Sissy Cumslut Stories

7,812 results
Orientation
Length
Source
Infinite Scroll

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Sissy Crissi Ch. 01

by sissycrissi on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need of a place to stay, and Erika was in need of someone to help w...

Girl's Night Pt. 06

by DifferentBreed on Sep 14, 2017
Fetish

This is a continuation of an earlier story. It contains themes of feminization, humiliation and other fetishes that don not appeal to all. If you are a fan of these, please read on and leave comments as to how to improve the story. Hope you enjoy it. ~ DB ********* Fisher climbed up the stairs to the brownstone, Sophie's jeans creeping down his ass for wha...

Mindy's Moving Day - CFNM Ch. 02

by BuckyDuckman on Sep 25, 2017
Interracial Love

Author's note: I think this works as a stand-alone. I get my lily white ass reamed by a big black bull in front of my wife, her friend and my swim team. Delicious humiliation! Mindy's moving day signaled a huge change in her life and the relationship I have with my wife, Debbie. That was the day we put on a real life show of me offering up my sissy ass wh...

You're Like a Little Boy at Times Ch. 03

by Myneed on Aug 30, 2017
Fetish

This is a slight twisted femdom love story that will make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** My heart ached for Mel. It had been another long week another long week of edging and chastity at Mel's instruction. Th...

Neighbors Sissy Son Ch. 05

by newfield1981 on Apr 18, 2018
Transsexuals & Crossdressers

For as long as Tiffany could remember she always envied real girls sexy curves. Clothing looks so much better on a girl with a nice set of tits and ass. Tiffany spent the night thinking about all the options Dr. Landry offered her. The most compelling option was that he could increase her bust size or ass size, without surgery and that counted for a lot. B...

On a Scale of 1 to 10

by His_fag_wife on Apr 17, 2019
Transgender & Crossdressers

He couldn't help himself, it was a new office environment for him and she truly was stunning. Even her little sister Claudia was delightful and sexy, but in a more understated way. The fact that she worked for Georgia her sister, set the hierarchy, but even more so, Georgia towered over her younger sister, and then there was Georgia's innate sense of style a...

Sister Mistress Ch. 15

by LilLindaMelons on Sep 19, 2017
Transsexuals & Crossdressers

Pulling back Kathy patted Jenny's still sore cheeks. "Catch ya later girlfriend." "MMMMM bye, you know I'm going to dream about you Mistress Katherine." "I hope so Baby." After watching Jenny disappear through the garage Kathy walked up the service steps and into her bedroom. She was eager to checkout the surveillance of her mothers' bedroom. Deborah ha...

Good Little Bitch Pt. 02

by Baron_Cumhausen on Sep 25, 2017
Transsexuals & Crossdressers

Author's Note: Many thanks to all who've voted, favorited, and commented on Part 1. Your kindness brought me great joy and inspiration. Below is Part 2 in gratitude. I hope you like it as much as the first one! If you haven't read Part 1, I urge you to do so before reading on. ***** Ben and I sat on the bench in the center of the apartment complex. The s...

A Mistress to Obey Ch. 03

by gbr2004 on Sep 12, 2017
BDSM

I woke up when she whipped the cover off the cage. I had been able to curl up enough to sleep on my side but when I tried to move I was very stiff. She opened the cage door and I backed out. She told me to go take a nice long shower and that my clothes would be on the bed when I finish. She was wearing a pair of tan slacks and a yellow blouse and looked like...