Content Tagged with "boy"

favorites 11
Sexy:
Added: 05/04/2015

Playboy's Amateur Mash-up

More naked hotties than you can shake a stick at. On second thought that may not be true. I'm sure some of you are masters at shaking sticks.

favorites 4
Sexy:
Added: 04/21/2015

Sexy Bunny Kaley Kade

Cute Kaley Kade has dressed up as a sexy Playboy bunny just so she could strip down, just for out viewing pleasure.

favorites 25
Sexy:
Added: 04/13/2015

Playboy Casting Session at the Playboy Mansion

Have we got a treat for you to start the week! A long video showing just how much fun a Playboy Mansion can be. Spoiler: a ton of fun.

favorites 0
Sexy:
Funny:
Added: 04/08/2015

Playboy TV 7 Day Free Trial Offer

This just landed in my inbox so I had to share it with you. Playboy TV is the best site out there for fun sexy content. We'll be featuring a clip from a different show each day for a week!

favorites 5
Sexy:
Funny:
Added: 12/24/2014

Twas the Night Before Christmas.. as Read by Playboy Models on a Sybian!

The guys at Simple Pickup have outdone themselves yet again. I'm actually amazed YouTube lets this one ride (ha!)..

favorites 3
Sexy:
Added: 10/02/2014

Hottest Playboy Girl on S&F

We took the 50 best rated Playboy galleries and made what is possibly the hottest battle yet out of them. Lets see who comes out on top of this very fine bunch of ladies.

favorites 3
Sexy:
Funny:
Added: 09/15/2014

Cocky Cowboy - Must Watch

In the Wild West, we follow the comings and goings of a cocky cowboy who falls in love with a Diva. This was really, really well done. Best viewed in Full Screen mode with HD on.

favorites 6
Sexy:
Funny:
Added: 05/26/2014

Two Topless Girls Tell Dirty Stories

Playboy Radio did this competition for March Madness (they creatively called it March Badness). Which story do you think is badder, sneaky shower sex or mile high threesome?

favorites 8
Sexy:
Funny:
Added: 04/25/2014

Topless Tricycle Obstacle Race on Playboy Radio

Two girls take on the obstacle (to getting laid) course, which includes a whiskey dick, time of the month and my favorite, cock block.

favorites 17
Sexy:
Funny:
Added: 11/05/2013

Know It or Show It Stripping Game

We haven't had a clip from Playboy Radio in far too long, so here's a good one to make up for it. As with all games where hot girls strip, we are the real winners..

favorites 12
Sexy:
Added: 08/05/2013

Naked Playboy Bunnies Take on a Water Jet Pack!

Now that's badass, which is kind of appropriate given that's the name of the show. The second chick has quite an impressive wipe out.

poll favorites 11
Sexy:
Funny:
Added: 06/28/2013

Spelling Bee, C's and DD's

Spelling Bee with a difference. That difference being that the ladies take off their tops to reveal their various sized boobs if they get words wrong.

favorites 7
Sexy:
Funny:
Added: 06/24/2013

Count the Mooseys Contest Solution!

So despite all the entries nobody got it spot on. However two people were only one away, and as per the rules the first one is our winner! And that person is...

favorites 5
Sexy:
Funny:
Added: 06/17/2013

Count the Mooseys Contest! Win a Playboy Plus Membership!

All you have to do is count how many times a moose appears in this Playboy Ass Compilation video and you win a membership. Simple right? Read under the video for the full rules!

<< < 1 2 3 4 5 6 7 > >>

Spotlight

favorites 185
Sexy:
Funny:
Added: 11/05/2011

Fast Car Causes Girl to Bust out of her Shirt (Extended Version)

We posted this video on Halloween, but thanks to a tip off by GBW, we can now bring you the extended version which shows more boob!