Teen Sissy Stories

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Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

Das Leben als süßer Sissy Sklave

by Captain Simpel on Oct 30, 2020
Miscellaneous

Justus war ein durchschnittlicher Junge mit etwas längeren schwarzen Harren, der gerade zu übers Wochenende zu Marie wollte. Die beiden waren schon seit der fünften beste Freunde und unzertrennlich. Etwas beneidete er sie für den Reichtum ihrer Eltern, die ihr mit 18 ein Leben in einer eigenen Wohnung ermöglichten, obwohl sie im Moment nie viel verdiente. Al...

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Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Teen Boy Becomes a Girl for his BFF

by SissyKelly on Nov 23, 2017
Transsexuals & Crossdressers

Okay so this is the story of the first time I revealed my identity to someone I knew, this ended up being quite an important relationship in Kelly's life, so more stories from this will come! Names have been changed to protect the identities of everyone!! Let me know what you think and if you want to know mor stories from my life :) So Ryan went to my schoo...

Teen Boy Becomes a Girl for his BFF Pt. 02

by SissyKelly on Nov 26, 2017
Transsexuals & Crossdressers

I ran into Ryan's bathroom and quickly transformed back into boy me. I nearly ripped my hair extensions as they came out, furiously scrubbed my make-up and tossed my pretty clothes into my bag, replacing them with my normal jeans and t shirt. I looked in the mirror, I was a boy again. Kelly was gone. Downstairs I head Ryan talking to his mum, casually menti...

Teen Boy Becomes a Girl for his BFF Pt. 03

by SissyKelly on Dec 5, 2017
Transsexuals & Crossdressers

I was fucking stressed. After fucking me in the ass and filling me with cum at his house, then cumming all over my face at the tree, me and Ryan hadn't had another chance to hook up in weeks. Sure, we still texted and exchanged photos and jerked off to each other like crazy, but since my parents divorce that was harder to do as my mum gave me little privac...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Town of Hidden Desires

by Birbfinchy on Oct 27, 2020
Fetish

A U-Haul van pulls up outside a beautiful blue house in the suburbs of Setgow. Skylar, just turned 18, steps out of the van and relishes the cool breeze on his face as he stretches' his thin legs after being trapped in the car for the past 4 hours, the wind pushes his neck-length dirty blonde hair past his bright blue eyes which he gently brushes aside back...

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Cyber Sissy Ch. 05

by missvicky53 on Sep 25, 2017
Fetish

A fantasy by Miss Vicky Part 5 (The Last One) The rest of the evening passed with the two of us cuddling on the couch, each with a glass of wine. Megan had changed into a black floor length nightgown with a lace inset running diagonally across the front. This meant that with each movement of her body, I would catch a glimpse of various parts of her body. T...

Candy's Day

by daisyboi_sissy on Sep 13, 2017
Transsexuals & Crossdressers

This contains Sissy porn and sex acts. Leave now if you should....everyone here is above 18 years old. Love ya! * I have always loved the feeling of something lacy or sexy on my body. I call it a passion of some sorts, wearing these things made me feel very special and desirable. I was raised by my mom and the closest family we had was my Aunt Trish and h...