Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
Source
Infinite Scroll

Easy in Japan Ch. 02

by Spiritogre on Sep 16, 2017
Fetish

Chapter Two: Easy Money The young Japanese girl watched tentatively her friend's nude chest being fondled vigorously by an older, strict looking man with greying hairs. She stretched her arms over her head arching her back with the result that the hem of her short blue dress almost rode up to her tiny waist displaying a simple white thong. Ryuchi's left han...

Trust Ch. 03

by kellyhockey on Sep 16, 2017
Loving Wives

Chapter 3: The Accident Mike went to work on Monday. Around 9:30 am Mike got a call from Jamie. Mike's voice mail system recorded the whole call. "Hey dick head. I am going to fuck your wife tonight. That's right Marine boy. I am going to butt fuck and then cum in her mouth." Jamie went on for about twenty minutes when Mike figured out where he may be call...

How Ashley J. Changed Her Image

by Sunqueen on Sep 14, 2017
Erotic Couplings

Copyright 2002, 2003. All Rights Reserved. I didn't know anything about him except that his name was Brent, and that he was cute, funny, played the guitar and wore tight black pants. I liked his butt, and giggled about it to my girlfriends after track practice, on the plane, or on the bus on the way to competitions. They laughed at me, and went out on dates...

Penny Wise, Pound Foolish

by clinton09 on Sep 14, 2017
Loving Wives

[©2010 BY CLINTON09; ALL CHARACTERS OVER THE AGE OF 18; NO EVENTS DESCRIBED ARE TRUE; THIS STORY HAS A 'HARDER EDGE' THAN MOST; BE WARNED: HERE BE DRAGONS; FOR AGES 21 OR ABOVE] [Husband's only asset is his gorgeous wife; he also has a failing dance studio; why not save the cost of an instructor by having incredibly sexy wife teach slow dancing to well-hung...

Francis Meets a Black Stud Ch. 03

by FrancisAlba on Sep 16, 2017
Transsexuals & Crossdressers

Sorry it took so long. Thanks for the all the wonderful comments, they certainly do entice me to share more of my story. Please feel free to post or write me additional comments. I don't care what you right as long as you talk to me like the cum slut that I am. As I washed myself in the women's bathhouse, I began to regret everything I had done. I had alr...

Hate Crimes Inc. Ch. 01

by NOIRTRASH on Sep 16, 2017
Loving Wives

All characters are adults. ***** The first time I collided with Janet Douglas I was in my car parked in a space beside the Come & Go store, with a cup of coffee and a Crispy Cream Donut for supper. Janet strolled over, leaned on the door, and kinda stuck her head and tits in the window. I put down the file I was reading. "Gotta light?" She asked. It was e...

Awakening

by timewarp69 on Sep 16, 2017
Group Sex

Let me describe myself. My name is Tony. I am about 5'7", 153 lb., brown hair, blue eyes and have a 7-inch cock with an average body. I usually love extreme sports and am up for anything new or exciting. Another day as usual. After work, I headed to the bar I usually frequent to grab a few beers. I had just been dumped by my girlfriend of three months. I de...

Fear!

by gentle_man on Sep 14, 2017
Erotic Couplings

He awoke with a start. Had he been having a bad dream? It seemed so real. He dreamed he had been wrapped up tightly in a sheet and carried away. Somewhere. He tried to think. It was all a blur, as if seen through a drug haze. "No matter," he thought, "a warm shower will clear my head." Tensing his muscles, he stretched out his arms, only to find he couldn't...

The Music Teacher

by justincbenedict on Feb 12, 2019
BDSM

Serendipity looked at Trevor, her student, smiling. "You keep making the same mistakes, and I don't think you are truly devoted to the piano." "No, really, I love the piano, and I want to play-" "Trevor, you like the idea of playing the piano." "Really, please, Serendipity. I can pay more-" "And all these excuses, Trevor? One week you told me your metro...

Lust During Quarantine Pt. 02

by ClosetSissy2020 on Apr 13, 2020
Transgender & Crossdressers

Thank you all for the ratings and comments. It seems like you all like the story so far, so as promised, here's part 2. Again, I hope you all enjoy and let me know what you think as I work on editing the next installment! ************** Pt 2. Soft light filtered into the second story room and Nico didn't yet feel like getting out of bed. His head hurt a l...