Sissy Chastity Stories

12,331 results
Orientation
Length
Source
Infinite Scroll

Save Some Punch for Me Pt. 03

by chenwanli on May 12, 2020
Transgender & Crossdressers

Jo-Sei and Marina take me out on the town... Marina left the room to get changed, leaving me in an uncertain, yet familiar predicament: Jo-Sei standing over me after having just fucked my brains out. Except this time, she'd locked a metal cage around my cock and brought her friend Marina to the party. Jo-Sei reached for her black mini backpack again and bro...

Mikey’s Decision

by VeraCBlake on May 12, 2020
Transgender & Crossdressers

Mikey's Decision: A Feminization Story By Vera Blake Part I The Meeting During the third week of quarantine, I took a jog out into the deserted Carolina night and felt inconceivably light on my feet. For just a moment then, as shameful as it was liberating, I forgot I was a man; I forgot I was anything but a pair of eyes hovering just above the mist. Of c...

Casey's Rise Ch. 03

by velcrofist on Sep 28, 2020
Exhibitionist & Voyeur

Casey had the house to herself for a change. Greg had a new supercharger that he wanted to fit to the Trans Am and decided a complete tear down of the engine was in order. He had a few days off before his next shift so he'd decided to go back to his parents' house to use his father's workshop. Jolene and Cassandra were out shopping and weren't expected back...

Meeting Raquel Ch. 03

by Floydman1 on Sep 15, 2017
Transsexuals & Crossdressers

After that, I didn't have much in the way of discipline problems with her. Raquel still got off in a big way on being punished, so I would incorporate it somewhat when we were having sex, but mostly I fucked her after she was tightly bound. Out of nowhere, one day she asked me, "Have you ever thought about bringing somebody else in to play with us? Like a re...

Slut Wife - Join the Club Literally

by policywank on Sep 13, 2017
Loving Wives

Sophie is a 35 year old french Canadian woman. Fluently bilingual, she speaks english with only a hint of an accent. She was raised by a single mom who was a contradiction in the eyes of her contemporaries. She provided Sophie with a safe and loving home and was at all times fiercely devoted to her. Yet personally she was a free-spirit, flighty and self-indu...

A Drow's Dilemma Ep. 75: Inflitrate

by DrowsDilemma on Apr 10, 2019
Sci-Fi & Fantasy

Author's Note: A Drow's Dilemma began as a one-on-one roleplaying project and has been converted into a chapter-by-chapter format for weekly posting with the permission and assistance from my partner. It will contain a considerable amount of sexual themes such as femdom, lesbian, straight, 'reverse' rape, BDSM, group sex, romance, and other themes. The mai...

Footing the Bill

by NoJo on Sep 24, 2019
Fetish

This is a femdom story with the themes of foot worship, financial domination, hypnosis and mind control. If that’s not your fetish, please don’t vote this story down, please hit the back button instead! It’s a black comedy for feeble foot-fetishists, pathetic paypigs, mindless addicts, abject losers, weak-willed wankers, hopeless chastity slaves, hypno jun...

Husband has a Limit

by lover1953 on May 7, 2019
Loving Wives

To try and forget about human nature is difficult and likely will result in a bad decision. This is a story of a couple where human psychology was ignored by one of them and resulted in the eventual disintegration of the relationship. I saw some websites on the web, when I was doing some research for another story, that talks about FemDom marriages and the...

Office Feet Femdom Ch. 02

by Andre_Sillitoe on May 15, 2019
Fetish

"You're right on time," Mrs. Sheridan said as she opened the front door. She was wearing a white silk blouse and a short black leather skirt with sheer black stockings. I kept eye contact with her and tried not to look down at her feet even though it had been more than a week since I last saw them bare, and I missed them dearly. I was carrying her dry cleani...

Finding Travis Ch. 08

by Katiekatsman on Sep 19, 2017
Fetish

Travis urinated again. The tug around his waist grew as another cup or two of fluid moved from his bladder into the make-shift diaper. He thought he'd been sequestered for at least a day before he finally heard something. When the unmistakable sound of hands gripping his head-covering reverberated in his ears he perked. His pulse quickened at the excitement...