Gay Wedgie Bully Stories

319 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

Alex and Tom

by sgc45 on Jan 22, 2019
Gay Male

It was the spring of 1995, I was 18 and growing up in suburbia. I was walking down the tree lined street with shaded sidewalks heading to the store to pick up some snacks. The street was long and straight and the tall Oak and Maple trees were just leafing out. It was a sunny but chilly day after rain had fallen the night before and I avoided the worms that h...

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...

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,...

The Master Swim Team Ch. 07

by cubscou88 on Jan 21, 2019
Gay Male

This is a fictional story about a young adult who joins a Master's Swim team full of older men. ***** THE SWIM TEAM, PART VII -- FIRST DAY ON THE JOB Dennis rolled over and found himself lying in a large, wet spot. Half asleep, he ran his hand down the length of his body until he got to his belly, which was also covered in the liquid. His fully erect cock...

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...

What Happened in Harvey's Room Pt. 01

by Robert_Furlong on Sep 14, 2017
Gay Male

The five of us gathered round Harvey's laptop, pulled our dicks out and he loaded up the movie so we could all wank off to it. I was new to the academy and I'd never been in a circle jerk before, so it seemed funny and horny at the same time for us all to be crouching round like this with our boners poking out from our flies. "This is so fuckin' hot," Harv...

Breaking in Kirk

by i8mym8 on Aug 18, 2017
Gay Male

It's a hot Saturday afternoon and I'm driving home from work. Just past the train station I see a kid hitch-hiking. I recognise him. It's Kirk, a boy who was on the local under-15 basketball team when I was assistant coach a few years back. He must be 18 or 19 now. He looks a bit like one of those skater types – long blond hair under a baseball cap, shapeles...

Notifications Gone Wrong

by SemiStraight on Oct 5, 2020
Gay Male

One of those stories that comes to you at the least suspected time and interrupts what you're supposed to be working on in a series. The ADD kicks in and all of a sudden it's just sitting there ready to be written with your only job being filling in the details. This is fiction with bits of true sprinkled in from what could have been. It's also got a rough,...

Adventures Of A Mormon Missionary Ch. 01

by Coxswain on Aug 18, 2017
Gay Male

Part 1: I can tell it now [names have been changed] I was always timid. Don't know why. Just never the rough-and-tumble sort. And I was a homosexual before I even knew what the word meant. I liked cocks even before I knew they could do more than piss, clear back when the only word I knew was "peepees." The Mormon church, of course, taught me that I was on...