Gay Wedgie Stories

983 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Caught with a Wedgie

by marriedhubbi on Oct 8, 2019
Gay Male

I never knew that my straight-laced life could take such a turn. Until that day I thought my hidden life of masturbation would remain undiscovered forever. You see, I have an unusual way of masturbating. When my wife and kids are out of the house, I often head to the bedroom and strip to my underwear. I prop up a couple of pillows in the middle of the bed,...

A Special Day

by Madelyne13 on Feb 11, 2019
Gay Male

I have been looking forward to today. It is my birthday and I have high hopes. Dan has been up to something and today I should find out what. Greeted by a cooked breakfast and a card. Dan says I will hopefully get the present later. I am supposedly on a day off but Dan has asked me to handle one appointment this afternoon. I am an estate agent and will go t...

My Buttslut

by thatrileyguy on Dec 16, 2019
Gay Male

This story is about a college guy named Keith who falls for another college guy named Maximillion, with you guessed it, a nice bubble butt. I'm writing this story because I noticed there is a lack of stories on this site about my #1 turn-on: a guy's ass. I hope this inspires others to unleash their love for the butt. I hope you enjoy the story and feedback...

A Summer of Firsts

by Turbidus on Aug 30, 2017
Gay Male

Everyone depicted in the story is over 18. All the characters are fictional; if you think you recognize yourself you're mistaken. The story is fiction is fiction of course but I hoped to capture some of the confusion and anxiety of discovering something new about yourself, especially in a small town. The story takes a dark turn. Not all first times end l...

A Summer of Firsts - Reimagined

by Turbidus on Aug 30, 2017
Gay Male

I posted a different version of this story a few weeks ago. It had a very dark ending. If you've read that story you can skip to ALTERNATE ENDING, the first section is identical. I'm curious to see if the story is better accepted without the grim ending of the first version. Thanks yet again to LarryInSeattle for his editing assistance. Everyone depicte...

Bully to Bitch

by Emily_sweetness on Jul 3, 2019
Gay Male

You know the phrase: 'Karma's a bitch'? Well, I didn't believe it until only recently, although I didn't think it would take me 10 years for me to learn that lesson, the hard way. The name is Josh, let's start from the beginning. 2008 15 years old and still living in the innocent world of secondary school, I was the top of the food chain. Having gone throu...

Picture Perfect Ch. 03

by tamgreen on Sep 25, 2017
Gay Male

"Are you sure you want me to be here for this?" He was sprawled across the bed in a posture that was an obvious attempt to look casual and careless, but I knew Aleksi well enough by now--he was posing for me, and delighting in being looked at. I couldn't help but look and appreciate. He was blissfully naked, with his white-blonde hair spilling around his pi...

Sweet Spot Ch. 02

by podga on Sep 14, 2017
Gay Male

"Not bad, Andy. You live here alone?" Paul sounded impressed. Andy opened the gate and motioned for Paul to precede him through it into the garden, then stood looking at his home, trying to see it as Paul probably did. He wasn't glib or artless enough to pretend that this was just a place to live, although it was that, as well, and had been for all 42 years...

Can A Straight Boy Be Turned Ch. 05

by Liquid_Dreamsxxx on Sep 14, 2017
Gay Male

Thursday April 16th On Monday I was on a job interview at our local supermarket. I think it went really well. They promised to e-mail me later this week. I've been applying for a job for several months but without success. I don't really care what kind of job it is, as long as I get paid. It's really frustrating going day to day without doing basically any...

A Learning Experience Ch. 02

by allsdude on Sep 14, 2017
Gay Male

I checked on my girlfriend one more time- she was sound asleep. Her shift at the bar wiped her out, she didn't even get up after our quickie. She laid there with her ass up, her cheeks red from where I thrusted against her. My cock straightened, more due to the thought of where I was about to go than the site of her freshly fucked pussy. I gently closed t...