Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...

Madame Jenoix

by Candour on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 1 --------- A young looking and slight 18-year-old boy sits outside the Headmistress's room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow "Come!" from...

Julia, Ben and Lisa Ch. 09

by chloejacobs83 on Mar 10, 2020
Transgender & Crossdressers

Ch 09: Wednesday A few quick notes: 1. this is the ninth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned We were both quiet and shy the next morning. How do you start after...

Married at First Sight

by komrad1156 on Oct 15, 2017
Fetish

*Note to readers: This story is about the fetish of attractive women who smoke. If you hate smoking, please move on to another story. Don't bother telling me about your poor Aunt Millie who died of lung cancer or your Uncle Joe who has emphysema from smoking as it won't change the way I feel one iota. We all die from something. **Intro: My girlfriend, Kay,...

A Boiled Frog Pt. 01

by noobdude on Sep 25, 2017
Transsexuals & Crossdressers

Author's Note: After three months of trying to find an editor or get some feedback, I'm giving up and will just post my story and see if I can get any feedback to help it out. It's my first attempt at writing a story and I know it needs work, so please be kind. Any helpful feedback is appreciated. ***** Chapter 1 With the last pass over my lips with a...

A Gift in Disguise Ch. 10

by Talespin on Sep 14, 2017
Novels and Novellas

The drive from Marta's home office back to my apartment took only about half an hour. Fortunately, traffic was light. By the time I pulled into my parking space at the apartment, I was feeling surprisingly invigorated. Marta had found no plagiarism concerns in my thesis, and then in an effort to help explain both my 'gift' and the reason for Emily's aggres...

Packback

by MetaBob on Sep 23, 2019
Novels and Novellas

1. Liaisons Many thanks to Emmeran for editing assistance. There wasn't time to make all the changes he suggested, but everything I did change made this better. I look forward to our next project. * * * I woke to my new life in a trail angel's house near the Mexican border. There were 20 of us on cots and the floor. A young woman with long strawberry-blon...

The Gentlemen's Panty Club Pt. 05 - Final

by joefelton on Aug 22, 2018
Fetish

Authors note: This is the fifth and final part of my story, and I believe I have saved the best for last. Thank you to those of you who've read the first four parts. For those readers who are new to The Gentlemen's Panty Club, I have included a short cheat sheet in this note, listing the major characters and a few significant details about them, that should...

Mrs. Montrose

by qhml1 on Sep 15, 2017
BDSM

Part one of this series is in Transsexuals and Crossdressers, "The Creation Of Shanna" might want to read it first. There isn't a lot of Bondage in this, mostly examples of domination and control. Enjoy the read. ............................................... Edie Montrose sat at her new[temporarily]desk, wondering what she had gotten into. This was a g...

An Affair of the Heart

by laffalot on Sep 19, 2017
Loving Wives

Prologue I couldn't sleep. Lying in the darkened room, staring up into the blackness, and listening to the steady, even breathing of my husband asleep beside me, I could only think about love. There are so many songs about love, but for every one of those songs that celebrate love, there is another song about heartbreak and love lost. I was lost in thought...