Sissy Stories Xxx Stories

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Mommy and Goddess

by force_transitioned on Sep 12, 2017
Transsexuals & Crossdressers

Andrew never saw the noose. He was uncomfortable around his new mother in law - his wife's new step mom. And rightly so - he was, after all, going through the woman's intimates since the day she entered their lives, some two years ago, shortly after the marriage. Had he overcome his guilty reaction, he may have noticed a recurring theme in their conversa...

First Time Blowjob

by MyWhoreWife on Dec 10, 2019
First Time

I'm a man and I love crossdressing. I love the feeling of nylons on my legs and wearing strappy high heel shoes. While wearing them I would wonder what it would be like to suck a COCK in them. Kneeling between a man's legs and sucking his hard and meaty COCK. I started to go to adult cinema's in the downtown area after accidentally discovering their existen...

XXX-Women Ch. 03

by scatwoman on Sep 14, 2017
Celebrities & Fan Fiction

NOTE: is you just wanna get to the nasty stuff, you can skip the marked-off section that deals with the background and set-up... * * * * * The Premise: XXX-Women After founding the original X-Men, Professor X was often found to be missing or believed to be dead or off on some secret mission he told no-one about. In truth, Professor X was training an enti...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Roxy house of xxx 2 the secretary pet

by Carterdruzba on Dec 31, 2020
Interracial

I onced worked at a porn shop called Roxy house of xxx until I met the love and goddess of my life Sandra or mistress Sandra she picked me as her new secretary a sissy secretary for her company and her big black cock I never had a better life than this get paid more and get fucked more by Sandra big black penis.What's next? How it all st...

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Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

Faye's Official CHYOA Story Contest 2025

by Spindizzy on Apr 29, 2025

Hey there, sexy readers, it's me again, Faye, your faithful flirty filthy CHYOA librarian. Gosh, it's been simply ages since we've had a chance to chat, but I've been so busy filing away all your delightfully dirty stories I've hardly had a moment to relax. What I really need is a little me time. A chance to unwind with my favourite toys and the highest qual...

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High School Dilemma Ch. 03

by LaurenWestley on Sep 15, 2017
Transsexuals & Crossdressers

(Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. I suggest those who don't like this kind of story not to read on. I know I make both grammatical and punctuation mistakes. I promise all of you I will try harder every time to get it right. Hey what else can a sub...

First Time Meeting Master Gene

by sissysubTiffany on May 29, 2018
Transsexuals & Crossdressers

First off a little about myself as I am bi having been with both sexes, but lately only men. I have always it seems to have been attracted to a male cock, but not to men as weird as that may sound. For awhile now I have been going to an XXX Theater Book Store in a town about 45 minutes from me hoping no one would know me there sucking cocks and getting mine...

Going Gurly Ch. 01: Cara's Clitty

by anna_subCD on Sep 16, 2017
Transsexuals & Crossdressers

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...