Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

Bad Tidings

by Maxwelzal on Apr 14, 2018
Transsexual

Rememberance ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ All characters mentioned herein are of at least eighteen years of age or older. Bad Tidings is a story that contains various for...

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PJ's Cucky Husband

by cuckytoher on Sep 17, 2017
Loving Wives

PJ had it all. Long red hair that cascaded down her back reaching almost to her gorgeous bubble butt, big tits that she loved to put on display by wearing skimpy or see through tops, a pretty face, and a gorgeous shaved pussy that could lure any man she wished. She reveled in the power she had over men and especially over one special man, PJ's cucky husband....

The Sexy Cuckold Couple Pt. 09

by cuckcpl4play on Sep 19, 2017
Fetish

Part 8: The Ceremony We arrived home and almost like clockwork, a text came in to Miss Jenny's cell as we pulled up the drive. Master's text read...time is fleeting slut so you will have visitor's at your place shortly to help with your final task before dressing and officially submitting and devoting yourself to me as my owned slut Oh, and make sure slave...

Anklet Adventure Pt. 04

by dometoo on Nov 27, 2018
Interracial Love

Editor's note: this story contains scenes of incest or incest content. *** The last time Lynda and I returned from our romantic getaway cruise, she came back black bred and knocked up, cuckolding me and keeping me in chastity much of the time. I'm now the proud father of a three-month-old black boy, Mark, her bull's namesake; with strong prospects of havin...

Cherry Pt. 03

by Cirkle7 on Dec 25, 2019
Transgender & Crossdressers

We made it to the final installment of Cherry! You may want to read the other two first... I am working on a few more. Finding time is difficult, but I really like sharing my dirty thoughts with you all! Of course this story has no person under the age of eighteen. Thanks for the comments, I like the bad ones the best... makes me happy that I made you sick!...

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...

Cuckold Story

by Grey Eagle 286 on Sep 19, 2017
Loving Wives

I watched my wife of ten years as she entered the den where I was working on a report for work. She was looking very good. Grace wore a light brown leather skirt with a pale yellow shell and Cardigan sweater set over brown boots with high stiletto heels. Her body is amazing, and is centerfold quality for playboy. I am very proud of her. I smiled at her, "Yo...

The Birthday Party

by today_i_am26 on Jul 27, 2020
BDSM

Chapter 1 - The Negotiation We sat, the four of us, in a coffee shop on the high street. To the causal onlooker, we probably looked like university students meeting their parents for a catch up. The reality was something quite different. My Wife, Goddess, Dominant, Keyholder, had answered an online advert on my behalf; a couple looking for a Sissy to att...

Counselling Changed Our Marriage Ch. 02

by Quietoldie on Dec 1, 2017
Transsexuals & Crossdressers

I am grateful to another member of Literotica for the story line and about half the content of this story. I have thoroughly enjoyed the collaboration and have found working with a woman has informed my own writing. Chapter 3 will follow shortly. ***** Third Joint Interview Emily and I arrive at their marriage counselling session a bit earlier than their...

Sissy Awakening Ch. 03

by Torbjornson on Oct 5, 2020
Transgender & Crossdressers

Standing at the living room window with the windex and paper towels, I teetered on the ridiculously tall Mary Janes. It were as though I were standing on the balls of my feet and toes only. There was no relief. My other pumps felt like heaven compared to these! She said to wash inside and out, and not to miss a spot. That meant I'd have to go outside. It wa...