School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

The Cock Clock Ch. 04

by HarveyMarcus on Sep 26, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Alex to Alexis Ch. 01

by TransPrincessMorgan on Sep 25, 2017
Transsexuals & Crossdressers

Thanks to Jack Murphy for being our volunteer editor! Enjoy! ***** Chapter 1: Feminization Alex was late home again. Once, maybe twice would have been acceptable, but this was the third time this month. His mother, Daniella didn't know what to do with him, especially considering her other children, the eldest, Hannah, who was 25, and the youngest, Amelia,...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

The Journey Ch. 02

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

(You may want to read The Journey before reading this so you will know the background of Tom/Tonya and Jason. These stories are a combination of real life and fiction. Thanks for sharing your comments.) Tonya was content as she stretched across Jason's lap. She had given Jason a long slow blow job and now Jason was rubbing his sissy slut's smooth ass a...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...

Neighbourhood Terror to Sissy Pt. 09

by Fibaro on May 27, 2019
Transgender & Crossdressers

While Mark was going through his night time ritual and sleeping Lisa was at CC's getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The th...

Jasmine - Sissy Slut Transformation Pt. 01

by BillyBaroo4you on Jun 1, 2020
Transgender & Crossdressers

A Sissy Cumslut Transformation Part I - The First Taste (of cum) Nervousness crept into his mind like a snake, slithering its way down toward his stomach. He felt scared, worried about the night ahead, worried about how this one night would change his young life forever. His gentle hands began to tremble as he applied the hot pink nail polish to his finger...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

My Sissification Ch. 02

by sissy171 on Aug 31, 2020
BDSM

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation. My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon...