Sissy Enema Stories

10,114 results
Orientation
Length
Source
Infinite Scroll

Becoming a Sissy Maid & Slut Vol. 03

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Seven: Another Day in Chantel's New Life. It's 7:30am and the alarm clock goes off. I awake to my first morning in my new sissy slave home and life as a sissy maid and slut. I get out of bed, stretch and strip nude for my enema and shower. My butthole still hurts from last night's gang rape session, but I won't protest, nor do I really wish too. In...

Making of a Porn Queen Ch. 01

by Scribler on Sep 25, 2017
Transsexuals & Crossdressers

When I think back on my life I can't see how I ever came to this juncture. As a child my life wasn't so much different than most of the other boys I grew up with. In the end it took a radical turn that I'm sure very few other boys lives took. My mother was a very warm and loving person. She always made me feel safe and I knew I was loved. Tragically she di...

Tables Turned at the Mall Ch. 02

by sissysherry2 on May 1, 2018
BDSM

Steve had just finished an amazing orgasm which Sissy Sherry had facilitated by the use of her mouth. But he and the girls had other plans. This involves some forced sex. If that offends you please move on. For those who read on, I hope you enjoy this second part of the story! ****************** Steve stood over Sherry, watching her swallow his cum. "Go ov...

My Life with Little Sparrow

by DomAlphamann on May 11, 2020
Fetish

I almost never come home early unless it's for a good reason. I have two reasons today; one of those being to keep you on your toes, of course, the other one is to give you news. If you followed the rules, as you should always, you might have heard the car pull up, but just in case you were busy doing anything for your own sake and enjoyment and didn't hear...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

Wife in Control Ch. 01

by wifetoy on Sep 25, 2017
BDSM

I originally posted this story almost two years ago, but lost the other parts of the story when my computer crashed. I am reposting this part and will be posting the other parts of the story over the next few weeks as I finish retyping them. While I may post some fictional stories in the future, all of the events in this one and the other parts to follow are...

Hung like a Grape Ch. 02

by sissysherry2 on Apr 10, 2018
Transsexuals & Crossdressers

The story of our sissy heroine continues... We left things in the last chapter where a female coworker uncovered "Sherry's little secret" and proceeded to humiliate and dominate her. This is part two of three. Thank you to those who reached out for suggestions and hope you enjoy this chapter. I am still new at this and appreciate any guidance either below or...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Wife in Control Ch. 04

by wifetoy on Sep 25, 2017
Fetish

This is the fourth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please review the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I did not think she would actually perform all of these cruel punishments on m...

Brian Becomes Brittney Ch. 01

by BrittneyCummz528 on Sep 14, 2017
Transsexuals & Crossdressers

My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before college. The program was something my neighbor told me about. My n...