Hyper Sissy Stories

11,464 results
Orientation
Length
Source
Infinite Scroll

Charlies Sissies

by Bisexual Zam on Apr 29, 2025

Once upon a time, there were three very different little boys... who grew up to be three very different Glammed-up, twerkalicious, super slutty Booty Boiz. They have three things in common: They're brilliant, beautiful... and they work for me. My name is Charlie. The sissies were hired, trained, and given new identities. Their old identities are lost to the...

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Do You Wanna Be A Ditzy Bimbo Barbie Doll!?

by Crissy on Apr 22, 2025

The Rise of a Sissy, Bimbo Barbie Doll! What makes & is a Bimbo? Bimbo is term or slang word for a conventionally, _'golden/bleached blonde, attractive, buxom, sexualized, naïve, and unintelligent woman'. Bimbo culture, or bimbofication, exemplifies the character type of “a conventionally attractive, sexualized, naïve, and unintelligent woman.” The term...

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Cockland Island Pt. 03

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I think my dreams that night were pleasant. I was kind of still just transforming back then. But when I woke up, I remember the feeling of my butt plug in my ass was pleasing and that my caged cock was perfectly sissy cute and I was good with that. It was kinda a trip to look in the mirror and see it all. And walking with the plug, sitting with the plug....

Femboy Autocracy

by Azaylia on Mar 1, 2021
Science Fiction

In 2027, a mad horny scientist unleashed her diabolical weapons in an attempt to turn the world into her sexual paradise. She released two custom-made viruses. one that would affect men, and one women. They rapidly spread to the entire population, brining their effects with them to all but 0.00001% of the population. For women, the effects caused futaficatio...

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Sissy College Ch. 03

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

Standard disclaimers apply. I'm indebted to Puzziboi for writing the first half of this chapter: Thank you! I really do enjoy your feedback, so please keep it cumming! Lastly, I encourage you to read the previous chapters before you delve into this one. Mr. Blackwood slapped his large veiny cock against Lenni's smooth lily white face with an audible smac...

Sissy College Ch. 01

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All characters 18 and above. This series will eventually be filled with all the raunch you desire, but I like a little foreplay first. So sit down, slip down your panties, and enjoy! I love your comments! Chapter 1: Mathematics Welcome to Chester College: An exclusive all-boys Sixth Form College catering to talented young men from across the country aged...

A New Life Ch. 02

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

I closed my eyes and took a breath, which was far from easy. The steel boned corset, which I was made to purchase and learn to lace myself, was quite tight and pulled my body into the curvy shape that both Mistress Sally, and the men who have been encouraged to watch me on Skype, all enjoyed. The cursor moved across the screen as Mistress Sally's Skype call...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Mommy's Boy? Ch. 03

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I minced into the kitchen in a new dress, feeling terribly nervous. My small pink butt plug added somewhat to my wiggle, reminding me at every step that sissies need constant training. I brushed my hands against the skirt of my princess dress one more time, smoothing out again all the wrinkles that my imagination created, and again touched the hair of my wig...

Sarah's Husband

by JJEroticas on Mar 30, 2020
First Time

Sarah's Husband I was nineteen sitting at a table of other nineteen-year-old degenerates. We sat outside, drank rounds of coke, and everyone had their Marlboro packs obscuring the red and white striped table cloth. I ordered a TGIF burger, greasy, a favorite. My body had a secret inside shimmering of nerves, dehydration, and malnutrition from last night's k...