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Stacey Poole Secretary Costume
All the busty chicks are celebrating Halloween on Pinupfiles this year, and that includes Stacey Poole! She is playing the sexy secretary with the tiny tie which actually makes her boobs look bigger than they already are. Now all I can think about is diving face first into those puppies. -
Monica Mendez Halloween Dress
Halloween 2016 is turning out to be amazing already, because Monica Mendez busts out her sexy orange dress for Pinupfiles. I mean she literally busts out of that dress, letting her huge milk pillows hang out and look like the most delicious melons in the world. I'm all about innuendos today. -
Jana Defi Busty Proper Pinup
When I think of Pinupfiles, I think of Jana Defi in a blue sparkle dress, dancing around the microphone and pulling her top down. Pinup is more than a beautiful woman, it's a seduction and an erotic story that show us beauties like Jana are really naked gems. -
Stacey Poole Red Tie Costume
Halloween is starting early at Pinupfiles and I'm glad, because Stacey Poole is playing the red tie secretary. She's the kind of secretary who answers calls while topless, thus halting business so people can see what happens with her boobs. Hint: they sway and bounce a lot! -
Demmi Blaze Ripped Blue Dress
Demmi Blaze is really heating things up lately, you know being a trail blazer and all. Sorry, I had to do a pun, but there's nothing funny about this ripped dress she is wearing today. Sure you might smirk, but once Demmi's huge boobs come bouncing out, you'll be drooling like it's your first time. -
Miriam Gonzalez Sweater Pinup
When I posted Miriam Gonzalez' Playboy set, I got many requests for more. Many of you may not know that Miriam also poses for Pinupfiles and she did a lot of seductive sets like this sweater and body dress gallery. Tight enough to give Miriam mega cleavage, but covers enough to make her a teaseworthy vixen. -
Chloe Kendall Is Back In Red
I'm doing a happy dance right now because Chloe Kendall is back on Pinupfiles! Even better is that she's wearing a sexy red bra and booty shorts, making her ass really pop but I know what you came here for: Chloe's big boobs coming out to play. It happens, and it happen up close. -
Cara Ruby String Bikini Pinup
Summer '16 is proving to be damn good for busty girls and tiny bikinis. Cara Ruby has a brand new gallery on Pinupfiles which showcases her curves in a very tiny red string bikini, so tiny in fact that Cara feels like rolling around in the grass as if she were naked. -
Beth Lily Freedom and Boobs
This week has been all about freedom, so who better than Beth Lily to show us the real definition of independence as she frees her large boobs from that tight dress. I've seen many tight outfits in my life, and very few touch what Beth is wearing today. -
Beth Lily 4th Of July Boobs
This one goes out to all the Americans celebrating the 4th of July, and Beth Lily is too! I love the idea of freedom and independence because when Beth sets her boobs free, my pants start to understand independence. Get it? Ah hell, just look at Beth's big bouncy boobs. ;) -
Demmi Blaze Big Wet Boobs
The first time we saw her, we were just getting started. Now that Demmi Blaze is warmed up, she is more comfortable in her skin and takes her big bouncy boobs for a nice dip today. As Demmi slowly gets out of the pool, we can watch water dripping down those perfect pillows. Who else loves that? -
Demmi Blaze String Bikini Tits
Since finding Demmy Blaze on webcam, I've fallen in love with this curvy Ukranian beauty. Then I hopped on Pinupfiles and saw Demmi in Los Angeles, at the pool in an extremely tiny silver bikini that barely covers her huge boobs. Luckily for us, it's hot outside and Demmi cools off in the pool topless. -
Sha Rizel Upclose Nudes
As I was browsing around Pinupfiles today I came across a set of Sha Rizel I've never seen before. Let me ask you, do you like upclose pictures? Good becuse the camera gets REALLY close to Sha's big bouncy tits and her freshly shaved pussy. Yep, these angles are about the sexiest damn thing I've seen. -
Samanta Lily Lap Dance Videos
I'm ready to enjoy Samanta Lily in motion, starting with her blue stretch lap dance where tons of groping goes on. Then we move onto Samanta's other intense red rider lap dance where she proves big boobs really are more fun to play with. -
Stacey Poole Perfect Pinup
Stacey Poole is back on Pinupfiles to prove that she's more than just big boobs, because her ass looks so fucking good in that lace thong. In fact, I am seriously thinking this set shows off her curves perfectly as she strips down and puts her big boobs right up to the camera. It's like you can practically taste them. -
Katie Marie Cork New Model
Put a cork in it they say, so Pinupfiles did one better: they found Katie Marie Cork. She is a brand new british model who has similar features to Jana Defi but she is easily one of the sexiest new models of recent times. This is just the preview too, so wait until next week and the unveiling of her huge boobs. -
Leanne Crow Plays Games Topless
Next time you play a video game and get angry because you got beat, just watch this video. It's actually Leanne Crow on the other end and she plays games with her boobs out. I can't attest to her skill level but I bet she would pwn many noobs if everyone saw what we see today: big bouncing boobs and a lot of fun games. -
Jo Paul Pink Pinup
I feel like we are seeing a different version of Jo Paul than we did last week. She plays the perky pinup next door, wearing the tightest tank top possible because if there's one thing that Jo Paul loves, it's busting out of her clothes. If part one is this good then I can't wait until part two! -
Beth Lily Busting Out Bikini
I gotta hand it to Beth Lily, she can be the most interesting person just by holding her boobs. It also helps that she's literally busting out of this string bikini today, which leads me to believe that Beth buys clothes one size too small for this very reason. -
Pinupfiles Holiday Boob Videos
When it comes to celebrating the holidays, the ladies of Pinupfiles know how to do it right. We start off with Sha Rizel's infamous christmas set, then quickly move onto Tessa Fowler shaking her boobs, and finally one of my favorite christmas videos of all time: Stacey Poole's boobs popping out of her christmas corset. Ahh I love the holidays. -
Erica Campbell Christmas Pinup
Merry Christmas, Happy Holidays, and Happy boobs! I decided to choose Erica Campbell for our christmas eve pinup because she is one my favorite models of all time, looks damn good in her bra and panties, and she always gets naked with a big smile on her face. That's what the holidays are all about. -
Anya Zenkova Bubble Bath Pinup
As I was browsing around the Pinupfiles archives, I found an amazing set that Anya Zenkova did and it ignited the spark I have for her. Let me just say this, I miss Anya and her huge boobs, natural body, and the rare time she sported a landing strip. It's now made even better in the bubble bath. -
Chloe Kendall Bikini Pinup
Third time is definitely a charm with Chloe from Pinupfiles. She wants to show off her new gold bikini this week, and I have a feeling Chloe bought this from the "Bikinis so small, they don't exist" store, which is actually a store I want to exist. So on that note, what do you think about Chloe by the pool? -
Beth Lily Firewoman Costume
I don't think Beth Lily will be putting out any fires wearing this firewoman costume, infact I believe things will be heating up. That's ok, this is just a preview of what many busty girls will be wearing for Halloween, but not many will be able to top Beth's incredibly large boobs spilling out. -
Samanta Lily Sexy Cop
Imagine if you got pulled over and saw Samanta Lily dressed in this sexy cop outfit. I won't lie, I wouldn't mind if she frisked me dressed like that. We've seen our fair share of models playing the frisky cop, but Samanta really takes boob enforcement to a whole new level. -
Chloe Topless Studio Shots
You know it's going to be a good day when you see Chloe from Pinupfiles completely topless. The simple things in life really are the best, and when it comes to true busty beauty, Chloe is the ideal. Can you tell I'm crushing on her like crazy? -
Samanta Lily Lapdance Rider
The screencaps were amazing, but the high quality pictures are even better. Of course I'm talking about Samanta Lily's lapdance for Pinupfiles, which is filled with tits, ass, and plenty of groping that I wish I was doing! Seriously, I'm jealous. -
Summer 2015 Pinup Videos
It's that time to showcase the latest Pinupfiles models in motion, which includes Chloe's test shoot, Beth Lily's strip tease and saving the best for last, Samantha Lily's insatiable lap dance. These videos just keep getting better and better! -
Beth Lily Tiny Bikini
Beth Lily returns to Pinupfiles in the most awesome bikini ever. Yes I'm saying that because I have fantasies of rubbing lotion all over Beth's body, but after you get a look at her massive cleavage and tanlined booty, you will have the same fantasy. -
Samanta Lily Lapdance Screencaps
This is the moment we've all been waiting for, ultra rare screencaps of Samanta Lily (aka Samantha Lily) giving a very sensual and long lapdance as her boobs get oiled. Ever imagine groping this lovely lady? Look no further, that fantasy has come true. -
Chloe Bubbly Pinup
Chloe from Pinupfiles returns with some high quality pictures, and she is looking damn good in that test studio. Sometimes all you need in life is a bubbly girl with huge boobs, slowly taking off her top until those puppies come bouncing out. The simple things count. -
Beth Lily Topless Pinup
Welp, it's safe to say that seeing Beth Lily topless in her newest Pinupfiles gallery proves she is wifey material. Imagine waking up to that cute smile and huge boobs every morning, talk about the perfect morning. Hell I would even skip coffee for Beth's boobs! -
Chloe Pinup Test Model
Pinupfiles is keeping things fresh with it's influx of amazing new models (Beth Lily and Jo Paul), so when I found Chloe debuted today as a test model, I nearly fell out of my chair. This small preview feels like something big because Chloe is beautiful, busty, and having a damn good time. -
Jo Paul Blue Lingerie Boobs
I knew Jo Paul's return to Pinupfiles would be fruitful, considering how quickly she lets her huge perky boobs out to play, and yes, she puts them real close to that fish eye lense. Let's just say if your dream is to get a faceful of Jo's boobs, mission accomplished. -
Beth Lily Pinup Debut
Beth Lily (aka Charlie B) may not be new to the scene, but her Pinupfiles debut is definitely her most mind blowing piece of work. I thank whoever invented the fisheye lens because seeing Lily's boobs this close up is giving me the goosebumps, and I love her choice if panties. A nice thong for a nice round butt. -
Stacey Poole 4th of July Bikini
Today is all about stars and stripes, but there's a third theme that is thinly veiled in american culture: BOOBS! That's right, today is the day we also celebrate big bouncing boobs in the form of Stacey Poole wearing a skimpy bikini. It doesn't end there because September Carrino and Antonella Kahllo join in on the freedom from clothes fun. -
Ellis Attard Bikini Pinup
It's been a good year for busty newcomers and Ellis Attard is now added to that list. This busty bikini beauty is quite happy to be posing for Pinupfiles, and this is a chick who is a bit prude but she has no problem flashing her boobs for the site, and I must say, they are awesome boobs. -
Jo Paul Blue Lingerie Pinup
Even though we've seen Jo Paul naked already, I feel like we are getting a brand new view on her Pinupfiles debut. Jo is ready for the summer and decides to hang out by the pool in her sheer blue panties, which shows off that legendary landing strip in the sun light. -
Jana Defi Pinup In Bed
What started out as a gloomy day for me turned amazing instantly when I saw a brand new gallery of Jana Defi on Pinupfiles. The bow in her hair seals the deal, and the low cut top really brings her huge boobs out, quite literally.
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