Sissy Boss Stories

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Infinite Scroll

The Sexy Cuckold Couple Pt. 05

by cuckcpl4play on Sep 19, 2017
Fetish

Ceremony Preparation Continues as Does slave's New Life at Work (Day One) part 5 Background: we are a cuckold couple and one of our past Bulls ordered cucky to write a long story that included creative ideas that he could employ with us as a couple. As such, much of what is written here is based on fantasy and we would not live out many of the situations he...

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...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

XChange Seminar, X-change, X Change Ch. 02

by Grabenork on Feb 6, 2018
Transsexuals & Crossdressers

"Good morning, everyone! I am Dr. Welcott, and I am very happy to welcome you to X-Change Technologies, Inc. You are all here because you attended one of our X-Change Seminars run by Dr. Brewer at the Comstock Institute. He reports that you all participated in the seminar enthusiastically and then signed a list to volunteer to become future demonstrators at...

PARTYBOY and His Bitch Wife

by Goddess_Meanie on Mar 13, 2018
BDSM

I'm didn't take the time out to describe myself. I often skip over my features. They are both a gift and a curse. Young girl, very timid, secretive and shy. Early masturbator, enjoyer of porn and as my youth went about, and more and more aggressive, into my teen years. At that same time I found boys to be boring as hell, and always needing to be led. I had a...

Afro Stress Relief Ch. 08

by llts1970 on Nov 11, 2019
Transgender & Crossdressers

It was Monday evening, again, and I hurried home from work to get ready for my shift at 'Babes With Asstitude' (BWA). My new Afro-boyfriend, Drake, rang to chat about our new venture as soon-to-be Brothel-keepers and tell me not to work 'too hard' on my shift as a whore at Drake's uncle, Leroy's, place, BWAs! Drake wanted to come over but I said I wouldn't b...

Dancer Turns me out Pt. 03

by pantiepervMI on Sep 28, 2020
Transgender & Crossdressers

After a restless night, I finally dragged my tired and sore body out of bed. My asshole was on fire and I could feel the pain with every step I took. I thought about skipping the insurance sessions to catch-up on my sleep, but after tonight I did have to return to my real life, my job, and my asshole boss. I downed several cups of coffee and got dressed in...

Brad's Return Ch. 01

by grizzley123 on Sep 29, 2020
Loving Wives

Brad's Return, Chapter 1 ****************************************************** This is a continuation of the "Brad's Suggestion" stories I wrote a while back. It has similar cuckold and bisexuality themes, along with some lesbian and light BDSM fun thrown in. It emerged from my never-ending desire to put off the real work I should be doing. I hope you enj...

The Pool Party

by JamesMiehoff on Nov 19, 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...

Wendy The Haitian Sadist

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Salutations, dear readers. It has most definitely been a while, hasn't it? The name is Wendy Stefania Polydor, and I'm a young Haitian-American woman living in the City of Boston, Massachusetts. Mother of two, divorcee, college graduate and nurse, I am all of these things and more. I have been delving into the world of BDSM, and more fun things like swinging...