Playboy Stories

4,151 results
Orientation
Length
Source
Infinite Scroll

Adventures of Hollywood Jim Ch. 14

by hollywoodjim on Sep 18, 2017
Celebrities & Fan Fiction

I was trying not to look embarrassed as I followed Bridget and Laura out of the Palms Playboy Club. They were giggling the entire time at what they'd done to me under the table there. Bridget took us to the private elevator reserved for VIP's and we started down. As soon as the doors closed they were all over me again, rubbing my pants and giggling. I had th...

The Convenient Marriage Pt. 02

by CamilleShaw on Jun 2, 2020
Romance

"I know pronounce you Mr and Mrs. Carrington." Miri and Carter looked at each other in the courtroom. This was really happening, their marriage of convenience to save Miri's company. "Well," said Miri, "I'll be returning to the office to inform the board I now have control of the company." Carter paused, "You don't want to celebrate a little first?" Mir...

Erin on the Right Side of the Law

by BrettJ on Sep 15, 2017
Celebrities & Fan Fiction

Author's Note: While I actually received permission from Playboy model Erin Fox to use her name in the writing of this story, it is entirely a work of fiction. ~~ BrettJ * Erin Fox was not a happy girl. She had only been in Toronto for a day and had already got herself in trouble with the law. It wasn't her fault, the guy had it coming. Just because she wa...

1963

by cerection on Sep 16, 2017
First Time

I love to jerk off. I loved it the first time, and I love it thirty six years later. I hope I'll always love it. No matter what my lovers have thought, yes it's sexual, but it has absolutely nothing to do with my sex with them. My masturbating has nothing to do with whether I like sex with them, it doesn't mean I do or don't want sex with them. It's just tha...

No Contest

by JonJon237 on Sep 16, 2017
Celebrities & Fan Fiction

I, Travis Paul Johnson have been advised of my Miranda rights and my attorneys have been involved in my decision to make this statement. I am confessing of my own free will. The County Prosecutor has made no guarantee of the outcome of the felony charges pending against me. (Signed) Travis Paul Johnson, defendant (Witness) Arby Van Dyke, Detective, Chicago...

Crystal Clear Ch. 03

by Romantic1 on Sep 12, 2017
Group Sex

This story is part of a continuation of my Road Trip series (see the end of 'Road Trip – California' for a list of the chapters of that series, in order to be read). You need not read that series to enjoy this one. Although real places and celebrity names are used for realism, this story is fiction. Please 'read, enjoy, vote, and comment.' Synopsis of This...

I'll Be Around Ch. 02

by Rockwell on Sep 2, 2017
Erotic Couplings

The Centerfold Girl Jack and Jill picks up where they left but… Jack was in the shower singing along with the song “Bring Back The Pieces” by the Spiral Staircase playing in the phonograph in his room. After the shower, he dried himself with the towel and wrapped it around his waist. He looked into the mirror and asked himself whether to shave or not. He d...

Wife drinks cum at party

by aca089 on Jun 1, 2020
Loving Wives

Hi, I'm Jason and I would prefer to use this outlet to describe what has happened in my life, especially with my sex life with regards to my wife Beth. I wrote one previous story about what happened last year at my wife's college reunion (see "Her Bad College Days"). Since that weekend, I have done my best to forget what I saw. It had been on a video tape t...

The Wild Blue Yonder

by Moonraker_Bond007 on Sep 12, 2017
Exhibitionist & Voyeur

TO THE READER: this story includes several characters from the series of Jason Garrett stories; however, this story is not part of that series. Furthermore, with the exception of Hugh Hefner and Larry Flynt, all characters and occurrences in this story are entirely fictional. This story is not designed to be a true portrayal of military policy; however, th...

Bijou & Mackenzie Ch. 1

by ThomX on Sep 16, 2017
Celebrities & Fan Fiction

Mackenzie Phillips, who starred in the classic TV sitcom One Day At a Time, was finally getting her life back on track after years of drug and alcohol abuse. She was starring in a new TV show called So Weird (which was being described as a kiddie version of The X Files) and had other TV and movie deals in the works. Her sister, Bijou Phillips, had her own ac...