Gay Challenge Stories

1,577 results
Orientation
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Infinite Scroll

The Grand Duellist

by meris on Jun 28, 2016
Gay

Fierre is an 18 year old French Duellist in the city of Demacia. Standing at 5'10 he is smaller than many other fighters his age. Clothed from neck to toe in a skin tight black bodysuit which hugs the plump cheeks of his bum enticingly. Two long silvery white boots, the edges lined with a gold tint. Some leg guards coloured the same with a matching pair on h...

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Seduced: A New Experience

by alias_the_archangel on Aug 18, 2017
Gay Male

So there I was; naked, blindfolded, and tied loosely to the four legs of a waist-high chair. Matt would be home any minute from the store, he had only gone to grab a few snacks for watching a movie. I’m sure he thought it odd that I hadn’t accompanied him, but I was fairly sure he would never guess my reasoning. In the short time that he was gone I changed t...

Chore Bitch Pt. 01

by travelsforfunxxx on May 12, 2020
Gay Male

I've been using an app to hook up with guys for over 15 years, and I'm a true switch. I genuinely enjoy both being in charge and being a complete and total bitch. As a way to keep myself entertained during COVID 19 and to give something back to the kink community, I decided to share some of the stories about guys I've hooked up with. One day, I was feeling...

Jungle Fever Ch. 4

by ozeboi69 on Aug 31, 2017
Gay Male

Moaning. It escaped from Boi's lips like a gentle breeze passing through the tree tops. Groaning. I couldn't tell if the sounds he emitted were of pleasure or despair. His eye's closed, lips parted only enough for the sounds to escape, Boi's facial muscles were contorted in a way difficult to read from my vantage point above, where I stood tied to a tr...

Sam's Cousin Ch. 01

by downupdownup on Mar 25, 2019
Gay Male

My name is Sam. This is a story about my cousin Jay and I from the not-so-distant past. Hope you enjoy! *** Taking advantage of the end of senior year and the new warmth of early summer, Jay and I made our way through our neighborhood's forest. He and I had grown up close, and we spent a lot of free time together, especially in the warmer months. We both h...

My Own Devices

by ndeavour on Oct 6, 2020
Gay Male

I have a private space I can go to indulge myself and my fantasies -- it's my RV. Parked in the country, I leave it there on land I own. Since I've put in a power line, water and septic, I can live there any time. And if I'm not living there, I can stay there and soak up the quiet and privacy. And indulge. It's also where I can indulge in some of my fantasie...

Opportunistic Fellatio

by SgtBuzfuz on Oct 16, 2018
Gay Male

I walked into the house from my normal morning at the gym. It was 7:15 AM and the house was all but silent, the only sound, a gentle susurration from the central air conditioning. I knew Lucas, our houseguest, was downstairs in the media room. He was staying over for a few days...not for the first time. We had been family friends since he was born. He had...

Bathhouse Lures Ch. 03

by glory_first on Sep 14, 2017
Gay Male

Weekends, the local bathhouse opens at 2pm, and this Sunday, I was there at 2:15pm. My weekend had already been enhanced by Friday's visit here, spending an exquisite time in the whirlpool, ending with the incredible balance of excruciating pleasure and unstoppable desire as he played with my cock slit, a feeling beyond orgasm under the total domination of...

Anticipation

by ndeavour on Oct 24, 2018
Gay Male

Look, I don't think I'm all that unusual. I think that there are at least a few men out there like me. What's that mean? Well, here's what I am talking about -- you tell me if you identify with me, okay? I hit my twenties in the beginning of the 70's. I smoked pot. I experimented with other drugs. And I actively explored my sexuality. Somewhere I read a cha...

Bear Hunting

by blue_mirage on Nov 2, 2020
Gay Male

Author's note: If you like this story please leave a comment. I enjoy reading them and I like receiving feedback on my writing. Enjoy the story. Bear Hunting I saw him at a party once, and I knew I wanted to make him mine. He was a bear, a massive man in his thirties always looking for younger twinks. I would often sit at the bar and look at the crowd, th...