Sissy Crossdresser Stories

7,061 results
Orientation
Length
Source
Infinite Scroll

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

Weekend Games Ch. 03

by SissyAndi on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: My stories contain explicit descriptions of consensual and Non-Consensual sexual activities and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexual activity, cross-dressing and other fetishes and perversions. All characters and events are complete and total fiction a...

Linsey Gets Used

by linseyCDslut on Sep 13, 2017
Transsexuals & Crossdressers

It was one of my first times in public dressed as a girl, and I was feeling nervous and insecure. As other guests at the party milled about around me, I stood by the snack table, clutching my drink with one hand while tugging at the hem of my miniskirt with the other. Was it too short? What do people here think of me? Do they even notice me? And where's my f...

How Nathan became Natalie Ch. 03

by saintlycd on Dec 31, 2017
Transsexuals & Crossdressers

Friday came and after classes and eating a light meal it was a little after five in the evening when I paid for and checked in the room where I was going to meet Kevin. I gave myself plenty of time to get ready for him. I had decided besides wearing Jennifer's dress I would go even further and try my hand at completely dressing as a girl. I purchased some...

Uncovering the Sissy Beneath Pt. 03

by jefferyscott745 on Jun 25, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part three of my previous work. Be sure to read parts one and two if you wish to understand the background of this section. *** I hesitate to follow him out of the bedroom, as my anxiety is out of control. "Have I just been kidnapped...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

The Retirement Party

by DrLuverotica on Sep 18, 2017
Transsexuals & Crossdressers

April 3 Jo had been singing it for days and it was driving me mad! "It's all about the bass, about the bass..." On and on she went until finally I screamed: "Enough already!" "Oh hubby. Do you not like my song?" "Well, I like the way you move to the song." Jo looked hot swinging her big sexy curvaceous ass in a short micro skirt and flicking it up occasi...

Sarah Gets Soaked and Meets a Girl

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. *** I was on vacation in Florida. On the second day, I decided to visit the 'glades. I wore a matching red bra and panty set, with a...

Stephanie's First Time

by swinship28 on Apr 4, 2018
Transsexuals & Crossdressers

Disclaimer: All events in this story took place with people above the age of 18. ***** It was a Tuesday morning and I had begun my usual routine. I woke up, put on some girly clothes, watched porn, and started masturbating. When I get aroused enough, I would grab my lube and dildo and I would start fucking myself until I cum. It was mostly satisfying, but...