Sissy Wedgies Stories

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Orientation
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Getting caught

by Dat_boy on Apr 22, 2025

Your a college student who finally has the day alone with your step sister out of the house and your mom at work. Youd get up early and get dressed into your sissy outfit complete with a pink chastity cage and a metal buttplug as you set up a chair in your closet for a hanging wedgie. You set the key to your cage on the dresser where you could see it, grab a...

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You and Juri Han

by wedgiefrmluckyfetish on Nov 27, 2017
Fetish

You wake up wishing you could fall back to sleep. For a wedgie fetishist, so much of life is dreams. Fantasies of every variety can not only come to life in the land of dreams, but they can stay that way. Animated by your desires you can spend an indiscernible amount of time among a horde of people permeated by lust for wedgies. Surrounded by the barely clot...

Wedgie Fetish, an Introduction

by wrbsuperman on Sep 14, 2017
Fetish

~~~~~ Hi! I don't know about you, but I have a serious wedgie fetish. It's my hope to continue to write on this theme and share some fun (fictional) sensual stories that will really get your juices flowing. First though, I wanted to give a little background on the wedgie fetish. Read on, hope you learn, then get ready for the REAL sexy stuff. Feel free to PM...

Being My Roommate's Sissy Pt. 02

by SubTessa on Sep 19, 2017
Transsexuals & Crossdressers

Waking up this morning was just a mix of feelings - shame, pleasure, defeat, embarrassment. Tanner's display of 'power' over me was three days ago, and in that time - according to his brags and occasional light-hearted messages he likes to show me - he has convinced Kara to come over to 'hangout' tonight. My mind was so confused, I told myself I would stand...

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...

Bully of a Boss

by Vacantuser on Apr 22, 2025

Just another day at your awful, terrible job at a company owned by Val, the worst woman you had ever met. You had taken the job when it first opened a few years ago to support the only company around with a young woman as CEO. As a nineteen year old woman, you had wanted to support soneone close to your age and thought that since sge was so young she'd be th...

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AJ’s Wedgies and Other Humiliations

by BrightLord96 on Apr 22, 2025

AJ Brody was now a freshman in college and considered to be an adult. Now he was free to do whatever he wanted without his family and other adult figures getting in the way. The idea of him entering a completely new setting fueled his perverted imagination like never before. He had several fetishes to act on including wedgies, ENM, small penis humiliation, g...

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Wedgie on an Island

by wedgiefrmluckyfetish on Sep 16, 2017
Fetish

They had been on the island for a few days. Their boat, pieces of which had been washing up on shore. Neither of them were sure what had happened for all they knew their ship had crashed, sunk, and maybe even imploded. There was a lot of running, alarm bells; they had explained safety procedures and what to do if there was ever an emergency but when the cris...

Wedgie in the Apartment

by wrbsuperman on Aug 18, 2017
Fetish

There was nothing like a crisp autumn day to clear out the cobwebs. Quite literally in fact, since the rays of sunshine cutting through the window highlighted any and all lint or spider webs in corners missed in last week's once-over. One could almost let them pass, but the beautiful foliage created such contrast to any dusty disorder it was impossible to le...