Bimbo Sissy Stories

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Orientation
Length
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Infinite Scroll

A good fuck

by sissygasm on Feb 10, 2016
BDSM

This story will contain : bdsm, fantasy and sifi elements, gay sex, sissifacation, transformations and various other kinky things. You have been warned. First a description of the world this story will take place in: In this world things are simple, there was a natural order to the way the world worked: real, strong, masculine men were at the top and then as...

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Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...

The twisted DM

by Nobody567 on Nov 21, 2019
Fantasy

Authors notes: please like and comment my stuff I desperately desire your feedback and approval. I am new at this and recently redid the intro hope you like it. A being beyond space and time whose goal is to torture, torment, pleasure and change his players in ways that you cannot begin to fathom for his entertainment and pleasure. He sits at multiple tables...

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Mom's Big Black Hobby Ch. 03

by MiddleKoala on Jun 15, 2020
Transgender & Crossdressers

This story has with incestuous and homoerotic themes. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned! All characters in this story are over the age of 18. The entire story is fiction as are all characters....

The Night He Started Showing Me

by SissyCinnamon on Sep 16, 2017
Transsexuals & Crossdressers

Mistress walked into the kitchen where I was cleaning and informed me that I was to stop and get ready. "Get your swishy ass upstairs and clean up. You have a date tonight." Mistress said. "A date, Mistress?" "Yes, you ditz. There's a man in town who very much wants to meet you. And you WILL behave for him! Understand?" Mistress was quite stern. "Yes, Mi...

Dani's Night Out

by Jemina004 on Sep 26, 2017
Transsexuals & Crossdressers

Danielle Winona was very nervous. Maybe it was because he was standing outside the door of a strange man's house at night in a mesh top, tiny skirt and thong panties. Maybe it was because he had just rang a stranger's doorbell and he had no idea of what awaited him inside. Whatever it was, and whether he enjoyed it or not, Dani had to be as pleasing and sexy...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

Jasmine's Slutty Weekend

by sissyslutjasmine on Sep 16, 2017
Transsexuals & Crossdressers

James squirmed uncomfortably in his seat on the train. His discomfort was for many reasons, the plug in his ass, the cage on his cock and the feeling of soft satin panties he was wearing. However the main reason he was squirming was in anticipation of what was to come on his weekend away. Earlier that day James had packed his bag full of all his toys and cl...

Black New World Order

by Wildone101 on Oct 14, 2018
Interracial

(Quick Disclaimer: This story will contain a lot of triggering fetishes. Things such as cuckoldry, raceplay, light BDSM, bisexuality, sexual domination, bimbos, racial superiority, and other things of the like. If any of those offend you, this may not be the story for you. Also, I'm not that good of a writer. I just want to get the outline out there for the...

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A Gooner's Tale

by changoparati on Sep 16, 2017
Transsexuals & Crossdressers

While waiting for the party to start, she had me getting naked and jacking off for her while she talked about the many dicks she's had in her ass, pussy and mouth, and the technique she employed in each case to get cum from them, pumped into her slutty fuck holes as quickly as she wished, even proposing to show me how. While the 6 or 7 men she'd invited ove...