Sissy Wedgie Stories

1,000 results
Orientation
Length
Category
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Infinite Scroll

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...

Ballet Erection

by pixiemuledonkey on Sep 14, 2020
Fetish

Author's Note: Long ago, I roleplayed a play-by-post erotic fantasy with a girl named Christine, who amazed me with her deviously humiliating responses. What follows is a reconstruction of the scenario we roleplayed, which has ever since remained a favorite erotic fantasy. Wherever you are now, Christine, i hope you're enjoying powerful orgasms! You gave thi...

How I went from Domme to Slut Ch. 05

by Ms_Allison on May 29, 2018
BDSM

Over the following few months from my first night waiting tables at the club things continued and amber and I fell into a comfortable rhythm with things. The first Friday of the month amber would wait tables during "men's night" and on the third Friday of the month I would wait them for the Ladies. When amber waited tables I was typically dressed in somethin...

American Mom Ch. 20

by Hardplay on Sep 25, 2017
Celebrities & Fan Fiction

Having left Afghanistan in the cloak of darkness, an unmarked CIA Lear jet approached company headquarters in Virginia early Monday morning. Arriving home a full week early following his successful mission, Stan Smith was literally shaking at the thought of seeing his wife Francine now that they had entered a breathtakingly exciting new phase of their rela...

Mistress Encounter

by WellBehavedMan on Sep 15, 2017
Fetish

Eva gets back to her hotel room from her business meeting, glad to be back, the meeting went ok, could've been better, they could all be better she reminds herself, as people don't give everything for nothing. As she flicks on the main lights she jumps as she see's you on her soft double bed, right where she left you before she went out, however she did not...

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...

Poor Little Zentai

by Guestnames on Apr 22, 2025

You have always kept your fetish closely guarded; you've given previous girlfriends subtle hints to try and get them to act accordingly, but have never disclosed the true nature of your fetish. You are addicted to tights. To pantyhose, leggings, bodysuits, catsuits, zentai, bodystockings….to any spandex or nylon garment that tightly hugs the legs and crotch....

Old Friend, New Slave

by livingforfun on Sep 12, 2017
BDSM

Home for the summer, well part of it anyway, and boy was it hot out. I'd forgot how humid it got at home compared to at school. Just over 80˚ and it was sweltering, too hot to do work without dripping in sweat. But the lawn at home grew so fast, unless it was mowed once a week it got entirely out of hand and the mower would jam on all the grass. I always mo...

A Domme at the Colfax Inn

by justincbenedict on Jun 19, 2018
BDSM

Nibs wearily tried to stay polite with the touron on the phone. Nibs, since childhood had referred to most of the tourists who came to the Colfax Inn as combinations of "tourists" and "morons", thus "tourons. "That's right sir...We are near Lake Colfax. My family has owned the Colfax Inn since the seventeen hundreds...No, that's the Buttermilk River. Yes,...

How I went from Domme to Slut Ch. 06

by Ms_Allison on Jun 26, 2018
BDSM

I would like to thank the darlin mymantoy999 for his editing and insight and in particular keeping my math and thought process straight while writing these! ***** As amber had suggested she and I settled into our new normal relatively quickly. Now on top of waitress duties every other week, house cleaning trips and the random frustration amber experienced...