Sissy Wedgie Stories

7,074 results
Orientation
Length
Source
Infinite Scroll

Flashing at the Hospital

by Julie_S on Sep 18, 2017
Exhibitionist & Voyeur

I'm definitely not your typical exhibitionist. I don't enjoy openly flaunting myself or flashing just any passerby. I prefer what I call "discreet," or "accidental" exhibitionism. I really enjoy giving an unsuspecting male an "accidental" peek down my blouse, especially when I'm braless. I'll pretend to be unaware as I give a show, as long as the guy behave...

Head Fantasies Ch. 01

by boogieman10469 on Oct 13, 2017
Mature

For as long as I can remember, I've fantasized about the women I've found attractive. The following is a series of some of those fantasies (at least the ones that I can remember) about teachers, co-workers, classmates, women and girls from my neighborhood, etc. Although I'll accurately describe people, places, situations, and circumstances, I will (of course...

Enjoy the Silence

by Ironnick on Oct 14, 2017
Sci-Fi & Fantasy

Jeremy strolled into the busy coffee shop. He looked around at the customers and smiled smugly. It was a target rich environment. He went to the counter and ordered a large coffee with a shot of espresso. After receiving his drink, he concentrated then everything went silent. Jeremy had a special gift. He could stop time. Time was not really stopped, more...

The Ultimate Smother

by hithere222 on Sep 12, 2017
Fetish

Samuel gracefully rolled over in his bed, flashing his eyes open to take in his surroundings. Closing them again, he quickly yanked them open, gasping at the sight. His bed was enormous, his pillow giant enough to engulf him, and his clothes had not shrunken to his size, leaving him wrapped in his shirt. He struggled and fought his way out, and surfaced, try...

ENF-Geschichten.

by PaolaENF on Nov 26, 2019
Exhibitionist & Voyeur

Hier ein paar Geschichten zu Paola. Im Folgenden schreibe ich aus der "Ich" Perspektive auch wenn die Geschichten nicht wirklich passiert sind. VG bedeutet, dass es eine (kurze!) Vorgeschichte gibt, bevor das eigentliche Thema beginnt. Erstmal Allgemeines: Mein Name ist Paola. Ich bin 19 Jahre alt und wohne in einem kleinen Dorf direkt am Waldrand....

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Jeanie with the Light Brown Hair

by acgolf on Sep 17, 2017
Loving Wives

story I am about to post was written as a contest entry. The rules of the contest were to use the inspiration of the picture of a kneeling woman clothed only in shear thy high stockings and a white feather boa draped over her shoulders. There was a caption under the picture, "you want me to do what? with this boa?" that had to be used somewhere in the story....

Touhou Mind Control

by plorbus on Nov 22, 2020
Fan Fiction

This story is fiction! All characters are over the age of 18. Gensokyo is a land of possibilities and opportunities, even for a lowly mundane human such as yourself. At the very least, strange things can happen and fortunes can change. You are down on your luck, at your lowest, but things are really about to turn around. You find yourself in the local pawn s...

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Gay Fem Boy Finds His Man

by Clintdear on Sep 14, 2017
Transsexuals & Crossdressers

Chapter One It was lunch time and I was leaving a service call for the day. I was about to lift some test equipment into my car and I noticed one of the inside techs was heading my way. I assumed he was heading to his car, so I ignored him and got back to loading my gear. "May I help you with some of your things?" he said kindly. I glanced up at him. My...

Young Guy Goes To College Ch. 05

by pantysubsissy on Sep 26, 2017
Transsexuals & Crossdressers

Sorry that this took so long to post. I will try to get the next chapter out quicker if there is positive response. * The sound of my sister Robin and her incredibly hot roommate Kelly coming down the stairs to my hopefully new girlfriend, Julie's room had me scared to death. It's not that either one of them scared me but it was the predicament that I was...

Jessica's Change Management Ch. 27

by Cathartico on Oct 19, 2020
Exhibitionist & Voyeur

-- Saturday -- This was it! The grand finale was hitting the home stretch! Time for a status update. It was make-or-break time, 'cause I was down a buncha scores. It was all-or-nothing, 'cause I had totally gotten outmaneuvered by Ortega. Despite everything that had happened, the task was still the same. I had to broker new contacts for LGZ. The goal was...