Interactive Wedgie Stories

1,269 results
Orientation
Length
Source
Infinite Scroll

Caught in Ex-GF's Underwear Pt. 01

by HiddenThoughtz on Oct 6, 2020
Transgender & Crossdressers

Hello everyone...welcome to my crazy kinky life lol. This origin story takes place right before my 21st birthday. This all started when I finished my junior year at college. School had ended and I was taking summer classes so my workload senior year would be easier and I could enjoy my last semester. My two roommates had gone back home to work for the summe...

Clothing Hunt: Battle Royal

by lewdman03 on Aug 1, 2019
Exhibitionist & Voyeur

The president of the United States of America stepped into the stage. he placed his sheets on the table as people from across the world tuned in. "ladies and gentlemen...I Donald J Trump am proud to tell you all about the new world wide CH event. due to the popularity of the video game Fortnite, great game, great game, we here at the Whitehouse are prou...

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Surprise Hanging

by Pantyqueen23 on Dec 3, 2017
Fetish

Before I met you I'd never heard of a wedgie fetish, the thought of it when you finally mentioned it, not only made me curious, but also very nervous. I didn't know what you mean by that, as far as I knew wedgies were for embarrassment or to hurt someone, something bullies did to people to make them feel small. Which now makes sense to me, during sex you lov...

The College Hottie: INTERACTIVE

by System32 on Dec 19, 2010
Erotic Couplings

Consider the following adventure more as an interactive game rather than a story. In order for this to work, you will need to visit the following URL: http://www.wizards.com/dnd/dice/dice.htm When instructed, you will be required to roll 1 x D100 die to find out what happens to your character. All my stories will work in the same way. You are 19 year old...

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Death By Fucking Ch. 21

by thebullet on Sep 14, 2017
Romance

Chapter 21: Interactive Love Deirdre’s Story Our little girl has changed our lives. Something – hypnotism, magic, psychic brain surgery – has moved our relationship to a place we never knew existed. It’s what I suspected about our children all along. But I never expected it for my husband or my sister or myself. We long ago had recognized that the childr...

Virtual Sex with Jennifer Anniston

by lenux on Aug 12, 2003
Fan Fiction

Welcome John Doe to "virtual sex with Jennifer Anniston"< you will soon find out for yourself that this is one of the most detailed and descriptive interactive sex scenes you will ever have the privilege to witness. The first ten or so steps of the story are to set up your specific sex scene, out of the options that we provide you. The first opt...

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Doctor Wedgie

by Leon_Regis on Feb 2, 2019
Fetish

_A/N: Just a few things before diving in. While I would prefer at least the first few chapters of any given story-line to focus on wedgies, you're free to add to this story in any way you see fit. Everything from juvenile kinks to the most disturbing fetishes to regular intercourse will be accepted. Also, there will be a separate story-line for Old Who added...

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Public Pool Indecency

by palehorse666 on Sep 14, 2020
Erotic Couplings

This is a work of fiction. All characters are over the age of 18. Chapter 1: A Bit Too Snug It was the hottest day of the year. A record shattering 101°. I was sitting alone at home, literally baking in the heat. Our air conditioner was acting up, and a repair man was supposed to come after the weekend was over. It was Friday. My parents were away on a bus...

Ms. Jiggles Ch. 01

by Cappadonna on Sep 25, 2017
Mature

Her name was Glenda Johnson, but the neighborhood knew her as "Ms. Jiggles." She was one of those women that you fantasized about when you were young. All the boys had a crush on her. "Hey boys!" she would tease when we passed her yard. We always responded with respect, even though we wanted to fuck that pussy senseless. In her mid 40's, she was very attra...

Eliminated CYOA

by Deathcon on Apr 3, 2021
Fetish

It was a seemingly normal day in my life, when I heard a banging on my door. Not expecting any visitors, I go to look through the peephole at who it could be. But instead, I simply open the door! Gasping at my bodies incorrect action, a tall woman in robes brushes past my stock still form, into my house and beyond. Picking my jaw up off the floor, I slam the...

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