Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
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Miles's Counseling

by justincbenedict on Sep 16, 2017
BDSM

My chastity tube hangs heavily between my legs. It resembles a water faucet, and looks a little odd. Gretchen used to have me in a plastic thing, but she felt that I was too disrespectful in having big erections... And the tube makes it quite cramped! Really, it is. When I get a hard on, it's quickly contained. Then I feel this unpleasant squeezing fro...

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

The Domme Diet Plan Pt. 01

by subm_atty on Sep 11, 2017
Fetish

Day 1—The Plan I have been fat as long as I can remember. I have tried various diets with no lasting success. Being uncomfortable with my body was probably one of the many factors that drew me into being a submissive. Two years ago, I met the Domme of my dreams. My Mistress was about 5'10" but towered well over 6' tall in the heels she usually wore. Her hai...

Another Submissive Slut Ch. 10

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

The sleazy Indian clerk wouldn't leave. As soon as I let him into my place he made himself at home. At first I was afraid that he would force himself on me but after watching him indifferently trash my apartment I was wishing that he would do whatever it was he wanted to do and go. I stood helplessly fuming as he rummaged through my belongings. I couldn't...

A Look Into My Mind: Uncle Sissyboy Ch. 05

by rickiee_2002 on Aug 31, 2017
Fetish

Lori and Lauren led me into the bathroom. They were giggling and talking to each other so quietly, that I could not figure out what they were saying. My wife, Serena yelled to them as they walked me to the bathroom. "Girls, I bought a liquid depilatory at the drug store. It's in my purse." "We can spread the liquid all over his body and watch the hair just...

Butterflies

by marybethsanford on Sep 15, 2017
Transsexuals & Crossdressers

There were a lot of good reasons to be out this early, but none as wonderful as seeing this first Giant Swallowtail awakening, and John smiled as it moved. Magnificent, he whispered, in awe of this giant as it slowly unfurled it's Forewings against the sun's morning warmth. It was, as they always were at this time of day, lethargic and calm. "Papilio Cresph...

The Worst Smell

by RANDYCRIME on May 14, 2020
Fan Fiction

Contains: hypermess, hyperstink ____ DONG! DONG! DONG! The church bell signaled that it was 3 PM in the quaint suburban neighborhood of Fouler Hill. Cars rolled along steadily in the streets, a dog or two here and there poking their heads out of the windows. An old couple crossed the street where a school bus stopped to release some children, who raced each...

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Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

Staffing the Mailroom

by justincbenedict on Sep 17, 2017
BDSM

"Polly, we have a candidate for the mailroom, darling." Pierson Albemarle Upshur IV was distressed. Certainly he went by "Polly" at home when Brie had him in his garter belt and stockings, but at work he was supposed to be a name partner and be called "Piers" if not "Mister Upshur" It was distressing enough that Piers was leaving the firm that his father "...

Winning Big in Las Vegas

by marykay9 on Feb 6, 2018
Transsexuals & Crossdressers

I was in Las Vegas staying at one of the "lesser" hotels, playing the slots to kill time waiting for a "Shemale" show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surr...