Sissy Diapers Stories

8,322 results
Orientation
Length
Source
Infinite Scroll

Letter from Trenton

by justincbenedict on Sep 23, 2019
BDSM

Dear Shoeblossom: I'm a Jersey girl from way back and no one suspects how unconventional I am, living in the suburbs...but I thought you'd get a kick out of this little missive! And yes, like so many others, it's a recording. My hubby has no idea that I've surprised him like this, but Mistress Figgy is a relentless chick! Figueroa Salvini "Hey, there baby...

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...

Mistress Marisa's Estate Pt. 11

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... ******************************** The matron sits at the front of the room, gorgeous and tailored perfectly. She's wearing a tight short black dress and nee...

Family Chastity Story Ch. 04

by antares34 on Aug 13, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** 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+. ***** My girlfriend Christina has been staying with me for the past sev...

Chuck

by wajawhiii on Jun 5, 2018
Erotic Couplings

My name is Marjerie. I'm thirty-nine years old. I was married to George when I was only twenty. He left when I was just twenty-three and Charles was only two. I got an uncontested divorce three years after he disappeared. Charles is the only thing George gave me and the best thing I've ever received. Charles is now eighteen and just graduated from high scho...

Spellbound & Sissified

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

SISSY FOR A SPELL The Omega Psi Phi Fraternity loomed in front of him. The lights were on in almost every room. Frank's hopes, that maybe the brothers of Psi Phi were at the Halloween party across campus being thrown by their sister sorority Sigma Gamma Rho, were dashed. He took a step forward. His hand was shaking and the child's Jack O' Lantern bucket...

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...

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...

Lady Esolen

by justincbenedict on Jul 30, 2019
BDSM

Esolen smiled at Claude. She shook her short dark hair. It was a bob, easy to control, but quite thick, and a bit curly. Claude stood in front of her, weeping slightly, and holding the thick leather strap. "Claude, we talked about this." Esolen's soft voice resonated. Esolen never raised her voice. "There are rules and consequences. When I moved in with you...