Gay Predicament Stories

474 results
Orientation
Length
Source
Infinite Scroll

African Nightmare

by briboy2008 on Aug 18, 2017
Gay Male

This story takes place in Nigeria. The year is 1968 and the country was in the midst of civil war. The Ibo's, a tribe that lived in the eastern region on Nigeria had broken away following the assassination of the Nigerian Premier. The Ibo's called their territory Biafra and as this area contained Nigeria's oil reserves tensions were running high. In the nort...

Adventures with Kevin

by houston_man_28 on Aug 18, 2017
Gay Male

Let me begin by telling you a little bit about myself. I would define my sexual orientation as "bisexual" (sort of). I love sex with women. When it comes to men, I am only really sexually attracted to them for the thought of being submissive to a dominant guy. I have no desire to put my dick in another guys ass, but I LOVE sucking cock and getting fucked in...

My Brother's Keeper

by tvdude17 on Jan 23, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** I look pretty in my mother's clothes, I thought to myself as I stared into the mirror. An old grey skirt of wool was draped over my long legs and an orange top fitted tightly around my flat chest, only sagging where my boobs were supposed to be. I never identified as a woman but s...

Coffee .. And Maybe More ..

by MecumMhor on Aug 18, 2017
Gay Male

The Tim's was full when I got there. I mean full. This particular Tim's is usually busy, but this morning .. not a seat to be had, let alone a seat at a table. Well, no, there is one seat. Guy I recognize from the gym. Sitting alone, but obviously waiting on somebody. He nods and I nod back. I'm in line, waiting on a server. 'What are you doing? What are yo...

A First Taste Of Manhood

by spurt-reynolds on Sep 19, 2017
Gay Male

I've never considered myself to be gay, and even after the events described in this tale, I still don't. But, having said that, there's definitely something to be said for the feel of a nice hard cock! It all started one Christmas Eve, we (that is myself and my mother and father) were all at home as normal with my folks banishing me to my room for a couple...

Groom-To-Be & Me

by pdxjo on Aug 18, 2017
Gay Male

I answered the classified ad with trepidation. I was married, everyone assumed I had the perfect life and here I was answering an ad from a guy looking to have sex with "bi-curious" men. In the letter to the blind box address I accurately described myself as 6' 1", with brown hair, brown eyes, a swimmer's build and a great tan - except for my brilliant white...

The Price

by dreamweaver705 on Aug 30, 2017
Gay Male

I was in a real fix, I thought, as I sat staring dumbfounded at the computer screen and its multitude of pop-up screens, each filthier with triple-x porn than the last. Every time, I closed out one window, it seemed three or four more popped up to prove that I was beaten. I'd been surfing online porn and sure enough had landed in a site that had infected by...

First Meeting Ch. 02

by cutewht26mtoplsyou on Sep 14, 2017
Gay Male

*all references to characters, locations and events are fictional. Any similarities between this story and real life are purely coincidental* With my mouth and tongue occupied with your dripping cock, my mind begins to take in the details of my predicament. Here I am on my knees in front of you, my lips spread into a large O by the ring gag fastened around...

Lulls

by emoboi on Aug 17, 2017
Gay Male

(Inspired by AA's WYW.) * PROLOGUE "Unh!" With a final cry of carnal bliss, he came inside his newest conquest. A pretty blonde thing, with a face that was innocent and angelic. Definitely young-looking, maybe not even legal. But what the hell. He plopped on top of the boy to recover. He was breathing pretty hard into the boy's ear, but most of his part...

Behind the Equipment Shed

by princeof_parties on Sep 14, 2017
Gay Male

Gregory was the son of the wealthiest man in the county. When his family would visit the estate they were bestowed not only an extraordinary dinner, but also given the nicest rooms to stay in, an endless sea of compliments from their hosts, and sometimes even a series of nonchalant gifts. Cyrus had always hated Gregory even though at the urging of his mother...