Playboy Stories

4,151 results
Orientation
Length
Source
Infinite Scroll

An Open Letter to Anja Josephsen

by MasturbationSuperstar on Sep 16, 2017
Letters & Transcripts

Anja Josefsen is my all time favorite Penthouse Pet. In the past I have emailed the folks at Penthouse asking how I could write to her and was told that they had lost touch with her and don't know of a way to contact her. Since Penthouse hasn't kept in touch with her, I'd like to present this open letter to Anja Josefsen in hopes that she is out there, Goog...

Lesbian Empress

by LesbianMuses on Sep 14, 2017
Humor & Satire

You know you're a Lesbian Empress: When you realize anytime someone messes with you, it's like Helen of Troy. There's an army of LezBro's crossing oceans to battle for your honor. When your LezBro kicks the A$$ of some jerk-off that won't leave you alone, you starting singing, "Hey now, hey now. My LezBro's back!" You sing this unfazed in the middle of the...

Adventures of Hollywood Jim Ch. 13

by hollywoodjim on Sep 18, 2017
Celebrities & Fan Fiction

Bridget Marquardt and I slowly regained our strength. The cool air of the bungalow made it easier. I rolled over and looked at her lying there, naked as I was. "I forgot how good that felt." She said with a smile as she looked at me. "Me too." I replied. Bridget sat up and stretched her arms out, her tits still looked so inviting. But my dick needed time...

GTA: Bitches of Liberty City Ch. 04

by Buzzboy on Jan 23, 2019
Celebrities & Fan Fiction

"Retrieve" In the last half-hour, Allie does an occasional glance at the manager's office door when not distracted by the strippers on the stage or the strippers who just happen to casually walk past her and Hector's table. Her focus switches back to the office when she spots a black man in a mostly red but gaudy multi-colored hoodie walk out thought the d...

Erotic? No. Soporific? Yes.

by fardreamer on Sep 16, 2017
Reviews & Essays

Warning: This review deals with a DVD which contains "erotic" material, and as such contains references to nudity, sexuality, and other topics which may be offensive to some readers. Part One: Sex, Money, and Balancing Budgets, or, Why I Own this Awful DVD... Like most adults my age (I'm 41 as I write this), I've had more than a passing interest in sex, n...

Tell Me A Story

by isfly on Sep 13, 2017
BDSM

"Tell me a story," Daddy whispers in my ear. It is our second night in Vegas and my man and I are lying naked in bed after an evening at the Playboy Club. As I rub his cock, I open my mind and let the fantasy that's been hiding there flow out... Daddy can see me surveying the club, my eyes wide taking everything in. Then he sees my focus narrow and sharpen....

The Amnesiac Overlord

by TheNextGamer on Nov 3, 2019
Fetish

It all seemed like a blur, to be honest. I have no idea what the hell just happened to me. One moment, I was driving my parents to my sister's high school graduation ceremony, and the next thing I could remember was some sort of explosion. Some glass from the front panel must have lodged itself into my face or something. I distinctly remember that much, at l...

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First Explorations

by MrShyTown on Sep 12, 2017
First Time

The boy was newly 18, and had the run of his father's house for almost a full week. His newly acquired, and for that matter his "girlfriend" Melissa, his first ever, was prone to showing up at his door late at night unannounced, essentially looking to make out. The boy didn't mind this at all, of course, but as the living room was bounded by windowed French...

Adventures of Alice and Alex Pt. 01

by AlexCarroll on Sep 14, 2017
Exhibitionist & Voyeur

These are some of my sexual adventures with Alice in the late 1970s, beginning when we had just moved into a new shared rental with a few friends, after already living together for about 18 months. Up to this point our sex life had been active- but irregular; as a nurse Alice worked shifts and we had to make the most of our opportunities. Sometimes this was...

Unbreak My Heart

by TexPlayboy on Sep 16, 2017
Romance

How do you start a story that has no beginning? How far back do you go when everything has been a part of this moment? Do you start with the first time you fell in love and your heart was broken? Do you start with the fears of abandonment when you first learned of your parents pending divorce? Or do you start with the phone call that scared and excited you w...