Wedgie Spanking Stories

23,051 results
Orientation
Length
Source
Infinite Scroll

Bondage Burglar Ch. 01

by TheFluffyX on Jan 21, 2020
BDSM

This is not a true story nor is it realistic, this is complete fantasy so do not re-enact nor take it too seriously. Chapter 1: An interesting target Michael looked to be a normal person from outside appearances, he had a seemingly ordinary if not spectacular job working as part of the IT admin team in an office working 9-4 Monday to Friday. Most people ju...

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...

Doubleheader

by wickedlorelei on Sep 13, 2017
BDSM

The Cubs were losing the game 9-4, and it was the bottom of the 7th. A rally looked unlikely. The players seemed to just be going through the motions today. Considering that it was the second game of a doubleheader against the Cardinals and the temperature was in the 90s in St. Louis, Anya couldn't really blame them, and it was nice to be watching the game...

Penny's Comeuppance

by jlorthia on Sep 16, 2017
Fetish

This is another story from my former username "newfavorite," I only added minor tweaks to this story, I corrected some grammar and spelling. There is not much sex in this one and it is shorter than my normal story. *** The job market wasn't doing so hot in Megan's hometown. She had gone to college upstate to become an HR professional, but after weeks of j...

Teresa Scalia: Riot in the Ring

by obo on Sep 13, 2017
Humor & Satire

Mark Anderson and Dominic Scalia were meeting in Dominic's office planning a major fundraiser for their Men's Club. The club was providing financial assistance and support to construct a new recreation facility for the youth of their city. The event, catering to the more affluent male population, was to be a night of boxing followed by an auction of donated...

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...

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...

The Goth Girl Ch. 02

by CopyCat13 on Sep 16, 2017
Fetish

The other day I decided to finally confront the Goth girl who assaulted me in the bathroom and made me do...things...to her about a month ago. Since then I'd been avoiding her like the plague but with the encouragement of some friends I'd met online while chatting about some of my kinky fantasies I'd decided to confront her. I didn't really want much from th...