Messy Wedgie Stories

18,859 results
Orientation
Length
Source
Infinite Scroll

The App

by QuirkyPriya918 on Jun 4, 2020
Fantasy

The morning began just as any other did for Cindy. She woke up, brushed her long brunette hair out of her face, and checked her phone groggily. Although there was a notification Cindy had never seen before; the icon that of a sparkling wand, the notification itself reading: "Setup complete! YourWish app is fully operational!" "Probably Brielle...

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House-Sitting Panty Lover Pt. 01

by sissydn on Sep 15, 2017
Transsexuals & Crossdressers

Finally Friday! The day I have been waiting for, for so long. A month ago my sweet and hot neighbours, Megan and Sophie, knocked on my door and asked if I would watch their house and feed their dog when they left for an extended weekend. I immediately replied yes and suggested I could do some house chores since I had no plans that weekend and were low on m...

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...

Strip Fight

by Octave on Jan 12, 2021
BDSM

Julia und Sabrina waren gute Freundinnen die beide zusammen studierten. Sie verabredeten sich regelmäßig zum lernen in Sabrina's WG. Sabrina wohnte mit einem Studierenden aus deren Universität zusammen. Sein Name war Joshua. Ein sehr schüchterner Typ. Er war meistens in der WG am lernen und blieb in seinem Zimmer. Julia hatte ein Auge auf ihn geworfen und wa...

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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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Nora’s Naked Nightmares

by Lysanderoth on Apr 10, 2020
Exhibitionist & Voyeur

Eleanora Nancy Fackler, or Nora as she is better known, is your typical high school wallflower. She has long brown hair, blue eyes, and dresses modestly. She almost never socializes, largely ignored by the general populous, and only ever seems to interact with a few close friends. That and her bullies of course, not that she enjoys it. Often teased for being...

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A Tale of Two Sisters Ch. 01

by eddievalquez on Sep 26, 2017
Exhibitionist & Voyeur

Before Kim and I had been dating for almost two years, and if things kept going the way they were, we wouldn't see year three. Kim was working full time at a coffee shop and I was coasting on student loans. She was stressed about drama at work, but I was so busy worrying about whether or not English Literature was really my passion anymore that I didn't off...

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...