Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
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Infinite Scroll

Wet Dream Pt. 02

by sissymissyct on Jan 21, 2020
Fetish

After breakfast, Gayle said she would drive me to the doctors office. It was across town but shouldn't take too long to get there. "How did you find this doc?" I queried. "Oh, one of the gals at the gym mentioned her. She is the doctor that got me on the HRT treatment I started recently. I think you will really like her." "Her?" "Yes her. I thought you wo...

Ultimate Sissy Weekend Ch. 04

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Susie is lying in the store supply closet next to Tinkerbell. It's six in the morning, and they've only just finished cleaning the entire supermarket. After changing each other into fresh diapers, and using the few left over to make pillows for them both, the two exhausted sissies lie side by side in the cramped supply closet. Tinkerbell's right hand, handcu...

My Medical Vacation

by sissymissyct on Jul 10, 2019
First Time

BRENDA'S MEDICAL VACATION by Brenda Finally on the way to the airport. My first trip to Europe. I wish my wife was coming with me but she was just dropping me at the Laguardia international terminal. I certainly hoped we would get to go to Europe together and do the normal sightseeing and partying that most couples enjoy, but this was a special trip for me....

Mistress Training Guide

by Kerrysslave on Jan 1, 2019
How To

Slave Training basics Let me start by saying that I love my husband. Some people have a desire to submit, some have a desire to dominate. This is the way I trained Allen. People very quiet a bit. I will explain why I have these basic rules and steps. The most important thing is to be consistent. 1. Never let him know what your ultimate goal is. Never e...

Turning into His Toy Ch.03

by vaultdweller111 on Sep 13, 2017
Transsexuals & Crossdressers

My heart raced as I saw the tray one of daddy's maids held. On it were a wooden paddle, a pair of handcuffs, a pair of nipple clamps, and a pair of white cotton lace panties. "Alright Ashley come wait with the tray by my side and Lilly put your hands on top of your head so I can get a good look at you." He commanded us both. "Yes daddy." We both answered...

Amanda Adams becomes My Queen Ch. 09

by ShyDenZen on Sep 15, 2017
BDSM

"Yes, Ms. Deborah..." I almost stammer, "I think the kind of procedure I'm here for today is called a 'Prince Albert.'" Her pretty blue eyes grow very wide as she stares at me. She blinks at me once, twice- maybe four times... She knits her eyebrows. Finally, she shakes her head a little- flipping her amazing hair. She says, "That's a piercing I can only d...

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...

Earning His Keep

by Compliant1 on Sep 19, 2017
BDSM

I punched in the code and waited. I knew that I was being charged $1.99 for each minute, but I didn't care. I listened to the recorded music until a woman's voice came over the phone. "Tell Mistress Monica, have you been a naughty little sissy?" "No, but apparently my husband has." There was a long pause on the other end. "I just spoke to the manager. He...

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...