Sissy Wedgie Stories

7,074 results
Orientation
Length
Source
Infinite Scroll

Wedgie on an Island

by wedgiefrmluckyfetish on Sep 16, 2017
Fetish

They had been on the island for a few days. Their boat, pieces of which had been washing up on shore. Neither of them were sure what had happened for all they knew their ship had crashed, sunk, and maybe even imploded. There was a lot of running, alarm bells; they had explained safety procedures and what to do if there was ever an emergency but when the cris...

Marina

by clthongclthong on Dec 10, 2018
Fetish

Marina sits quietly at her desk and types at her computer as she spends her Saturday at work. On this particular day she has gone in to catch up on some things and is the only one in the office, along with two other women, Jodie and Christie. All three women are in their late 20's and are working on the same project which has been quite a stressful part of t...

Sarah's Bully

by humiliationstation on Feb 1, 2020
Exhibitionist & Voyeur

Sarah is sitting at her desk in her dorm when her roommate comes in. She recognizes her roommates look, feeling a bit of dread in her stomach.What's next? Bedwetter Punishment Wedgie! Public Humiliation What's next? Bedwetter Punishment Wedgie! Public Humiliation...

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To the Manor Bound Ch. 04

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This probably won't make too much sense unless you've read the other chapters first. Like the other chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless, do comment and email me to let me know what you think, or just to say hello! ***** Chapter 4 - Five Weeks After Transformation Peter held the d...

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...

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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PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

Renee's Training

by UniversalReader on Sep 26, 2017
Transsexuals & Crossdressers

AU: The age of the characters in this story are not listed so that you can make the age fit you're desired age group. Assume by default that all characters are over 18. Nathan was an average teenage boy. He was slightly shorter compared to most of his friends at school; but other than that he was average height. He was thin, he wasn't very muscular but h...

Creating Ginger Ch. 03

by Ms_Allison on Jun 1, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into, cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consiste...