Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Becoming Daddy's Girl Ch. 02

by Sungmehetu on Aug 20, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** After the groceries were put away, I was allowed to shower. The warm water was instant relief to the stickiness I felt in every pore of my skin. I was still aghast on how I had been altered so permanently in just the last 48 hours. A liter of warm water was now being pushed into m...

The Prisoner Pt. 05

by Jamie77917 on Mar 16, 2020
BDSM

Martin has been stripped naked, photographed nude, electro-shocked, bound to a table, had his cock and balls shaved smooth and has been now placed into chastity. A woman, known only to Martin as Warden, was now heading his way with a leash! It became clear to Martin that Warden was attaching this leash to his chastity device. She was going to lead him outsi...

Donna's Ultra-High Heels Bk. 02 Ch. 11

by SHAFERLINE on Sep 15, 2017
Fetish

Author's Note 'Donna's Ultra-High Heels, Book 2' is a continuation of Book 1 and can be read without reading the first book, although it is highly recommend that Book 1 be read first since it would be helpful in understanding the character development of the main players. I tried to make the transition to Book 2 as seamless as possible by briefly summarizi...

The Facility Ch. 06

by spankmehard1984 on Sep 14, 2017
BDSM

Chapter 6: The Dungeon Tim and Vanessa's relationship blossomed. They became frequent clients of The Facility. Their sessions almost became routine. They would make small chat with Cassandra, be taken to the Changing Room, handcuffed together in the Spanking Waiting Room. Miss Kate would take them to her Spanking Room where she would spank them with a vari...

Slavery Philosophy

by honourableboy on Apr 11, 2018
BDSM

i identify as a slave. i'm a slave. That's who i am. It's what i want to be. It just feels right. i'm a slave and i have some opinions on what that means. Now, understand, a slave's opinions are exactly what you think they are, worth only the amount that an Owner, my Master or Mistress, wants to give them. Master=Mistress=Master/Mistress=Owner i think the...

Ms. Alexandria - Interview No. 02 Pt. 02

by gasissynora on Dec 3, 2019
Transgender & Crossdressers

This is the third part of the Ms. Alexandria series and part two of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2a. This part starts with the last paragraph of the previous part. Ms. Alexandria: The Second Interview -- A day out. Part 2b Mistress walks up behind...

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...

Slave Ella Ch. 10 - Jade's Denial

by SlaveMasterDom on Sep 13, 2017
BDSM

We awoke mid-morning, and I drew back the curtains to another sunny Dorset day. "Good morning beautiful ladies," I said, waking Ella and Jade with kisses. "Good morning, Master," Ella said with a big smile. "Good morning, Daddy," Jade said, stretching and yawning; "What time is it?" "About ten-thirty," I said. "Shit, I have to be at work at the pub at m...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...