Gay Challenge Stories

1,577 results
Orientation
Length
Source
Infinite Scroll

Like The First Time ...

by MecumMhor on Aug 18, 2017
Gay Male

"Fuck", I say to him, "if you had a pencil dick, you'd be sliding in there now, right up to your balls, all nine or ten inches of you." "Ten," he says in my ear, nuzzling me. "Ok, ten," I say, my mouth now at his ear. "Whatever," I smirk. 'Ten' I know it is. It's our private joke. We'd measured it how many times. I'd run the tape from his pubes to level wi...

Bio of a Bully

by ozeboi69 on Sep 14, 2017
Gay Male

I am so fuckin’ hot. I mean it, no kidding. It’s not vanity or nothin’ like that. It’s true. Plain and simple. I am fuckin’ a-grade hot. It’s like at school, everyone wants a piece of me, you know. The chicks giggle and gawk when I walk by and all the blokes – they all wanna be just like me. Even some of the teachers - no bullshit! It’s great being lik...

Winners and Losers Ch. 07

by bawdybloke on Sep 15, 2017
Gay Male

If you have missed the previous instalments the premise of the story is that after a football match, the losing team must provide sexual relief for the victorious players. Previous chapters for Winners and Losers are on Literotica. * * * * * There was no denying that the last minute loss to AFC Kerlon had dented confidence in the dressing room, but when...

Game of Love Ch. 01

by vanalas on Jun 9, 2020
Gay Male

Game of Love Ch. 01 Comments, critiques and tips are welcome! *** Love.... Love is a game that both can play and win. But we always have to remember that games are deadly serious and you do not play them to enjoy. There's a saying, 'Not knowing what you want is one thing but not knowing what you want and getting a person's feelings involved is another thi...

Shattered Boundaries Ch. 08

by Humilifuck on Sep 14, 2017
Gay Male

Sex is a kind of opium for the masses. We are intoxicated yet keenly aware. The solution to every problem is suddenly evident. We blindly leap towards our bliss and our inevitably downfall. "Your ass is so fucking tight." Jim huffed. I replied, "Sorry Sir." Being careful to keep the tone of my voice respectful; without any hint of the apprehension I...

Forever Yours Ch. 12

by vanalas on Sep 19, 2017
Gay Male

Welcome to the twelfth chapter of my story. It's been really wonderful having you wonderful readers with me. I hope this chapter entertains you like the others. I love you and I look forward to more ratings. Don't forget to drop your comments at the end of this chapter. Enjoy... ******* "Ahhh..." Ramon's mouth gaped in a silent scream as Marcos pounded in...

My Intro Into Long-Stroking...

by hornyTCbicple on Aug 18, 2017
Gay Male

My intro into long-stroking and more... I'm a bi bottom who as my girlfriend says "is a natural bottom". Now there are several encounters I could tell you about but there is one specifically that sticks out and will never be forgotten by me or my girl; and probably not in yours after you relive it with me here. The night started like normal, my girl and I...

College Roommates Meet

by tomthewriter on Sep 14, 2017
Gay Male

Chapter 1 Today marked a new chapter in Devante's life. Today was move in day, and all summer Devante had dreamed about what life would be like on a college campus and today he would find out. He had only dreamed about getting out of his parents’ house and out of the watchful eye of his younger sister. His only concern was being an African American going...

With Kieran, Life was Never Boring

by alexcarr on Aug 18, 2017
Gay Male

I just don't know what I'd do without Kieran. He mans everything to me, He just has to put on that cheeky dimpled smile and I am anything he want to do. He has a wonderful disposition and for a guy coming on forty can still be a very remarkable lover. Especially after a glass of Schnapps or two, Then he becomes very blue and I adore it when he tells me - no...

Straight Guy Sucks His First

by fakename1221 on Sep 14, 2017
Gay Male

One evening a couple of years ago, my girlfriend had been out of town for a few days, and I had been taking advantage of the privacy to look at pussy porn and jack off like 3 times a day. At some point I got to thinking it would be great to have a jack-off buddy like I did in junior high school with my best friend. So I went on a local message board and star...