Wedgie Stories

582 results
Orientation
Length
Source
Infinite Scroll

Vanessa's New Life Ch. 05

by VanessaEvans on Sep 19, 2017
Exhibitionist & Voyeur

This is part 5 of my Journal. I started writing it when I made a bold decision to change my life. I left my dull existence in North Wales and went to work as a Housekeeper for a man in the East Midlands of England. It is a decision that I will never regret. I have never been so happy and never had so much pleasure. Vanessa * Saturday August 8 I woke up...

Drool

by redmaxxx on Sep 26, 2017
Group Sex

CHAPTER ONE ONE A thick strand of drool glimmered in the light. It stretched from his cock to her hungry tongue as he playfully pulled it from her eager mouth. She was naked, lying flat on her back on the dining room table, each limb tied to a table leg. Her head was not allowed to rest on the table; instead, around her neck she wore a collar and he held t...

A Passion for the Game Pt. 02

by Carrie1 on Sep 12, 2017
Exhibitionist & Voyeur

If you haven't already, I serious suggest you read the first part so this makes more sense. * I didn't go back to watch the tournament the next day deciding to take some time for myself and try to relax, but first thing Monday morning I was on a plane heading to NYC with Tanya and Didi. The last minute cross-country tickets had seriously eating into our r...

Appreciating Cory

by Panthergirl on Sep 4, 2018
Erotic Couplings

It was a very hot and humid summer day. I dressed up in one of my sexiest dresses, a flashy emerald green number that clings to my curves and leaves a lot of skin exposed in such a way that it cannot be worn with underwear. I'm not just talking about a bra, wearing even a thong with this dress would look a bit tacky. The shoulders were straps, the fabric was...

A T-Girl and a Tomboy Pt. 03

by AlexBailey on Sep 14, 2020
Transgender & Crossdressers

A Surfer and a Swimsuit Model _____________ Hello! This is part three of a full length novel in four parts. It's a gender-fluid, 'what if everything fell into place,' fantasy about self-discovery, coming out and coming of age. It explores pansexuality, cross-dressing and several fetishes - especially for things like swimsuits and athletic-wear. Some part...

Teen Stud and the School Therapist

by dominanceaddict1 on Mar 3, 2020
Transgender & Crossdressers

I was about to leave work early when my phone rang. It was one of the school administrators. They also served as my secretaries. "Mr. Caldwell? A student is here to see you." No, I hadn't seen this student before. The student hadn't wanted to describe his issue with the admin and instead wanted to speak to me directly. My name was Sam Caldwell and I worked...

Boy Sorceress Pt. 01

by sycksycko on Sep 25, 2017
Sci-Fi & Fantasy

This story contains a gender-bending element, but it is not your typical transgendered story. If you're looking for that kind of fare, there's plenty of it on this very site. Edited by Over_Red ************** On the day after my twenty-first birthday, I was determined to get shitfaced for real and Greeley's was as good a place as any. Or, so I had thought...

Fresh Pt. 02

by PurpleMonkeyDishwash on Apr 24, 2018
Interracial Love

Disclaimer This is a four-part white woman, black man cuckolding novel. It is written based on fantasy sexual scenarios. Some characters are written as stereotypes in order to advance this fantasy. The cuckold character behaves weakly and doesn't stand up for himself. The black bull characters behave aggressively, and are not written as living human beings...

Gym Milf Affair

by jeffincognito on May 2, 2018
Mature

She was momentarily blinded as she exited the well-lit gymnasium and stepped into the night. She squinted, waiting for her eyes to adjust to the dark parking lot that was nearly empty by now. "Damn light." She cursed under her breath. She had complained to the boy at the front desk about the burnt-out street lamp weeks ago. He had told her there was noth...

Basketball Diaries Ch. 09-10

by Kellog on Sep 15, 2017
Group Sex

Part IX Playing Man Coverage Keith Cole had just settled into his easy chair to watch some golf on television. Really, there wasn't much else on this time of day and he was all alone. Kevin was out of the house at practice, his wife was out of town at a conference, and his daughter -- who was still sleeping upstairs -- had said she had plans to go out shop...