Gay Jack Of Spades Stories

22,814 results
Orientation
Length
Source
Infinite Scroll

The Shopping Trip

by NYCBoi2 on Mar 26, 2019
Gay Male

All characters in this story are over the age of 18. *** Jack was getting a bit bored. He had been shopping all afternoon with his girlfriend Amy. They had already purchased a new pair of sheets and she had purchased some new clothes as well. He was ready to head home, however Amy had told him that there was one more shop that she wanted to go to. He follo...

Sharing Jack

by nextbestthing on Sep 14, 2017
Gay Male

I have loved my husband Jack since shortly after we started seeing each other. For whatever reason, when we were first dating he had told me that he had a jerk-off session with another guy when he was a teenager. I was shocked at first, as I couldn't figure out the relevance of why he was telling me what he did 25 years ago. As is my habit, I read between th...

Jamies Saviour Ch. 02

by alexcarr on Aug 18, 2017
Gay Male

Jamie could hardly sleep being so excited about tomorrow. He felt himself rising like never before, with carnal images in his mind about how it would be, going all the way with Jack. He wondered if it would hurt first time with Jack, he imagined how it would feel with Jack penetrating deeply inside him, he thought about too; that Jack asked for him to suck c...

Work Out Buddies Ch. 03

by eyelevel123 on Sep 14, 2017
Gay Male

I'm that 49-year-old guy from the Midwest wondering how I got into this position. Jack climbed on the bed as close to the headboard as he could; he wanted to have room for Matt to come up on the bed also. Thank god his wife made him get this king size bed the thought while smiling. Jack put his hands behind his own head and put his head on the pillows that...

Jack and Oliver Ch. 02

by tgrlily317 on Aug 18, 2017
Gay Male

Jack lost his balance and fell back onto the floor as Oliver shot up off the couch, tossing his shirt into his laundry basket and tucking his dick back into his pants. Pulling a fresh shirt from the closet and slipping it on, he waited until he had shut the door almost completely behind him before turning and muttering, "I'll be back later, man, don't wait u...

Gay Fills In for the Secretary

by walterio on Sep 16, 2017
Gay Male

INTRODUCTION Pete Jenkins and Jack Lewis were wrapping up things at the office on a Friday afternoon. They both worked for an investment banking firm and shared a satellite office. The secretary of three years was getting married that weekend and she would not be returning to the firm. Under normal circumstances the guys and their wives would have attended...

An Older Jock in the College Sauna

by jtwy on Apr 13, 2020
Gay Male

It was 5:30pm on a Friday night and Jack was exhausted after a long week of classes. A junior in college, he was studying hard to get into graduate school while working part-time to help pay his tuition. He definitely wasn't energetic enough to go out later that night with some friends, but still needed an endorphin boost. Might as well go to the gym, he tho...

Jack and Oliver Ch. 01

by tgrlily317 on Aug 18, 2017
Gay Male

The clock ticked mercilessly on the bedside table. It had been exactly twenty-two minutes and four months since Oliver had said goodbye to his lover of one and a half years. Sometimes he still played their last argument back in his mind, in the quiet, lonely hours of the morning. It was rarely quiet in the dorm at his university in Southern California, being...

Influencer to Sex Slave Ch. 05

by dreamymark9 on Jul 30, 2019
Gay Male

Author's note: This is erotic fantasy and completely fictional. The main character, Jack, is a fictional, generic social media star / influencer, and is not a real person. As always, would love to get feedback in comments and messages. Today was Jack's first day as a sex slave when his master was at work, and it was pretty eventful. He got a ton of embarras...

Consumed Pt. 04

by myoregon on Sep 14, 2017
Gay Male

WARNING AND NOTICES: This is a work of fiction. All characters appearing in this work are fictitious. Any resemblance to real persons, living or dead, is purely coincidental. Do not read if you are underage according to the laws in the country, state/province, county, city/town/village or township where you live. Copyright © 2008 Debra Diane; Permissi...