Sissy Doll Stories

23,968 results
Orientation
Length
Source
Infinite Scroll

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...

Candi's Conversion Ch. 04

by CandiCumminz on Oct 24, 2018
Transgender & Crossdressers

It was early afternoon when we pulled up at the mall. Mistress Luna had me drape myself sluttily over her car while she took some photos for my Instagram. I was still dressed as a sissy bimbo doll, having been styled by Crystal, a much more experienced sissy in servitude to another dominant, Goddess Furia. Mistress had given me a lollipop to wrap my glos...

From Husband to Man's Sissy Wife

by Pantypansy on Jul 8, 2019
Transgender & Crossdressers

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door. He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down. I felt a chill of fear, but tottered down the stairs in my...

A Sissy Saga Ch. 17

by Snurge on Sep 15, 2017
Novels and Novellas

Titled people were a weakness with Miriam Hancock. She frequently spoke of them with harsh condescension, but the snob in her heart secretly rated them higher than wealthy businessmen, and so it was with some delight she agreed to the visit of the ennobled Marchioness of Wiggleswick. The delight had doubled when she discovered that in both Debrett's Distingu...

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...

Candi Gets an Upgrade

by CandiCumminz on Dec 11, 2018
Transgender & Crossdressers

This story follows the 4 part "Candi's Conversion" series. - A useless, inattentive husband is sissifed by his wife, Mistress Luna. Now named Candi, she has been fitted with a sophisticated set of tools that will mould her into the sissy her mistress desires. Mistress Luna's new friends, Sasha, a makeup artist and budding domme and her boyfriend Dom are al...

Candi's Conversion Ch. 03

by CandiCumminz on Oct 3, 2018
Transsexuals & Crossdressers

Please read Parts 1 & 2 first. - Candi has had a long night and tomorrow she begins her sissy life properly. First thing? Shopping of course! - I hadn't slept well. I'd gone to bed horny and frustrated, and Lucy's screams of ecstasy in the other room weren't helping. Just as I'd got to sleep, a few hours after I'd crawled into bed, a loud phone notif...

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...

Mistress Joan Ch. 01: Punishment

by slutty_sissy_nikki on Mar 10, 2020
BDSM

BASED ON A TRUE STORY! All characters are over the age of 18. This is my first short story and I welcome constructive feedback. PRELUDE The cane cut through the air to deliver another mark onto my plump bum. I tried, unsuccessfully, not to flinch when I heard the wish sound of the cane travel through the air. Knowing it was coming was the worst part, or ra...

A Sissy's Joy in Being Fucked

by MissDeeLiscious on Sep 16, 2017
Transsexuals & Crossdressers

We were in the back room of our local drag club, "Miss Thing's", a very special place where only the seasoned and initiated drag queens and sissies are allowed after hours when the queens have finished performing. As one might imagine putting on an erotic performance going as far as the law will allow all painted up in all their glory makes them aroused in d...