Bimbo Sissy Stories

10,300 results
Orientation
Length
Source
Infinite Scroll

The Double D Ranch Ch. 02

by JDBones on Sep 15, 2017
Transsexuals & Crossdressers

Jeff Malville awoke slowly, moaning softly. He almost forgot where he was in that moment where sleep and being awake clashed. However, after that split second, it all came rushing back and he moaned in delight. He was a captive on the Double D Ranch, and even though he was considered an employee, the only thing that he'd come to be good for was a sex slave...

Jezebel's Magic: Becoming Josephina

by twiddershins on Aug 31, 2017
Fetish

Jeff was just a regular dude when he met Jezebel. They had lived together for a few months and at first they seemed satisfied with each other. They got along fine and would have appeared like any normal couple in public, but that was now long ago. Even then, Jeff had felt lucky to have her because of his tiny penis! One Saturday night, Jezebel came home lat...

Turning into His Toy Ch.03

by vaultdweller111 on Sep 13, 2017
Transsexuals & Crossdressers

My heart raced as I saw the tray one of daddy's maids held. On it were a wooden paddle, a pair of handcuffs, a pair of nipple clamps, and a pair of white cotton lace panties. "Alright Ashley come wait with the tray by my side and Lilly put your hands on top of your head so I can get a good look at you." He commanded us both. "Yes daddy." We both answered...

Crystal: A Sissy Set Free Pt. 01

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

Chris was a pretty standard excuse for a man, 19 years old with a thin face and a wiry frame, lacking any sort of muscle. He would have been just another man in a huge sea of others at his local college, but he was different, he refused to keep his mouth shut and refused to behave. He would strut around like he owned the place, hollering at girls, wolf whist...

Girl's Night Pt. 05

by DifferentBreed on Sep 14, 2017
Fetish

This is a continuation of an earlier story. It contains themes of feminization, humiliation and other fetishes that don not appeal to all. If you are a fan of these, please read on and leave comments as to how to improve the story. Hope you enjoy it. ~ DB ************************** Fisher awoke gradually, blinking at the morning sun as it peeked through th...

Begging for a Pegging Pt. 02

by Cirkle7 on Oct 12, 2020
Fetish

This story is dedicated to the muse who inspired it. I think she would most certainly enjoy taking the reins in the bedroom. In fact, I think she may have pleasured herself while she read the last story. Thanks again I'm speechless, but I love your dirty mind! All characters are above the age of eighteen, please this story may not be for you, but don't read...

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

Sissy's First Time

by Sonjas_pet on May 23, 2018
First Time

By the time my wife, S, and I had been married for fifteen years, there was not much that we didn't know about each other. If you're going to make it that long, you're going to have to learn to be honest with each other. This is what had led to me recently, cautiously, come out to her as being bi, turning at once tepid physical relationship into one of ongoi...

Letter From Montgomery County

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom, Loving your "Taped Confessions" series. I am known as the Bitch of Bethesda, for I've really trained a lot of hopeful couples in the femdom life, all over Maryland, D.C. and Northern Virginia. Enjoy! Rhyce, torturer of Chevy Chase Crybabies... "So how goes it with Milton? Did you up the ante like you said you would?" "Jesus, Vermillion,...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...