Gay Underwear Stories

6,363 results
Orientation
Length
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Infinite Scroll

Boxer Briefs Left Behind

by BeltBuckle on Mar 11, 2019
Gay Male

I carefully stretched my arm muscles while flexing my entire body before the mirror and check myself out for a while. I could easily afford to do that - at this time, the gym locker room was deserted. Very few people came here this late at night, and that's what I liked. Privacy. It was almost absolute - I saw nobody else in the gym at this time and there wa...

Underwear Friends Ch. 02

by ramon25 on Sep 16, 2017
Gay Male

I couldn't stop thinking about my encounter with Mark. I was pretty sure I still liked girls, but I was so hot for Mark! I longed to kiss him, undress him, stroke his cock and slide it in my mouth again. And have him do the same for me. I got to see him four days a week in gym class, and loved watching him strip to his boxers and A-shirts. The rest of the g...

Hypno Reversal

by TheNakedGinger on Apr 15, 2020
Gay Male

Rob was expecting a pretty exciting night. He had heard of x-rated hypnosis shows but was pretty convinced it was just paid actresses more-or-less stripping with a storyline. He didn't care though. The idea of hypnosis always turned him on a bit and even if fake, the idea of some hot babes being hypnotized to do some naughty stuff ensured Rob bought a ticket...

Truth or Dare Turns Gay

by TightWhiteHole on Aug 18, 2017
Gay Male

On Thomas's 18th birthday he decided he was going to ask his number one crush to his last winter formal, in a super way. So he put on his superman t-shirt and went to her house with a sign. After all the asking Emma agreed to go to the dance with Thomas. The night of the dance was finally upon them. Thomas began to get ready a few hours before. He took a sh...

I Had Anal Sex With A Man

by oldmushroom on Aug 18, 2017
Gay Male

I am now at the age of 63 and after retirement don't feel to live retired life , so working on contract. Though I am yet smart and energetic and don't feel much tired after long hectic office job, but some times do feel cramps in legs and shoulders. Three months before on weekend evening was sitting in TV lounge along wife and she saw me feeling uncomfortab...

Underwear Friends

by ramon25 on Sep 16, 2017
Gay Male

I was dreading taking a gym class in my senior year in high school. I missed gym in my junior year due to some surgery, so I had to take it as a senior in order to graduate. All of the other guys were juniors that i didn't know very well, but I had to make the best of it. Partway into the school year, a new guy transferred to our school from Texas. Mark...

Cock Worshiping

by alexhj1962 on Aug 18, 2017
Gay Male

I was always bi-curious but it wasn't until my 40s that I really started exploring. I sucked a handful of cocks through glory holes but never had the chance to fully worship a cock and balls. During a trip I placed an ad on Craigslist and agreed to host in my hotel room so I could have all the time needed. A guy in his mid-40s with a nice 7" cock, cut and sh...

Halloween Cruise: Night 01

by Bright_Star on Sep 1, 2017
Gay Male

I needed to get away for a few days, so I decided to book a cruise. I figured that would be a great way to escape the problems of the real world, and I would be able to relax for a fun-filled seven days and get to visit some great destinations and do some things that I hadn't been able to do before. And who knows, I figured, I might be able to meet someone n...

The Highland Festival Ch. 01: Train Ride

by BareBearsFan on Apr 3, 2019
Gay Male

This story contains elements of non-consensual relations, and abuse. This story is a fantasy and should be taken as such. If you don't like my story, then don't read it, or better yet write your own. This is my first story and something I'm trying out. For those wishing to add nice comments, or HELPFUL critics they are always welcome. I Hope You Enjoy ---...

Higher Education Ch. 01-02

by MelvinMhk on Aug 17, 2017
Gay Male

Chapter one : College Brings New Experiences I earned my Masters Degree in the first semester of my colligate life. Okay I can sense that most of you are rolling your eyes and saying something like, 'My oh my, doesn't he have a high opinion of his intellect.' Well let me try to explain that a little better. I am using the term 'Masters Degree' in a little d...