Sissification 101 Stories

2,009 results
Orientation
Length
Source
Infinite Scroll

The Intern Ch. 01

by FrostShard on Sep 14, 2017
BDSM

The intern was not your usual 20 year old. Mengxia looked sharp in her crisp white blouse, black skirt, stockings and heels, particularly at this tech company where casual wear was the norm. Her sharp eyes roved around the room and finally landed on me, her manager. She approached with a professional smile. "Hello Mengxia," I said, reaching out my hand, "we...

Captain's Choices

by CaptainX on Dec 22, 2020
Cheating Spouses

Chapter 1 - The Beginning Your name is Captain, well that is what you prefer to be called, and this is your story, your life has been a crazy rollercoaster living a double life and most people on the surface think, You're just this normal guy who doesn't know much but if only they knew how wrong they really were. After having a fallout with your ex, You nev...

Open in Reader

Finding Her Secret Emails Ch. 01

by Quietoldie on Sep 26, 2017
Transsexuals & Crossdressers

Julie, my wife's mum and I have never got on. When I first started seeing Carol she did everything she could to split us up. I thought she was jealous and believed I was going to take her away from her mum and monopolise her time but nothing could be further from the truth. I wanted Carol to see her mum regularly. I knew they were very close and confided in...

Mommy's Boy? Ch. 03

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I minced into the kitchen in a new dress, feeling terribly nervous. My small pink butt plug added somewhat to my wiggle, reminding me at every step that sissies need constant training. I brushed my hands against the skirt of my princess dress one more time, smoothing out again all the wrinkles that my imagination created, and again touched the hair of my wig...

Training of a New Sissy Ch. 01

by npbear on May 23, 2018
BDSM

I'm not sure who was more surprised at my reaction to the surprise party. Certainly She expected that I would enjoy my time, She is very considerate like that. But I think it took even Her by surprise at how much I, for lack of a better word, gushed like an excited teenager when telling Her about the experience. I think that's partly why She insisted I write...

Making a Sissy

by kittycalamity on Sep 13, 2017
Fetish

Once upon a time, I dated a guy with muscular dystrophy. True story. I didn't know much about MD or neuromuscular disease in general at the time, so I never asked which form he had. Looking back on it, I'd say with about 90% certainty it was Becker. God, he was gorgeous. I'm six feet tall and he was an inch or two taller than me, but he probably only wei...

The Rendezvous Ch. 03

by CassidyCaine on Sep 26, 2017
Transsexuals & Crossdressers

(Author's note: I have tried to get an editor for this story but failing that after over a week of looking I'm publishing it. Please be aware this work has some fictional coercion and other sissification elements.) The car drove through the city as the night pressed around Nick, watching the buildings flicker by as he wondered what was in store for him....

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...

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...

Mood Slime Ch. 37

by maestro84 on Sep 19, 2017
NonHuman

As the class dismissed every just seemed to leave with their heads down not wanting to talk about what just happened. There were a few hours before the next class so Doll was trying to see what other fun she could have as she heard a knock on the door. "Excuse me Mr Crowley... oh I'm sorry I was looking for someone else!" A young man said standing in the do...