Chastity Crossdresser Stories

7,593 results
Orientation
Length
Source
Infinite Scroll

The Spirit of Lady Macbeth Pt. 07

by alyssawinters on Oct 19, 2020
Transgender & Crossdressers

The campus still empty for holiday Tracy his backpack replaced with a catch-all purse walked across the quad gripping the strap looking to kill some time reading before returning to home and Mistress Lisbeth. Spotting the couch in the near empty coffee house he planted down in the middle of it ready to open his book of Shakespeare's 'the Tempest'. Nervous...

Life and Time of Lady Vargos Ch. 07

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"The New Bitch of Vargos Manor" Written by: Rikki Lady Vargos begins to exert his new found powers as Lady of the House. He is able to channel many of his frustrations and anger through being tough and almost insulting to those try to accept him as the Baron's wife. As a result, word spreads and Martin is slowly becoming the Bitch of Vargos Manner. "Thank...

Erika's Story Ch. 06

by Quantarx on Mar 2, 2020
Transgender & Crossdressers

This is the sixth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. *** I slept like a baby that night, I think I was worn out from all the excitement of the day before. Mary h...

Trapped and Trained Ch. 05

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

There I was, Saturday morning, back in the driveway of my quote/unquote "Master", as he liked to call himself. I turned off the key to the ignition of my car and prepared to step out. He had sent me an email the previous night telling me to show up in the outfit that I had left in during our last session. I looked down at myself and shivered as I saw the s...

The Roommate Pt. 11 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Josh/Lori, having lost her virginity to Miranda's penetration, and feeling even more like a woman, settled into teaching again. The rewards of passing on his passion for literature to young students was considerable, and now he could increasingly see characters from male and female perspectives. He was especially interested in learning how his female student...

Life and Time of Lady Vargos Ch. 08

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"Lies, Truth, and Innuendo" Martin was pressed into attending to his duties that week as Lady Vargos. With little or no manly pride left to swallow or cling to, he performed his daily routines dressed as a woman, both publicly and privately. Each day seemed to bring more heart felt shame and humiliation into his life as he stepped out and displayed his ema...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jeremy is get...

A Morning's Service Ch. 02

by Philippasubmaid on Dec 10, 2017
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive crossdresser. If you are offended by tales of BDSM and sex between consenting adults then read no further... other wise enjoy. Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue... ***** As I laid on the floor I strained to hear what m...

A Week End with Mistress Pt. 03

by gasissynora on Nov 6, 2018
Transgender & Crossdressers

Dear readers this is part 3 of my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. ***** Once we are on the way I feel a wonderful vibration in my ass. I then realize that the device Mistress inserted in my ass is remotely controlled. I sit back and enjo...

Life and Time of Lady Vargos Ch. 04

by rik581 on Mar 13, 2019
Transgender & Crossdressers

The Martin Hastings Saga" is a work of erotic fantasy/fiction in three distinct pieces and is not based on any beliefs/realities or are any of the characters based on person's alive or dead. This story contains elements of b/d, s/m, forced femininity, and some explicit scenes of gay sexual activity, some non consentual in nature. The story is meant to be a p...