Sissy Couple Stories

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Infinite Scroll

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

The Cock Clock Ch. 04

by HarveyMarcus on Sep 26, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Legally Binding

by MistressMtoyou on Aug 31, 2017
Fetish

As I explained in my first story (My first submissive), I'm fortunate to have a high paying job at a large well known firm. While my employer is equal opportunity and all of that, even the most open minded employer wouldn't react well if they learned they had an amateur dominatrix on their senior staff. Accordingly, before going much farther with my little h...

The Prostate Exam Pt. 06

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

"Just as it should be, now walk to quickly to the Langham hotel. Make sure you keep the bag out in full view, for all to see, it cannot go in your back pack. I want anyone who sees you to know what a slut you are.." "Go straight to the bar and order a triple G&T and 3 shots of good tequila. If the bar man asks you what you're doing you will tell him that yo...

Sissy Chantel, New Reality Ch. 08

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving on to my life at 'The Agency' Some Interesting New Things. It's 5:00pm sharp, we all must be present and ready to enter the eating area. As we all enter a small but purposeful eating area for us sissy girls, we first get a tray and a plate and mug or glass. The sissy maids who prepared our basic dinner have the food out for us. Today i...

From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

Sissy Panty Handjob

by CrossdresserCaitlyn on Jun 19, 2018
Transsexuals & Crossdressers

When I woke up in the morning I saw my girlfriend getting ready for work. She sees me awake and reaches out and rubs my penis outside my panties. While rubbing me she tells me if the house was spotless when she got home sissy would get a special treat tonight. She let's go of my dick, smiles and leaves for work. Still hard I jumped out of bed immediately a...

Riley's Bar Ch. 07

by Just Plain Bob on Sep 15, 2017
Loving Wives

When I got back to my apartment there was a message on my answering machine to call my brother. I called him and he told me that what we had talked about at the courthouse was doable and I told him to go ahead and do it. Then I went to bed and slept like a log. Friday was a busy day at work and even though I had my hands full trying to finish the job I was...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...

Holly's New Start

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

I love Jamie so much it hurts. I mean there's a lot of things that would have people freaking out over this relationship of ours especially how I am and how we started. Jamie loves me despite my past. And like he really, really only has a sort of little picture of just how bad I was as Holt. Only he found reasons why Holt ended up so broken. No, no excu...