Permanent Chastity Sissy Stories

27,304 results
Orientation
Length
Source
Infinite Scroll

Spanking Jay

by Kimberleigh65 on Sep 17, 2017
BDSM

"Let's stop here." "Jay, I'm tired of being in the car." Melissa gazed out of the car window. "We're out in the middle of nowhere. We can pull over, get the picnic, walk for a few minutes then have something to eat and relax. Then find the place. It's on this road – County road 67, we just haven't driven far enough." Jay pulled the car over to the verda...

Lynne Takes Revenge

by Morpheuse on Sep 17, 2017
Loving Wives

I'm enslaved by my wife and her lover. What can I do? What do I want to do? Lynne decided she should learn to drive about five months ago. We're both in our late twenties and I was very encouraging. That would mean we could share the driving, always a benefit on long trips and maybe even the chance of a glass of wine for me on a night out. She asked around...

Virgin Ch. 01

by SissyKirsty on Sep 13, 2017
Transsexuals & Crossdressers

Turning twenty-one next week and still a virgin, is it really that sad? Not a kiss-less virgin at least, but I'm not sure if a drunken kiss with some random girl a few years ago at a random party goaded on by the crowd counts. Almost everyone kissed everyone that night, most more than once, but just the once for me. She was really short and average looking.....

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...