Wedgie Dare Stories

42,476 results
Orientation
Length
Source
Infinite Scroll

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...

Surprise Hanging

by Pantyqueen23 on Dec 3, 2017
Fetish

Before I met you I'd never heard of a wedgie fetish, the thought of it when you finally mentioned it, not only made me curious, but also very nervous. I didn't know what you mean by that, as far as I knew wedgies were for embarrassment or to hurt someone, something bullies did to people to make them feel small. Which now makes sense to me, during sex you lov...

Those Jeans Don't Fit

by whostheboss on Sep 12, 2017
Anal

Molly lies on the bed, wiggling her way into her new pair of jeans. "Almost there," she grunts. She's got this habit of buying clothes online that don't quite fit her, but she never wants to declare defeat. She's squeezed the button shut somehow and jumps up from the bed. She's got a bowlegged stance and looks pretty uncomfortable. "Not bad, right?" she say...

Doctor Wedgie

by Leon_Regis on Feb 2, 2019
Fetish

_A/N: Just a few things before diving in. While I would prefer at least the first few chapters of any given story-line to focus on wedgies, you're free to add to this story in any way you see fit. Everything from juvenile kinks to the most disturbing fetishes to regular intercourse will be accepted. Also, there will be a separate story-line for Old Who added...

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Public Pool Indecency

by palehorse666 on Sep 14, 2020
Erotic Couplings

This is a work of fiction. All characters are over the age of 18. Chapter 1: A Bit Too Snug It was the hottest day of the year. A record shattering 101°. I was sitting alone at home, literally baking in the heat. Our air conditioner was acting up, and a repair man was supposed to come after the weekend was over. It was Friday. My parents were away on a bus...

Ms. Jiggles Ch. 01

by Cappadonna on Sep 25, 2017
Mature

Her name was Glenda Johnson, but the neighborhood knew her as "Ms. Jiggles." She was one of those women that you fantasized about when you were young. All the boys had a crush on her. "Hey boys!" she would tease when we passed her yard. We always responded with respect, even though we wanted to fuck that pussy senseless. In her mid 40's, she was very attra...

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...

Under The Table

by Nat_Needs_Humiliation on Apr 15, 2020
Fetish

My friends and I are always making stupid bets with one another, or giving each other juvenile, puerile dares. The stakes vary wildly, from a simple thing like buying someone's dinner to something far less platonic. One forfeit that always sticks in my mind was the time we made Amelia put most of her meal into her knickers to eat later. I remember watching...

Home Movies with Patsy

by LitEroCat on Sep 1, 2017
Exhibitionist & Voyeur

This story was hijacked, or maybe even inspired without my knowledge, by my WONDERFUL, GENEROUS, BEAUTIFUL AND DISCRETE(?) Muse, Lois. Right, my goddess? ARE YOU LISTENING? "I'm ALWAYS listening. Flattery will get you EVERYwhere." "I'm so whipped! And I don't get any tail from you" "Don't you wish? Get on with the story I gave you." "Yes, my idol." Grrrr...

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...