Sissy Hell Stories Stories

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Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...

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...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Boredom and Therapy

by oldhippie1949 on Aug 31, 2017
Group Sex

The following is a true story. Naturally, all the names have been changed but all the events described took place just as I have written. If a bi-sexual threesome is not to your tastes then move on. If you are too young to be reading this, then move on. ***** I was so bored. Even my dog couldn't shake me out of it and. believe me, he tried. I didn't care t...

How to Become a Sissy/Cuckold

by Quietoldie on Sep 14, 2017
How To

This is a How To Guide for Sissies and Cuckolds. Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, drivi...

Becoming Mindy Ch. 02

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Thank you for the positive feedback from my first story. As I recall things I wrote about in my diary, I am not going to be writing on all of them. Just the ones that are important to my story and/or just some memorable events (i.e. the first time I..). I hope I am able to write them in a way that you find as enjoyable reading as I had living them. I have se...

Aficionado Gets in Trouble Ch. 03

by His_fag_wife on Sep 23, 2019
Transgender & Crossdressers

As his WhatsApp call rang to the contact simply named Master, Pete had no idea what faced him. His senses were full of Marks cum, the distinctive metallic taste, it's manly musky aroma were overwhelming for him. He was still high from the poppers and thought he should just sit for a few minutes to recover a little, although the nearly full bottle of poppers...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

The Naked Bleached Blonde "Sissy Barbie Bimbo"

by Crissy on Apr 22, 2025

Did You Know? According to a study conducted on 293 female college students at the State University of New York in Albany, exposure to semen can lower symptoms of depression. And it’s mighty healthy: One teaspoon of semen contains over 200 proteins and several helpful vitamins and minerals including vitamin C, calcium, chlorine, citric acid, fructose, lacti...

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