Plaid Skirt Stories

113,885 results
Orientation
Length
Source
Infinite Scroll

Naughty Kate Ch. 02

by randomspaces on Sep 13, 2017
BDSM

Authors Note: This is part 2 of Naughty Kate, reading part 1 will give you a better idea of the story. You don't have to read it but if you like this, then you'll like it as well. All characters are over 18 and sexually transmitted diseases and other unexpected negativity from sex doesn't exist in the, very, fictional universe this story is set in. Enjoy....

Jury Duty Ch. 02

by vastiesmith on Sep 17, 2017
Loving Wives

Mary dressed for Tommy's enjoyment that first day she went to his house after instructing his wife to go to the office and work on the project. She almost had her breasts hanging out of her low cut off the shoulder blouse. With no bra on, her nipples showed against the white blouse as they pointed against the material and the dark circles surrounding the fat...

Netsex with a Twist

by YDB95 on Aug 31, 2017
Erotic Couplings

Late spring 1994 -- Cobain was dead, Clinton was president, and Becky's ritzy New England college was still a few years away from installing computers in all the dorm rooms. That last point was rather frustrating to Becky when the library closed down that Saturday evening in May and she had to return to her room, for she was in the mood for some fun. Private...

Meeting Hannah Again

by peacekeeper25 on Sep 14, 2017
Erotic Couplings

I hadn't seen Hannah since the last time I was in New York to do a poetry reading my brother had arranged at the library. That was two years ago and I didn't know whether I would see her on my return visit to read now that my book was published. She had been careful not to tell me where she lived or give me any information about her so I had no way to let he...

Bench Seat Wife

by away443 on Sep 15, 2017
Anal

There I was, lurking in the company truck for a whole hour. It was dark and I was parked on the curb by the university parking garage. Just waiting. Not even really sure for whom. It could have been a prank, an ugly transvestite, an old fat man. Someone laughing at the thought I'd come out and drive an hour and then wait longer to meet a fake person. Everyo...

My Son In My Clothes Ch. 03

by LeggyVicky on Sep 14, 2017
Transsexuals & Crossdressers

"Shit, that'll be Adam. I forgot, I told him he could watch the football with me." "Well, in that case you had better let him," I said. Two frightened eyes stared in my direction. "I guess he'll be a little shocked, but you two are friends. Just make sure he keeps his hands to himself." The scared eyes were now joined by an open mouth, and a look of tot...

Maggie's Slutty Fantasies Ch. 08

by thesecretslut on Dec 3, 2019
BDSM

Oh god, what was coming next? I turned around and thought for a second, I could leave right now, head back to the apartment, end this before I got in even deeper. But the video would be released, with all my information and god knows what else they had now and the world would know the side of me that I've been trying to hide for years. My friends, family, t...

The Neighbour's Son Pt. 04

by ChrisyCrossy on Dec 16, 2019
Exhibitionist & Voyeur

My name is Lynette, and I am a very successful businesswoman. I have returned home and have rekindled a new business with me ex-husband - no we will not be getting back together. We have worked together before, and we were a formidable team that made lots of money: he looked after the finances and paperwork while I was the saleswoman. This partnership just...

Michele Nylons' True Stories Ch. 05

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

New Punishment System Demonstration

by TUnicornLiterotica on Jun 15, 2020
Transgender & Crossdressers

DISCLAIMER: This story involves the degradation of a trans character, this is not meant to be read as transphobic scripture. The writer, being me, is trans, not that makes it automatically okay, but just understand, this is a fantasy, and it fulfills some of my submissive desires. Characters all 18 years old above etc. * * * * * Carla had just been pulled...