Sissy Wedgie Stories

7,074 results
Orientation
Length
Source
Infinite Scroll

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...

The Boss vs. The Man Ep. 01

by wrestlingisreallycool on Jan 15, 2019
Celebrities & Fan Fiction

Hello there, I hope you enjoy this, this is the first series in what I hope will be a collection of wrestling-focused erotic literature. I have seven different series in mind to start which hopefully will all be unique and interesting. Also, admittedly, this is my first time writing a full-length piece of fanfiction/erotica, so I hope it's not too bad. Anywa...

Manacite

by TheCanadian on Aug 26, 2018
Miscellaneous

As you return home from work one evening, you find a large shipping package waiting for you in front of your apartment. Bringing the package inside and opening it, you find a letter and hundreds of vials containing a mysterious red powder. You decide to inspect the letter. -- WARNING: PROPRIETARY INFORMATION. DISCLOSURE OF THE CONTENTS OF THIS PACKAGE AND TH...

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House-Sitting Panty Lover Pt. 03

by sissydn on Sep 13, 2017
Transsexuals & Crossdressers

... As I stood there in the parking lot I felt like all eyes were on me. But why wouldn't they be? I had substantially bigger breasts than the average busty girl and were wearing a skirt shorter than that of the high school slut. As I had been standing still for a moment Megan got impatient. "Come on pretty. Don't let me get over there and grab your thong...

The Long Resignation Pt. 01

by AndersonCoombs on Oct 22, 2019
Exhibitionist & Voyeur

Chapter 1 – The Surface The dream had always repeated itself with a surprising specificity. Nicole was at the bottom of a pool – the kind with those miniature tiles, mostly white with the occasional blue tile in the mix for the sake of contrast. She was never quite sitting on the bottom, just drifting, fluid like the water all around her, inches from the ti...

Just a Taste, Nothing More

by StrayingZombie on Sep 17, 2017
BDSM

It was fate that they happened to meet at work. He had spotted her first, unconsciously rubbing her pussy on her chair, trying to cum. He waited for the perfect day, the day she left last. She was surprised when he confronted her in the hallway, as she should be. He was one of the best looking men there, and she...she could be described as a plain girl. But...

Trying Something New

by aliiceinwonderland on Aug 18, 2017
Fetish

Well, my name is Alice. My boyfriend's name is Ben. And Ben had a secret fetish he decided to let me in on recently... We're living on the same residence hall floor and have basically just been staying in the same room for a bit now... yeah, with his roommate in the room as well. Dorms suck. But knowing he might come home at any time is interesting on its ow...

Curse of the Living Clothes

by calx86 on Jan 8, 2020
Fantasy

There are several stories out there involving living clothes but I want to leave this open to allow many collective authors to be as creative as possible. For example, you can write a story about clothes simply coming to life and stripping their wearer, leaving them nude and embarrassed or maybe the living clothes forces someone to wear them and turns them i...

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Enm at Work

by Onlysorta on Dec 6, 2017
Exhibitionist & Voyeur

Call me, Ahab, this is the tale of my embarrassing day at work, a humiliating story in which the lady I've been pining after for quite some time now, a sharp, attractive businesswoman with a flirty side, saw me completely naked. I was never absolutely certain where it was that she worked, but, my crush Ming Zhao's routine involved passing by my workplace, an...

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A Sissy's New Daddy Ch. 06

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

A loud crack of thunder broke the silence and Billie smiled in his bunk. Lights had been out for almost an hour and he couldn't sleep. The prison had gotten a new influx of prisoners. The first night was always the hardest and it was hard on Billie too, he could never sleep listening to the crying. Plus Billie had gotten a new cellmate in the process, a cell...