Sissy Diaperboy Story Stories

142,289 results
Orientation
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Infinite Scroll

How I Became My Neighbor's Diaperboy Ch. 01

by dl2424 on Sep 19, 2017
Fetish

My parents had left town for the week and I meant to have alot of fun. Little did I know where that fun would be found. I had been home for most of the summer after my first year of college and I was a little tired of some of my parents house rules. It wasn't that they were outrageous, they just made me feel like a little child. They wanted to always know...

How I Became My Neighbor's Diaperboy Ch. 03

by dl2424 on Sep 19, 2017
Fetish

Miss Hunt returned a short while later still dressed in her panties and garterbelt. "What have you been up to diaperboy?" she asked with a big smile. "I uh.. nothing really MMMMommy," was all I could manage. My diaper was really full and she was sure to notice rather quickly what I had been up to. "Have you noticed all the mirrors in this room?" she asked...

How I Became My Neighbor's Diaperboy Ch. 02

by dl2424 on Sep 19, 2017
Fetish

I'm not leaving the house like this!" I practically screamed. "Let's not make a big fuss honey," Miss Hunt replied. "We can just sneak through our backyards. Noone is gonna see us." "But I uh.." I tried to reply. "Enough!" she ordered. "Mommy says we're going home. You can put on a t-shirt if you like, but you and your diapered butt are going to my house....

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

Becoming a Sissy Maid & Slut Vol. 14

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Three: Sissies at Work, Sissies as Sluts at the Farm. 4:00am and the alarm clock goes off. We three sissies must wake and begin our day of long, hard labour of degrading sissy maid and sissy slut work. Off comes our sleeping lingerie and soon three naked with only our chastity devices dangling on our sissy dicks we must quickly and together s...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

Becoming a Sissy Maid & Slut Vol. 04

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Preview: Here is another chapter of my multi-part "Becoming a Sissy Maid & Slut Story." I so hope you all are enjoying this story. I'm no professional writer so excuse me for any writing errors. But I have a flood of sissy maid, slut, crossdressing ideas, thoughts and fantasies to share. I will add more chapters to this unfolding multi-part story now ONE cha...

Breaking with Traditions

by Canadagander on Sep 17, 2017
Loving Wives

Copyright © 2005. All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved. - - - - - - - - - - - - - - - - - - - - - - - Writer's Note: It's time for Canadagander to make a public disclosure, to come out of the writer's den, so to speak. 'Gander is not a real person....

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...