Wedgie Boy Stories

105,330 results
Orientation
Length
Source
Infinite Scroll

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...

The App

by QuirkyPriya918 on Jun 4, 2020
Fantasy

The morning began just as any other did for Cindy. She woke up, brushed her long brunette hair out of her face, and checked her phone groggily. Although there was a notification Cindy had never seen before; the icon that of a sparkling wand, the notification itself reading: "Setup complete! YourWish app is fully operational!" "Probably Brielle...

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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...

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...

Sailor Moon Ch. 02

by embarrassednakedmale on Feb 3, 2020
Transgender & Crossdressers

The alarm had been buzzing for a solid two minutes when a bleary-eyed Scott finally rolled over and slammed his hand down on the offending device. The harsh noise ceased immediately, and Scott groaned as he rolled back again and cautiously stared at the ceiling. It was still dark in his bedroom, although a single beam of light cut through a tiny gap in his...

House-Sitting Panty Lover Pt. 01

by sissydn on Sep 15, 2017
Transsexuals & Crossdressers

Finally Friday! The day I have been waiting for, for so long. A month ago my sweet and hot neighbours, Megan and Sophie, knocked on my door and asked if I would watch their house and feed their dog when they left for an extended weekend. I immediately replied yes and suggested I could do some house chores since I had no plans that weekend and were low on m...

Strip Fight

by Octave on Jan 12, 2021
BDSM

Julia und Sabrina waren gute Freundinnen die beide zusammen studierten. Sie verabredeten sich regelmäßig zum lernen in Sabrina's WG. Sabrina wohnte mit einem Studierenden aus deren Universität zusammen. Sein Name war Joshua. Ein sehr schüchterner Typ. Er war meistens in der WG am lernen und blieb in seinem Zimmer. Julia hatte ein Auge auf ihn geworfen und wa...

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Wardrobe Malfunction- Mikheala

by CopyCat13 on Aug 18, 2017
Exhibitionist & Voyeur

Mikheala shifts uncomfortably from foot to foot trying to relieve the wedgie that is slowly working its way further into her butt. It would probably be easier for her to manage if she wasn't playing Ping-Pong in front of an audience. After all, Mikheala has quite a bit of experience dealing with uncooperative panties and by now she was pretty good at subtly...

Rosa Diaz Humiliation

by Cosmicpinkbeautie on Mar 29, 2021
Fan Fiction

Since this interactive is female-only, there are a few characters changes I'm making to allow for that. Also, this interactive will be very unrealistic, obviously. The Captain: Amy is acting as the precinct's captain due to the fact that the last captain (Captain Nikki Martin) requested a precinct change after she was publicly humiliated by detective Diaz. G...

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Sensual Weekend Getaway Ch. 04

by Sexy_Boy_90 on Sep 28, 2020
Exhibitionist & Voyeur

Hannah and Brandi walked me back to their hotel room and made sure I was visible for anyone to see in only my red thong. As soon as I entered the room, Hannah glared at me. "I hope you're not ignoring the dress code!" she exclaimed. "No, ma'am," I replied and slipped out of my thong, once again completely naked. Brandi grabbed it from the floor. Hannah sat...