Sissy Wedgie Stories

7,074 results
Orientation
Length
Source
Infinite Scroll

Bethan's Wedgie

by wrbsuperman on Aug 17, 2017
Fetish

When it starts getting cold outside you either suffer, put on more clothes, or go inside. Now, depending on the house, going inside might not provide the relief you hoped for. Let me tell you something; freezing houses equal butt cheeks covered with goosebumps. I don't care if you're just climbing out of bed (because of course you sleep nude) or if you're si...

A Sissy's New Daddy Ch. 08

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

As I finish this chapter and prepare to start on the final ninth chapter I want to take a moment to thank everyone that has sent me letters of support. You have really helped keep me going in writing this and I hope you have enjoyed the ride as much as I have. ***** Chapter 8 - The Prison Billie was being pulled through gates faster than his feet could ke...

A Sissy's New Daddy Ch. 02

by sissyneko on Oct 8, 2019
Transgender & Crossdressers

I hope you enjoy this second installment of 'A Sissy's New Daddy'. I worked hard on it and hope that it brings all of you the same pleasure reading it that it has brought me writing it. There are some extreme moments in this chapter but also some very tender ones. There was a line in the first piece that gets expanded on at the end. I hope you enjoy what I h...

Young Sissy Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"Pleez...por favor...pretty pleez...fuck me..." I looked up at her with tears in my eyes, pleading to be penetrated. I didn't have to beg...nothing in the world would have stopped Lola from spraying her seed deep inside my ass...but I know it's what they wanted to hear. I regretted it immediately...well almost immediately...nothing can take away from the pur...

Son of a Witch Pt. 05

by Jwood23 on Jun 15, 2020
Sci-Fi & Fantasy

***if you like my stories please consider leaving a comment or rating. Any feedback is always appreciated so i can improve my writing. Thanks all :-)*** All characters depicted here are 18+ Jay was in shock. Even without the spells holding his feet in place and hands over head, he didn't feel he could move if he wanted too. His entire world had come crashi...

Review: The Dukes of Hazzard

by Rev_Lovejoy on Sep 13, 2017
Reviews & Essays

I just saw the "The Dukes of Hazzard" movie and it was so thought provoking that I felt compelled to offer my review. It's a story about a family of inbred southerners that takes the law into its own hands and creates chaos . . . No, wait a minute, that's "Fahrenheit 9/11." "The Dukes" is more about serious environmental concerns and the power of the people...

Caught with a Wedgie Ch. 02

by marriedhubbi on Oct 8, 2019
Transgender & Crossdressers

While my life looked the same on the outside, I noticed that my masturbation habits had changed. Ever since my 28 year-old neighbor, Alejandro, had caught me masturbating and had coerced me into sucking his cock, I began to notice my wife's sexy underwear and high heels in a different way. I was drawn to my wife's panties. I didn't just want to see and fee...

A Double Thrashing

by Hammer356 on Dec 9, 2019
BDSM

Note. This is a POV story and a work of fiction. *** Hello, my name is Saba and I work as a hall monitor here at Fencer High School in Glendale Arizona. I like the climate of this state because it reminds me of my native homeland of Lebanon. And yes, I am Muslim. One of the three on the school staff, but that doesn't bother me much. The bell rung which s...

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...

Offering up The Wife

by StoneKidman on Sep 14, 2017
Fetish

Karen grunted out as her opponent hammered a forearm into her back, sending her to the mat. She grimaced when she felt her blonde hair being pulled as the large black woman she was wrestling helped Karen to her feet only to scoop the petite woman up and body slam her to the canvas with a deafening boom. Jerry sat ringside with a massive erection in his pant...