Plaid Skirt Stories

113,885 results
Orientation
Length
Source
Infinite Scroll

A Bunny to Play With Ch. 04

by ChrissieLecker on Sep 12, 2017
Novels and Novellas

* Author's Note: This chapter is one of fifteen in a novel. If you want to enjoy it fully, please start reading at the first chapter! * "Let's hit the road, Bunnie!" That war cry was so Anne, with her spontaneity and fable for the dramatic. For some unknown reason, I thought back to the moment the name 'Bunnie' had come about. It was actually a bit embarra...

Pleasing Her Forever

by Bigchicklover on Sep 13, 2017
Erotic Couplings

Many thanks to sunshinesdevotion for her editing even if she had a shitty weekend. My father, who was very conservative when it comes to sex, told me one important thing about sex. That if you can please a woman she will be yours forever. I was a normal college boy; nineteen years old and no longer a virgin, having lost it to a skinny drunk girl last year....

The Sportswriter and the Ad Exec

by patricia51 on Sep 17, 2017
Celebrities & Fan Fiction

(Crossover story My Boys/What I Like About You. PJ wakes up in New York with someone she certainly didn't plan on. Femslash. PJ/Val Tyler. The incident Val refers to in Connecticut takes place in my story "Visitors from New York". Not my property. PJ belongs to TBS and Val to the WB and CW.) PJ Franklin cracked open one eye and glared at the sun streaming t...

Adventures after Dark Ch. 01

by classmate1119 on Sep 16, 2017
Transsexuals & Crossdressers

-Author's note- I started crossdressing in my teens, but coming from conservative South-east Asia, it was definitely my darkest secret for many years. I would often dress in my mother's dresses, and put on her makeup when I was home alone, but I stopped crossdressing when I moved away to start college. When I won a scholarship to study in the UK, I did no...

Sunday Afternoon

by millieteases on Sep 14, 2017
Transsexuals & Crossdressers

On Sundays he always wore panties. If he planned on spending the afternoon alone, he'd get out and wear the rest of the clothes – pantyhose, pumps, a skirt, blouse, bra and a slip – but either way – women or men's clothes – he always wore a pair of women's panties on Sunday. It was a little strange, but it aroused him and at the same time, at least he'd tell...

The Bet

by cybele_13 on Aug 19, 2017
Exhibitionist & Voyeur

So, I get into trouble in school. What kid doesn't? I'm 18, about to graduate, so what's the big deal. How am I gonna learn if I don't make mistakes? Well, at least argument works on Daddy... I got caught after school today in one of the storage rooms with two of the guys from the football team. They literally had their pants down. I was jerking off the o...

Doggie Time with Kayla

by cowboy109 on Sep 17, 2017
BDSM

Her chin rested against the fabric of my jeans as a comforting weight. Her big eyes looked up at me. They followed my face intently as I relaxed looking at the TV. Her red hair piled high on top of her head. Many mini curls fell into every which direction. Her hands were poised next to her chin in my thigh. Her elbows were tucked in, like a person hiding the...

The Rake Ch. 01

by scooze64 on Sep 15, 2017
Loving Wives

Intro: The Rake is a man who is clearly dishonest, disloyal, a risk taker, and has no interest in marriage. They live in the moment; they give you no time to think or to worry about the consequences. The Rake never worries about a woman's resistance to him, or for that matter about any other obstacle in his path – a husband, a physical barrier. Robert Gree...

Trapped! Ch. 01

by EffieMeow on Jun 4, 2019
Transgender & Crossdressers

Note to the dear reader: Written over a lazy Sunday afternoon. I've found that my favorite stories here are the ones that delve deeply into the various sensations of crossdressing. So here's one to us girls who enjoy every step of the transformation. *** My heart felt like it would burst out of my chest as I stepped out the front door. Halfway through, I...

Surreptitious Love Ch. 07

by BenGarland on Jun 19, 2019
Erotic Couplings

Chapter 7 -- Black After the rumpus at Thuy's house, Nguyet and I took a break. We let almost a month pass by before we even spoke to each other again. I guessed neither of us wanted to be the first to propose another threesome. Anyway, I believed we needed a session without Thuy first. Just to tickle Nguyet's fancy a little bit, however, I suggested she bu...