School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

A Freshman's Summer Class Ch. 09

by CapnSteelBoy on Jul 6, 2020
Transgender & Crossdressers

**All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventures at home draw to a summer conclusion! Sorry this may be it for a bit, its very difficult to decide which direction to take this story at now. I mean, can't keep calling it a "Freshman's" anything now that he is a sophomore...I may...

Futanari Academy Ch. 14

by TheOrcKing on Jun 10, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Halloween Special, 2018 Danielle walked up the steps to her friend Maddie's house, still wearing her Westbrook school uniform which now consisted...

A New Way Of Life

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

This story begins as many do. I stared to dress at an early age in my mom's things. Then I started to buy my own things as I got older; panties, bras and high heels. I was always small for my age taking after my mom, she was a small woman with a nice figure and so was I. I was only 5'4 and 110lb, blue eyes and jaw length blond hair. They loved me in high sch...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...

Jock Princess Ch. 04

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

Logan carries me down the hall of his place like i'm some little feather making me feel definitely thrilled and small but he's a really huge guy honestly like one of those guys that was big in high school but he really worked out and got bigger still in college. I like the way that all feels. I like that he carries me all the way into his bedroom and sets...

A New Way Of Life Ch. 02

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

A Big thank you to Chris & Scott for the great eaditing job. This is the 2 part please read the firts New Way I looked at Everett, "Ok, are you sure?" "Yes, Carine. Now go get ready. I'm hungry." I headed off to the bathroom to fix my make-up and hair. Looking at myself, I can't believe what had happened. I was loving it! I had never felt so alive, tu...

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...