Sissy Chastity Cage Stories

23,357 results
Orientation
Length
Source
Infinite Scroll

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is 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. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

Caught

by ImpureChastity on Sep 13, 2017
Transsexuals & Crossdressers

I had been planning my downfall for weeks. Putting together the right outfit, working out the best place to be in the house, practicing my lines to appear convincingly surprised, everything was lined up perfectly. For a few months the relationship between me and my fiancé, Janice, had been just a little kinky. She had cottoned on to my submissive tendencies...

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

Superstars Rise and Superstars Fall Ch. 01

by felicia_rene on Oct 6, 2020
Transgender & Crossdressers

Superstars rise and superstars fall 1 Part 1 of 4 By Felicia Rene This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy the story Synopsis: The underlying theme is transformation and sexual punishment of the main character for his anti-gay womanizing feelings. For his heinous actions initially making h...

The Wedding Ch. 06

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 6 -- Haberdashery, Hedonism and Highlights... We were into Patti's second week being overseas with Dean -- where by day they were supposedly riding around in expensive luxury cars yet by night? I had to figure, or it was safe to assume that is was more like Patti was riding Dean on their shared hotel room bed, stra...

Truth or Dare Takes a Turn Pt. 03

by Cutiepie183 on Sep 21, 2020
Transgender & Crossdressers

I pull up in Luke's driveway and get out of the car, I retrieve my suitcase from the boot and make my way over to the back door, only to be stopped and greeted by Brent before I can enter the house. Brent leers at me and says "hey there sexy little cocksucker" before he pulls my pants and panties straight off me, locking my cock back in the little pink chast...

Made to Obey Ch. 13

by madetoobey on Sep 9, 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). I'd been forced into a chastity cage and made to start wearing panties all the time. Furthermore, a curious email I'd sent to "Bowser" before I was married led to my past fraudulent activity being unco...

The Backpack

by ~Etoile~ on Jul 31, 2011
Fetish

Moving to a new place is always rough, but it can be rewarding as well. The Nuwisha Design College in Seaside City is a smallish school, but is known for its art and design classes. A lot of literature and word-of-mouth shows that graduates from this school often get very lucrative and popular jobs. Lucky for you, you were able to get in with some of your gr...

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Mark & Lisa Pt. 01: Key-holder

by LockedSissySubmissive on Sep 25, 2017
Fetish

When the doorbell rang I honestly thought I was hearing things, I'd lived in my apartment for two years and I don't think anybody had ever rang it before. It's not that I don't have any friends although if I'm being honest I don't have many, it's just that I live in a secure block and any visitors would ring the bell at ground level and then I would either c...