Cuckold Chastity Shemale Stories

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Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

Mommy's Slave

by Futafan567 on Dec 7, 2019
Transsexual

You are Jim. You are 18 years old and live in an average sized home with your mother Jennifer (Jen for short). Being homeschooled for most of your life, you never went outside very often. In fact your only “friends” are the two girls Amy and Mary who live across the street. You are really only friends with them because they live so close but you were never t...

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The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

Male Chastity Device

by CuckoldGuy on Sep 12, 2017
Toys & Masturbation

Janice and Mike (not their real names) are a married couple in their mid forties. Married about twenty years. About ten years ago they started playing with a male chastity device and discovered they were having a lot of fun with it. They have been using it ever since. The device is a stainless steel or plastic tube about three and a half inches long and abo...

Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...

Black Bulls in Chastity!

by Samuelx on Oct 3, 2018
Interracial Love

Meet Bartholomew "Bart" Jones, a big and tall young Black man living in the City of Ottawa, Ontario. Born in the City of New Orleans, Louisiana, Bart moved to the Canadian Capital to expand his horizons and explore new things. He had a Business Management degree from Louisiana Tech University, and felt like giving life in Canada try. Life in Canada had alway...

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

One of the Girls

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and the transsexual/cross-dressers niche. This is my first attempt at a story so go easy. ***** I couldn't believe my situation. I had signed up for porn, but I had not signed up for this. I was standing naked in the dressing room and the c...

Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...