Wedgie Punishment Stories

31,807 results
Orientation
Length
Source
Infinite Scroll

Wardrobe Malfunction- Mikheala

by CopyCat13 on Aug 18, 2017
Exhibitionist & Voyeur

Mikheala shifts uncomfortably from foot to foot trying to relieve the wedgie that is slowly working its way further into her butt. It would probably be easier for her to manage if she wasn't playing Ping-Pong in front of an audience. After all, Mikheala has quite a bit of experience dealing with uncooperative panties and by now she was pretty good at subtly...

Rosa Diaz Humiliation

by Cosmicpinkbeautie on Mar 29, 2021
Fan Fiction

Since this interactive is female-only, there are a few characters changes I'm making to allow for that. Also, this interactive will be very unrealistic, obviously. The Captain: Amy is acting as the precinct's captain due to the fact that the last captain (Captain Nikki Martin) requested a precinct change after she was publicly humiliated by detective Diaz. G...

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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...

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...

Under The Table

by Nat_Needs_Humiliation on Apr 15, 2020
Fetish

My friends and I are always making stupid bets with one another, or giving each other juvenile, puerile dares. The stakes vary wildly, from a simple thing like buying someone's dinner to something far less platonic. One forfeit that always sticks in my mind was the time we made Amelia put most of her meal into her knickers to eat later. I remember watching...

Sweat

by MrBlack86 on Sep 3, 2017
Fetish

God, it was hot, unbearably hot. Sweat beaded up against Lydia's skin but offered no relief from the heat. She tried to cry out but the gag in her mouth held her jaws open, her poor lips and tongue dried and cracking from the relentless heat. The heat that was only made worse by the rubber suit covering her head to toe. It held her tightly, seeming to shrink...

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...

I'm Being Blackmailed Ch. 06

by VanessaEvans on Jan 23, 2018
Exhibitionist & Voyeur

Author's Notes: - Before you read this part I strongly suggest that you read the earlier parts before reading this. It will give you the background that will make this part a lot more enjoyable. V ***** Tony thought that it would be a good idea for me to wear that collar with the rectangles skirt at work the next day. I'm sure that you can imagine the co...