Sissy Chastity Stories

12,331 results
Orientation
Length
Source
Infinite Scroll

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

My Wife Turns Me Out At Book Club

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been 3 days since the event, and my mind is still reeling. I can't believe my wife took me as far as she did in one night. Sharon had told me a few weeks ago that the neighborhood book club she attends was having a special couples night. Apparently the wives had discovered that their husbands enjoyed the idea of group sex and partner swapping, and eve...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

The Training of Sissy Paula Ch. 2

by submissive~pet~ on Sep 14, 2017
Fetish

Mistress carolyn patted me on the head and said i did good. Then she sent me home. The chastity belt still on me, and the cucumber still in my bottom. I logged on line yet no e-mails from Mistress carolyn. It was 4 days before she sent me another e-mail. Hello my pet i bet you thought i had forgot about you. i replied with a yes Mistress i was be...

Neighbourhood Terror to Sissy Pt. 08

by Fibaro on May 20, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Chapter 9 Once off the bus Mark snuck to his house as good as he could. Hiding behind bushes and hedges whenever he spotted someone. He really didn't want to run in any of his neighbours with this big pink shopping bag. It would mean nothing but trouble since he realised f...

Transforming Brent Pt. 04

by sissymissyct on Dec 2, 2019
Fetish

In the morning I showered and dressed casually as directed by Mistress Wendy. My new black skinny jeans and a plain blouse with light day make up and my cork wedges. Some jewelry and my handbag and I was ready. Mistress wore leggings and a tunic top with her long hair tied up in a bun. Wearing flats, she was still much taller than me. We had a light breakfa...

Humiliation Journey Never Ends

by Subkoksukr4u on Jun 25, 2019
Transgender & Crossdressers

Here I am once again looking up into the eyes of my tormentor, my superior in every way, especially his cock, 10 1/2 inches to be exact. I know because when I first met him he made me measure it with a ruler. He made me measure mine too. I was embarrassed, humiliated and shamed for being so small. It hasn't been called a penis or anything remotely masculin...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...