Femdom Sissy Diaper School Stories

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Orientation
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Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

The Women in My Life Cuck Me Ch. 02

by Philyssis on Mar 18, 2020
Fetish

Continued from part 1, right in the middle of a sex club... I was relieved when my wife grinned. Then I was a bit concerned as it turned into an evil grin. "Wow Phil" my wife said to me. "I knew you had a dirty mind, but I didn't know you had THIS in you!" Amy, my wife's little sister, leaned over and kissed me on the cheek, then looked at Tara, "I'm s...

Sissy Truth or Dare

by BimboBarbie on Dec 23, 2017
Transsexual

You wait nervously outside the front door of Samantha's house, your heart pumping as you still can't quite believe your luck. Just a small, nerdy guy like you being invited over to the most popular girl at school's house! Finally gathering up the courage as you tentatively press the doorbell, hearing the sing song chime through the door. A whole minute passi...

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Behavior Modification Institute Ch. 09

by NancyPan on Sep 12, 2017
Fetish

I want to finish the story since I have some avid readers and I don't want to leave you "hanging," so to speak. However, I've noted a significant drop in the number of votes and the rating of the last couple chapters - so if you want to encourage me or have constructive suggestions, please vote and/or leave a comment. ***** Confined to the cage and in tot...

Tales of Feminization

by AnonWriter on Jun 11, 2014
Fetish

In a seemingly normal town, a new social movement is taking place. White boys are encouraged to act, dress, and be feminine. You are a student at this school, and this is story of how you become a dirty sissy slut. Choose a boy to play as and be feminized. (All characters in this story are of legal age) (I'm only working on Mark's story right now, but feel f...

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Butterflies

by marybethsanford on Sep 15, 2017
Transsexuals & Crossdressers

There were a lot of good reasons to be out this early, but none as wonderful as seeing this first Giant Swallowtail awakening, and John smiled as it moved. Magnificent, he whispered, in awe of this giant as it slowly unfurled it's Forewings against the sun's morning warmth. It was, as they always were at this time of day, lethargic and calm. "Papilio Cresph...

Ultimate Sissy Weekend Ch. 05

by SissyTwinkleToes on Jan 21, 2020
Transgender & Crossdressers

Susie can feel her diaper getting warm as she fills it with more pansy pee. 24 hours ago, she posted an envelope containing five keys, and still has another 48 hours until they arrive at her house. Those keys are for the lock that keeps her in her dress, the handcuffs that keep her right hand locked to this sissy on her left, and the tiny pinching chastity c...

Wet Dream Pt. 02

by sissymissyct on Jan 21, 2020
Fetish

After breakfast, Gayle said she would drive me to the doctors office. It was across town but shouldn't take too long to get there. "How did you find this doc?" I queried. "Oh, one of the gals at the gym mentioned her. She is the doctor that got me on the HRT treatment I started recently. I think you will really like her." "Her?" "Yes her. I thought you wo...

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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