Hanging Wedgie Stories

94,881 results
Orientation
Length
Source
Infinite Scroll

Mom Makes My Bully into My Boss

by I_Love_MILF on Jul 8, 2019
Mature

My mom, Charlotte, was the owner of The Fan, a popular sports bar where I earned extra money for my college classes working as a busboy. She decided to promote me to a managerial position, and as such, we put out an ad for a new busboy to fill my old position. My mother went through potential applicants, and to my horror, the last person interviewed was Todd...

Stephanie Wants to be Seen Pt. 01

by alittlecloser69 on Sep 26, 2017
Exhibitionist & Voyeur

She sat there quietly contemplating how she had gotten to this point. She knew what she was about to do was risky, but she couldn't help herself. She loved the thrill. The chills that she got deep down in her bones every time she got away with it were what gave her an indescribable high. She waited patiently in front of her high school for the beginning of t...

Adventures in Gaming

by CumBalloon123 on Feb 20, 2020
Fetish

The Players Anna: Shy, crush on Barry, 4’11’’ Dirty Blonde hair, long, 130 lbs. 30A-30-32 measurements blue eyes secret fetish size queen/excessive cum, straight Katy: Raging nympho 5’6’’, black hair, medium, 140 lbs. 32B-30-32 Green eyes secret fetish giantess, bisexual Chloe: Rich Popular, 6’0’’ long blonde hair, 155 lbs 34C-32-34 green eyes secret fetish...

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Her Panties and a Wet Spot

by daves40004 on Sep 18, 2017
Toys & Masturbation

Jennifer heard the office door open along with a male voice, "I can't imagine what was going through her mind...I mean, seriously, who exercises in a public gym wearing a thong leotard?" Jennifer's hands froze over her keyboard. She recognized Joe's voice. Another male voice responded, "Was she wearing tights or something underneath?" That voice belonged to...

Amazon Bully

by LoveAmazonBullies on Aug 19, 2018
Fantasy

You walk into a Amazon ruled school. The office doors are up to seven feet tall and the office has no one in it. You look confused and look around the office and see a average height chart. Looking at the top you see the tallest female is 7 foot and the looking down you see the shortest is 6 foot 5. You dont see the boys average until you look all the way do...

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B + P Sleepover

by allyouneedislove95 on Feb 26, 2019
Fantasy

*Ding-dong* The cry of the doorbell rang throughout Sarah's house. Her head immediately perked up and a smile began to spread across her face. She sprang up from her living room couch and ran to answer the door. She was a short but well-built girl with dirty-blonde hair, 38E tits, and a nice ass to compliment the rest of her attitude. Tonight she is dressed...

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Danganronpa ENF

by Unbacked0 on Mar 7, 2020
Fan Fiction

Hope's Peak Academy. For most people, coming here is the best thing that can ever happen to them. Graduating guarantees success for the rest of your life. Any student immediately becomes one of the next big celebrities known the world over that is talked about online across the world. Very few people ever get a chance to come to this school, those who do are...

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Mrs. Hanson Ch. 02

by velvet hammer on Sep 25, 2017
Mature

"Oh, hello Johnny!" Mrs. Hanson said cheerfully as she answered his knock on the door. Johnny's jaw dropped; at how stunningly beautiful Mrs. Hanson looked this morning! She wore a sort of collared halter-topped white dress - a VERY revealing halter-topped dress - that flared out to a full, wide skirt ending right below her knees. Mrs. Hanson's white dress...

She Sucks She Cock by the Sea Shore

by FredTR on May 21, 2019
Transgender & Crossdressers

It felt like it had been years since Liz had been able to take a day and just relax. Her first year at college had been a whirlwind of papers, tests and classes. And her job at the bookstore. Sure she'd gotten laid a few times (okay, maybe more than "a few" times), but that just seemed to stress her out more because she always felt guilty and worried her boy...

Make Me Believe

by northcountrylass on Sep 13, 2017
Anal

I was in the kitchen cleaning up when you got home from work. I heard you come through the front door, and I tried hard to stay focused on the task at hand and pretend as though I hadn't been waiting for you to come home all day. It was a blatant lie, of course, and my clothing fairly well advertised the fact. After all, who cleans kitchens in flirty, ruffly...