Diaper Sissy Bondage Stories

21,766 results
Orientation
Length
Source
Infinite Scroll

Homeward Bound Ch. 04

by Joe456 on Dec 19, 2018
Romance

The medic and the Russian had stopped for the night. Bearing in mind that he was a city boy, the Russian was not so squeamish, the medic though. If he had to walk, he walked, if he had to sleep, beneath the sky, on the dirt, he slept. Even the medic was a city man, but he had more experience about the life in that country. Especially about how much it took t...

Coffee Shop Syrup

by FemFreak on Apr 9, 2019
Transgender & Crossdressers

Summary: After seeing her boyfriend/employee break regulations, she decides to take his training into her own hands, and remind his of who's boss. ~~ It was difficult being a female business owner. Agatha's small business, a coffee shop at the outskirts of a large metropolitan area, had to compete with the larger franchises. Despite being taller than avera...

Agnes Dourville Ch. 14

by ValoryG on Oct 12, 2017
Transsexuals & Crossdressers

The Gauss family, Anton and Suzy, become an increasingly important part of my young life. Anton and I keep our little (big) secret at work, and no one seems the wiser. We carefully maintain our distance (even though I sneak looks at his fly and buns from time to time) and he grants me no favoritism. After our time in bed (with Suzy away), I return to the dai...

Letter from Tanglewood Springs

by justincbenedict on Jan 1, 2019
BDSM

Dear Shoeblossom, How can I start this? I was raised to be a spoiled brat, and I always seemed to get what I wanted when I had tantrums, even into adulthood. My parents always let me win when we played games, and I learned how to cheat in school and subtly sabotage other players in athletics, such as kneeing in basketball, to make me a star academically a...

Jessica's First Time at the Bar...

by Lion24655 on Jul 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Jessica followed Tom into the bar, walking carefully, feeling very self-conscious. Already she had received a number of strange looks, smirks, as she had slowly tottered across the car park in her high heels. Not just the high heels. The bright red lipstick. The eyeshadow. Nail va...

A Sissy is Born

by gtanya on Jun 19, 2019
Transgender & Crossdressers

We were really excited for our first family vacation. 20 years of my life and I had never visited another country. Jessica and I had been raised by our parents in the small town of Derby-shire, England. Jessica was 1 year younger to me and we had both moved out of our parents' house a couple of years back. Both Jess and me were good at studies and had gotten...

Crossdresser Evolution Ch. 04

by pantyhigh on Aug 7, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. I could feel the arousal but at the same time was ashamed that I was wearing my wife's panties knowing that I would soon be cumming in them. There was this part of me that was telling me, "I CAN'T like this," but there was...

Crossdresser Evolution Ch. 05

by pantyhigh on Aug 7, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. Though there was still a feeling of shame surrounding it, I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

Slave Girl Pt. 01

by KrierWitz on Feb 26, 2019
Transgender & Crossdressers

There's a snap, then "Wake up!" I slowly open my eyes. I feel dizzy, confused. I'm sitting on a bed, and in a grey armchair in front of me, a young woman is sitting. She's wearing a long, green dress, and her black hair is swept to one side. She's staring at me with a big smile. Where am I? I try to open my mouth to speak, but can't. My head is stuck too...

Sissy Arlene's Soul Mate

by SissyArlene on Feb 26, 2019
Transgender & Crossdressers

I was alone for the evening. I decided to spend the evening pampering myself with some wine, Sarah McLachlan in my ear buds, and shaving my legs in a soothing bubble bath. Cindy, my wife, had gone out for drinks after work with some coworkers. This usually meant that she would be home around 2am, and she would be very drunk. It was now 9pm. I was through...