Gay Prostate Milking Stories

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Infinite Scroll

Ben Loves a Challenge Ch. 07

by PDreadful on Nov 18, 2019
Gay Male

By late afternoon on Sunday Ben worried he'd pushed Dean too far, he hadn't heard anything from him. He, himself, was having a hard time processing exactly what happened before dinner the night before. He thought about how Dean had stalked him the second he was in the door, sure Dean liked him, too. They had some excellent chemistry, he'd never come so hard...

A Boy Who Came In from the Cold Ch. 03

by SadieRose on Apr 3, 2019
Gay Male

Part Three – "The Payoff" (c) Sadie Rose Bermingham 2005 "Any unauthorised use of the whole or part of this story in any format constitutes theft of copyright. If you are not reading this story on Literotica.com it is posted illegally." UPSTAIRS AT THE FALCON... "I was gonna pay you back, Johnno. I swear it. Every penny, I just need some time…" Rayne w...

Had to Improvise - Prelude

by trybiman on Dec 19, 2018
Gay Male

There will come a day when I will have to improvise during filming, but that day is still far from the events I'm about to share. This is all about the build up to that fateful day. Here I'm still wading slowly into new waters. The very beginning: We were just hanging out one day when we had a conversation that would change so much and lead us down a long...

New Neighbor Ch. 01: Steve Pt. 01

by rimaday on Nov 18, 2019
Gay Male

My name is Steven Vincent wife and I had been married for eight years and lived in a newer middle-class housing development outside of Dallas when this story began. We were one of the original units in the development that now had over 150 houses with plans to double that in the next eight to ten years. We had lived next door to an older couple that retired...

My Erotic Education - A Journal 09

by rae121452 on Feb 6, 2018
Gay Male

For Gracie's Daddy * * * * * * Philip had been a part of our household for almost a week. My uncle, Will, Philip and I were having our breakfast in the bedroom on trays that Will and Philip had thoughtfully provided. "I had meant to tell you earlier but it somehow slipped my mind," my uncle said, "that I need to be away most of the day on business. The al...

Calluses Pt. 01: Friction

by MrMister23 on Dec 10, 2018
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** "Fuck..." I heard myself say as the blue-red lights lit up the gray sky behind me. I'd been lost in my music, coasting down the highway, three hours into a six hour road trip back to my college dorm. My foot had gotten heavy as I distracted myself; I'd been going well over...

Carved by Angels

by Rinique on Apr 3, 2019
Gay Male

*.:Carved by Angels:.* A curse to the cold weather. Dark brows twitched in annoyance as snowflakes continued to sprinkle down from the fairly clear, night sky above. If its snowing there should be more clouds... Sajery hiked up his light beige coat, loosening the black scarf that was wrapped around his neck to ease his temper. Someone brushed past Sajery j...

Behind the Bookstore

by LikesOlderMen18 on Aug 31, 2017
Gay Male

You have to be careful how you answer some questions or at least make sure you understand what is being asked. The question in my case was answered based on the knowledge of an eighteen year old kid; not knowing what was really implied or how it would change my perception of sex. The question has also brought about many of the stories that I write -- many of...

DJ Pt. 26

by o2byoung on Apr 10, 2018
Gay Male

In Part 26 Jamal and Rusty explore their Feelings Bryan and Phil 'Borrow' DJ's Bed Matt & Marie's First Date Randy & Daryl's Party DJ Part 26 Jamal arrived on campus about 8:45 AM on Wednesday morning, he parked in his usual area and was looking around for that 'special' pickup truck, and didn't see it. He's hoping that Rusty hasn't changed his mind. A...

A Bend in the Road Ch. 02

by Oldguy45 on Sep 14, 2017
Gay Male

The phone rang. I opened my eyes, disoriented for a few seconds. Then I remembered where I was. I was at Tad's, sleeping with him in his bed. The phone rang again, and Tad sleepily answered it. "Hello?" he said. "Oh. Hi Chris. What's up? Oh. How bad is she? Is she on a ventilator? Okay. All right. I'll be there as soon as I can. Bye." I glanced at the cloc...