Diaper Cuckold Chastity Stories

14,837 results
Orientation
Length
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Infinite Scroll

Holding for Life Ch. 03

by Adrian69702006 on Oct 16, 2018
Fetish

This is a newly written story which I've shared elsewhere too and I expect to form part of an ongoing series. It is completely a work of fiction and any resemblance to real persons, living or otherwise, is entirely coincidental. All characters are well over the age of 18. I hope you enjoy it. ***** Tuesday Morning -9.00am in a classroom/group setting. Con...

Britney - Les Avocat

by call_me_dana on Sep 16, 2017
Transsexuals & Crossdressers

The Court awards Eight Million Euros ... The courtroom in Paris erupted all around though Britney Clark merely stood in place with a feint smile across her lips. She had won. She had expected to win. She almost always did. A couple hours after the verdict and having done the requisite press interviews, Britney was arriving at the offices of her firm with t...

Afternoon Delight Turns into More

by TammyPanty on Jun 5, 2019
Transgender & Crossdressers

How an Afternoon Delight Became Much More I was born into a large trust fund and had the good fortune of never having to work a day in my life. I would always have as much money as I needed and could do whatever I wanted. As it always is in life, when something good happens there is always something on the other side of things that happens to level things o...

Slave Immigrant Ch. 23

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. I guess Human Recourses had me figured out correctly. All those years in BDSM chat-rooms and webs...

Cuckold Birthday Present

by upswing on Sep 12, 2017
Loving Wives

My husband Dave and I had been married for 25 years. We were both 48, still attractive and healthy. And our sex life was still good, even if it had fallen into a routine after all those years. Dave's sex drive was always higher than mine, and I tried to keep him happy the best I could, but I always knew he wanted a little more. Shortly before his 49th birth...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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The Sexy Domme Next Door Ch. 05

by rickiee_2002 on Sep 19, 2017
BDSM

I was stirred from my sleep by my doorbell ringing. I quickly got out of bed and hurried down the stairs. I hadn't thought about it until I was on my way down, but my diaper was soaking wet and weighed a lot. It was so wet that a little bit of pee was dripping down my inner thigh having escaped the elastic leg band of the diaper. I had on Miss Carissa's litt...

Humiliated Stable Sissy

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

After a long week at work, I was looking forward to a quiet weekend of relaxing in front of the TV with a beer, but my fairy godmother had other ideas. "Good morning sissy," came her stern voice as soon as I woke up Saturday morning. I whimpered, immediately knowing I was in for a humiliating weekend. She frowned, not pleased with my whimpering. She's an ol...

Black Dreams

by Bakeboss on Sep 14, 2017
Interracial Love

My girlfriend Charlene was spending yet another weekend out of town working with her boss. I didn't like it at all but what could I do about it, to be honest her boss scares me. It's not only because he a black guy he is also huge and muscular and the look he gives me lets me know he could kick my ass easy. While Charlene is out of town she has me clean her...