Latest Updates
Thursday, December 29th 2011
13
Playboy Leola Bell
We featured a gallery of Leola not long ago and now you get to see a behind the scenes look at one of her photoshoots.
Monday, July 23rd 2012
25
Boob Shennanigans with Sabrina
Apparently Sabrina likes her boobs so much she just can't leave them alone. Her favorite thing seems to be squeezing them in between things!
Wednesday, June 24th 2015
15
Jo Paul Gets her Sizeable Breasts Out by the Pool
Behind the scenes footage of a topless photoshoot for Pinup Files. We are not kidding when we say sizable, those things are huge!
Friday, January 13th 2017
13
Lexi Washing Her Impressive Tits
Lexi's midway through a bath which puts her in the perfect position for a look at her curvy body. I wonder if she needs help rinsing off..
Thursday, November 26th 2015
24
Study Time Turns Into Make Out Time
Aurora was busy on her laptop when Ava decided she wanted some quality time. I think these two have done this before.
Monday, October 2nd 2017
30
Milla Plays Basketball and Proceeds to Strip
Her shooting technique may need some work but her stripping game is on point. Also those boobs are on point too.
Monday, May 11th 2015
14
Cara Strips Out of her Lingerie
We introduced you to English model Cara a few weeks (click here), but this video by Playboy may just be even hotter. 2 isn't a great sample size but she seems to like her red lingerie.
Tuesday, August 2nd 2016
16
Nicole and Anikka Take Off Each Other's Jeans
Two hot blondes, tight jeans and lots of attitude. They don't even make it past the door before undressing each other and getting personal.
Wednesday, May 27th 2015
10
Singer Flashes her Boob at a Live Concert
We skipped it right to where the magic happens so you don't have to sit through 3 minutes of the song. You're welcome.
Tuesday, August 23rd 2011
14
Jasmine Sinclair Scenic Boobies
What a view! And I'm not just talking about glamour model Jasmine Sinclair, although she helps too..
Tuesday, August 9th 2016
Jemma Trades a Look at Her Boobs for a Ride
Jemma's excited about going out but not about paying for a taxi. She wants a ride but her roommate's got his own needs.
Friday, July 26th 2019
16
Lauren Has a Treat for an Old Crush
After a night out at a college reunion, Lauren's old flame was optimistic. It didn't work out like they thought but they got a helluva consolation prize.
Thursday, March 16th 2017
21
Elizabeth Takes Off Her Fuzzy Sweater
Elizabeth likes an audience when she's getting undressed and that's great because we like watching her. Fun girl with big, natural boobs.
Wednesday, February 1st 2017
Any Ivy Gets Pranked By her Boyfriend
She takes it well but plans revenge right away. The best part is watching her bounce around after she gets out of the shower.
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