Playboy Stories

4,151 results
Orientation
Length
Source
Infinite Scroll

Black Women and Me

by mgwauthor on Sep 12, 2017
Interracial Love

It started when I was in junior high - my excitement whenever I saw a hot black woman. There was a Playboy special issue I somehow got my hands on, with cover to cover photos of girls from all around the country. While I loved all the Playmates, my attention drifted to a few - black girls. Playboy, then and now, specializes in white girls, so it was always a...

Office Sluts: The Flight

by sandymonroe on Sep 19, 2017
Group Sex

I could hardly believe it; we were the only ones sitting at first class. Our flight attendant told us something about the current economy and the night flight, but I didn't really pay her any attention. I enjoyed the large space and I was happy Walden, Inc. paid the first class tickets for the three of us. There were Bonnie, Carl and me arranging our bags i...

Octo Pie

by PrevertOne on Sep 12, 2017
NonHuman

(Inspired by Deep Diving 2 by Octopus 2099) by The Preve Thanks to Jon B 1969 for the edit. Rikki Jorgensen, a 21 year old Minneapolis college student, was vacationing on the Caribbean island of St. Dellacroix, when she unexpectedly vanished. As she was a beautiful young blonde haired, blue-eyed woman, her disappearance made front pages stateside. St. Del...

Adventures of Jenny McCarthy Ch. 1

by jzelger on Sep 13, 2017
Celebrities & Fan Fiction

Chapter 1: PLAYBOY [The following is a never-before-printed excerpt from a magazine interview with Jenny McCarthy. It was never published for obvious reasons. Other excised portions of the interview will be revealed later, if readers are interested] Posing in Playboy changed my career, but it changed me personally, too. INTERVIEWER: How do you mean?...

The Deviant Girls Go Wild Pt. 01

by Obobby on Jan 20, 2020
Group Sex

Almost three years after the events of The Deviants Club, much has changed for the three young, sex-positive, bisexual women, but their hunger for sex has not. A Mile High Halfway through the flight to Cancun, Heather sat in the comfort of her first class seat, her long, red hair falling down the left side of her freckled face, concealing from the man on h...

My First Time

by uticanyrick on Aug 18, 2017
First Time

My first time was with a big girl, and I've been a chubby chaser ever since. I remember the first time I had sex as if it was yesterday even though it was a long time ago. My parents had a summer home on Otsego Lake in upstate New York . Which is the lake Cooperstown N.Y. is on. The baseball hall of fame is located in Cooperstown. Our summer home was about...

Momentum

by RelentlessPerversion on Sep 14, 2017
Group Sex

The Metro The metro car lurches slightly, its momentum causing Carolyn to brush against me ever so slightly as we grip the poles to keep from toppling into each other. There is electricity to her skin, I can almost feel it radiating off of her. "It isn't about the sex," she says softly, the last word nearly a whisper as we hold the handrails tightly. There...

Adventures of Hollywood Jim Ch. 47

by hollywoodjim on Sep 18, 2017
Celebrities & Fan Fiction

East Coast Image had shut down operations for the Holidays. Chris and I were heading back east to see our families. I was eager to get out of town for at least a week. Ever since the Dark Hills project, things between us had started to sour and there was a definite edge to everything. I felt like anything I said or did would set him off. Chris and Marty O'Br...

Red Rock Canyon Ch. 06

by LuciousBi-Writes4U on Sep 13, 2017
Exhibitionist & Voyeur

Red Rock Canyon ~Ch 6~ "The Magnum Man" ***** The fun and games couldn't help but continue outside the tent. After Paige and Rex listened to the muffled sounds coming from the tent for more than an hour as they tried not to let it get to them. They tried not to look at the shadows that rose from the sides of the tent in the glow of the lantern light. They...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...