Spanked Sissy Stories

24,820 results
Orientation
Length
Source
Infinite Scroll

Luke's Field Trip

by LucyAnn51 on Sep 16, 2017
Transsexuals & Crossdressers

All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Hope you enjoy, love you dolls! Xoxo ------------------------------------------------- Luke was a sissy. The kids at school called him mean names and threw things at him. They played keepaway with his book...

How Low Can You Go?

by Compliant1 on Sep 16, 2017
Transsexuals & Crossdressers

Be careful what you wish for; that's a popular phrase in these Literotica stories. I found out the hard way the import of this message. I have always had a submissive streak a mile wide, but in my twenty-eight years I'd never experienced the feeling of completely surrendering to another person. With the Internet and its free personals web sites, I decided t...

A Sissy Saga Ch. 04

by Snurge on Sep 15, 2017
Novels and Novellas

The highly polished writing table was uncluttered, the only item encroaching its pristine surface being the letter of application Miriam Hancock had received from Emma Twist, the young woman who now sat stiff backed in the chair facing her. Miss Hancock folded her hands over the pieces of paper and gave the impression of ignoring them as she assessed the ca...

Tales of Sub Asian Sissy Ch. 03

by subASIANsissyJADE on Apr 23, 2019
Transgender & Crossdressers

(Thanks so much for taking the time to read my story! This is just my third post and I'd love to hear any feedback, questions or comments. Also, please feel free to contact me if you just want to chat with a very submissive asian sissy. XXX, jade) *** While it's only about fifteen minutes away, the drive back to my apartment seemed to take forever. I had t...

Mandy's Reward

by sissymaidrose on Sep 12, 2017
Transsexuals & Crossdressers

There was a sharp, heavy rap at the door. Mandy scrambled out of bed as Mistress Charlotte pushed the door open, hastily smoothing the tiny, soft, pink and green nightdress that barely went past her hips and surreptitiously tugged the matching knickers down from where they had ridden up into her bottom. As Mistress sashayed past to the throne like chair in t...

Slut for All Pt. 06

by Knightofround on Sep 19, 2017
BDSM

"That's it baby! You are such an amazing cock sucker!" Anthony stands towering over me from my knees. Like a proper slut, I make sure to keep eye contact with my new master. I moan around the cock in my mouth as I bob up and down quickly. Anthony puts his hands on the back of head to grab my hair and stops me from moving up and down the amazing nine inch c...

Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...

Mommy's Boy? Ch. 03

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I minced into the kitchen in a new dress, feeling terribly nervous. My small pink butt plug added somewhat to my wiggle, reminding me at every step that sissies need constant training. I brushed my hands against the skirt of my princess dress one more time, smoothing out again all the wrinkles that my imagination created, and again touched the hair of my wig...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Young Master Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

There I was, still impaled on a shemale's cock, one belonging to what was supposed to be my sissy slave, wearing her bra, her cum on my cheek along with my post-fuck smeared make-up, and my cum running down the full length mirror. "I fell" wasn't the best explanation for what happened, but it was all I could think of with my step-father's hulking frame loomi...