Gay Underwear Stories

6,363 results
Orientation
Length
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Infinite Scroll

Freshman Year Ch. 01

by RO10589 on May 12, 2020
Gay Male

Hey there! Thanks for checking out my first Literotica submission, I hope you enjoy. This will be an ongoing series containing some of my favorite kinks, notably, light humiliation, DDLB, sock/foot play, and of course, some very passionate and complicated love! Enjoy Chapter One! * I tap my steel-toe boots against the floor with loud clacks as I look aroun...

Drunk Plaything

by randystoner on Sep 14, 2017
Gay Male

"You can crash at my place if you want." He said. I was completely drunk. It seemed like a good idea. Let's backtrack. I was 19 years old, and this was my first job. I was a barback at a pretty busy bar and he was the bartender. This being my first week on the job, I didn't really know how the place ran. It was a busy Saturday night and he had been feeding...

Tales of a Cock Slave #12

by dprb65 on Oct 6, 2020
Gay Male

I was in the main area of a booth store in Chicago, about to leave as there was no good men there, when a group of men wearing wedding rings, all tall, handsome, looking like the CNN reporter, Scott McLean, entered and walked by me on the way to the back room. I'm sure my mouth dropped opened and my eyes popped out! The last one, a tall hot redhead, turned...

The Park Ch. 02

by RobertSeattle on Aug 18, 2017
Gay Male

This is a continuation of the same park visit that occurred after a ruined meeting with a man from an online dating and hookup site. ***** As I laid on the blanket that I had spread out on the grassy area the wait to see who would approach it wasn't going to be long at all before I had company. I had noticed at least three couples two male male and one two...

Private Tanner

by TightWhiteHole on Aug 18, 2017
Gay Male

"Okay, okay Gabby I promise I won't jack off for 6 months," Tanner said regretting is words as soon as the left his mouth. Tanner was a young 18 year old, with brown hair and a nice build. Tanner and Gabby had started dating almost 6 Months ago and Tanner was getting tired of waiting for sex. Gabby agreed to have sex with Tanner if he could go six months wi...

Big Dick - Highway Restroom Pickup

by cut7nchlookn on Sep 14, 2017
Gay Male

Back in the 80's I was basically a traveling salesman in Ohio. I had worked the day in Canton, Ohio and was headed back into central Ohio, traveling on SR 30. I picked up a 6 pack of beer to enjoy so had to pee after a couple. There was a rest area near the intersection of SR 30 and I 71, so I stopped. It was a warm afternoon, so several people and cars were...

A Good Time With My Friend

by a_thick_dick on Sep 16, 2017
Gay Male

Well...I want to relate a story about the time a friend of mine and me enjoyed each other in the woods next to a creek. It all started when my friend and I were driving around looking for a place where we could get naked and have our way with each other without any disturbances from others. We came upon this wooded area near our high school that I had part...

A Pleasurable Discovery

by markshubby81 on Aug 18, 2017
Gay Male

"There's no way Jim's gay, Bryant," Vincent told me. "I'm pretty sure he is, Vinny. I have ways to find out." "I'll bet you a hundred bucks he's not. Just look at him." Vincent and I both turned our heads across the room to Jim's direction. The man was drop dead gorgeous. He was over six feet tall, and had curly blonde hair and the most sexy blue eyes one...

The Right Size

by REINER BENT on Aug 18, 2017
Gay Male

I used to work as a salesman at a fashionable menswear store. Hundreds of men would shop each day and I was in the habit of fantasizing about having sex with every single one of them. When a handsome guy would walk into the store, I would check him out trying to figure out if he was gay. Then, naturally, I would try to guess the size of his cock. I wondered...

ENM Intertwined - Jack Pt. 04

by SpecialtyM3 on Jan 22, 2020
Gay Male

Apart from being almost naked, I was having one of the best days of my life. I once took a yacht out on the Caribbean for one of my father's parties and met a celebrity from my favorite movie while eating lobster at the buffet. That time couldn't compare to how I felt when I was with Zayne just doing ordinary things. He showed me how to cook microwavable piz...