Sissy Wedgie Stories

7,074 results
Orientation
Length
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Infinite Scroll

The Popular Girl

by minus12 on Apr 13, 2017
Amateur

As beautiful and "hot" Peyton was she had never been modest about any of her blessings and always carried a haughty attitude. She had come from rich parents and had never had to work for anything in her life. She was already committed to play division 1 soccer and was the captain of the cheerleading and varsity soccer team. plus was dating the star...

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Office Obsession - His POV

by POVscribe on Mar 12, 2019
Anal

Aargh! My tablet just blew up with calendar reminders. I love my work, but lately it's been overwhelming. I have been a corporate attorney for nearly 25 years and also sit on several non-profit boards of directors. While I get to do pretty much what I went to school for and trained to do, the lifestyle doesn't leave much—or any—room for a personal life. I've...

A Sissy's New Daddy Ch. 05

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

When the loud speaker blared that Billie had a visitor he was tied to a stool. Billie had become a plaything for a few of the more business savvy residents of Blofield State Penitentiary. When prisons became smoke free buildings cigarettes were no longer the illicit currency of choice. Stamps had come into fashion because they couldn't keep you from mailing...

Banging the boss

by dannythefunny on Dec 19, 2017
Fan Fiction

You sit on a balcony crying and eating ice cream,you are upset. Why? Because you don't feel appreciated for what you do for Star City. All because of Cat Gaunt,you want revenge,time for you to take action."No more crying" you realize,it's time for revenge! So you go to Cat's office through elevator you don't want to girl give her a heart attack. &q...

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Sarah humiliated

by 9844 on Jul 29, 2020
Exhibitionist & Voyeur

You wake up, exited for the big day, but also worried about what you bully has in store for you. *Side note: This story is public, please feel free to add any chapters or storylines that you want.What's next? Last day of school! (Female bully) Sleep away camp (group of bullies) What's next? Last day of school! (Female bully) Sleep away camp (group of bul...

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Morty’s dream dimension

by Soappaper on Mar 22, 2021
BDSM

ALL CHARACTERS PORTRAYED ARE ABOVE 18 Morty feeling extra horny one night decides to go on the search for a dream dimension. After a couple hours he’s able to find 3 dimensions as his favorites. One is a dimension where he can get payback on summer for all the things she’s done to him. Another is a “regular” world with women who are into extreme punishments....

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Goth Girl Rivalry

by Myds6 on May 1, 2019
Fantasy

(Author's note: Feel free to add chapters. I will publish if they follow the guidelines.) It was a big night at the club. A famous band had just played in town and Blackmail was holding the afterparty. Everyone who was anyone was there, and that meant feathers would be ruffled. Not only did everyone's friends show up, but everyone's enemies as well. The bar...

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Embarrassing/ Humiliating Naked Stories

by Jdoe201207 on Apr 13, 2020
Exhibitionist & Voyeur

This is where others and I can share embarrassing/ humiliating naked stories we’ve either experience or been told about.What's next? To much freedom for a 18 year old girl The hazing of a 18 year old girl The Neigbhorhood Flirt Online Classes With Webcam Girl gets lonely over winter break Revenge Gone Overboard Girl gets locked out on spring break Revenge...

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Sister Catfight

by JingleheimerSchmidt on Oct 13, 2014
BDSM

It's a hot July day. There are two sisters hanging out in their house, Jena and Riley. Jena is 18, 5' 1", Chestnut hair, fairly skinny with B-Cup breasts and a small but firm ass. She's wearing a pair of pink and white striped panties and a black camisole. Her Sister Riley is 19, 5' 7", Strawberry Blonde, she has a very well toned body with D-Cup b...

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Faced

by Ailsie on Nov 4, 2019
Fetish

This next match was one that I actually helped set up. It was a friendly bout between myself and another one of the other women in the circuit. She was having a bit of a rough patch, so I offered, well, an easier match up. Myself. At this point, I'd actually won a few matches, so I wasn't entirely on a losing streak. So it was arranged. For this one I actu...