Messy Wedgie Stories

18,859 results
Orientation
Length
Source
Infinite Scroll

Alice and the Looking Glass Ch. 05

by LeopoldNicholas on Sep 12, 2017
Sci-Fi & Fantasy

Alice must have fallen asleep quite quickly. She had no recollection of anything after the lights went out and awoke alert and ready for more plundering. "Glease Gurn Ghe Gights Gone." Her tongue was feeling a little sore from the constant pressure of the depressor but she was sure a good soaking in piss would cure any problem. "Gan, Gete, Gis Gat Goo?"...

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...

Art in the Dark

by rjordan on Sep 14, 2017
Mature

I never would have taken the art appreciation class if my friends hadn't convinced me that it was a snap. "Hey, it's Art in the Dark, man. All you do is watch a bunch of dumbass slides in a dark lecture hall." Cool, I thought. I picked a seat in the last row. It was dark, farthest from the prof and closest to the door. The prof, an older woman in her late 4...

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...

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...

A Helping Hand Ch. 01

by brans on Sep 15, 2017
Exhibitionist & Voyeur

This is my first story here and it's going to be an ongoing saga, so bear with me. Please feel free to review with praise or criticism. All characters are 18+ years old. ***** Ellie and Samantha had gone to a temporary bazaar a few blocks down from Sam's house. The bazaar had just appeared one day-no advertisement. Ellie loved places like that. The stall...

Jenny's Holiday Income Ch. 02

by StoneKidman on Sep 5, 2017
Fetish

Ch.2: the giant Jenny arched her back up off the mat after she was just slammed again by Giselle. The 6'7" giantess once again hauled my 42 year old girlfriend up by her long, dark hair. Giselle guerrilla pressed Jenny high in the air, one thick hand wrapped around Jenny's throat and the other digging into her crotch. The giant had light brown hair just a...

Beer Thursday

by barkirk on Sep 13, 2017
Erotic Couplings

"What did you say? Where did that come from?" "I'm sorry, really, really sorry." Tom said. "I should leave." "No, you stay right here. You can't say I want to fuck you, just out of the blue that way. We've know each other for 5 years and never even flirted with each other." "It must be the beer, forget I ever said it." "Seriously? You think I will ever f...

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...

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...