Diaper Ai Sissy Stories

24,751 results
Orientation
Length
Source
Infinite Scroll

Mommy's diaper sissy

by Bornagirl on Apr 22, 2025

This is my first story and would really appreciate your input on the story if I'm making literary mistakes please tell be if I'm not differentiating the characters properly making it difficult please give me an example and a rewrite for the chapter so I can understand what your saying and apply it to the rest of the story. You wake with a soaked diaper at 19...

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The Diaper Sissy Project

by AlyssaDb on Apr 29, 2025

Jordan rolled over in bed and looked at his phone. It was 6 am; time for him to go to work at his fast food job. He hated this job and the way his life was going. He got out of bed, got ready and went to work. He made it on time and started his day. A few hours later, just before lunch, his boss called him into the office. "Hey Jordan, thank you for tal...

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Landlady's pet leashed diaper sissy

by Bornagirl on Apr 22, 2025

I had been speaking to a lovely woman for some time now, down the local water meadows. We talked about life the universe and everything, just Smalltalk really when she came out and said your quite submissive aren't you. I was slightly taken aback because although I am softly spoken I view myself as more of a gentle soul than a submissive one. we got talking...

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The Worst Smell

by RANDYCRIME on May 14, 2020
Fan Fiction

Contains: hypermess, hyperstink ____ DONG! DONG! DONG! The church bell signaled that it was 3 PM in the quaint suburban neighborhood of Fouler Hill. Cars rolled along steadily in the streets, a dog or two here and there poking their heads out of the windows. An old couple crossed the street where a school bus stopped to release some children, who raced each...

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Harmonyville

by drteddyro on Apr 22, 2025

In the quiet town of Harmonyville, lived a young girl named Lily. Lily was unique in more ways than one. Born as William, Lily grew up with little interest in traditionally masculine pastimes and sports. Instead, he found joy in playing with dolls, an activity that perfectly suited her delicate physique and graceful mannerisms. The boy's interests and demean...

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Ultimate Sissy Weekend Ch. 03

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Before today, Susie had only ever spanked herself. Nothing could have prepared her for the 220 spanks she'd received earlier, her first serious sissy spanking. Still her butt burns, even in its new pink poofy diaper. And now it's joined by fresh welts and lines on her inner thighs from the cruel canings of the redhead's ruler, as she happily decorates the tw...

Daddy's Little Sissy Diaper Slut

by Satanicsissybitch on Jul 14, 2020
Transgender & Crossdressers

I absolutely love wearing my adorable pink pull-ups for Daddy and I really love being his cute little sissy diaper slut! Daddy had always loved playing the dominant role with women but it was me who has him addicted to sissies and I've always been a little diaper slut. Well, a pull-up slut anyway. I always felt the adult diapers were not only boring and blan...

Ultimate Sissy Weekend Ch. 02

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...

Hypnotized

by Satanicsissybitch on Sep 23, 2019
Transgender & Crossdressers

Warning: there's a lot going on here, diapers, sissies, interracial sex so if any of those things are an issue you may not like this story. *** Where do I even begin with this story? I don't know why but I feel absolutely compelled to share my recent experiences online and I can only assume it has to do with that horrible hypno-therapist one of my supposed...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...