Sissy Schoolgirl Stories

13,642 results
Orientation
Length
Source
Infinite Scroll

The Visitor Ch. 07

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

Thank you for all your support and comments on my story so far. ***** Whimpering, my face on fire, my body quivering in an almighty panic of humiliation, I had no choice, I needed something to hide behind, something to cover my glaring nudity with. I put on the flimsy sheer baby doll nightie and it's panties in a trembling nightmare of impending doom, the...

How I Became A Girly Slut Ch. 02

by richfun71 on Sep 13, 2017
Transsexuals & Crossdressers

Copyright 2008 I couldn't believe what was happening to me. Here I was a normal straight guy dressed in a tight pink t-shirt, stockings and suspenders and black lacy panties under my jeans, wearing bright red lipstick and with a transvestite's cum dried onto my face, and the taste of another man's cum in my mouth. I had a piece of paper with an address on i...

Humiliated Sissy Husband Ch. 05

by rik581 on Nov 16, 2020
Transgender & Crossdressers

Max and Tonya walked in the front door after a morning outing in which Max spent the entire time complaining about wanting to go home. Max stood there wearing a little girls dress and high heels, with his wrist tied to his upper arms and hanging limply near his shoulders. His shoulders, waist and legs strapped extremely tight to the pole. They needed to be...

Mamma Mia - Forced Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"We need a little more feminine energy around here." The words hung in the air as Tommy's devoted licking of Mia's ass slowed to a stop. "You mean another woman?" Mia hooked her legs behind Tommy's head and pulled his face back into her ass. "No, I mean you, you dumb sissy bitch." Once Tommy finished with pleasuring Mia, she led him into her closet. She...

Time for a Kit Kat Ch. 04

by cashcrunch on Sep 17, 2017
Fetish

"All ready for me you naughty little whore?" Kat asked, standing in the entrance to Evan's room. She wore her black "fuck-me" boots, a black bra, and her new pink strap-on dildo hung obscenely from her waist. Evan had been caught in a blissful reverie; fantasizing about his gorgeous, blonde next-door neighbour. The cock-ring tight against the base of his di...

Touched By Magic

by HighGrove on Jan 19, 2020
Fantasy

Throughout history, man has been driven by two primal goals: Getting Something for Nothing and Having Sex with Everything. Every great advancement in human civilization, from fire to philosophy to the electric guitar, can be understood as some combination of trying to fleece or fuck one's fellow man. And no single pursuit has more perfectly encapsulated the...

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A Small Problem

by Rbhy2 on Mar 2, 2019
Cheating Spouses

"Hey baby I'm home" you said as you walked into you apartment. The building wasnt much, just an old converted motel that you and your girlfriend Kay had scraped enough money together from your menial, part time jobs to afford. "Hey babe I'm in the shower" you hear coming from the bathroom on the back. "I'll be out in a sec" You...

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Stepsister's Whim

by wintermute on Jan 13, 2016
Science Fiction

You close the door behind you and walk into your parent's house, finally back after driving home from your first semester away at college. Finals week was rough, as you'd expected, and you've been looking forward to being able to relax at home. Your hopes are shattered, though, when you turn into the kitchen to see your stepsister, Sarah, standing in the cen...

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Booted for Daddy

by booteddesire on Jul 15, 2020
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Danny adjusted the skirt as he walked into the club. It was his first time dressing... and truth be told he wasn't really sure why he was dressed up. His girlfriend was at a bachelorette party for the week and he decided to say screw it and go out and to wear his girlfriends cloth...

Just Like My Friend

by purekink on Sep 12, 2017
Transsexuals & Crossdressers

I suppose it all started after my friend told me his girlfriend liked to dress him in her clothes before sex. I couldn't quite believe it - he was masculine and muscular, a real man's man. He'd confided in me and I teased him about it unmercifully. I mean, really? Being dressed in women's clothes? That was supposed to be a turn-on? He seemed to think so, bu...