Crossdressing Chastity Stories

7,823 results
Orientation
Length
Source
Infinite Scroll

Hotel Panty Slave Pt. 01

by hotelpantyslave on Sep 16, 2017
Fetish

As a traveling consultant, I have found fun ways to indulge my fetishes while on the road. Because I stay at the same hotel for 12-18 months at a time I can leave a bag there with my favorite clothes and toys which means I don't have to take them through airport security every week or risk my wife finding them. Although my fetishes are not that wild, she has...

Serving the Dark Lady Ch. 07

by Certeis on May 27, 2019
Sci-Fi & Fantasy

"Twenty gold for the engagement ring." Karee looked up with a start at the Tiefling who ran the jewelry stand. "You were staring at it, cutie pie. Hoping to get one from a special someone?" She smirked at him coyly. Karee laughed nervously, and then blushed when that didn't work. "No... just daydreaming." "About your future..." She paused, letting the word...

Love Your Readers: Categories

by Tx Tall Tales on Dec 9, 2019
How To

============================ Help Your Readers. Categorized Your Story Correctly. In Love Your Readers, I wrote about things you do to improve the reading experience for your readers. In Love Your Readers: Categories, I'd like to share my ideas on making it easier for the readers to decide to give your stories a read, by placing it in the right category....

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Lost in a Female's Pleasure Pt. 03

by LucysFox on Mar 11, 2019
Transgender & Crossdressers

Synopsis: Damien had been looking forward to a relaxing weekend free from his abusive father, but things quickly take a downward turn when he's kidnapped and wakes up in a confusingly elegant room and learns that his life is about to change forever. After a confusing few hours of fear and pleasure he collapsed, and after waking up he is dressed and led towa...

Made to Obey Ch. 06

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

The Club Pt. 01

by Paulateevee on Jul 13, 2020
Transgender & Crossdressers

This is a continuation of 'The Trap'. It would be best to read that story (5 parts) first before reading this one although I will try to make this story as stand alone as I can. Background - Paul has been outed as a cock sucking sissy to his friends, family and work. He's lost his job, his wife and friends. Louise offers him a way out. Usual disclaimer. An...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...