Playboy Stories

4,151 results
Orientation
Length
Source
Infinite Scroll

Playboy Files: Sable Gets Her Wish

by dfg1980 on Sep 16, 2017
Celebrities & Fan Fiction

This story is obviously of a fictional nature. It is not suitable for anybody under the age of 18. I hope you enjoy it. Feel free to email me with any thoughts or comments that you may have on this piece. The Playboy Files: Sable Gets Her Wish This is part one of a series that will take place over the course of nearly a decade involving various women of th...

Cougar and her Five Virginal Cubs Ch. 07

by SusanJillParker on Sep 19, 2017
Mature

Chapter Seven - Virgin No More "I thought you were a gentleman. You weren't supposed to peek, Freddie," she said giving me a serious look that wanted to make me get up and leave. "You weren't supposed to look. How dare you ogle my naked body? You knew there was no door to the bathroom, yet, you disrespected me by taking advantage of me by looking. How could...

Down the Rabbit Hole

by Jack_Love on Sep 15, 2017
Illustrated

"Micky, this is Tiffany, my friend I was telling you about," Jessica said, introducing a breathtakingly gorgeous girl I'd never met before. Jess was an old friend of mine from high school. Now we went to college together, and had come to a huge bush-party at one of our friend's parent's farms. There were over a hundred people there, many of which we knew, an...

Picture Perfect Playmate

by didier on Sep 17, 2017
Celebrities & Fan Fiction

You were having an online discussion with a fellow Playmate fan, discussing your all-time favourite Playmate, the sweet Black Playmate of June 1996, Karin Taylor. Of all the beautiful Playboy Playmates, that dark exotic Karin Taylor is the one that makes your white boy’s cock throb the most. You were discussing how good Playmates look in lingerie. But you we...

A Day to Remember Pt. 01

by StoryTeller1959 on Apr 15, 2020
First Time

I was a senior in high school at the time. My mother had kept me home an extra year as a child, so I was already well into my 18th year, and I was especially ready to move beyond the local school culture. We lived in a small neighborhood of Town Houses, a popular design of the 70's era, We had moved into the house when it was new just 5 years earlier. I ca...

Crystal Clear Ch. 01

by Romantic1 on Sep 18, 2017
Group Sex

This story begins the long-awaited continuation of my Road Trip series also posted on this website (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 I do make references to events and characters in that story to tie this story and that one toget...

Divorced in South Florida Ch. 06

by BoRaFL on Sep 13, 2017
Mature

I had discovered three wonderful women who showed their affection by sharing their asses with me, but I was having difficulty finding other new bedmates on my own. I was discounting the blindfolded lady because Lynn found her, and I did not know who she was. My failure to find bedmates was not caused by being overly selective or insisting on assplay games....

No Apologies Ch. 02

by ThomX on Sep 16, 2017
Reviews & Essays

Well, I had another conversation with my mother about my porn habit. It went pretty much the same as our previous conversation. She implied that I was somehow "disrespecting" her beliefs by looking at porn. I told her that that wasn't my intent, and she said she realized that (then why did you bring it up? I wondered). She emphatically stated that she had ne...

Semper Fi!

by Moonraker_Bond007 on Sep 13, 2017
Exhibitionist & Voyeur

To The Reader: Some scientists postulate that more than one universe exists. In fact, there are those who believe that there may be an infinite number of parallel universes that exist side-by-side. This would mean that an infinite number of you exist, in multiple different universes. This theory is so popular that a movie was actually made about it - 2001's...

The Circle Ch. 33

by SteveWallace on Sep 12, 2017
Group Sex

Chapter 33 – Renee does Playboy. Ellen The photographer and set that Renee was to use for Playboy were in Chicago, right near the Playboy mansion. Renee and Ellen were there three days, and most of that time from nine in the morning to six or seven at night, Renee told us she was either naked or wearing some frilly piece of lingerie that wasn't too differe...