Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
Source
Infinite Scroll

Locked Away

by johnlocke1123 on Sep 17, 2017
Fetish

I don't know whether I should have been surprised or terrified but when I finally presented my new, most-extreme-to-date, chastity plan to my wife she instantly agreed and insisted that we start right away. I should probably go into our background a bit to put things into perspective... My wife and I have been married for ten years and we have three great c...

Story to My Cuck

by Miss_Delila on Sep 17, 2017
BDSM

This is a story I've started writing to my submissive about you would exactly happen if he came for a visit in real life. It started out as a fun project and I keep enjoying it more and more. Once you make your way to the baggage claim area you will see me waving at you. I walk toward you and take both of your hands in mine and kiss both of your cheeks....

Slave Immigrant Ch. 18

by OldGuy1026 on Sep 14, 2017
Sci-Fi & Fantasy

After receiving a cloned body I immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either I become an Unskilled Labourer or a Sex Slave. In the end I guess Human Recourses had figured me out correctly. All those years in BDSM chat-roo...

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

My Cuckold Wedding

by CuckinChastity on Sep 16, 2017
Fetish

Note - this is a piece of fiction. The characters are not real. The scenario is purely a fantasy and does not describe any actual relationship. Laurel is not my actual wife. Enjoy! ***** I stood at the altar alone with Rev. Carl, the minister, looking out at the wedding guests. It wasn't a large wedding, still to me it seemed there were a lot of people l...

Jerry becomes Jill Pt. 03: It Gets Serious

by gasissynora on Mar 2, 2020
Transgender & Crossdressers

This is the third part of my story about how I became Jill. My relation with Rikki takes a serious turn and I learn more about what life with her will be like. Each day Rikki gives me an article about a female led relationship. The article on Monday is about a couple in their thirties who are dating. The woman makes most of the decisions when they are in pu...

Mistaken Identity

by goodlittleboysub on Sep 17, 2017
BDSM

I awoke to find myself naked, hanging from the ceiling by two hooks. Dazed and confused, I tried to lift my weary eyes. The last thing I remembered was walking out with that hot girl from the bar. Was I drugged? I felt misty and couldn't seem to focus. Suddenly, I realized that I was naked and in a strange place. In front of me, drinking wine from a glass, w...

Mistress Marisa's Estate Pt. 27

by keptsissy on Sep 13, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** "Please Mistress, please...so sorry, I had to go so bad, couldn't get you on the phone, couldn't hold it, couldn't, please...

Breckyn's Bashful Boss

by justincbenedict on Jul 4, 2018
BDSM

Loudon and Jeanelle Gaskin waved at their baby sister as she walked down the hall of the big law firm. "Make us proud, Breck, baby." Jeanelle called. The legal secretaries of their formerly white-trash family had been enriched by this amazing place... Juanda, Riva and Desna, Breckyn's great aunts were "document specialists" whatever that meant, and had rec...

Adversity in Buttermilk Falls

by justincbenedict on Sep 17, 2017
BDSM

When Blume and Chloe got home from their BDSM party, they were still shaking their heads over the odd goings-on at the dinner party. But Chloe had a funny smile on her face. "You know, Blume... What's this porn stuff about?" Blume blushed. "Chloe, you have to understand, there's fantasy and there's reality... The whole chastity thing is kind of a fanta...