Sissy Wedgie Stories

7,074 results
Orientation
Length
Source
Infinite Scroll

Being My Roommate's Sissy Pt. 02

by SubTessa on Sep 19, 2017
Transsexuals & Crossdressers

Waking up this morning was just a mix of feelings - shame, pleasure, defeat, embarrassment. Tanner's display of 'power' over me was three days ago, and in that time - according to his brags and occasional light-hearted messages he likes to show me - he has convinced Kara to come over to 'hangout' tonight. My mind was so confused, I told myself I would stand...

Wedgie Fetish, an Introduction

by wrbsuperman on Sep 14, 2017
Fetish

~~~~~ Hi! I don't know about you, but I have a serious wedgie fetish. It's my hope to continue to write on this theme and share some fun (fictional) sensual stories that will really get your juices flowing. First though, I wanted to give a little background on the wedgie fetish. Read on, hope you learn, then get ready for the REAL sexy stuff. Feel free to PM...

You and Juri Han

by wedgiefrmluckyfetish on Nov 27, 2017
Fetish

You wake up wishing you could fall back to sleep. For a wedgie fetishist, so much of life is dreams. Fantasies of every variety can not only come to life in the land of dreams, but they can stay that way. Animated by your desires you can spend an indiscernible amount of time among a horde of people permeated by lust for wedgies. Surrounded by the barely clot...

Discovering Amber Ch. 07

by Ms_Allison on Mar 25, 2019
Transgender & Crossdressers

Mistress notes: The morning after is always fun, people tend to get caught up in the moment, sissies included, and amber was no exception. The fact Jenn and I were there to remind her of all of it just made it better! The fact amber seemed to really enjoy humiliation only added to the whole experience. Ms. Allison ~~~~~~~~~~~~~~~~~~~~~~~~~~ The following...

Dancer Turns me out Pt. 03

by pantiepervMI on Sep 28, 2020
Transgender & Crossdressers

After a restless night, I finally dragged my tired and sore body out of bed. My asshole was on fire and I could feel the pain with every step I took. I thought about skipping the insurance sessions to catch-up on my sleep, but after tonight I did have to return to my real life, my job, and my asshole boss. I downed several cups of coffee and got dressed in...

Wedgie-Self

by wrbsuperman on Aug 18, 2017
Fetish

~~~This story got rejected 4 times, because the paragraphs were too long and because they thought I was advertising for sites I'd mentioned. I prefer real-world stories that other members of the wedgie fetish community can relate to, and apparently I can't do that. The story isn't the same since all these "revisions" but I hope you can find some enjoyment no...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

Mike the Gang Bang Bitch

by sissyneko on Mar 17, 2020
Transgender & Crossdressers

Standing in the bathroom wearing just his little pink bikini panties and stockings, Mikes gaze was transfixed. Not on the panties, the usual draw of his lust, or even his white thigh high stockings with their little pink bows at the top. None of that drew his attention, it was the bathroom itself, it was run down, dingy and in the worse part of town. But non...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...

Wedgie in the Apartment

by wrbsuperman on Aug 18, 2017
Fetish

There was nothing like a crisp autumn day to clear out the cobwebs. Quite literally in fact, since the rays of sunshine cutting through the window highlighted any and all lint or spider webs in corners missed in last week's once-over. One could almost let them pass, but the beautiful foliage created such contrast to any dusty disorder it was impossible to le...