Sissy Schoolgirl Stories

13,642 results
Orientation
Length
Source
Infinite Scroll

Away with the Lads

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You're invited to Dublin, Ireland with 10 other lads from your village. It's planned as a weekend of copious quantities of drink (Guinness), fast food (beef burgers and chips) and cultural interest (Girls). You fly from Southampton and costs are kept to a minimum. Aiden, The only Irish born lad in the group fails to show – selfishly this is good news, as unl...

Rene and Gene

by Bakeboss on Sep 16, 2017
Novels and Novellas

Part l My first Friday as Jean: Although I work at home, I still took the day off to make sure all the housework was done. Rene called on her lunch hour and said she bought a surprise for me, that she felt naughty and wanted us to spend the weekend doing naughty things. I was hard at the word naughty; my beautiful wife is such a tease and enjoys role-playi...

The Path to Happiness

by brendachaplin2000 on Sep 23, 2019
Transgender & Crossdressers

Author's note, none of the characters are below the age of consent. *** Here I was staring into a full-length mirror, seeing myself glowing in my wedding dress. At 44 years old I never thought the day would come when I would be a blushing bride. As I stared my mind wonders back to my childhood. I was born a boy, Brian Cole. From an early age I knew I was d...

The Executive's Wife

by Original_Aramis on Oct 15, 2017
Erotic Couplings

Randy Evers had nothing but sympathy for his next door neighbor, Sissy Ryan, an absolutely beautiful woman caught in a bad situation. Ever since he had moved into the neighborhood six months ago, he knew that something was amiss in the Ryan household. Sissy's husband, Bruce, was a corporate executive who was at least fifteen years her senior. From the conver...

Kinky Adele Mummy Fucker

by Sissy Adele Howells on Sep 17, 2017
Fetish

Being in love with a married women is so rewarding. Wet dreams about Adele Howells is one of the rewarding pleasures left in life. When this fantasy became true, a warm and satisfying glow engulfed my body. Her husband Tony was not aware, that is sexy wife was texting me, as we chatted at the same table, in the local cafe. I hope by describing Adele to you...

Magic Panties Ch. 06

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy! Here's the last recap for you loyal readers out there (I apologize for the delay, life got hard, un...

Cheap Sissy Whore To Call Girl Ch. 02

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

The day I woke up after being knocked out was a strange one. I didn't know how long I had been missing but I felt my body had been completely transformed. My skin felt softer, I had breasts, my lips were filled with collagen. I remember waking up in a what seemed like a hospital room and walking up to a mirror and looking at a gorgeous bald woman with a peni...

Pay for Pleasure - Prequel

by Pleasure_the_slut on Sep 16, 2017
Transsexuals & Crossdressers

I had written about how Sandy turned me into a $50 whore before writing about how I got to that point with her. I was cruising an online posting for sex one Thursday evening and I came across a posting for TV looking for big cock. Well that got my attention, I'm 8" and very thick. So, I shot a reply right away. Not a minute later Sandy and I started chatti...

Marine Girl Ch. 03

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3 - Dressed for class There's a sudden noise from the changing rooms. I make out a banging of doors. Steve yanks his thumb out and kicks me onto the shower floor again. 'Come on you horrible lot,' Sir screams from outside the showers. 'What's the hold-up? I've another lesson in 5 minutes. I want you out in 60 seconds. 59, 58, 57...' Sir began count...

Snowbunnies

by tori_tgirl on Oct 12, 2017
Transsexuals & Crossdressers

I was finding it hard to concentrate on my picture... the creaking sounds from the box spring grew louder with each passing moment, making it harder and harder to keep my crayons inside the lines. I didn't have long to finish my coloring, maybe another minute or two but it was already the prettiest unicorn I'd colored yet, and surely they'd be happy. I strug...