Gay Predicament Stories

486 results
Orientation
Length
Category
Source
Infinite Scroll

Bad Deal Ch. 03

by skip5236 on Aug 18, 2017
Gay Male

Let me start out by saying Skip is not special...he is convinced that he somehow bumbled in to his predicament, but honestly he followed a well designed path that yields the same result every time...a guy naked and on his knees, his dick is hard and drooling, and he is agreeing to everything and anything I tell him to get his mouth on my dick. Nothing about...

Frat Party Costume Sex

by SluttyBisexualGuy on Mar 2, 2020
Gay Male

This is the story of how 19 year old Caleb Jensen found himself in the sexual predicament of a lifetime. It was the fall rush season and Caleb had been accepted as a pledge at the USC frat of his choice: Tau Kappa Epsilon. Their off-campus reputation was legendary and they threw incredible parties that people talked about for weeks. The girls that attend...

Cocksucker: Cum Slut

by silkstockingslover on Sep 14, 2017
Gay Male

You do not need to read the first four chapters of this story to enjoy this story of a straight man that gets submerged into the drag queen world of San Francisco (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first four chapters of "Cocksucker": Chapter 1: Cocksucker...

When Darkness Falls Pt. 1 Ch. 03

by Kay Derwydd on Sep 14, 2017
Gay Male

Chapter Three The driving rhythm of the bass vibrated the walls of Elixir and the music spilled out into the street. The doormen seemed oblivious as one checked IDs while the other collected the five dollar cover charge. Jordan shivered as he waited in line. No doubt the others—Matt, Jessica, and Parker—were already inside, drinking without him. As the line...

The Steam Room Ch. 02

by velokev on Sep 5, 2017
Gay Male

As Mike strolled leisurely toward me, I backed up into the corner next to the Steam Box. No doubt sensing my rapidly increasing anxiety of the situation, James got up and walked toward the door, blocking my only exit. They both had evil grins on their faces and confidence was flowing from them freely. "Why don't we just relax a little bit and get a little b...

Sweet Spot Ch. 05

by podga on Sep 14, 2017
Gay Male

Paul wasn't looking forward to visiting Andy's parents, and no number of toe-curling blow jobs was going to change that, though he didn't discourage Andy from making a repeat effort first thing in the morning. Unfortunately, he couldn't let go of his nervousness. "The problem is that I've never met anybody's parents before," he explained his predicament alo...

Renovation

by reddirtwriter on Aug 31, 2017
Gay Male

Also this story contains fantasy scenes of unprotected sex. This is fiction, not real life. Always protect yourself and wear a condom. My heart was pounding, my ass convulsing and my cock dripping as the stud behind me rammed his massive plum-headed cock hard and fast into my gaping ass. My head was reeling as I backtracked to how I ended up in this deli...

Hard On the Trail Ch. 11

by ketup on Sep 14, 2017
Gay Male

It had been so long since I had been fucked in the ass it felt like I was being ripped in two! I screamed out in pain. More of a loud primal grunt that echoed back in the woods. I struggled against Daddy who pinned me down harder. I slipped and my face hit the mud. As I fell he fell with me and landed to the hilt in my ass. He didn't move for a moment. I t...

Live and Let Live

by STLwriter on Aug 17, 2017
Gay Male

The human struggled in his binds, trying to break the rope tied around his wrists and around a thick wooden spear impaled into the ground. Sweat dripped over his naked frame as the cool night air kissed his tan skin. His muscles flexed as he moved, the toned canyons and valleys tensing and relaxing as he tried to break free. A fine looking black hair traile...

A Submissive at Heart Ch. 05

by hotbottom1 on Sep 2, 2017
Gay Male

Final Chapter I awoke the next morning to the feeling of Gerald gently grinding against me. His arm was wrapped around my chest and his body was intertwined with my own. As a straight man, to have this large black man spooning me in such an intimate manner made me feel more than a little awkward. As my consciousness became more salient I thought of all the...