Sissy Bondage Stories

20,137 results
Orientation
Length
Source
Infinite Scroll

Truth or Dare Takes a Turn Pt. 03

by Cutiepie183 on Sep 21, 2020
Transgender & Crossdressers

I pull up in Luke's driveway and get out of the car, I retrieve my suitcase from the boot and make my way over to the back door, only to be stopped and greeted by Brent before I can enter the house. Brent leers at me and says "hey there sexy little cocksucker" before he pulls my pants and panties straight off me, locking my cock back in the little pink chast...

The Right Girl for the Job

by Stephen_Heathcote on Oct 13, 2017
Transsexuals & Crossdressers

"If you aren't here for sex, then why are you here?" Lacey asked. It was a reasonable question, given that we were sitting in the bar area of a brothel. "I have some very specific fantasies, things that I would never ask a civilian to do," I said. "Why not?" "Too embarrassing. I don't even know if I can tell you," I said. "There's nothing you can tell me...

Mommy Adriana and the Video Booth

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, I never imagined to get so far but funnily the more I write the more ideas I get. I hope you still enjoy the ride. * I closed my eyes. Not wanting to see people staring at the bound and gagged bundle which I had no doubt they were, especially when we stopped at red lights. In fact I didn't see where we were going. The only thing I...

A Cuckold Earns His Horns Pt. 02

by lapraline70 on Sep 16, 2017
BDSM

This is part 2 in a series of letters about my cuckolding. For context, read part 1. We open with O/our Bull knocking at the door on the fateful evening. ==== Already on my feet, i walked to the door and, fumbling with the handle a bit, opened it to see Him. Our eyes met. i saw His immediately slide down my nightgown as His grin widened. "Ah, good evening...

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

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...

A Deal Offered

by LockedSissySubmissive on Sep 25, 2017
Fetish

I was sitting in the kitchen drinking coffee wearing my dressing gown when Emma left for work. We'd had a pleasant morning chatting about the various inconsequential matters that married people chat about but she had to leave for a meeting and looked fabulous in a smart dress suit and jacket. Even after almost two years of marriage I was still totally smitte...

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...

My Sissification

by sissy171 on Jul 6, 2020
Transgender & Crossdressers

Chapter 1 Summer after High school I was a sexual submissive with my very first girlfriend, Mary Jean. Mary Jean had an aura of sexuality; sensual and seductive. All her summer clothes were tight and revealing, and I was drawn to her like a moth to flame. We hung out a lot, and sex was all I wanted to talk about. She implied that she wouldn't fuck me, b...

The Making of a Dominatrix Pt. 01

by teamorangecrush on Sep 17, 2017
BDSM

The Making of a Dominatrix; how I turned my timid, soft-spoken, submissive wife into a Dominatrix. This experiment started as an attempt to add a little BDSM in my marriage. We had experimented a little with BDSM in the past with positive. I did some research and planning and then executed my plan during our next love making session. The first experie...