Diaper Sissy Chastity Messy Stories

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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...

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...

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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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...

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...

Pro Domme Assignment Pt. 02

by Dprboy4Dominant on May 7, 2019
BDSM

I was shocked and embarrassed and immediately put in headspace from her direct words. Embarrassed not only by my very full diaper but that I had been caught disobeying a direct order. Head Mistress S walked over to me as I hurried to get back on my knees. She was dressed in a very beautiful business suit. She came very close to me, wrapped her hand around my...

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...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

Behavior Modification Institute Ch. 08

by NancyPan on Sep 12, 2017
Fetish

It seemed like I was going to have plenty of time to contemplate not only why I was experiencing such arousal at being treated like a helpless infant and a domestic pet, but time to consider my future fate with Kelli. Here I was, diapered and locked in a 4 X 4 X 6 wire dog cage with a solid plastic floor and a doggie bed. I tried to ignore the sensations fro...