Literotica Crossdresser Videos Stories

351,514 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

I Adore Crossdressers

by Ab9095 on Nov 26, 2018
Transgender & Crossdressers

I adore crossdressers. Adore!! Pretty little pantied asses up in the air. Shaved dicks and balls hanging down. Pretty little assholes. Fuck Yeah!!! I love seeing their hard dicks flopping when they are riding a cock. Fucking A, when they are hot they are HOT!!! They don't have to be perfect any more than any woman does. They are ALL good. But I do love it...

My Wife, My Tormentor

by Sissyjackie2008 on Sep 16, 2017
Transsexuals & Crossdressers

I am excited by the . One of the most humiliating experiences I sufferer was caused by my first wife. I had been a crossdresser since I was little. Actually my mother started me when she dressed me as a girl for Halloween. When at 7 I started to protest, She said she had no daughter and once a year I could let her have fun. I could never refuse her so I re...

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

My Name is Raquel Ch. 02

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. Well, at this point, I didn't know I was Raquel, just yet. I was just a thirty-something guy with a serious secret addiction to wearing and masturbating in panties. Secret that is, until my 19-year old stepdaughter caught me in the act. Now we share a panty drawer in her bedroom. We also have lots of masturbation par...

Crossdresser In Picnic Area

by Lovinhose on Sep 13, 2017
Transsexuals & Crossdressers

This is my first attempt at a fictional/fantasy story. All my stories thus far have been true, honest, and accurate, as much so as I can recall. But I kind of ran out of true stories that were worth sharing (for now, but I've got some 'irons in the fire' and hopefully I'll have another true story to share fairly soon). The story I will tell here is something...

My Story of Degradation

by Philippasubmaid on Aug 28, 2018
Transsexuals & Crossdressers

A Story of Degradation. This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. I was 47, just divorced for the second time and for the first time in years able to be myself and enjoy what I wanted to do in my own time. I should explain...

From a Husband to a Dutiful Sissy Ch. 08

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Readers, I so hope you are enjoying my story here. It sort of allows me to live vicariously through my words as Chantel. This story has been outlined to allow me to write it in an encompassing and linear way. I try not to wing it but to paint a story that is life-like without being boring, well at least I hope it's not. I hope my characters are believable an...

A Crossdresser Gets Fitted

by Vennessa on Sep 16, 2017
Transsexuals & Crossdressers

Not long ago I was out shopping and stopped at one of the clothing outlet stores that I frequent when looking for sexy clothes and shoes to wear when I go out clubbing or to wear in my adult videos. I was looking through the display rack of my favorite brand of pantyhose, trying to find the colors I wanted in my size, when I noticed a cute guy checking me ou...