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Year 1999 Archive — Digital PDF Downloads Available Now

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1976 … 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 … 2009
Playguy Jan 1999
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Playguy January 1999
Features
Coverman Cory: The Butt Next Door
Jason Dicaprio: Runaway Fame
Uncut Football Player's First Dirty Snapshots
Carlo Sartini's Fur-Lined Bottom
Playguy Feb 1999
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Playguy February 1999
Features
"I'll Show You Mine"
Plus: Junio Salazar Chris Madas Tito, Tony, Dylan & More Cute (And Eager)Guys!
Shopping Mall Confesses
Playguy Mar 1999
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Playguy March 1999
Features
Our Coverguy Talks About His First Double Penetration
The Return Of Brandon Lee
Sniffing Ryan's Privates
-Ethan Dain's First Time - "I Lost My Cherry To A Sailor At The Y"
Playguy Apr 1999
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Playguy April 1999
Features
Coverguy Jonnie Perrino
Jordan Austin Butt Sale
Plus: Peter, Jesse, Bob, Ash And Hiroshi Strip Down To The Bone
The Best Of 1998 Our Dirty Yearbook
Playguy May 1999
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Playguy May 1999
Features
9 Naked Newbies
Meet XXX Video Star Emilie Sands
Superhung Superstar Tony Donovan Spreads It
Video Virgin Chip Noll Loses It
Playguy Jun 1999
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Playguy June 1999
Features
Naked Horseplay With 9 Guys
Watch Playguy Pups Josh, Victor, Dirk, Lance, Steven And Kurt Rollover!
Coverguy Ladislav: First - Time Photos
The Return Of Beefalo Brad Houston
Playguy Jul 1999
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Playguy July 1999
Features
Coverguy Troy
Ken's Kinky Quickie
Our Dirty Map Of The Smut Superhighway
Adam Young's Growth Spurt
Playguy Aug 1999
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Playguy August 1999
Features
Coverguy Rick Darius
Blond Brian Begs: "Bang Me"
Amsterdam Strip
Plus: Naked Sammy's Email Address
Playguy Sep 1999
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Playguy September 1999
Features
18 Year-Old Czech Import Josef +9 Other Heavenly Bodies
Vic, Tim, Jake, Jose, Davey And Angel So Many Butts, So Little Time!
You Can Email A Playguy Model!
Comix, True Stories Website Madness And Way More Cool Stuff!
Playguy Oct 1999
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Playguy October 1999
Features
Coverguy Mark Logan
Dudley: Open 4 Business
James Reece: Open 4 Anything Wrestling Nephews
Raymond: Pet 4 Hire Dylan, Leo, Tommy And Trevor Burning Hot!
Playguy Nov 1999
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Playguy November 1999
Features
Coverguy Tyler
Little Brother Strips
Plus 5 More Playguy Pups: Josh, Jason, Gus, Mike And With Drop Trou!
Comix Websites, Dirty Flick And Other Neato Stuff
Playguy Dec 1999
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Playguy December 1999
Features
Coverguy & Centerfold Ashton Ryan Photographed by Rad Video
Homegrown: A Reader Strips
Sex Advice: How Can I Get Him To Rim?
Putting Out On Prom Night
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