This story contains m/f, pegging and some crossdressing. So, for those of you who aren't aware, I've taken to wr...

Marion Turns Me Out Ch. 02

by jomar on Sep 13, 2017
Fetish

If gentle femdom, crossdressing, strapon and male-male sex isn't to your taste, please back out and try one of my other stories. And let's imagine this is set in a world where unprotected sex is safe. ********** It was looking to be a glorious day. Marion and I were on vacation in the tropics at a five star resort. We started the day with Marion touching u...

A Demon's Revenge

by SnoopWorg on Nov 20, 2020
Fantasy

Prologue When Aron Steelside began adventuring, the golden years were already past. Almost all the High Demon lords had long been defeated by the heroes of old, whose statues now resided in the cities they had made safe. There was still some money to be had clearing out nests of goblins and protecting smaller villages from bandits, but fame was a pipe dream....

Faye's Official CHYOA Story Contest 2025

by Spindizzy on Apr 29, 2025

Hey there, sexy readers, it's me again, Faye, your faithful flirty filthy CHYOA librarian. Gosh, it's been simply ages since we've had a chance to chat, but I've been so busy filing away all your delightfully dirty stories I've hardly had a moment to relax. What I really need is a little me time. A chance to unwind with my favourite toys and the highest qual...

Michele and Buster: A Tranny Tale

by MicheleNylons on Sep 14, 2017
Illustrated

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

Marion Turns Me Out Ch. 01

by jomar on Sep 13, 2017
Fetish

Marion Turns Me Out Ch. 01 by jomar If gentle femdom, crossdressing, strapon and male-male sex isn't to your taste, please back out and try one of my other stories. ********** "There, baby, that does it. Your toes will be dry in no time. A nice shade of mocha. Do you like it? It'll go perfect with your new bathing suit." Marion put the lid on the finger...