Wedgie Dare Stories

42,476 results
Orientation
Length
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Infinite Scroll

Heidi's Diary: Day 01

by koala011860091 on Sep 26, 2017
Exhibitionist & Voyeur

Dear Diary, The most humiliating thing happened today. I can't believe what my assistant Justine did to me. It all started after lunch. I was sitting in my office, preparing some briefs for the McIntyre case, when Justine brought me a cup of coffee. I thought it was so nice of her, little did I know! She came around behind me for a few moments, and then s...

Girls Just Wanna Have Fun!!

by RickDeville2 on Jan 6, 2018
First Time

She fiddled furiously along the highest notes of her fiddle as the drums and saxophone kicked in behind her to support the tone. She angled her chin to brilliantly smile at the gathering crowd while striving to maintain a firm grip on her violin. An old lady with chickory coffee from the left, an eager young man staring at her legs and compressed breasts fro...

Caught Relaxing Pt. 01

by StephaniePlayland on Aug 6, 2019
Transgender & Crossdressers

This is going to be a short series of stories. This one really starts the journey out, they won't all be in exact order or have a proper linear flow to them. Just depends on what's has caught my interest that day, and needs to flow out of me. It's Friday night, no plans or anything to do a perfect night to dress up. Hangout have a drink and relax being Ste...

Just Across the Hall Pt. 04

by EROTICbearscribe on Aug 6, 2019
Transgender & Crossdressers

Chapter Five ACCEPTANCE The assortment of clothes in my pink suitcase reflected my taste and my curiosity about feminine attire but I didn't own a lot of things. Not as much as I would have liked, anyway, especially at this very moment. That is to say, I didn't own any 'sexy' lingerie. Or, what, in my mind would be considered sexy. It was just I never fel...

The Freshman

by playbabyf on Sep 13, 2017
Erotic Couplings

I was a dork during high school. Not in looks, or in personality really, but I studied a lot. That was my parents' expectation. So I got good grades. I didn't party. I had a few friends, and they studied a lot and got good grades as well. We were all going to be successful. Of course, I was a little pent-up, so the summer after graduation I had a beer, tried...

Best Summer Job Ever!

by amaleSwitch on Nov 7, 2017
Fetish

For 30 days so far this summer my job as a lifeguard at Spankas County Country Club had sucked. Stuck with the early shift it was my job to watch the pool from 6AM to noon and clean the men's changing room and toilets both before and after my stint on the pool. Needless to say it wasn't quite what I envisioned when I applied for the job. All the hot girls in...

Petulant Pia Ch. 01

by Mind Imperator on Sep 17, 2017
BDSM

Copyright Mind Imperator 2005. All Rights Reserved. Part One I have decided to take you for a while to the Château d´Eperon in the region of Reims. The owners are friends there from my time in Paris. They are also in the hierarchy of the commissariat and I share some leisure interests with them. Our car pulls up along the stable-flanked gravel entran...

Tracy

by velvet hammer on Sep 16, 2017
Novels and Novellas

This was some years back, I was in L.A. for a week, so I looked up this girl I knew from school. Tracy had always said to give her a call if I was in town. Tracy was so excited to hear my voice. "Where are you staying?" - I told her I was calling from the airport - Tracy said "Don't get a hotel room - save money and stay at my place!" She had this nice ol...

My Best Friend's Exposed Pussy

by zip33 on Jun 11, 2019
Exhibitionist & Voyeur

My husband John and I have been married for 10 years. John is a tall slender man and the love of my life. My name is Karen. I am 5'2" about 110 pounds with long auburn hair about 2' below my shoulders. My husband always says how beautiful the color of my hair is and women would die to have that color. I never thought of myself as sexy and actually I am very...

A Tale of Two Sisters Ch. 01

by eddievalquez on Sep 26, 2017
Exhibitionist & Voyeur

Before Kim and I had been dating for almost two years, and if things kept going the way they were, we wouldn't see year three. Kim was working full time at a coffee shop and I was coasting on student loans. She was stressed about drama at work, but I was so busy worrying about whether or not English Literature was really my passion anymore that I didn't off...