Gay Vacation Stories

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Orientation
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Infinite Scroll

The Fallen Ch. 07

by Acacia_wolf on Sep 14, 2017
Gay Male

Note from the author: I'm happy to bring you another chapter of The Fallen! I have so much planned for our pair. Please bare with me! I do have another short story coming soon. Thanks to a fan I'll be starting paranormal short stories of different varieties! Any other comments, suggestions, or requests feel free to message me! Thank you and please enjoy!...

My Gay Crossdressing Vacation Ch. 03

by Flame666 on May 11, 2020
Gay Male

I woke up. My bra undone, panties covered in lube and my nylons pushed down my legs. I felt as if I had been used. As I became more aware, I realized that I had been used and really enjoyed it. On the first day at the gay resort after getting dressed, I had walked over to a gay bar and been picked up by a nice guy, named Paul, just a bit older than myself. H...

My Gay Crossdressing Vacation Ch. 05

by Flame666 on May 12, 2020
Gay Male

As I was falling asleep, I realized that the egg and the plug were still inside me. Terri must have put the plug back in after fucking me. I wonder where the remote for the egg is. Oh well off to sleep. I was dreaming, I could feel soft hands on my back and running over my panty clad backside. Then I realized that it was not a dream. A pair of delicate hands...

College Break at Home

by jtwy on Oct 5, 2020
Gay Male

Jamie was a senior in college, back home from school for Fall break. Normally, he would've stayed at school for the vacation so that he could just relax and get drunk with his roommates. But this year, his parents were throwing a big, black-tie event at the house and they'd requested he come back to help out. Although not his ideal vacation, Jamie figured th...

Strangers Off the Street

by KeithD on Mar 6, 2018
Gay Male

That was the first thing Diego Medina said to Brett Williams upon meeting him in the arrivals area of the Barcelona-El Prat airport. "Your guess is as good as mine," Brett answered. "I haven't seen him for six months or more. I've been in London. I haven't been in New York for more than a year. You two are business partners, so I probably would be asking yo...

Boy in the Banana Hammock

by timmywells on Aug 29, 2017
Gay Male

A slightly strange tale about a man in a loveless marriage and the neighbors next door. *** It was my fault, all of it. It was just an ordinary week in August, or so I thought when my vacation began. My wife Jill and I were planning on taking a couple little jaunts in the northeast and just hanging around the house in lieu of a real vacation because she...

Little Guy with a Big Surprise Pt. 02

by Str8SensitiveGuy on Aug 24, 2020
Gay Male

It's been four months since the night my three housemates grabbed me, held me down, stripped me, tickled me, measured me and jerked me off. It had all begun early in the year with some verbal teasing and taunting about how small I was. I am only 5'5" and shy of 100 pounds. Mark, Sam and Chad are all good looking, well-muscled jocks. Mark is the biggest at ab...

The Pretender

by JaycobMatthews on Sep 14, 2017
Gay Male

(so this is my first attempt, and I was unable to find an editor, so if anybody finds mistakes, or has suggestions, be as harsh as you wish... THANKS!) The Pretender I'm gonna rent myself a house In the shade of the freeway Gonna pack my lunch in the morning And go to work each day And when the evening rolls around, I'll go on home and lay my body do...

Cumslut Diaries - Third Encounter

by bigal999 on Mar 18, 2020
Gay Male

Another entry in the Cumslut Diary. I just got an email from the first guy that I met at the Hyatt. He said the salesmen said I was a keeper. He told me he saw the video and that they were going to show it at their weekend poker game. I'm getting a sinking feeling. He said that the maintenance techs were going to be in Savannah on Monday and that he would...

First Time with Family Friends

by jtwy on Jul 6, 2020
Gay Male

It was Christmas break of James' senior year of high school. Just two months earlier, he had turned 18 and made a pact with himself to finally get laid this year. He knew it was stereotypical, but it needed to happen. And being in the closet certainly didn't help. James was tall at 6'1'', with dirty blond hair and blue eyes. He was pretty skinny, but not la...