Gay Vacation Stories

1,191 results
Orientation
Length
Source
Infinite Scroll

All-Inclusive Vacation and Sex Ch. 01

by walterio on Sep 14, 2017
Gay Male

As the plane approached the landing at the Caribbean Island airport, I quickly dismissed my disappointment with my former girlfriend Andrea. At the last minute she had bailed on me and I was headed to an all-inclusive resort vacation by myself. I didn't blame her for cancelling as the other guy she was seeing had put pressure on her not to go on the trip. I...

Beach Trips: The Final Chapter

by Universal_Thirst on Aug 22, 2017
Gay Male

The final chapter of Beach Trips, after Beach Trips & Road Head, Beach Trips & Sex On The Beach and Beach Trips & True Romance. A burst of sunlight coupled with the sound of blinds being opened woke me suddenly. I sat up, aware of the smell of coffee and the sensation of nakedness. Chad sat on the edge of the bed, wearing a tank top, shorts and a huge grin....

My First Time in Hawaii

by cowboy109 on Aug 18, 2017
Gay Male

I swerved left and right at slow 20 mph. The Jeep Wrangler dipped deeply to the sides, much more like a dingy in waves than a car on steady land. The shocks of my rental were worn out. I wanted to at least get a feel for the jelly pudding of a car on the deserted airport ancillary road before hitting life traffic. It was my first time in Hawaii. What? Was I...

A Pound of Flesh Ch. 02

by SEVERUSMAX on Sep 14, 2017
Gay Male

The next day, Nicky went to work as I had instructed him and officially resigned, giving them two weeks' notice (that way, if something happened to me, he'd still have good references). His supervisor was nice enough to count the day before to his credit despite him being ill and using it as a personal day, and he also permitted Nicky to use up some vacation...

Jake and Toby Ch. 09

by kmillerk1 on Jan 14, 2018
Gay Male

For the Fans of Jake and Toby, For the time being this may be the end. They have their Happy Ending. But there maybe more. As you will read in chapter 9, I created a new character that might need to show back up later in Boston. I also am "thinking" about writing, HAVE NOT yet started. Again, "thinking" about maybe writing Jack and Toby's story, but we wi...

Naples

by undergear37 on Aug 18, 2017
Gay Male

This story is intended for a mature audience who can legally view this material. It is not intended to be viewed by minors or anyone else prohibited by law to view such material. No part of the story may be reprinted or reproduced electronically without the express written permission of its author. I always enjoy the feedback. * I dreaded the news that I...

Becoming a bitch

by Testytesterton on Nov 28, 2019
Gay

(Skip this if you don't like boring behind the scenes stuff. Wow! Over 3000 likes and story of the week for my first story here! Thanks to everyone who has liked, bookmarked or commented. The feedback lets me know what works and what might need work. I would love for this to be the most popular story in its category, so if you like the story, "like&quot...

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Meeting Ian Ch. 03

by evolvingslowly on Sep 19, 2017
Gay Male

This one is far shorter and far less fraught also no sex. The topics bounce around because my life, contrary to this story's impetus, is not that interesting but I wanted to continue updating. I hope that you enjoy it all the same. Be aware... this story depends on my life actually occurring so it won't be the most consistent upload schedule (as well as gett...

Family Cabin Ch. 05

by BeltBuckle on Oct 7, 2019
Gay Male

=== Friendly warning: Parts of this series include incest between a man and his father === ***** I was woken up from the blissful sleep by the familiar sound of raindrops hitting away at the window screen. I opened my eyes and tried to get my thoughts in line for the first couple of seconds. It seemed hard to remember what was the reason why I had arms of...

Converted to Bisexual

by walterio on Oct 15, 2017
Gay Male

xAndrew and his best friend Chuck were touring wine country in Napa Valley. They had decided to visit Northern California and they were staying in Sausalito. Andrew was gay and for the most part Chuck was straight. However, Chuck was okay with Andrew sucking his cock and recently he had been fucking him as well. Chick was not into cock at all but that was fi...