Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
Source
Infinite Scroll

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...

The Computerized Bed

by submissive~pet~ on Sep 14, 2017
Fetish

The year is 2020 all sorts of new inventions have been created. The time machine in which John Paul traveled was from the year 2002. He had no idea what was in store upon his arrival to the future. His machine carried him into a large bedroom. It was a very lovely room done in pinks and light blues. The bed was enormous in size, 4 times the size of any he...

Another Submissive Slut Ch. 11

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

My land lady's knowing look held me transfixed. Quietly Mrs. Lehrer purred, "What are you?" A spasm of trembling shook my body before I could mew out, "I am a sub sissy slut, Mrs. Lehrer." "Hemmmmm," She hummed, "And what else are you slut?" Her voice was quiet, soothing, inquiring. "I am a wanton cum whore, Mrs. Lehrer," I admitted, blushing at such an a...

Pro Domme Assignment Pt. 01

by Dprboy4Dominant on May 7, 2019
BDSM

I once served a daddy dom for quite a while and he set up a meeting with a Pro Domme for me. The following is part 1 of the email report that I sent to him. You had scheduled me to meet Head Mistress S at 5pm so at 3:45 I showered thoroughly, re-shaving my entire diaper area as you directed. I tried hard to scrub around the base ring of my chastity and spr...

Isabella's Reversion Pt. 04

by silverbackteddy on Sep 11, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...

Ultimate Sissy Weekend Ch. 07

by SissyTwinkleToes on Mar 10, 2020
Transgender & Crossdressers

Ruby is sat flicking through a magazine. Mid-twenties, she's been working in the tattoo parlor since college and is soooo bored. So her face lights up when two sissy dumplings mince into the tattoo parlor. She gasps at their ridiculously effeminate outfits that no woman would be caught dead in. She can't believe they've handcuffed themselves together and loc...

Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...

Isabella's Reversion Pt. 03

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have...

Yes, Mommy

by searic on Sep 13, 2017
BDSM

My wife/Mistress, Heather and I had over the years developed a large repetoire of ways of playing together, with me, of course, always in a submissive role. One of our favorites was her as Mommy and me as her obedient little sissy boy. What a delightful combination of humiliation and safety it created in me. However, as frequently was the case, she had deci...