Jack Stories

29,957 results
Orientation
Length
Source
Infinite Scroll

Kicking and Screaming Ch. 01-02

by SevMax2 on Jul 27, 2020
Loving Wives

Chapter 1 "Alright, you wanted to sit down and talk, Jill. We're sitting. We're talking. With no lawyers around, either. I hope that this doesn't put me off my appetite, because it's a shame to waste great falafel and tahini sauce," I told my estranged wife, Jill, as she sat with me in my favorite Greek and Middle Eastern cafe. "Look ... Jack. I blew it. O...

After Church Ch. 02

by alien_freak_nugget on Feb 11, 2019
Transgender & Crossdressers

I spent the whole week walking around like some kind of zombie. My asshole was sore from that long night of being fucked in the ass and every time I thought about Mike's cock in my mouth or ass, I had to go in the bathroom and jack off. Mike had told me not to cum without him but there was no stopping it. I had to touch it. Friday night rolled around and as...

Wayward Wife Ch. 05

by Out_of_Bounds on Apr 8, 2019
Fetish

Cindy reached into the back seat of the beater Honda and grabbed her shorts and thong panties as she slid off Sunny's deflating dick. "Man, that was good baby," Sunny said in earnest. "Yes, it was baby," Cindy cooed. "You're such a hot fuck." she said, definitely trying to inflate Sunny's ego a little bit. She did enjoy Sunny but he was similar to her husb...

Goodbye, Earl Ch. 04

by Tara Cox on Aug 31, 2020
Mature

***Note*** This story is part of my Trouble Texas Style series that includes Night Walker's Woman, Tight Fittin' Jeans, One Night Stand, and Ready to Run. It will be appreciated more when reading in context with those. ***TRIGGER WARNING*** This story deals with the life-long after-effects of rape. Both the heroine and hero are rape survivors. There will b...

A More-Men Wife Ch. 01 Pt. 02

by PolySwingerWife on Dec 14, 2020
Interracial Love

I met my husband on a Monday night. He proposed to me on Tuesday night, and by Friday afternoon we were married. Early that Friday evening, I lost my virginity to another man while my husband watched. And now me and my husband, Ray, were looking for an apartment. As we looked through the paper, I mentioned to Ray that Carl, the man I lost my virginity to, sh...

Witness

by oneiria on Feb 6, 2018
Erotic Horror

INTAKE It was a dark and stormy night. John Shaftsman's thumb was growing heavier by the minute as he plodded though the puddles in the breakdown lane of Route 30, also known as Conestoga Road after the wagons of the first settlers that set out west on this very road in search of a new frontier . Shaftsman was soaked, as God Himself seemed to be pouring b...

Reunion 1993 Pt. 01

by Barb36D on Sep 13, 2017
Mature

The following story is based on characters and events from "First Time Fun on the Farm" and "Retro Moresome." Prologue +++++ Home from another uneventful workday, I flipped through the daily mail until I stopped at a greeting card sized envelope addressed to Ms. Barbara Rogers. "Okay, this looks suspicious." Having been married and residing under my marrie...

His Sissy Bitch Ch. 02

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

The next day at work I felt my face flush every time I saw him, felt embarrassed and felt like stammering every time I spoke with anyone in the office. His office is across from mine, he's my boss and I have to see him daily. It felt like everyone in the office knew! I was so nervous I didn't speak to anyone, avoided everyone as best I could. He didn't say a...

Webslut Madison Ch. 01

by Rockwellray0 on Sep 26, 2017
Exhibitionist & Voyeur

Madison Kendall Holt sat on her bed with her phone in hand, thumb hovering over the "submit" button. Her heart was pounding with excitement and terror at the prospect of actually pressing it. Thoughts were racing through her mind as her left hand slowly crept down her pajama shorts and stroked her eager, throbbing pussy. "I can't believe I'm actually doing t...

Adam & Mike: The Story Continues

by mikeman341 on Sep 17, 2017
Loving Wives

(This is the continuing story of Mike and Adam, best friends who had suddenly discovered their new found sexual attraction to one another. They have had a couple of rounds of hot sex together, including a mutual jack job on the golf course. They are now headed home to cyber chat with their families. The first installments in the story are under the gay/bi se...