Diaper Sissy Stories

8,305 results
Orientation
Length
Source
Infinite Scroll

Postscript: The End to PIG

by fexhominum on Jul 27, 2020
Fetish

Goddess Ashley met me outside of a Panera Bread for the ostensible reason of returning my credit cards to me. She was sitting alone at a small table, drinking a mango smoothie. She wore a white halter top, black shorts, and white high-heeled sandals. Sunglasses stylishly perched atop that luxurious blonde hair. As I approached, I could see her ruminating on...

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...

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...

Uncovering the Sissy Beneath Pt. 06

by jefferyscott745 on Jul 31, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part five of my previous work. Be sure to read parts 1-5 if you wish to understand the background of this section. Sherry and I sat on the couch for a while watching fashion shows again. There was no discussion about what had just ha...

The Marriage

by zeta515 on Sep 17, 2017
Fetish

Acknowledgements: My very grateful thanks to AngelLove for agreeing to edit this story, for her very timely work, and her valuable suggestions and corrections. Copyright 2006 by Zeta. All rights reserved. Rose turned and looked at the red numbers on the clock: six-seventeen a.m. The bedroom was beginning to lighten as the sun rose, heralding the new day a...

His Sissy Bitch Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

He makes sure they all get a good look at my rear end. He pinned my skirt up in the back, large safety pin holds my skirt up at the top. It's a large baby diaper safety pin, one that women used in the 1950s, pink plastic shows at the top. Kind of cute, the pink plastic matches my ear rings. I could just take my skirt off but he says it's way sexier this way,...

Mistress Marisa's Estate Pt. 22

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... *********** I hear the female chatter as I come down the hall from your kitchen and main bar area. I have a tray full of margaritas. As I enter the room I...

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...

Changes: One Spell at a Time

by Guy_Faux on Aug 31, 2017
Fetish

Author's note: This story involves themes of incest, mind-control, the abuse of magic, and transgender. If these don't appeal to you then don't read it. Otherwise please enjoy. * I was still young when I lost my virginity. She was older than me, a high school girl in fact, but she was so impressed by how large my dick was that she gave me a shot. I imagin...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...