Plaid Skirt Stories

113,885 results
Orientation
Length
Source
Infinite Scroll

Studying with Kelly: Pt. 01 The Assignment

by Legman173 on Sep 13, 2017
Erotic Couplings

All characters in this story are above the age of 18 years old and are legally consenting adults. All characters in this story are purely fictional and any similarity with actually people or events is purely coincidental. I hope you enjoy it, any and all feedback is welcome! * The bell rung as Stan made it into his history classroom. The day had been hect...

Schoolgirl Confessions

by miss_cheevious1 on Sep 12, 2017
Erotic Couplings

I have heard it said that you can never be too rich or too thin but whoever said that obviously didn't know Angela Tubinello. We all watched her waste away to nothing, her hair growing lifeless, her skin patchy as she convinced herself and her body that she didn't need food, her Daddy's money or anything or anyone here at St. Charlotte's. Her whole life she...

Alexandra Makes The Grade Ch. 01

by peechka on Sep 14, 2017
First Time

Alexandra, Alex to her friends, wasted as much time as she could fiddling around inside her locker as the school building cleared of students and faculty. It was Friday afternoon and the weekly inhabitants of St. Brendan's Catholic High emptied in a hurried wave, glad to be free from yet another week of school. She listened absently as her friends talked ex...

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

Back In Class Pt. 01

by Tiffany8 on Oct 15, 2017
Exhibitionist & Voyeur

Every person I mention in this story is fictional and everyone involved in this story is eighteen and older. ***** So here Tiffany was inside the halls that once her domain. The disgust that came across her face to see the sorry state of her alumni. The poor female body was stuck wearing long plaid slacks, not even skirts anymore, and were forced to wear l...

My Best Friend... Or More?

by RedSquirrel84 on Sep 12, 2017
Romance

Stacy quickly cleaned herself up in the bathroom, blending in her concealer under her eyes. Why was I born with such fair skin, she wondered as she covered the dark circles that seemed to perpetually stay no matter how much sleep she got. David would be there any moment for dinner. Tonight, she had prepared grilled swordfish and asparagus, one of his favor...

Punk Princess

by gizmo52242 on Sep 19, 2017
Erotic Couplings

A few years ago, I started talking to this girl online. Her name was Toni, and she lived and went to school in Utah. Mormon country. Toni was not your typical little Mormon girl, though. Oh no. What first started out as just idle conversation soon turned into a full-on cyber relationship, complete with webcam shows, e-mail exchanges, and AIM cybersex. Toni...

Thrills in the Night

by melanieatplay on Jul 24, 2018
Transsexuals & Crossdressers

I pressed the 'ground' floor button on the elevator and checked my look one last time in the mirror. White button-down shirt, brown leather pants, and brown oxfords... It was a classic, yet contemporary look that the ladies seemed to love. The rain started to fall again. Sunshine all week long. Then, light drizzle all weekend. Isn't that always the way? It...

New Student Escort Loses Her Pubes

by KissedMany on Sep 12, 2017
BDSM

This is the sixth instalment of an 18-year-old music student's, Clare's, sexual journey. In the first instalment, she was hired by the husband and wife team of escort agency owners who discover during some sexual high jinx she is still a virgin. In the second, she sets out in a limo to her first appointment with her new escort name, "Celeste", to a man who h...

Jill and Uncle Roger

by fantasyboy on Sep 16, 2017
Transsexuals & Crossdressers

Jill had realized that whenever her Uncle Roger visited, her panties kept mysteriously disappearing. She had told her mother who smiled and explained that her brother had always had this little weakness for panties. When Jill had asked about what Uncle Roger's wife Fiona would say if she knew about his fetish, her mother became quite alarmed and explained,...