Playboy Stories

4,151 results
Orientation
Length
Source
Infinite Scroll

Country Gin

by darvon86 on Sep 12, 2017
Humor & Satire

- Friday, October 31, 2013, California, just outside of Los Angeles - I finished up my email and closed the laptop. It's getting late, I better go carve the pumpkin and set it out for the kids to see. Why oh why did I ever buy this house out in the burbs? My accountant thought Real Estate would be a great investment for my sudden millions from the stock op...

The Bimbo Bunny Costume

by LincolnAndSunset on Sep 12, 2017
Fetish

Bunny Maria stood behind Tracy and sternly ordered, "Drop the towel." "Yes Mistress," Tracy said, happily letting a towel wrapping her naked body fall onto the oriental carpeted floor. She stepped out of the piled towel and continued to face forward looking at a painting above the room's fireplace that showed naked nymphs at play in a dark forest. She focu...

Salvation

by Ilbfita on Sep 17, 2017
Non-Erotic

I guess I was no different from any other guy growing up in the bad old '80's. Those were the days when greed was good, nice guys came second, and political correctness was yet to be thrust upon us. Life in middle class suburbia was comfortable rather than excessive, but with the increasingly intrusive advertising and an ever growing focus on lifestyle, wea...

An Englishwoman in Japan Ch. 05

by hal_tee on Sep 11, 2017
Novels and Novellas

I wrote this story for Tiffany. Thanks for all your help, Tiff. I hope you're pleased with the outcome. Chapter Five Yoko's telephone call this afternoon had come as a surprise. So did her invitation to tonight's dinner. There was a purpose behind the sudden arrangement, she'd said, something to do with an important client who had unexpectedly arrived i...

Hollywood Jim: The Early Years Pt. 09

by hollywoodjim on Aug 30, 2017
Erotic Couplings

Before he was "Hollywood Jim" in Los Angeles, he was a geeky kid with a funny nickname in the Connecticut suburbs . And before he had numerous starlets as friends, he had various girlfriends. Here then are the "Adventures of Hollywood Jim-The Early Years" * The New Hampshire small town I was in that summer was definitely your typical small town. Their ver...

Erotic Halloween Masquerade Ball

by HarryPerry on Sep 2, 2017
Exhibitionist & Voyeur

This is the first true story that I'm submitting to Literotica - well, it's mostly true. Real life is rarely as erotic as our fantasies, but this story exceeded my expectation. So that you know, I have only modified it to change the names of the people involved. With that said, here's a story of an Erotic Halloween Masquerade Ball that I attended back in the...

Amateur Photography

by Cold_Eyes on Sep 12, 2017
Exhibitionist & Voyeur

The best thing about the neighbor's pool wasn't that it was the biggest on the block or that it had a brand new heating system, but that Barbara Hamilton owned it. Now that summer had come and her husband had gone, it was time for Barbara to make the most of the warm weather. She lay face down, sunbathing on her raft. Thirty feet away, a shutter clicked. St...

Teenage Shenanigans

by JohnnyTightLips on Mar 3, 2017
Amateur

You are an extremely hot teen that has many friends, at least half of the school has either a crush on you, or once had a crush on you, possibly all genders, and the other half? They've probably thought about you many times. Your name is Ellis, your 18th birthday was on the 4th of December, which was yesterday, after many gifts from your family, and a rather...

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the bull, the legend

by Kaede on Feb 12, 2019
Erotic Couplings

this story is about Henry, a Millionaire who genuinely wants to be a playboy. He has an abandoned Adopted younger brother who never really lived in the spoils of the parent. they need to deal with their issues and help each other. Sascha is a Russian mobster who is a 3rd generation Russian mafia who also shares the same luxurious dream as Henry since his new...

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His fantasy

by Sexyml2015 on Jun 16, 2016
Fetish

Your sitting in a library one afternoon reading what appears to be a cookbook but your hiding a playboy while carefully playing with yourself. On the other side of the room is your friend Cindy and she sees what your doing so she takes the opportunity to get some blackmail on you she takes out her phone and starts taking pictures of you and by now you have y...

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