Sissy Diaper Chastity Stories

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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...

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...

The Business Trip

by OOAA on May 11, 2020
Fetish

My wife and I had been married for about 3 years when I first developed an interest in enforced male chastity. I had always had a very kinky and active fantasy life to fuel my almost daily masturbation habit. I was a 22-year-old virgin when I met Irene and I was looking to resolve that problem. Irene seemed like an exciting 20-year-old girl and I thought tha...

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...

Letter from Carker's Rents

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- Since I taped this, I also have enslaved my brother-in-law Santiago and his basketball team. So I have real progress going on here in Carker's Rents! Love, Sugar Perez "Sugar, I am having a devil of a time getting these thorns out of my, um--" "Your diaper. Say it, Esteban." "Don't--don't you think it was punishment enough for me to...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

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...

Letter from Frost Haven

by justincbenedict on Dec 11, 2018
BDSM

Dear Shoeblossom, Enclosed is a journal I kept after hiring a dominant couple to supervise me for a period of time. I actually first read about Sergei and Kyrsten from "Letter from Maui" and was determined to meet them and hopefully hire them. And it was financially quite steep! And, Sergei and Kyrsten were fun and lively, but they were a tough pair. (I ca...

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...