Gay Wedgie Story Stories

146,167 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Caught in Ex-GF's Underwear Pt. 01

by HiddenThoughtz on Oct 6, 2020
Transgender & Crossdressers

Hello everyone...welcome to my crazy kinky life lol. This origin story takes place right before my 21st birthday. This all started when I finished my junior year at college. School had ended and I was taking summer classes so my workload senior year would be easier and I could enjoy my last semester. My two roommates had gone back home to work for the summe...

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...

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...

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...

Life of Leigh Ch. 01

by Lee_Bee on Sep 1, 2017
Erotic Couplings

Authors Note: So this is a true story but I do have to change some things so that it's not blatantly obvious who I am and where I'm from. Contrary to popular thought Canada is actually a pretty big place and that's as specific as I'm getting. I would also like to forewarn people that where this is my life, a real life, not everything works out the way you wa...

Wedgie- at the Party

by wrbsuperman on Oct 12, 2017
Fetish

~~~Just a quick story before my class starts, sorry for any typos/awkward phrasing~~~~ So there I was, a few beers in and feeling sexy. Kinky too, if you must know. I'd had a bit of a dry spell recently and I gotta tell you there's not much like the heady high of strong hops to get me light headed and frisky. Now don't get me wrong, the warm fuzzies of wine...

Sissy Secrets

by DawnCutie on Feb 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Every Sissy is just a cross-dresser until someone stronger takes advantage of them. Either they give themselves to a Dom or a Dom takes control of them. This is my story of how my dom found me and turned my life into what it is now. If you're not a sissy let me tell you how we...

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...

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...

A Good Day for a Wedgie

by SerenOsmond1 on Sep 25, 2018
Fetish

Hello Everyone! So this is my first attempt at writing erotica. I am NOT an English/Writing guy. However, I truly do enjoy the wedgie/transparent clothing/humiliation/spanking fetishes and wished I saw more of that on Literotica! So with my girlfriend's blessing, I have started and completed the first part of my first story series. I would appreciate any fe...