Sissy Enema Stories

10,114 results
Orientation
Length
Source
Infinite Scroll

Walk-In Clinic

by ColinGraham on Sep 26, 2017
Transsexuals & Crossdressers

I don't know why I forgot to wear men's briefs that day, perhaps I was just so used to the comfortable feel of silk and lace that I didn't even think about it when I dressed. Or maybe I had an unconscious desire to be caught; to finally have my little secret uncovered. So here I sat at the walk-in clinic, debating whether to leave, or to risk the off chanc...

Ms. Tanaka Fixes Me Ch. 02

by chenwanli on May 4, 2020
BDSM

Chapter 2- Ms. Tanaka Takes Charge Ms. Tanaka stood up, straightened her sheath dress and bowed to her daughter Hiroki to say goodbye. They exchanged a few final words in Japanese that I didn't understand, gesturing at me and smiling then Ms. Tanaka laughed throatily and demanded the rest of my clothes. I took my pants off from around my ankles and gave her...

Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...

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...

Jacki's Journey into Sissyhood Pt. 02

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is a continuation of: Jacki's Journey Into Sissyhood. Thank you for reading a continuation of that series. ***** I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm draped across my shoulders and the large cock poking at my backside. I tried to slowly slide out from unde...

Cassy's Game Ch. 5

by wormwood on Sep 19, 2017
BDSM

Mistress Lindsay took no crap. Her orders were precise, her manner direct. I went from quiet subservience on the kitchen floor to quietly licking the grime from her street shoes in the living room. The taste was terrible and the grit on my tongue and my teeth made me nauseous. I took advantage of my actions to survey Mistress Lindsay, about forty years old...

X.S.X Experiment

by njcaptionlover on Apr 4, 2018
BDSM

All characters are over the age of 18 years old. ***** Hello. My name is Justine, and I'm a 25 year old single male whose fetish curiosity had finally gotten the best of me. My owner granted me permission to recount my story. I started collecting Playboy magazines at an early age. When I had my first computer at the age of 18, the world of porn opened...

A New Way Of Life Ch. 02

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

A Big thank you to Chris & Scott for the great eaditing job. This is the 2 part please read the firts New Way I looked at Everett, "Ok, are you sure?" "Yes, Carine. Now go get ready. I'm hungry." I headed off to the bathroom to fix my make-up and hair. Looking at myself, I can't believe what had happened. I was loving it! I had never felt so alive, tu...

Cucky Trained by CD DOM Pt. 05

by sndycd on Sep 15, 2017
Transsexuals & Crossdressers

It was 9:00 am, Sunday morning. I let you sleep since you had a busy day yesterday. Today would be nothing like yesterday. Today was the day you were going to be presented to your owner, you used to call her your wife, and her bull. I was standing in your door when you woke up. Cup of coffee in my hand. I had been up for hours and was fully dressed and read...

The Ex's New Toy Pt. 03

by Urtoy2be on Sep 15, 2017
Fetish

Wednesday afternoon and work was slowing down for the week. Sitting in my office bored staring blankly at my monitor waiting for 5:30 PM so I could cut out. I need a drink went through my mind. The weekend had been a blur. The events with my ex-wife and her new man had been crazy. Fantasies and thoughts had been awakened and now I was wondering who I really...