Wedgie Stories

582 results
Orientation
Length
Source
Infinite Scroll

Teresa Scalia: Riot in the Ring

by obo on Sep 13, 2017
Humor & Satire

Mark Anderson and Dominic Scalia were meeting in Dominic's office planning a major fundraiser for their Men's Club. The club was providing financial assistance and support to construct a new recreation facility for the youth of their city. The event, catering to the more affluent male population, was to be a night of boxing followed by an auction of donated...

A Little Wrestling Match

by Fred1177 on Aug 18, 2017
Fetish

On Tuesday, I was at the office, just another cubicle rat congregating with the other cubicle rats in the snack area. A couple of the women were talking about how they had been doing a little wrestling among themselves. My ears immediately picked up on this conversation. I found out that there were several women from the office who would participate and that...

My Ideal Morning

by atomicrocka on Aug 18, 2017
Fetish

I wake up on a queen sized bed. I was asleep on my back, belly up. I lay on the left side of the bed, and turn my head right to see you, still asleep. We are both under the bed sheets. Quietly, as not to disturb your slumber, I slowly slide the sheets off of me, revealing my sleeping attire. I am wearing nothing but baby blue panties and a white, short sleev...

An Unexpected Swim Ch. 01

by JackRabbit85 on Sep 13, 2017
Romance

I've always been one of those kind of guys that has the unusually high sex drive, and I know most guys will typically think that about themselves but mine has a bit of a twist and reason to it. For as long as I could remember I have been attracted to woman's panties, and for whatever reason... is unknown. But granted I do have my limits to what it is I am at...

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...

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...

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...

College Girl's Depravity Pt. 02

by DegradingGirlsStories on Dec 14, 2020
Exhibitionist & Voyeur

Thank you guys so much for the support! I honestly didn't expect everyone to love it this much. I plan on carrying this story out for a long time, so I hope it only continues to get better for you all! ------- It wasn't until the next day that Jessie would get another text from her brand new anonymous Master. "Hello again fatty. Hope didn't think I tossed...