Gay Measure Size Bet Stories

9,883 results
Orientation
Length
Source
Infinite Scroll

My First Penis

by yowser on Oct 15, 2017
Gay Male

The title of course is misleading; my first penis continues to be my own. This tale barely mentions my second, which belonged to my teenaged wank-off buddy Lenny, as both of us messed around with each other as horny, small-town adolescents. But somehow "My Third Penis" just doesn't make for a captivating title, however accurate it might be. The adjective "...

The New Gym

by BigJim1212 on Oct 15, 2017
Gay Male

My name is Bryce. I realized at an early age that my looks could open doors for me. I also realized that my big cock could close the deal. Most people would call the way I looked as classic all-American good looks. When I graduated from high school I was 6'4" with blond hair and ice blue eyes. You know the kind of eyes that can pierce right through the soul....

Hiding in Plain Sight Ch. 02

by beyondtheset on Nov 27, 2018
Gay Male

21-year-old Jason Charles found himself laying down on the bed in the hotel room that he was splitting with his line brother Deyonte. He was fully dressed for the cocktail hour that his Fraternity was hosting. He was a legacy and a recent initiate of Omega Psi Phi Fraternity Incorporated and this was his first conference. His fraternity was holding their St...

The Pictures Ch. 08

by Mike Cindy on Aug 17, 2017
Gay Male

Cindy left with Ms. Erin after eating breakfast. The only thing said to me that morning was to make sure I put the cream on my ass and to finish all the chores she left for me, written on a piece of paper. Cindy returned home about 6:00, told me she was taking a nap and to wake her at 7:00. She also told me to be showered and naked when I woke her. I sto...

Brent's Prep for the Prison Doc

by woofdaddy2 on Aug 18, 2017
Gay Male

After a few weeks of being used by first the prison ward and then rented by the prison to entertain local men, it was time for a full medical exam. The Warden did not want his rent boys spreading any diseases so they were tested every two weeks. The exams included tests of their mouth, penis, shit hole and blood. The exams were no too uncomfortable, it was t...

Improper Advances Ch. 03

by bjmichaels on Sep 14, 2017
Gay Male

It was a full week before the voice in my head finally went away. No, I wasn't possessed by a demon or anything super-natural. It was the voice of my girlfriend as I watched her body violently shake underneath Bruce's friend, Doug, as he rammed his hard cock in and out of her open pussy. "OH DOUGY, FUCK ME HARDER, SWEETIE, GOD I LOVE YOUR BIG COCK INSIDE M...

Yet Another Frat Initiation Story Ch. 05

by Cyanlot on Aug 18, 2017
Gay Male

Part 5: Morning Activities Long before my hungover mind wanted to, I heard an alarm go off in our room. The door sprang open and our six mentors came in with our morning instructions. We were all prohibited from taking a leak until each of us had given a semen sample. What the sample was for was not explained. We were given little cups to cum into and instr...

You Bet Your Ass

by kudzu41999 on Aug 31, 2017
Gay Male

There's nothing worse than two divorced guys sitting around watching television on a Saturday night. Lamar lost everything when his wife took everything he owned. All he had left after he got home from work that day was the car and the clothes he had on his back. I wasn't much better off. The only difference seemed to be in the bills that were left behind. I...

Fight Night: Round 01

by xzay24 on Apr 10, 2018
Gay Male

*This is my first story so please leave comments and let me know how I can improve. Thanks and Part two is on the way.* ***** How the hell did it come to this!? Why am I enjoying it so much!? Face down in a pillow I ponder these questions as the man I hated pushes his fat dick into me. "So tight." I hear him growl. "This must really be your first time hu...

Black Cock College Threesome Ch. 01

by TheOriginalAnonymous on Sep 14, 2017
Gay Male

Part 1 - Prologue, and Extending the Invitation It was my first year as an upperclassman, and I was finally the starter at shooting guard. Most of our players were upperclassmen; all of our starters except at point guard, where highly-touted freshman Marcus Washington was expected to earn the starter's spot. We had been a very good team last year, just mis...