Mature ladies with great experience

Holly Peers - Vol. 6 - Set 2


The amazing Holly returns with more fabulous new studio shots in her sexy bikini...

Actually, the bikini is pretty much gone in this set, so there's pretty much just Holly left, but we don't think you all will mind that so much.
Holly Peers
MILF
Pics: 20
Name: hollypeers-vol06-set02_full.zip
Resolution: 3000x2000
Size: 17 Mb
Format: jpg

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Rachael C - Test Shoot - Set 2


Time to bring back our latest new dicovery, the awesome 32GG Rachael C, the blonde UK bombshell with the fabulous all-natural big boobs and a beautful smile to boot!

This is the follow up photo set to her fantastic debut and we couldn't be more happy to bring her back, so check her out here and look forward to more from this very special lady. 


Rachael C
MILF
Pics: 23
Name: rachael-c-test-shoot-set-2_1280.zip
Resolution: 853x1280
Size: 2 Mb
Format: jpg

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Tessa Fowler - Vol. 8 - Set 2


It's midweek and that means it's time to get back to work here...

And we need a whopping dose of all-natural 32GG Tessa Fowler to do it!

Yes, she is back and she is awesome, as always...

And if you really want to get a whopping dose of Tessa, check out what she has cooking at her very own exclusive website, TessaFowler.Com -- you won't believe your eyes.
Tessa Fowler
MILF
Pics: 20
Name: tessafowler-vol08-set02_1280.zip
Resolution: 1280x853
Size: 3 Mb
Format: jpg

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Holly - Vol. 2 - Set 1 - Busty boobs Halloween!


Wait a minute
Holly Peers
MILF
Pics: 30
Name: holly-vol-2-set-1-busty-boobs-halloween-_1280.zip
Resolution: 1280x855
Size: 6 Mb
Format: jpg

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Danniella Levy - Vol. 3 - Set 2


We always need beautiful gals with awesome big boobs around here, mid-week like this...

Especially after a long holiday weekend, where no one really wants to go back to work at all...

So we're happy to bring back super-sexy and stupendously-stacked 32GG Danniella Levy to lift us out of our Wednesday blues!

Danniella is back in the shower, wetting down and soaping up those big tits and doing it like only she can.  

This is defintely the way to go!

MILF
Pics: 23
Name: danniella-levy-vol-3-set-2_1280.zip
Resolution: 1280x853
Size: 3 Mb
Format: jpg

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Marie-Claude Bourbonnais - Vol. 2 - Set 1 - Busty boobed awsomeness!


After we debuted her back in September of last year, we got a LOT of requests to see a lot more of 34FF Marie-Claude Bourbonnais and her perfect body and awesome big tits, so it may be a little later than we might have liked, but as long last she has returned! Marie-Claude's perfectly round big boobs and a awesome slender frame make it easy to take great glamour photos and for this one she returns in fine form yet again, so enjoy these great new photos of this awesome busty babe!
Marie-Claude Bourbonnais
MILF
Pics: 46
Name: marie-claude-bourbonnais-vol-2-set-1-busty-boobed-awsomeness-_1280.zip
Resolution: 1280x853
Size: 7 Mb
Format: jpg

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Katie Thornton - Vol. 1 - Set 1


Welcome to December everyone!  It is by far our favorite month of the entire year because allthe incredible holiday-themed goodies that we spend all year putting together for you finally get to see the light of day and today we have one seriously amazing goodie to give you as an early holiday present: our incredible new model, the lovely 32J Katie Thornton!

Katie is -- you guessed it! -- another busty British babe who is lovely and sexy and has a pair of astonishing huge boobs that will make your eyes pop out of your head and your lips whispter the words "goodness gracious" (or something along those lines!) because she is a stunner.   

Katie has huge, soft, pillowy breasts and a saucy smile to match and we figured, since she's our new model for December, we may as well get her into a sexy holiday-colored outfit and set her by a warm fire and let her work her magic.  Once you see those fabulous big tits of her's busting out of her white bra, that will be all you need to make your holiday season just a little bit warmer.

And last but not least, a really special thanks to Katie for being so incredible!  You have definitely made our holiday season brighter, Katie, so thank you!
Katie Thornton
MILF
Pics: 31
Name: katie-thornton-vol-1-set-1_1280.zip
Resolution: 1280x781
Size: 6 Mb
Format: jpg

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Sara Willis - Vol. 5 - Set 1


It is December and as you all know we love to celebrate the end of year holidays around here at PinupFiles,  and we always have a terrific holiday themed updates coming for you the entire month of December and even beyond so this year is no different as we ratchet up the holiday cheer once again with another fine installment from the lovely all-natural 32GG Sara Willis, whose big bodacious boobs fill up our screens and our boob-loving brains once again.


We entitled this shoot
Sara Willis
MILF
Pics: 30
Name: sara-willis-vol-5-set-1_1280.zip
Resolution: 1280x855
Size: 5 Mb
Format: jpg

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Katarina Angel - Vol. 4 - Set 1


34GG Katarina Angel returns to our pages today with more amazing new photos!

We always love showcasing sexy all-natural glamour babes with incredible big tits, and Katarina is the perfect encapsulation of that ideal.

For this one, she dons a very tiny silver stretch bikini and lets her fabulous figure and huge honking hooters do the rest!
Katarina Angel
MILF
Pics: 23
Name: katarinaangel-vol04-set01_full.zip
Resolution: 2000x3000
Size: 24 Mb
Format: jpg

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Alyssa - Vol. 1 - Set 2


We are getting ready to crank things up on a Monday with another super sexy photo bomb from the lovely 32GG Alyssa, who brings her irresistible girl next-door good looks and awesomely huge pendulous all-natural big knockers back to us here once more, and all the while dropping our jaws in the process.


Alyssa strips down out of her sexy pink bra and gives us the full gander of her awesome charms in this one,  further proving the inalienable mantra that we have always believed: that there is simply nothing that stacks up to a super-stacked and slim gorgeous babe with all-natural big tits
Alyssa
MILF
Pics: 25
Name: alyssa-vol-1-set-2_1280.zip
Resolution: 1280x852
Size: 2 Mb
Format: jpg

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Jana Defi - Vol. 20 - Set 3


She is an absolute legend of glamour and one of our most popular models of all-time (for very obvious reasons) and we are very lucky to be able to continually bring you all great new previously unpublished shots of her from our deep archives of shoots we did with her before she retired, so with that in mind we bring you the luciously lovely 32GG Jana Defi, the all-natural super marvel of big breasted goodness!

Jana is one of those models who, when she first hit the scene, instantly floored big boobs fans around the globe with her sultry bedroom eyes, approachable girl-next-door good looks, and her jaw-dropping slim and stacked frame topped off by a pair of simply stunning all-natural huge tits that were firm and huge, yet soft and pillowy at the same time.  Just perfect.

Her boobs were so perfect that many fans out there refused to believe her (or us) that they were real -- to the point that we had to finally take her to a doctor to do a live on-camera ultrasound on her magnificent breasts just to prove it... and she STILL had doubters after that. ;-)

Well, doubters be damned because she is and was the real deal 100% and this new set of previously unpublished shots is a true testament to her enduring beauty and the power of her spectacular chest.
Jana Defi
MILF
Pics: 32
Name: jana-defi-vol-20-set-3_1280.zip
Resolution: 1280x853
Size: 4 Mb
Format: jpg

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Karla James - Vol. 3 - Set 1


Yes, it
Karla James
MILF
Pics: 31
Name: karla-james-vol-3-set-1_1280.zip
Resolution: 1280x853
Size: 7 Mb
Format: jpg

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Cara Rose - Vol. 3 - Set 2


Beautiful 30GG Cara Rose is back with another stunning new photo set!
Cara Rose
MILF
Pics: 19
Name: cararose-vol03-set02_full.zip
Resolution: 3000x2000
Size: 23 Mb
Format: jpg

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Lana Kendrick - Vol. 3 - BTS - Set 1


Okay, so who is ready to kick off their week with another super sexy big boobs splash from 32GG Lana Kendrick?   We realized that Lana looks best when she
Lana Kendrick
MILF
Pics: 30
Name: lana-kendrick-vol-3-bts-set-1_1280.zip
Resolution: 1280x855
Size: 5 Mb
Format: jpg

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Katie Thornton - Vol. 1 - Set 2


She is just too damn sexy and mind-blowingly busty for us to stay away from, as the lovely and awesomely endowed 32J Katie Thornton comes back to us yet again with another winner of a photo set, this being the second set from her debut shoot with us.  

We love Katie's huge tits, her sexy smile and cascading blonde locks, and she does us all right yet again with another winning set of shots today, and definitely gets us further into the holiday mood!
Katie Thornton
MILF
Pics: 30
Name: katie-thornton-vol-1-set-2_1280.zip
Resolution: 1280x838
Size: 6 Mb
Format: jpg

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Rachel Aldana - Pinup Cami Special - BTS - Set 1


Heya there guys!  My pals at PinupFiles told me they were going to feature a new behind-the-scenes set here today, and they asked me to do the little write-up for it, so here I am!  

 

I've been rolling along with things at my site, RachelAldana.Com, and I know how much you guys like the sight of big boobs on a Monday to help jumpstart your week, and the good news is that I have that part covered... or maybe "uncovered" is the better operative word, right?  ;-)  

 

My already enormous boobs have gotten even more massive, as I am sure you all have seen or heard and the good news for you is that they are bigger now than they have ever been before, so here is a true eyeful for you to get the blood pumping.  

 

Hope you have a great week and come visit me at my site, too!  

 

xoxoxo -- Rachel
Rachel Aldana
MILF
Pics: 27
Name: rachel-aldana-pinup-cami-special-bts-set-1_1280.zip
Resolution: 1280x853
Size: 5 Mb
Format: jpg

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Maggie Green - Vol. 21 - Set 1


It's only appropriate that we kick off our 10th Anniversary celebration with the gal who literally helped start it all, and was our very first model FIVE YEARS AGO when we celebrated our 5th Anniversary and wanted to have a "special treat" for our members. Little did we know that the response to all-natural 36F Maggie Green would be so overwhelming that we'd have to keep it going, featuring her again and again and the rest, as they say, is history. We love Maggie and can't believe it's been five years since we started creating our own original pinups and we can't thank her enough for truly helping to make all of this possible. This new sset is another stunner, and Maggie has never looked better or more spectacular, showing off in a tight pink T-shirt and jeans and bringing that amazing girl-next-door charm and beauty in spades!
Maggie Green
MILF
Pics: 29
Name: maggie-green-vol-21-set-1_1280.zip
Resolution: 1280x853
Size: 6 Mb
Format: jpg

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Maggie Green - Vol. 25 - Set 1


Welcome to not just a new Monday and a new week, but also a bit of a special occasion here at PinupFiles: it's is our 15th anniversary of being online!  Yes, as hard as it may be to believe, we went live for the very first time on April 4, 1998 and have been going strong ever since, obviously.  

 

It's also the 10th anniversary of our "original modern pinups" work --  for the first five years of our existence we only featured the retro 60's and 70's stuff that we used to do, but then as part of our five-year anniversary celebration, we published our first original photo sets with Maggie Green and Miriam Gonzalez and Barbara Moore as our very first models.   That endeavor was originally supposed to be just a one-time "anniversary celebration" special deal, but it was so popular with everyone that we had no choice but to keep it going, so the rest is history, as they say.  

 

And so, to commemorate such a special occasion, and since she was our very first model, we felt it was only appropriate to have the always awesome 36DDD Maggie Green appear today for her 25th volume of photos (a bit of a milestone in and of itself).

 

Yes, the mighty mountain-sized mammaries of Maggie are back for our anniversary, if truth be told we have been lusting after Maggie and her luscious large lungs ever since she first unveiled them for us way back in April of 2003.  Maggie's cute, undeniable girl-next-door qualities combined with those big firms tits has always cemented her as a perpetual favorite of ours and of our fans and members here at PinupFiles, so we felt it was only appropriate to celebrate our 15th year online and our 10 year anniversary of creating our own original super-hot busty Pinups with a beautiful new photo set of the gal who truly helped launch it all for us.   Maggie and her big, round, robust rack have been a symbol and icon of everything we set out to do here at PinupFiles for 10 years now and we plan to keep at it and bring you more in the best of sexy big breasted babes for another 10 years and beyond, so thanks to Maggie and also to all of you for helping make it happen!
Maggie Green
MILF
Pics: 40
Name: maggie-green-vol-25-set-1_1280.zip
Resolution: 1280x855
Size: 12 Mb
Format: jpg

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Sarah Nicola Randall - Vol. 1 - Behind The Scenes - Set 1 - Beautiful busty encore!


Happy Friday everyone!  We always love making the weekends a little more special for all of you, and to that end we are very happy to bring back the lovely and talented and oh-so-amazingly busty 32H Sarah Nicola Randall!  Sarah's sizzling smile, charismatic beauty and perfectly shaped H-cup big boobs have made her nothing less than an absolute smash hit with our fans, and now she is back once again in another fantastic photo set, showing off her incredible frame and amazing beauty and making us gawk once more at those incredible giant all-natural breasts of hers... that look almost too good to be true. Thank you for making our weekend, Sarah! 
Sarah Nicola Randall
MILF
Pics: 34
Name: sarah-nicola-randall-vol-1-behind-the-scenes-set-1-beautiful-busty-encore-_1280.zip
Resolution: 1280x855
Size: 7 Mb
Format: jpg

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September Carrino - Vol. 5 - Behind-The-Scenes - Set 1


Since she made her debut with us back at the very end of April, the shining star that is all-natural 28F/28DDD September Carrino continues to burn bright and win over fans all around the world. This hot new Playboy SE cover girl is a fresh face with a killer bod and rockin' boobs and this new photo set is a terrifically fun new behind-the-scenes venture that is sure to please! We've got some great shots of September as she gets ready behind the scenes in her tiny bikini, oiling up to get ready to go on camera, clowning around in the makeup room and having fun with her fellow models.
Jelena Jensen
MILF
Pics: 24
Name: september-carrino-vol-5-behind-the-scenes-set-1_1280.zip
Resolution: 1280x856
Size: 5 Mb
Format: jpg

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