Playboy Stories

4,151 results
Orientation
Length
Source
Infinite Scroll

Cougar and her Five Virginal Cubs Ch. 05

by SusanJillParker on Sep 19, 2017
Mature

Chapter Five - The Seduction Cougar strips naked in front of her cub. I followed Kathleen to her apartment. Her place was nice but in disarray because of her painting project. Just a one bedroom flat with an eat-in kitchen, a living room, and a bathroom, her apartment was small but plenty big enough for just her and her little dog. Looking out her windows...

Sandi

by TDR2000 on Sep 13, 2017
Erotic Couplings

This is a story of one of those 'first-time' experiences that all guys have dreamed about having and, I should imagine, the kind a lot of girls fantasize about giving. It happened to me when I was a lot younger than I am now and sex was an entirely different game... At the time I was still a lustful and vastly inexperienced teenager living with my parents a...

The McGuire Brother's Sister

by Egmont Grigor on Sep 1, 2017
Humor & Satire

ONE A stranger came into town on a hot and windy day, just as drifters did in the Old West, well over 100 years ago. "Howdy, stranger," greeted the bartender, the tops of her breasts showing above scooped low neck of her flimsy top from Celine's of Paris (Texas). The height of the bar concealed her bare belly and scruffy tennis shorts. "Beer, or whisky?"...

Double Switch Ch. 16

by Just Plain Bill on Sep 16, 2017
Novels and Novellas

A Note to the reader: Double Switch is a full length novel with a Prologue, an Epilogue and 18 chapters. So it will take a commensurate time to read. It is erotic in places but not on every page or even in every chapter. So, a little patience is necessary. It is a love story, actually three love stories. I hope you will be rewarded for your time and trouble...

A Best Man's Duties Pt. 02

by dalton_rick on Sep 2, 2017
Exhibitionist & Voyeur

This second part focuses on the bachelor party and a comparison of the old porno films and the new ones. It is also about the generational differences and what was considered sexy through recent history. And of course, what is a good bachelor party without a little teasing of the groom? It is a bit twisted. I liked to rile up Steve. He got mad easily but...

Bionic Stud: When Lance Met Sandra

by Rubirosa on Aug 6, 2018
Erotic Couplings

NOTE: For those of you joining us for the first time, this story is a vignette from Rubirosa's series "C*ck Star." The chronicle focuses upon the private life of a public figure. As the most accomplished porn star of modern times, SAMSON lives out popular male sex fantasies on a daily basis. This story focuses on our hero's youthful exploits as an everyday h...

Sultry Sirens

by long on Sep 4, 2020
Interracial

Your first few days at State College felt lonely. One roommate was always away hanging at his older brother's fraternity. The other was already back at home, unable to be apart from his old high school girlfriend. But you came upon an intriguing poster at your entry way. The Sultry Sirens, State College's only all-girls choir, was looking for male soloists f...

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A Devious Woman

by Professorredbottom on Jul 9, 2019
Illustrated

This story is total fiction, occurring between those of adult age engaging in spanking that has the appearance of traditional discipline, but is turns out to be a platform for eroticism. Alberta Bennington watched through the crack in the bedroom door. She watched intently, delighted, as her plan came to life right in front of her. In a few minutes she wo...

Great Divide

by meganmurphy on Aug 30, 2017
NonHuman

Claire walked into her editor's office. "You wanted to see me, Sam?" she asked as she sat down in the chair in front of his desk. Sam looked at Claire over the top of his glasses. "I sure do. I had a great idea last night and I think you're the one to make it work." Claire started to get up. "Oh, no you don't. I remember your last idea all too well. 'A...

Playmate on Playmate Love

by didier on Sep 17, 2017
Celebrities & Fan Fiction

The Playmate of the 90s reunion photo shoot ended. Plied with liberal rounds of champagne, the buzzed Playmates did a fantastic shoot, in their bathing suits, in their lingerie, in the nude. As the day closed, the tipsy Playmates, photo crew, make-up artists, and hangers on all drifted away to party and to return to their separate pursuits. Karin Taylor and...