Gay Vacation Stories

1,191 results
Orientation
Length
Source
Infinite Scroll

Fire Island Vacation

by Dawns on Aug 18, 2017
Gay Male

Darrel and Tom walked along the trail through the sunken forrest on New York's Fire Island. They had both wanted to be there with a companion since long before they met at one of the city's more popular bars. They had been dating by now for six months. Together they enjoyed Broadway musicals, chick flicks, dinner at high class restautants, dinner at small...

The Vacation House Ch. 17

by 1Puck1 on Sep 14, 2017
Gay Male

I wish to preface this chapter by letting you know in advance that it was originally part of Chapter 16. Due to the excessive length of that chapter, it has been broken down in a more ingest-able size. Chapter 17 is now a set up for the following chapters to come. It may seem a bit off the beaten path for the saga of The Vacation House but I do hope you will...

A Vacation in Mexico

by luvcurious on Aug 18, 2017
Gay Male

When I started chatting with and mailing letters and stories to him, it was just fun sexy electronic play. We talked about everything. Most of the time it was real hot and we’d both cum to the stories and chats. Then after about three months of this we began making suggestions to meet each other. I live and work in Long Beach. Jerry lives in Cleveland....

Escapades of a Young Indian Bottom

by KeralaBottom97 on Dec 12, 2018
Gay Male

Youth is the time to experiment and like everyone else even I've had my fair bit of fun which is what I'd be elaborating today, this experience took place a few months ago a short while after I turned 21, though I'm not Gay in the strict sense I was still a virgin due to being the quiet kind and puberty didn't do me any favors as I was fair chubby and hairle...

Straight Guys Can Fuck Ch. 2

by Darksider on Sep 14, 2017
Gay Male

The week was coming to an end and Ryan's family and mine's joint vacation to Virginia beach in a nice big rented beach house was coming to an end. Close to the beginning of the week we had shared mind blowing sex, my only experience with a man, after Ryan told me that when there aren't any hot chicks around straight guys can fuck. Not that it would have mad...

The Customer (Dexter's Saga) Ch. 20

by JoyStick56 on Sep 14, 2017
Gay Male

Disclaimer: This story is a work of pure fiction. Names, characters, places, and incidents are either the product of the author's imagination or are used fictitiously, and any resemblance to actual persons, living or dead, events, or locales is entirely coincidental, and no harm or slanderous intent is implied or intentional. Other than that, the usual discl...

The Birth of a Sissy Pt. 03

by sissymedic1426 on Sep 14, 2017
Gay Male

By my sophomore year of college I had performed well enough in the class room that I had earned a few scholarships. This meant that my folks were saving money while I was getting my learn on. It also meant that my dad had promised me that if I rode it out for one more year in the dorms that by my junior year I could move off campus. The thought of finally ha...

The Vacation House Ch. 22

by 1Puck1 on Sep 14, 2017
Gay Male

Finding myself in the passenger seat of my pick-up truck, shaved smooth as a new born behind is mind blowing. How the heck do I keep getting myself into these bizarre situations? I don't think I even recognize myself today as the same kid that moved up to the family vacation house just months ago. Since I'm in this situation, I might as well go with it, not...

Unbreakable Bond Ch. 01

by adjoaq on Sep 13, 2017
Gay Male

Comments, critiques and tips are welcome. Chris Donovan vs. Shane Lewis Dedicated to Madisonkai (there's your clean ghost!) *** 'Fucking pull yourself together.' Shane Lewis screamed at himself silently. He couldn't believe his hands were actually shaking. As if that wasn't enough, his palms felt sweaty, he had a queasy feeling in his stomach, and he'...

A New York Cop Sucks Dick

by NYCSTUD on Sep 14, 2017
Gay Male

On the plane ride to my "unique vacation"—at least that's what the brochure had promised--I thought of what had brought me here. Job stress is something we all face, but I was feeling it ran deeper. Life stress, pushing 35, seeing dreams passing me by, it all seemed to conspire to compel me to this impulsive, two week vacation that I wasn't even sure I would...