Mature ladies with great experience

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Danielle Riley - Vol. 7 - Set 2

It is no secret that we absolutely love gorgeous women with all-natural 34DDDs, and that is why it is also no secret that we absolutely love 344DDD Danielle Riley, she of the British lineage (what is it with these U.K. gals anyway?) who is not only incredibly sexy but an incredible crack-up on the set as well. We love Danielle, we love her boobs and sexy body, and this brand new photo set shows exactly why...
Danielle Riley
MILF
Pics: 19
Name: danielle-riley-vol-7-set-2_1280.zip
Resolution: 1280x838
Size: 3 Mb
Format: jpg

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Sammy Braddy - Vol 04 - Set 2

Happy mid-week everyone!

We are back on a Wednesday here to get you pumped up and ready to head into the back-half of the week and the weekend with something extra special in the form of all-natural glam legend 32GG Sammy Braddy!

Sammy is back with the second half of her Vol. 4 shoot and wow... we really run out of superlatives when describing this amazing big bust babe.
Sammy Braddy
MILF
Pics: 20
Name: sammybraddy-vol04-set02_full.zip
Resolution: 3000x2000
Size: 24 Mb
Format: jpg

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Jana Defi - Vol. 21 - Set 1

Time to keep it going this Halloween season with a sexy Halloween-themed costume outfit from one of our hottest and most incredible glamour gals of all time...

The impossibly awesome 32GG Jana Defi!

Even though she is long retired, she lives on here at PinupFiles in the most amazing ways and this new set of shots is one of her best ever.

Channelling long-legged and impossibly busty cartoon icon Jessica Rabbit,  Jana Rabbit shows off her incredible frame and astonishing big boobs and her sulty beauty and dazzling smile...

And we'll just stop right there and let you see the rest for yourself!
Jana Defi
MILF
Pics: 28
Name: jana-defi-vol-22-set-1_1280.zip
Resolution: 1280x853
Size: 4 Mb
Format: jpg

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Brianna Jordan - Vol. 1 - Set 1 - New big tits babe at PinupFiles!

Happy Friday everyone! As you all no doubt know by now, bringing you a brand-new hot and sexy big breasted babes is one of our favorite pastimes here at PinupFiles and this month we have a gal who is not only sexy and not only has the big boobs, but also has a huge firm round booty to match!  In fact, she told us that guys seem to like her nice firm heart-shaped ass more than any of her other body parts!  Well, since we're always getting feedback from you all about how we don't feature enough of the booty, we figured this gal would be a nice welcome to that end (pun intended!) so please join us in welcoming the lovely and talented 34F Brianna Jordan!  Brianna bring the booty and the curves and the sexy in spades and is a fabulous combination of big boobs and bigger butt! ;-)
Brianna Jordan
MILF
Pics: 29
Name: brianna-jordan-vol-1-set-1-new-big-tits-babe-at-pinupfiles-_1280.zip
Resolution: 1280x854
Size: 6 Mb
Format: jpg

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Monica Mendez - Office Girl - Set 1 - Bringing the big boobs into the office!

Happy Monday guys!  It's me here, 34G Monica Mendez coming at you to start your week with a bit of a departure from our normal photo update in that I am here with a very special candids photo set here at PinupFiles -- it's me behind-the-scenes in the office!  As you can plainly see from all our amazing models, you know well that we have lots of big boobs in front of the camera but the other part of the equation is that we have plenty of big boobs behind the camera and behind-the-scenes as well!  A lot of our models work on the photos, on our photo crew, on wardrobe and outfits and hair and makeup and not only that, but we also do a lot of the photo and video editing as well!  This particular set is of me at the office having a little hair and makeup done (I do that every day at the office, believe me!  and then at the editing bay with all our computers where we edit all these terrific videos you see every week.  I was working on this upcoming one from our awesome new gal 32JJ Wendy Fiore and it is a hot one!  I know you guys are really going to like it, so I can't wait to show it to you.  And then of course I have to take my lunch break during the day, so I have a few shots of me in the car as well, just for good measure...  hope you like 'em and stay tuned for some awesome new behind-the-scenes video as well!  xoxoxo -- Monica
Monica Mendez
MILF
Pics: 27
Name: monica-mendez-office-girl-set-1-bringing-the-big-boobs-into-the-office-_1280.zip
Resolution: 855x1280
Size: 5 Mb
Format: jpg

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Leanne Crow - Boob Measuring 2017 - Set 1

One of the big questions we always, always, ALWAYS get asked is...

"How big are _______'s boobs?"

Well, obviously they are all different, and other than to say they range from "big" to "huge" to "massive" the one commonality is that they all belong to some pretty awesome women behind them, and today we feature TWO of them together as 32K Leanne Crow (or is she bigger? ;-) gets her humongous boobs measured by none other than 32H Monica Mendez!

We can't recall exactly what Leanne's measurments are, if only because our heads are still swimming after watching this go down, but suffice to say that watching Monica try to wrap her arms around Leanne's mighty chest is truly a sight to behold.

And don't forget to check out both of these fabulous busty babes and their own respective websites, LeanneCrow.Com & MonicaMendez.Com! 
Leanne Crow
MILF
Pics: 23
Name: leanne-crow-boob-measuring-2017-set-1_1280.zip
Resolution: 1280x853
Size: 3 Mb
Format: jpg

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Alyssa - Vol. 2 - Set 1

Great news for all you big boobs loving glamour fans out there, 32G Alyssa is back again here at PinupFiles with her slim and stacked charms.  Alyssa is one of the sexiest big breasted babes we have ever seen and that slender frame of hers combined with those incredible all-natural big tits definitely makes for a proper Monday wakeup call! 
Alyssa
MILF
Pics: 25
Name: alyssa-vol-2-set-1_1280.zip
Resolution: 1280x852
Size: 2 Mb
Format: jpg

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Tessa Fowler - Halloween Special 2014 - Set 1

32GG Tessa Fowler!  

From TessaFowler.Com!

Is there really anything else we need to say?  

Yeah, we didn't think so!  ;-)

This brand-new set of Halloween-themed photos pretty much say it all, all by themselves, so just check them out for yourself and check out a heck of a lot more of Tessa over at her very own personal exclusive site, TessaFowler.Com!

(drops mic)

 

 
Tessa Fowler
MILF
Pics: 31
Name: tessa-fowler-halloween-special-2014-set-1_1280.zip
Resolution: 1000x800
Size: 4 Mb
Format: jpg

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SarahRandall.Com - Pre-Launch Teaser Preview!

Hey there everyone!  It's me Sarah Nicola Randall -- yes, the real Sarah Nicola with the all-natural 32H big breasts that you all know and love -- I am here at PinupFiles to very happily present you with a special sneak preview of my very soon to be launching website, SarahRandall.Com!  Ever since I made my debut here at PinupFiles I've always had such a great fan response from all of you and so many of you asking when I was going to do my own site and the good news is that it is a very close at hand.  I have been working really hard on it and shot a lot of great stuff that I know your going love because I know how much you all like cute sexy girls with really big boobs and fortunately I fit that bill! ;-) I love posing and love showing off my big boobs for you, so here's a little sneak peak taste of what you are in for over at my site
Sarah Nicola Randall
MILF
Pics: 29
Name: sarahrandall-com-pre-launch-teaser-preview-_1280.zip
Resolution: 1280x855
Size: 6 Mb
Format: jpg

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Miriam Gonzalez - Vol. 9 - Set 2

It was one of our most popular photo sets ever when it first debuted at PinupFiles all those years ago, and now, at long last, the first wave of the unreleased extended photos is here! Yes, all-natural jaw-dropper 36FF Miriam Gonzalez returns to PinupGlam with a big bang, brandishing her awesome all-natural assets in a mind-boggling black bikini! It\'s no wonder Miriam fans around the world had their jaws drop when this set first hit and now the first part of the rest of the photos are finally here!
Miriam Gonzalez
MILF
Pics: 24
Name: miriam-gonzalez-vol-9-set-2_1280.zip
Resolution: 1280x856
Size: 4 Mb
Format: jpg

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Miriam Gonzalez - Vol. 6 - Set 3

She continues to make waves and a big splash even 7+ years after her Playboy debut as all-natural 36FF Miriam Gonzalez returns to PinupGlam with another new unpublished set from our archives. Miriam is one of those rare gals who sets imaginations running wild and it's not hard to see why. She fills out a stretchy yellow top like pretty much no one else on earth and strikes a hell of a pose, making her one of the greatest and most classic models of our time, or any time.
Miriam Gonzalez
MILF
Pics: 20
Name: miriam-gonzalez-vol-6-set-3_1280.zip
Resolution: 1280x858
Size: 2 Mb
Format: jpg

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Ana Rica - Vol. 3 - Set 1 - Oiled up big tits in a tiny bikini!

In the cold of winter, there are few sights more endearing to the eyes than a scorchingly hot big boobs babe in a tiny bikini top, and that is the case times two when the big bust babe in question is the awesomely endowed and incredibly sexy 32H Ana Rica!  Ana has lit up our website and our computer screens and our big tit adoring hearts ever since she made her debut with us last Halloween and for this one she really takes it up a few notches as she rocks our world yet again in this tiny bikini that will leave you gasping for extra oxygen!   For this one, Ana gets her mighty melons oiled up and ready for some serious big boob bikini action and boy does she deliver! 
Ana Rica
MILF
Pics: 29
Name: ana-rica-vol-3-set-1-oiled-up-big-tits-in-a-tiny-bikini-_1280.zip
Resolution: 1280x855
Size: 5 Mb
Format: jpg

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Sophie Coady - Vol. 1 - Set 1

Sophie Coady
MILF
Pics: 20
Name: sophiecoady-vol01-set01_full.zip
Resolution: 2000x3000
Size: 27 Mb
Format: jpg

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Glamourcon - Set 13 - 36DDD Maggie Green's huge tits have never looked bigger!

There's just something about a really incredible pair of big tits busting out of a corset top, with the cleavage bulging and ready to burst forth and few gals can pull off that look quite like 36DDD Maggie Green (who was more like a G cup in this shoot).  This was shot during one of our Glamourcon convention appearances and Maggie's huge tits have never looked bigger or fuller or rounder or more juicy than they do here... you just want to reach out and grab them!  ;-)  Trust us, there's been many a time in the past when Maggie has unleashed those big boys of hers and we have been tempted, LOL... can anyone say motorboat? 
Maggie Green
MILF
Pics: 34
Name: glamourcon-set-13-36ddd-maggie-greens-huge-tits-have-never-looked-bigger-_1280.zip
Resolution: 1280x855
Size: 6 Mb
Format: jpg

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Jo Paul - Vol. 3 - Set 1

We are back at it on a new work week here folks, and we need a serious hottie with some seriously awesome big tits to do the job, and that is why we have all-natural 32GG Jo Paul here to do exactly that!

Jo has some of the best and most perfectly form big boobs you will ever see and here she is, looking very pretty in pink and stripping down out of that top to show off those incredible boobs in another fine photo set.
Jo Paul
MILF
Pics: 26
Name: jo-paul-vol-3-set-1_1280.zip
Resolution: 1280x853
Size: 4 Mb
Format: jpg

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Beth Lily - Vol. 2 - Set 1

Just when you thought you had seen the last of her... she is back!

Her debut last month was so stunning and overwhelming that we couldn't help ourselves but bring back the lovely and pulchritudinous 32GG Beth Lily back for an encore performance, and what a performance it is.

We knew Beth would look good in a tiny bikini, but even we had no idea she would look THIS good... she is a true show-stopper and the way she wears this one can only be appreciated with the eyes, so feast yours on another fantastic new photo set from this stunning lady!
Beth Lily
MILF
Pics: 31
Name: beth-lily-vol-2-set-1_1280.zip
Resolution: 1280x853
Size: 5 Mb
Format: jpg

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Denise Milani - Vol. 6 - Set 1

She has quickly become one of the most incandescently hot models on the entire planet and she's showing absolutely no signs of slowing down as 32DDD Denise Milani mounts a breathtaking return to PinupFiles/PinupGlam today in this hot new new studio photo shoot. Denise's incredible, almost too hard to fathom curves, combined with her uncanny sexiness and amazing charm make her a winner through and through and this one, taken in one of our classic Pinup logo t-shirts, is definitely one to behold. Come inside and see exactly what makes Denise so incredibly special.
Denise Milani
MILF
Pics: 29
Name: denise-milani-vol-6-set-1_1280.zip
Resolution: 1280x911
Size: 4 Mb
Format: jpg

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Sarah Nicola Randall - Vol. 2 - Behind The Scenes - Set 1 - Busting your holiday blues!

Happy Friday and Happy New Year everyone! Our incredible month of holiday updates all December long wraps up today because we are very happily getting ready for the new year of 2012 to arrive but before we do that, we have one more awesome behind-the-scenes photo set of 32H Sarah Nicola Randall and her incredibly huge and firm breasts!  Sarah has that killer body that we absolutely die for and her big boobs are so firm and supple you can't take your eyes off them or help but want to reach out and squeeze them! Sarah's special red holiday lingerie and bra are just the thing to keep our festive mood humming along, so enjoy these fantastic photos of this phenomenally hot busty babe!
Sarah Nicola Randall
MILF
Pics: 30
Name: sarah-nicola-randall-vol-2-behind-the-scenes-set-1-busting-your-holiday-blues-_1280.zip
Resolution: 1280x855
Size: 6 Mb
Format: jpg

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Chloe Kendall - Vol. 3 - Set 1

We're back on a Wednesday here with another fabulous and sexy new photo set from our delightful big breasted babe, the lucious 32JJ Chloe Kendall!

Chloe returns with a sexy outdoor photo shoot in a roaring red bra and panties and she is looking GOOD in this one, with her fantastic all-natural big boobs and bedroom eyes, she's exactly what we need to get us over the hump and into the back half of the week.
Chloe Kendall
MILF
Pics: 28
Name: chloe-kendall-vol-3-set-1_1280.zip
Resolution: 1280x853
Size: 3 Mb
Format: jpg

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Denise Milani - Jaime Hammer - Set 2

So we finally got the photos from Denise & Jaime's trip to the beach up at PinupGlam today! We were so fixated on the awesome HD video of these ladies that we forgot we had some pretty sweet photos as well. Ever since we debuted the amazing HD videos of these gals having their day at the beach together, we kept getting requests for photos from it, so we're only too happy to oblige everyone who asked and thank you for your patience as we bring you the first set of terrific candid-style photos of these gorgeous ladies. Denise and Jaime have never looked hotter or more jaw-droppingly amazing than they do here so come insid and check these awesome busty babes out!
Denise Milani
MILF
Pics: 34
Name: denise-milani-jaime-hammer-set-2_1280.zip
Resolution: 857x1280
Size: 7 Mb
Format: jpg

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