Sissy Cum Stories

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Orientation
Length
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Infinite Scroll

Megan's Bitch

by magicrub on Sep 14, 2017
Fetish

"Why are your clothes still on?" demanded Megan as she smacked her bitch across the face. "I'm sorry Mistress..." bitch replied before being sharply smacked again. "I did not give you permission to speak bitch!" replied Megan. "Besides, a Mistress does not have a cock like this one! Does she slut?" "No Mistr..err Master?" replied the bitch, starring at t...

First Time Sissy Maid

by bart2077 on Sep 13, 2017
Transsexuals & Crossdressers

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for a sissy maid for ongoing service. I answered the ad, includ...

Sissy Chantel, New Reality Ch. 05

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, My Surprise. "Ohh, Ahhh...Wha...what." I say as I wake up and am lost with where I am and what is going on. "What the... What the Hell? Where am I and what is this? Huh, what the Hell? Why am I chained and padlocked around my waist?" I'm groggy and very confused as I look at the room, dimly lit with a single hanging light bulb, I'm on...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

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+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

My Girlfriend Made Me a Sissy Ch. 02

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Thank you to everyone who sent me messages about the last story, I've tried to include things people wanted to see in the sequel. Hope you enjoy ---------------------------------------- I woke up, stretched out and smiled as I felt the familiar sensation of my girlfriend's panties rubbing on my cock. The feeling instantly brought back memories of the night...

Sissy Sisters

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

This was the letter I wrote to an older Sissy in an attempt to convince Her to accept me as Her littler sister and use me. * Stop, You make me blush. I too luv wearing feminine luxurious things. I believe now I need to wear sensuous feminine things under the direction of some one else. Could that possibly be You. Please. You would treat me like a little...

Gym Submission Ch. 04

by AltErik on Sep 16, 2017
Transsexuals & Crossdressers

************ Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains Male/Male sex, Male/Female sex and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. I hope you enjoy it and fee...

Sissy Crissi Ch. 03

by sissycrissi on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 3 -- Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upwa...