Messy Wedgie Stories

18,859 results
Orientation
Length
Source
Infinite Scroll

Beach Interlude

by meltwater on Sep 14, 2017
Erotic Couplings

You close your eyes I'm standing behind you my arm comes round your waist and across your stomach. I kiss your neck as my hand trails lower reaching down; I undo your jeans letting them drop. My fingertips lightly brush the front of your thighs as they teasingly get nearer I proceed to nibble on Your ear as my hand finds your panties and slips beneath. T...

MILF in the Fitting Room

by lovematurebbws on May 7, 2019
Erotic Couplings

At 40 years old I recently had a baby with my second husband, but have three other children from my first marriage. So none of my work attire fit properly anymore. I'm a size 12 now and my measurements went from 36DD-32-38 to 42H-34-44. Needless to say, I receive dirty looks from women when their boyfriends or husbands sneak a glance at my assets. From old p...

Expectations be Damned Ch. 02

by Angelpenpal on May 18, 2020
Transgender & Crossdressers

I woke up with that gross feeling of makeup left on overnight. The warmth of my sweet seducers was nowhere to be found. In fact, it was quite cold as the covers were gone. As I attempted to reach for them I found my situation had changed quite a bit since my last moment of wakefulness. I was tied to the bed, hands over my head and feet stretched to the lowe...

ENF Prone Isabel

by Moonkisser on Feb 9, 2018
Exhibitionist & Voyeur

Isabel wakes up from a good night sleep and opens up the curtains to get the daylight into her room. The 5"7 tall 23 year old is ready for this new day. The blonde is so looking forward to this day, but little does she know that this day would become a terrible one, or a great one. That depends on which point of view one see it from, if it's Isabel or a...

Open in Reader

F&R University

by Forcas on Jul 30, 2020
Fetish

Welcome to Fallow and Roe, the best institution for mammalian learning. World renowned for our excellent methods of teaching, we ensure only the best for our students. Throughout your time at F&R you will be able to explore academia and yourself with hands on experience, so please, get stuck in! The Student's Guide to Free Use at F&R: The Tiers of Pr...

Open in Reader

Time Stopping Pervert

by wicker on Sep 27, 2015
Science Fiction

My name is Wesley Barron. I am 20 years old, 5'11, 155 pounds with dishwater blonde hair and brown eyes. Most people would consider me average looking. I just finished my sophomore year of college and was back home for the summer. I am majoring in history and plan on going to law school. I have a 4.0 GPA. I am also a loner who does not do well in social situ...

Open in Reader

Penny's Comeuppance

by jlorthia on Sep 16, 2017
Fetish

This is another story from my former username "newfavorite," I only added minor tweaks to this story, I corrected some grammar and spelling. There is not much sex in this one and it is shorter than my normal story. *** The job market wasn't doing so hot in Megan's hometown. She had gone to college upstate to become an HR professional, but after weeks of j...

The Boss vs. The Man Ep. 01

by wrestlingisreallycool on Jan 15, 2019
Celebrities & Fan Fiction

Hello there, I hope you enjoy this, this is the first series in what I hope will be a collection of wrestling-focused erotic literature. I have seven different series in mind to start which hopefully will all be unique and interesting. Also, admittedly, this is my first time writing a full-length piece of fanfiction/erotica, so I hope it's not too bad. Anywa...

Manacite

by TheCanadian on Aug 26, 2018
Miscellaneous

As you return home from work one evening, you find a large shipping package waiting for you in front of your apartment. Bringing the package inside and opening it, you find a letter and hundreds of vials containing a mysterious red powder. You decide to inspect the letter. -- WARNING: PROPRIETARY INFORMATION. DISCLOSURE OF THE CONTENTS OF THIS PACKAGE AND TH...

Open in Reader

Just a Taste, Nothing More

by StrayingZombie on Sep 17, 2017
BDSM

It was fate that they happened to meet at work. He had spotted her first, unconsciously rubbing her pussy on her chair, trying to cum. He waited for the perfect day, the day she left last. She was surprised when he confronted her in the hallway, as she should be. He was one of the best looking men there, and she...she could be described as a plain girl. But...