Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Casey's Submissive Journey Pt. 03

by corduroysissy on Dec 16, 2017
Transsexuals & Crossdressers

Angie & Debbie (Fag Night) Part One Audrey was dressed in a pair of tight black mid-wale corduroy jeans and had an 18" dildo sticking out through the fly of her pants. She laughed maniacally and grabbed Casey's balls. "I own you sissyboy. First I'm gonna yank on your sissy balls til you beg for mercy, then I'm gonna fuck your sissy ass with my big cock...

Wife's Early Return

by Jamie_in_dresses on May 9, 2018
Transsexuals & Crossdressers

We had been married for four years when my wife took on a new job, she was going to be the manager of a new insurance brokerage in our town but had to spend a few weeks of orientation and training at head office 180 miles away before she took on the responsibility. She spent the weeknights with an old university friend and would come home each Friday evening...

Initial Crossdressing Adventures

by vjak19 on Sep 19, 2017
Transsexuals & Crossdressers

Since the first article I wrote described the last time that I dressed as a woman was generally well received, I have decided to share some more of my story. To do that I will start the journey at the beginning and travel through to some of the first times that I ventured out into public dressed as a woman. For those that did not read my initial offering le...

Caught For the Last Time Ch. 09

by TGJamie on Sep 15, 2017
Transsexuals & Crossdressers

End of Series Notes While not the last chapter in this couple's life, it is the last chapter in this series. Finding the right theme to end a series with is not easy, but it was through the wonderful emails I received from so many, that is was easy for me to keep Jamie and Kelsey in love with each other, and only each other until the end. There were many r...

The Craigslist Killer Pt. 02

by thrillerauthor on Sep 15, 2017
Transsexuals & Crossdressers

© 2014 by Nom de Plume * "Missy, are you still there? Please don't hang up on me!" "I'm here." "I really want to see you." "I don't know, Ron...let me sleep on it, okay?" "Sure, Missy, whatever you say. Can I call you tomorrow?" "Okay. Bye Ron." I hung up before he could say goodbye. For a moment, I was actually going to give in to him! It did sound...

Caught by Kyle Ch. 01

by MzDeviancy on Sep 16, 2017
Transsexuals & Crossdressers

My stories tend toward the nonconsent/taboo side, but I want to be clear that I'm in no way suggesting that the acts in my stories are okay. Forced sex is a fantasy I enjoy and I write for other similarly minded people. Real rape is ugly and sad, and if it's something you're considering acting out you should seek help. * Alright, longest disclaimer ever, b...

Attaining Joy

by jackie_em on Sep 18, 2017
Transsexuals & Crossdressers

This story includes transgender and crossdressing. If either of those bother you, then this story is not for you. ***** Starting college was tough for me. I was Joey, 17 years old, but turned 18 around the end of the first semester. I was nerdy and withdrawn in school, and had moved a number of times growing up. I think I went to at least eleven schools in...

St. Clair Ladies Circle: Beginnings

by 1946EW on Sep 14, 2017
Transsexuals & Crossdressers

I Become A Woman (Author's Note: I Become A Woman is the true name of this chapter. Since Literotica's protocols do not permit long titles, I shortened the title used by Literotica. * My name is Valerie. Well, my en femme name is Valerie. For the past two years I've lived as a woman—dressed as woman, presented myself to the world as one, think lik...

Julia, Ben and Lisa Ch. 05

by chloejacobs83 on Mar 2, 2020
Transgender & Crossdressers

Ch 05: FRIDAY A few quick notes: 1. this is the fifth 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 "I knew I would tell you eventually. But I just couldn't for the longes...

The Doll Maker

by Fibaro on Jan 22, 2020
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (This story was one I wrote and posted on Halloween. It's a bit more gruesome than my other works as a result.) *** Intro Carl had always been different, he was a quiet somewhat effeminate looking boy, taking mainly after his mother. From an early age he had loved playi...