Sissy Enema Stories

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Orientation
Length
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Infinite Scroll

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Neighbourhood Terror to Sissy Pt. 18

by Fibaro on Mar 10, 2020
Transgender & Crossdressers

Chapter 20 Marcy had a wonderful night's sleep while she didn't realise it, the only reason she had a quiet night was because Lisa had demanded it. What he also didn't realise was that while he was sleeping peacefully John was setting up a website, turning him into a real pornstar. Once it was online John hoped he would make a good amount of money off his s...

The Training of Sissy Paula Ch. 3

by submissive~pet~ on Sep 14, 2017
Fetish

My eyes were blurry still from not getting enough rest. Mistress had me go shower, and make sure I was smooth all over. The outfit she had picked out for me was a wild looking mini dress. Black latex with half moons on each side that would be over my butt cheeks. She helped me with the outfit and bondage gear. Oh my sissy you’re going to have one hell o...

Becoming a Sissy Maid & Slut Vol. 04

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Preview: Here is another chapter of my multi-part "Becoming a Sissy Maid & Slut Story." I so hope you all are enjoying this story. I'm no professional writer so excuse me for any writing errors. But I have a flood of sissy maid, slut, crossdressing ideas, thoughts and fantasies to share. I will add more chapters to this unfolding multi-part story now ONE cha...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

A Week End with Mistress Pt. 04

by gasissynora on Oct 8, 2019
Transgender & Crossdressers

This is a continuation from part 3 of this series. To understand what is happening you should read the previous parts of the story. I hope you enjoy this and would welcome your comments. * Mistress Nikki grabs our hands and leads us to a room behind the stage. There are some lockers in the room, a bed, some bondage equipment and other kinky paraphernalia....

Sissy Pills Pt. 01

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

Some say it was some sort of experiment gone wrong. But it hit the streets and it changed everything. A pill a drug that you took that made you sexually submissive and made you especially sexually submissive to men. Semen made it worse apparently. And there were addicts that ended up not just being gay or fags but entirely sissies and that was fastly bec...

Neighbourhood Terror to Sissy Pt. 25

by Fibaro on Oct 5, 2020
Transgender & Crossdressers

Chapter 27 Marcy woke up with a loud groan as her alarm went off loudly and way too early. She really had to drag herself out of bed as she didn't look forward to her day ahead at all, but she couldn't afford to waste much time at all as she still had a busy morning ritual to take care of. It started off bad with the kiss to the dildo, although she had to a...

Once Upon a Laundry Ch. 02

by thekestrelkid on Aug 7, 2018
Transsexuals & Crossdressers

At 7 sharp I knocked on Jessy's door nervous and anxious still not entirely sure what I was doing. I couldn't believe how hot a time I had down in the laundry room with her making me finger my own ass like a "pussy" and jerk off for her. The thought of taking it to the next level was exciting. Jessy answered the door dressed only in an over sized t-shirt a...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...