Sissy Bride Stories

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Casey's Submissive Journey Pt. 01

by corduroysissy on Dec 14, 2017
BDSM

Karen walked into the bedroom and Casey thought he would have a heart attack. He was reading a book in the corner chair and looked up at his lovely wife. She was wearing a pair of dark red, mid-wale corduroy jeans. Casey had a corduroy fetish, corduroy turned him on a lot. He'd purchased many pairs of corduroys for her over the years and she knew the red o...

Not Sick Maid In Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

Cuckold Chronicles: Paul

by deltonaman2man on Sep 13, 2017
BDSM

Friday night is my night out with the guys. I go to a friends house and we have a small neighborly poker game. My wife likes the time alone, so she stays home and does whatever it is that she does. I don't get out much since my heart attack ( at the tender age of 48). I'm in my mid 50's now and we have been together for over 20 years. We are still very much...

Outed and Married Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

The head of his cock pushes hard against the back of my throat. I struggle not to gag. I struggle to control my gag reflex. I feel my throat spread open as he pushes his erection all the way into me, pushes deep into my mouth. It never gets easier no matter how many times he's done this to me. I feel that brief flash of slight pain as he deep-throats me. Fro...

Why I’ll Never Go Sharking Again Ch. 02

by tsfan84 on Sep 13, 2017
Transsexuals & Crossdressers

Earlier today, I was raped by a shemale. It was my first sexual experience with anyone not carrying two X chromosomes. It hurt like hell, at first and to be totally honest, I'm still sore. But it also felt really good after a while. The sensation of being.....what's the word I'm looking for here..."filled," while cumming is the best. Having your ass clench d...

Following My Heart

by Alexdino on Oct 9, 2018
BDSM

House sitting for my fiancé was supposed to be a nice way to ingratiate myself with her and get back into her good graces. Nothing I could do seemed to make her happy, including the way I jumped to do her favors, took care of her dog, and was generally supportive. No matter my efforts she looked at me with suspicion and doubt. That's why I spent much of the...

The Marriage of Martin Hastings Ch. 08

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Our Tale continues. Martin is not sure of all the why's. He is beginning to understand the realities though. The Tale continues to twist it's way through logical answers to unreal questions and expectations. Things are subtly changing............Hmmm * Martin didn't want Missy to leave. The realities of his situation were now too much. He reluctantly si...

Young Bride in Tights Ch. 02

by fanofpantyhose on Sep 26, 2017
Fetish

On Friday afternoon of the next week, I was in the store alone and had locked the front door to be able to develop some prints in the darkroom for a customer. Finally finished, I turned on the light and took out a little box from far back of my personal desk drawer that contained the special pictures I shot of Courtney, my secret former middle school crush,...

A Jamaican Vacation Ch. 04

by sissyashley4bbc on Dec 24, 2019
Transgender & Crossdressers

Rebecca studied me up and down. "What happened to you?" She asked. "I...uh...I..." Ty cut me off, "you look like you are in shock Rebecca. Let's fix you a drink and I'll explain everything to you." "Make it a double," she said as Ty started to make her a screwdriver. He handed her the drink, grabbed a joint, and ushered us outside. Rebecca sat down...

Jennifer's New Adventure Ch. 03

by JenniferTaylorTV on Feb 10, 2020
Transgender & Crossdressers

Jayne started easing her dress up over her thighs. They were tanned and muscular but in a very feminine way. With her dress resting on her hips, she reached out and grabbed Jennifer's lead from the fat woman. "Come here Jennifer. I want to see if you like the taste of pussy." And she forced Jennifer's head between her legs. Jennifer could see Jayne was turne...