Sissy Caption Stories Xxx Stories

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Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

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...

Dare You?

by Secretwriter25 on Mar 9, 2020
Loving Wives

You've gone away on business again, and, as we both like to do, I've given you a list of tasks. I love to dare you to do things. You'll usually manage at least one or two of them, and it's great for the inevitable phone sex or cyber sex later. There are the usual mild ones, like "Film yourself nude, in bed, playing with yourself", or "Send me a photo of you...

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...

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

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...

My Friday Night: Disconnected

by honey28 on Sep 16, 2017
Transsexuals & Crossdressers

Although it has been two years since I posted a short story, I never stopped writing. In 2012, our relationship was at its start, and I began feeling things that I was not ready to share with him yet. Those feelings were coming through in my writing, so I kept my stories to myself for a long time. I actually wrote a book, and was also busy with editing Nicho...

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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