Gay Cuckold Resort Stories

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My Gay Crossdressing Vacation Ch. 01

by Flame666 on Apr 21, 2020
Gay Male

It was mid-January and I was getting tired of the cold and I was horny so I started to think about planning a gay vacation. After a lot of thought I decided on Palm Springs in Mid-February. A bit about me, I am a straight looking and acting man 60 years old slim and fit. However, I love cock and like to dress up in panties and other lingerie. A few years ag...

Amy Cuckold Brian Ch. 05

by CuckoldGuy on Sep 19, 2017
Gay Male

"Honey, while I was upstairs changing, I went into our bathroom and I saw your douche bag hanging there. Are you having any kind of a problem?" Asked Brian. Setting the dinner table, Amy replied, "No I'm not but let's talk about it later. Will you tell the kids that dinner is ready?" "Sure thing", replied Brian. Later that evening after the children were...

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...

Daddy's New "Wife"

by Shadow Shark on Dec 4, 2019
Gay

Hello! My name is Tristan Wood, or Triss as my friends and family like to call me. I'm 22 years year old, recent college graduate, and unemployed. Right now I'm living with my old man Harry Wood, he's a thickset man in his late 40s. Though, pops has been living in constant sadness since mom passed away seven years ago. At first, he barely bothered to do anyt...

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Fetish Galore

by sr71plt on Aug 18, 2017
Gay Male

I had been banished. My wife would be joining me in a couple of months, but I was sent ahead—banished from New York—for my transgressions. April's father had known I was bi before he bought me for her daughter—and he also knew how I made my living, because he had been paying April's bills. But I suppose he assumed I would put all of that behind me when we we...

From the Frying Pan into the Fire 01

by walterio on Oct 15, 2017
Gay Male

PRELUDE Brad was in bed with one of his lovers when the telephone rang. He was annoyed because he was buried balls deep in his lover's ass. Brad rolled over to get the phone and as he did his cock slipped out of a shapely ass. "Hello," he said into the phone clearly disturbed by the interruption. "Brad, hi it's David. Sorry to bother you but I need some he...

Cross-Dressing, Gay & Lesbian Sex 05

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. * Daniel's one time bi-sexual fantasy consumes him "Maybe if you allowed me to have sex with Martin," said Emma to Daniel pausing without finishing her thought. She looked at him with teasing eyes and flirty sexiness in the way she used to look at him when t...

March Madness Ch. 09

by watchdwag on Sep 14, 2017
Gay Male

If you have been following my story, you know that Randy, a friend of mine since high school, has been blackmailing my girlfriend Sandy and me for the last few weeks. Sandy and I agreed to be his sex slaves for one month, as long as at the end of that term, he would turn over the compromising videos he filmed of me. I was the first to be blackmailed into ga...

Wow What a Night

by TheWingNut on Aug 18, 2017
Gay Male

The bulk of this story is true, however there are some embellishments. I remember the first time I met my wife. I was out of a straight relationship for a couple of years, after getting dumped by my girlfriend before the senior prom. I swore off girls, half-heartedly I admit. I kept myself busy sexually at circle jerks, adult movie theaters, and the occasio...

An Enjoyable Bisexual Encounter 01

by walterio on Aug 30, 2017
Gay Male

PRELUDE Kurt woke up Saturday with a morning erection and he rolled over expecting to find Sandy but the other bed was empty. Kurt was disappointed that Sandy had already left his bed as he would have loved fucking that curvy ass first thing that morning. He reached down and took a hold of his 7+" thick cock and stroked it slowly. He thought back to last ni...