Sissy Chastity Cuck Stories

13,492 results
Orientation
Length
Source
Infinite Scroll

The Key Pt. 01-03

by WantABWriter on Sep 12, 2017
Fetish

Part One Brenda stood on the back porch of her neighbor's home. She was looking in the window at Paul. He seemed to be crying. Brenda held an envelope in her hand and that was the reason for her visit that Saturday afternoon. She was debating on leaving to return later. Paul seemed so distraught she imagined he had just learned of some great tragedy, su...

Death of a Marriage

by ukresearcher on Sep 26, 2017
Loving Wives

My thanks to Techsan for editing this to a better story. * Twelve years ago I worked on the shop floor of a clothing factory and Shelley was the managing director's personal secretary. All the lads swore blind that he must be poking her because she was really too young to be in that position. Shelley was a really beautiful girl and that facial perfection e...

Rural Encounter

by ukresearcher on Sep 14, 2017
Loving Wives

This is another wife seduction story with a definite cuckold element. I have tried to give it a lighter touch because in writing about this particular scenario, I'm trying to exercise a personal demon. * Anne and I met when we were both just starting our final years, she was twenty one and I was two years older. I am slightly below average height; in fact...

The Role Players Pt. 01

by hollygurl29 on Jul 25, 2018
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21. This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. The main characters in this tale are as...

In Which an Elven Servant... Ch. 33

by Human_Primacy on Oct 24, 2018
NonHuman

In Which an Elven Servant Suffers a Succubus to Live in Her Home Chapter 33 "Yeah, okay. Why not," Lucy responds, in the most casually compliant, yet somehow personally fitting manner possible. At first I think she didn't understand Master's proposal, but no, she makes it quite clear that she understands what he he means to do. Lucy has a lot of character...

Pledging Alpha Kappa Betta Sorority

by phoenixcinders on Oct 3, 2018
Transsexuals & Crossdressers

All characters are over the age of 18. This is purely science fiction. It has a bit of a supernatural twist. I hope you enjoy. Finally finished moving into my dorm room! I'm so excited to finally start over and leave high school behind as well as all the people that bullied me. My best friend Casey is one of my roommates, we got paired with two other rando...

Eustace, College President

by justincbenedict on Sep 17, 2017
BDSM

As Eustace scrubbed his chest, his dick bounced between his legs, and he was overcome with the desire to touch it. I have to clean it, don't I? Eustace thought. But he'd already washed it a bit...too much! My wife will cause me grief, he mentally reminded himself. Opal had her rules. Just the other day she'd caught Eustace rubbing his Supertube, though t...

Scenes from a Marriage Pt. 15

by DopamineFan on Jul 14, 2020
BDSM

On Mother's Day, I made my wife breakfast in bed. She had a lazy day to herself, spending most of it upstairs in our room watching TV, while I took care of our son downstairs. Later in the day, she came downstairs and we all went out to hang out in the back yard. At one point, she pulled me down for a kiss. I think she could tell that I was really wanting...

Lion of the Desert

by Flatulent_Queef_Lord on Oct 19, 2020
Fetish

(Author's note: This story features willing cuckoldry, breeding, inferiority complex, cuckold chastity and an age gap. If any of these fetishes do not float your boat, please feel free to click away. You have been forewarned! Advanced vocabulary has been intentionally used here to complement the historical setting. It is not meant to be condescending. Th...

Christian College Sex Comedy Ch. 10

by FinalStand on Sep 25, 2017
Group Sex

*If I love women, I'm straight; and if I love men, I'm confused; does being Bi make me greedy?* Thank you Frontma for burning the midnight oil on this one. (Yes, this tale is supposed to be somewhat humorous and outrageous too. While not always comedic, I'd like to think it is mostly a good-natured romp.) We were late heading out of the dorm so, under Rha...