Gay Straight Bet Stories

13,269 results
Orientation
Length
Source
Infinite Scroll

The Roommate Ch. 03

by CalLorenson on Sep 16, 2017
Gay Male

This is a continuation of the story about my adventures with my girlfriend, Kara, and her roommate, Joyce. It takes place, once upon a time, when we were college students. Time-wise, this chapter occurs shortly after chapter 1. If you haven't read the first parts, I recommend that you do. However, if you want to plunge into this story, let me recap. Chapter...

The Handyman Ch. 06

by Bjsroxxs on Jul 6, 2020
Gay Male

"How do I look?" asked Matthew before he stepped into my truck. He wore a light blue polo shirt with blue skinny jeans. I had told him to wear something casual. Which he did. "Looks great," I said. Matthew opened the door and hopped into the truck. We had gotten used to not kissing in front of his house. For fear either his mom or neighbors would see. With...

Thomas and Niko Ch. 13

by kidboise on Feb 25, 2019
Gay Male

Thomas and Niko in the City of Trees - Chapter 13 — The house is pretty quiet the next morning. I think everyone is sleeping in a little. Thomas held me for most of the night. We're parted now, but the second he wakes up he sort of reaches for me, so I slip back into his arms. We're bare-chested. I can feel him through his underwear, pressing against my hi...

Straight Boy Gets Turned

by Newlybisub on Sep 14, 2017
Gay Male

This is the story of how I sucked my first cock. It was 7pm, just beginning to get dark, I knelt down and pulled the knot on my laces tight. Standing up I looked left then right before starting my evening jog. I kept up a leisurely pace towards the park where I liked to jog each evening. These days it's the only thing that keeps me in shape. Let me tell...

Lost Bet 07: Next Year

by dmoney4114 on Nov 8, 2017
Gay Male

Lost Bet Part 7: Next Year I was walking on a treadmill as a jiggly ass cycled in front of me. I had a perfect view of every movement and ripple which allowed my thoughts to wander to last year. My string of sexual experiences starting with a bet on a childhood game that I had made up, and culminating in, a bill for a destroyed dressing room, and the strang...

What Straight Men Want Pt. 04

by tvdude17 on Jan 15, 2019
Gay Male

What does one do when moving to a new city with a flourishing gay scene and more men that openly flirt with you in public and online? Behave, is what I did. I wanted to meet new people, make friends, but not combine them with sex. So every man that so much as openly admitted to only liking other men, was immediately friendzoned. I don't know why or what was...

TJ Ch. 03

by jt_hooks on Mar 6, 2018
Gay Male

"Hey there, Little Buddy. How are you?" Those seven words broke my heart. No, that's not it, it wasn't the words. It was the look on Josh's face that made my heart shatter into a million tiny pieces. How fucking stupid could I have been? There were signs everywhere, written with big, bold, red letters, warning me to proceed with caution. He played football...

The Changing Room

by velokev on Sep 14, 2017
Gay Male

In 1991 I was just barely 21 and working one of my first jobs as an assistant manager at a slightly trendy clothing store in the local mall. I wasn't paid well for it, but it was a little to put in my pocket, and I didn't have many expenses, so it all worked out. I was more frequently given the job close up, so I'd work the afternoon-to-closing shift, which...

If Motel Rooms Could Talk

by timmywells on Aug 18, 2017
Gay Male

The dingy and dated decor of The Skylane Motel on Central Avenue just outside the state's capital city hadn't been updated since Gerald Ford was President, but most of the people who stayed there didn't care. That was the case on the night of May 25th, when a nondescript 53 year old married man named Melvin Stark paid the $33.50 to rent room 108. The man ha...

Stallion Station Ch. 02

by sr71plt on Aug 28, 2017
Gay Male

"It sounds too complicated for you, Matt," Jason had said. "Getting a list would be the hardest part—impossible, I think. This is a small potatoes town. I think you should just keep it to the street and be happy when it works out. And get a job." I'll admit that getting a job was what got the plan rolling. Then getting a list turned out to be one of the eas...