Messy Wedgie Stories

18,859 results
Orientation
Length
Source
Infinite Scroll

Mistress Encounter

by WellBehavedMan on Sep 15, 2017
Fetish

Eva gets back to her hotel room from her business meeting, glad to be back, the meeting went ok, could've been better, they could all be better she reminds herself, as people don't give everything for nothing. As she flicks on the main lights she jumps as she see's you on her soft double bed, right where she left you before she went out, however she did not...

Jeanie with the Light Brown Hair

by acgolf on Sep 17, 2017
Loving Wives

story I am about to post was written as a contest entry. The rules of the contest were to use the inspiration of the picture of a kneeling woman clothed only in shear thy high stockings and a white feather boa draped over her shoulders. There was a caption under the picture, "you want me to do what? with this boa?" that had to be used somewhere in the story....

Touhou Mind Control

by plorbus on Nov 22, 2020
Fan Fiction

This story is fiction! All characters are over the age of 18. Gensokyo is a land of possibilities and opportunities, even for a lowly mundane human such as yourself. At the very least, strange things can happen and fortunes can change. You are down on your luck, at your lowest, but things are really about to turn around. You find yourself in the local pawn s...

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Accidental Cuckold Ch. 05

by Brass_ankle on Mar 10, 2020
Loving Wives

2001 Seattle, WA "Who are you?" Asked a couple stopping in front of Bob and Cassy. Cassy smiled, Bob set down his vodka and pop to leap out at them! "I'm Bat Bob!" Exclaimed Bob in a raspy voice as he flourished his cape about himself. The man and woman laughed, they were dressed as Zorro and Cat Woman; Cassy however was already sick of that voice he di...

Kinky Voyeur Husband

by YukonWolf on Sep 14, 2017
Loving Wives

The following is based upon a true story with exaggerations added to enhance the story interest: I write love songs so here goes. ***** Story: Kinky voyeur husband-Watching the wife seduced- It all started one day when I made the mistake of bringing a big, handsome, rouged looking friend home from work with me that looked like the twin brother of my wife'...

Jessica's Change Management Ch. 27

by Cathartico on Oct 19, 2020
Exhibitionist & Voyeur

-- Saturday -- This was it! The grand finale was hitting the home stretch! Time for a status update. It was make-or-break time, 'cause I was down a buncha scores. It was all-or-nothing, 'cause I had totally gotten outmaneuvered by Ortega. Despite everything that had happened, the task was still the same. I had to broker new contacts for LGZ. The goal was...

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 Store Slut

by fuckup77 on Aug 19, 2017
Exhibitionist & Voyeur

Henry always was fairly shy. Always scared to reveal his true self to the world. Terrified to find out exactly what the rest of the world might think of him. 6' tall, combed back shaggy hair, and a relatively average body. Never overly popular with the ladies, but still some experience. Henry worked at a local bookstore. One of the most exciting moments of...

Bliss

by IreneXXX on Sep 14, 2017
Erotic Couplings

His meeting took longer than expected and he was late picking me up. Nonetheless I was glad to see him after his busy week. He looked really tired. I was worried that he'd be exhausted since he'd just had a long day at work. But he insisted he was fine and despite a headache, wanted to dance, too. We were supposed to meet 2 girlfriends at Brix, so he decided...

Re-submit

by Mine0214 on Sep 16, 2017
BDSM

So there she was lying naked, exhausted, feeling the coolness of the bed clothes beneath her. She was in an intimate space all her own; completely satisfied, completely loved, completely owned. The memories of how she got there played out in her mind as she gradually drifted off. ------------------------------ She was wearing her favorite pair of panties,...