Chastity Cage Sissy Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Sandra and Stevie Ch. 43

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-third installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-two episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I stron...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

Sissification 101: Ch. 02

by silkstockingslover on May 18, 2020
Toys & Masturbation

Summary: Both Eric(a) and Joan discover the joys of toys. Thanks to the real Eric who requested and helped plot this lengthy story. Thanks to Tex Beethoven and Robert for editing this story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose wat...

Chastity with Ex as Keyholder Ch. 03

by chastity_sissy on Mar 12, 2019
Fetish

Back at my apartment, I wanted nothing more than to just get the chastity device off of me, but I still couldn't help but be aroused at my humiliating situation. Here I was, chastised by my previous girlfriend who now controlled not only my orgasms, but whether I could have sex with another woman. Suddenly, my phone buzzed, notifying me of a new text messa...

My roommate new sissy maid

by Carterdruzba on Dec 29, 2020
Interracial

I been living with Gina who happens to be muscular and stronger than me I haven’t paying my rent for 2 months so one day when I meet her in the living room “you been not paying for months so I have idea for you to repay me so I got this” it was a pair of pink panties heels and black stockings and a maid dress “I decided to should be my maid until you paid me...

Chastity Pt. 01

by thepeopleschamp on Sep 14, 2017
Fetish

Hello all! thepeopleschamp here with another story. Just so you know what's in store, this story centers around femdom, to be general. If you like femdom but are turned off by cuckolding and feminization, and if the phrase "sissy clitty" makes you cringe, then continue reading. Now, this story is going to be similar to my previous one, but I plan on taking t...

The Teasing Air Hostess Ch. 05

by footslave85 on Dec 29, 2017
Fetish

The week after my Goddess gave me the chastity cage was a very strange one, I would get home from work and put it on, then spend the evening trying to go about normal things and not have any naughty thoughts. It was really difficult at first, every time I moved and felt the cage in my pants it made me instantly think of my Goddess and I started to get arouse...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...