Gay Lost Bet Pegging Stories

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Infinite Scroll

My Sweet Bitch Ch. 03

by JasonClearwater on Jun 18, 2018
Gay Male

Author's note: After receiving instruction from Master Kleine on how to teach his slave to give good oral, Jaspar agrees to learn how to get the best from his slave's ass... * * * * * So, there I was, sitting on the side of Kleine's king-sized bed, about to learn how to get my slave to better service me with his ass. We were definitely going to use Sam fo...

Unworthy...No More!

by Corjix on May 16, 2018
Gay Male

The man in the suit bent down to ask me: "Is that okay with you?" He need not have bothered, for my fate was sealed and I knew it - at the age of seven I knew I was done for. Unworthy. My parents and I had been in his office for a while and they talked about my school experience...about my age...about my handwriting...about stuff. I sat on a small stool or...

My New F-Buddy's Big Cock

by DixeenormousToo on Jul 24, 2018
Gay Male

I'm married, "straight," and your typical suburban family guy. So is my neighbor buddy. The bonus with this neighbor, he has a big cock and is now feeding it to me regularly. Jeff, my neighbor down the street, is in his mid fifties, just a couple of years older than me, has a lovely wife and two kids in high school. Both my kids are in college and my wife i...

Even More with Stefan

by JustAStory888 on Mar 20, 2018
Gay Male

I did not plan to write a third story about my romance with Stefan, but after receiving a few more encouraging notes I decided to write one more to tell people a little more about our relationship. By the end of that fall semester, Stefan and I saw one another almost every day. Or at least every day we could. He would either drop by my place or I would meet...

Rory and Sebastian Ch. 19

by sebastiando on Sep 14, 2017
Gay Male

-- With great apologies for the delay and thanks for all the comments -- "Sebastian?" "I think so, Rory," I laughed. Half-laughed, I guess. Rory was staring at me in total shock and bewilderment, as if he'd somehow fallen asleep on his own life and woken up in a scene he didn't recognize. His silence lasted for another few seconds and his eyes were almos...

March Madness Ch. 09

by watchdwag on Sep 14, 2017
Gay Male

If you have been following my story, you know that Randy, a friend of mine since high school, has been blackmailing my girlfriend Sandy and me for the last few weeks. Sandy and I agreed to be his sex slaves for one month, as long as at the end of that term, he would turn over the compromising videos he filmed of me. I was the first to be blackmailed into ga...

College Daze Pt. 03

by The Avenger on Aug 30, 2017
Gay Male

College Daze: The Conclusion Chapter 1: The Morning After The morning after was definitely the icing on the cake. Dee woke up from a deep sleep to find his white room mate Jeri rolling a joint whilst Jeri's girlfriend, the pretty Stacy snored in his powerful black arms. Without a word, the two guys shared the joint. As the hot, horny events of the previous...

Office Top and Bottom Ch. 01

by 1077ad on Sep 16, 2017
Gay Male

Chapter 1 Caught in an Awkward Situation Steve twisted the lid off the tube of lip balm. He squinted and looked at the gap between the edge of the plastic tube and the waxy material within. Then he lowered it down to his cock, which was hanging out of his grey work pants. Squeezing the head of his half-erect penis, a drop of clear pre-come oozed out. With...

My Dark Angel Ch. 11

by tauger on Sep 25, 2017
Gay Male

**Previously** Louis' arms unwound from around my waist and in a few seconds I understood why. The door opened and the rest of the class began to pile in for the last 2 lessons of the day. I pulled on my red sports top and unbuttoned my beige chinos. I tugged them of my legs and pulled on my gym shorts. I headed for the door to the gym sparing a quick glanc...

Plotting a Course Ch. 09

by VaRiverWriter on Sep 25, 2017
Gay Male

Chapter 9: T-shirt and a Teddy Bear The wind was bitter across my face as I walked across campus back to my dorm. I pulled the drawstring tighter, trying to further protect my wind burned face. The sidewalks had been shoveled, but were slick with the compacted snow, turning them into a slick ice trail. I kept my head down, shielded from the wind. My phone w...