Diaper Sissy Bondage Stories

21,766 results
Orientation
Length
Source
Infinite Scroll

The English Ranch Pt. 01 Ch. 03

by slave_william on Sep 15, 2017
BDSM

(Warning –this and later chapters describe William's participation in Pony play and describes heavy BDSM and pain scenes which may not be enjoyed by all readers. Do Not Read if you cannot handle this type of fantasy and please remember, it is fantasy. If you do not enjoy this story or any of my writings, I'm certain that there are thousands of other stories...

A Sissy's Journey Ch. 02

by yukonnights on Sep 15, 2017
Transsexuals & Crossdressers

This work is authorized by the author exclusively to Literotica.com for publication. Introduction: A tale told in short vignettes which chronicle one young man's journey into self discovery. Please Note: This story series contains elements of homosexuality, cross-dressing, light femdom/submission and male feminization. All characters are fictional and port...

Lucy's First Submission Ch. 04

by StrictDom on Sep 12, 2017
BDSM

I would like to extend My thanks to everyone who has emailed Me with their comments. They have been filled with admiration, enthusiasm, encouragement, and different viewpoints which I have found immensely useful. Master. I had allowed My toy to come, after about six hours of light teasing and torture. For Me, it had been the most incredible evening of My l...

Marrying Sherry

by linedout5 on Dec 10, 2019
Loving Wives

SHERRY (Part 1 with Preamble) Words for our sexual nature have become established parts of our language. I am cuckold, submissive, sissy, and my wife is hot wife, dominatrix/submissive, slut wife. She loves controlling me but she also loves submitting to real men, bulls, studs. In the time period I'm writing about, we were in our early twenties, which wou...

Kim's Journey into Femdom

by humaleiated on Dec 24, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. *** Author's note: Please see Nana's Diary for the prequel to this story. Kim and her Mom have "the talk" Chapter 1. As Kim drove home, she mulled over the events of the day. She thought it would be like most other, but it turned into so much more after she had discovered Nana's Diary...

Adventures of Wyn Pt. 02

by Lyn_Wynn on Dec 25, 2019
Transgender & Crossdressers

These stories are my fantasies and how I'd love to live my life. Everyone who interacts in sexual moments is above 18 years old. Any person or company presented are fictional. Title: "Girly Thoughts" Sun shined across my bedroom. The last thing I remember was Craig hugging me from behind and kissing my neck. Here I was, in my bedroom with a stranger I just...

One Step Too Far Ch. 02

by LanaChu123 on Dec 3, 2019
Transgender & Crossdressers

I must have been standing there for awhile barefoot and terry-cloth robe with my eyes fixed on Alex and my mouth open. For some reason I was still on my toes even though Alex had let go of my chin. I lowered my feet and tried to say something but some feeling of fear and some feeling of being out of control confused me and I couldn't think of what to say. Ev...

Panty Boy Ch. 03

by AussieKev1 on Mar 17, 2020
Fetish

Author's note. As with all my stories, they are largely based on fact, with some embellishments to make them, hopefully, enjoyable reading. A very kind critic proposed that I had written myself into a corner in this series and I thank them for their constructive criticism, however when writing largely based on truth you are bound by that truth. Please...

Kathy and Manny

by BJB69 on Jul 6, 2020
Erotic Couplings

Manny was always a good looking kid. His Mother had named him Manuel, but his classmates dubbed him Manny in the first grade. His Mother was second generation Mexican and his Dad was second generation Guatemalan. He was just under six feet tall and weighed 184 pounds. He wasn't muscular in a weightlifter body style, but more of a swimmer or soccer player bod...

The Reunion Ch. 02: Thai Massage

by Valtikka on Jul 15, 2020
Anal

"Krissy! Long time no see! It's so good to see you. You look great girl!" As soon as I get out of the Uber, Micky comes walking to me with wide open arms and gives me a big hug. "Come let me help you with your bags. You're the first one to arrive so you have first pick on the rooms. The rest of the gang will arrive tomorrow." Instead of the overalls I'm use...