Pussy Wedgie Stories

247,397 results
Orientation
Length
Source
Infinite Scroll

The Lady and the Fat Man

by mstrhole on Sep 16, 2017
Fetish

A number of years ago, I knew a woman (on-line) from Germany who had a very (to me) peculiar fetish. She was a zaftig blond who could have been a stand-in for any Valkyrie Maiden swooping down on some ancient Norse battle field, plucking fallen warriors and transporting them to Valhalla. She was also a prostitute. A large (but not fat) woman herself, she was...

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...

Window Shopping Ch. 01

by kinki on Sep 12, 2017
Exhibitionist & Voyeur

…people really don't pay too much attention to whom is driving the big truck coming up next to them in traffic, but perhaps they should. Most of the male drivers constantly look down into the cars for a peek. Down a top, up a skirt…you would be surprised at how much you can see from up here. We call it "Window Shopping." As far as I go…I can't tell you how m...

Ana vs Joy - Payback or More of the Same

by Mag863 on Mar 26, 2019
Fetish

Joy was in a foul mood after the fight with Ana. She was definitely wanting a rematch. We would go to the community pool, and see Joel and Ana there enjoying themselves and chatting with several neighbors. Ana looked great in her tiny bikini flaunting herself around the pool. Joel and I would have some beers as Ana and Joy and some of the other neighbors wou...

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...

Bootycalled by McDreamy Pt. 02

by neuroslut on Dec 3, 2019
Erotic Couplings

Note: Thank you to everyone who gave feedback on my first story! To those waiting for the story with my professor, it's still coming I promise! Unfortunately things didn't pan out with him quite as I had hoped, so that story will be more fantasy than reality. In the meantime I figured I'd jot down another (true) encounter with McDreamy before I forget too ma...

Sally's First

by sally_spandex on Sep 16, 2017
Transsexuals & Crossdressers

My heart was racing a mile a minute as my hand reached for the door knob to open a whole new world to me. Altho I had been dressing for about 15 years, at 23 I still hadn't been outside or let anyone in on my secret. The last 3 years had been hell for me as I had started to play with dildo's and catching my cum in my open mouth, and craving the load of ano...

Book Porn

by librarianxxx on Sep 14, 2017
Erotic Couplings

"That's me finished for the day." Cythia the shift supervisor said as she walked out the librarian's office. "Remember you have to show that researcher the manuscript, and then lock up." "Of course Cythia. Enjoy your evening." Alice said with a smile, as she sat at the library help desk. She was just a library assistant and really shouldn't be left alone to...

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...

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...