Mature ladies with great experience

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Hot MILF Evelyne

Mommy Evelyne likes order at home and she cleans two times weekly. Recently she took the habit of calling the cleaning guy to take care of the windows and after he's done Mommy calls him in to pay him - but not by cash but by offering her wet pussy! She's still a hot woman and usually the cleaning guy can't turn down the offer and they end up fucking wildly on the sofa. Who knows a better way to save money?
Evelyne Foxy
blowjob, facial, milf, brunette, one on one
Pics: 126
Name: 78216.zip
Resolution: 1280x853
Size: 44 Mb
Format: jpg

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MILFs Love It Harder #02

Caroline De Jaie
Hardcore, Big Tits, Blowjob, Big Dick, Blonde, Mature & Milf, Open Mouth Facial
Pics: 56
Name: 44792.zip
Resolution: 1280x853
Size: 20 Mb
Format: jpg

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Glamour - Cherie DeVille & Alli Rae

Being a stepmother with a teenage daughter in the house can be difficult, especially when you're trying to win their trust. But in this case, Cherie DeVille needs to consult her friend regarding her stepdaughter Alli Rae; you see, Allie's father never spoke to her about sex and Cherie feels obliged as the mother figure to have this talk. Cherie notices Alli outside sunbathing, so she undresses and puts on her bikini to join her step daughter and find the courage to have 'the talk'.Observing Alli from afar, Cherie smiles, proud that she has such a beautiful stepdaughter whom she's grown so close to. Allie welcomes her mother to join her beside the pool. Cherie was careful choosing her words not to scare Alli and ruin her whole plan. Alli admitted she was very comfortable talking to Cherie and confided in her that she had a crush on a girl but was scared telling her dad afraid of his disapproval.Cherie reassured Alli that there was nothing to be afraid of and liking girls was perfectly normal. Now that Cherie felt she gained her daughter's trust, she manipulates her, by removing Alli's bikini top, insisting there was nothing wrong seeing her daughter's breasts.Cherie wanted to know more about this girl Alli was interested in, but Alli knew very little about the birds and the bees. Cherie saw this as a great opportunity to show everything Alli needed to know. Alli was scared the neighbors would catch them but Cherie was insistent that everything was going to be alright. How can it not be with Cherie Deville teaching her all she needs know?! Watch today and Enjoy!
Cherie DeVille, Alli Rae
Outdoors, Blonde, Big Tits, Masturbation, Natural Tits, Rim Job, Fingering
Pics: 49
Name: 59998.zip
Resolution: 1920x1280
Size: 45 Mb
Format: jpg

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Lusty busty Shyla Stylez

Busty MILF Shyla Stylez knows what's good for her. A big black cock is certainly amongst the things she can spend some quality time with, sucking it, riding on it, milking it for her own pleasure. Her kissable lips and pink pussy simply swallow the juicy dick, and the blonde bombshells cums again and again in front of our camera.
Shyla Stylez
blowjob, interracial, milf, Big Ass, blonde, one on one
Pics: 49
Name: 73437.zip
Resolution: 1280x853
Size: 13 Mb
Format: jpg

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Big Tit Office Chicks #02

Lily is a tattooed bad ass office worker that just doesn't give a fuck. Patrick is a nerdy boss that tries to get her to get to work, but she has other things in mind. She teases her little bitch boy boss and seduces him with her giant tits.
Lily Lane, Patrick Delphia
Latina, Hardcore, Big Tits, Deepthroat, Titty Fuck, Blowjob, Big Dick
Pics: 586
Name: 88267.zip
Resolution: 1920x1280
Size: 557 Mb
Format: jpg

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Glamour - Eva Notty

Ever since that fateful game of frisbee back in college, girlfriends Jenna (India Summer) and Nina (Eva Notty ) have been together through thick and thin. They are just about ready to move into their third house when Jenna pops the question! She surprises Nina with a huge diamond ring and Nina ecstatically accepts the marriage proposal. The ladies begin to celebrate their engagement with some foreplay that turns into full blown lesbian sex. Jenna sits on the floor in front of the sofa and Nina perches herself on top of her face. She gyrates her pussy on top of her tongue till she cums in her mouth. Nina kisses up Jenna's spread legs and devours her sweet pussy till her quivering clit explodes. Jenna's long hair tickles Nina's ass while she sucks another cum out of her. Nina climbs on top of Jenna kissing her future wife in gratitude. The couple entwine their legs till their pussies touch and they trib until they both orgasm. Nina prolongs Jenna's pleasure, trailing soft kisses from the rim of her ass to the nape of her neck. Enjoy!

Brunette, Big Tits, Girl on Girl, Natural Tits, Rim Job, MILF & Mature, Pussy Licking
Pics: 51
Name: 87910.zip
Resolution: 1280x1920
Size: 58 Mb
Format: jpg

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Glamour - Kayla Kayden

Innocent Alexis Monroe recently hitchhiked from small town Pennsylvania to Las Vegas where Madame Richelle Ryan plucked her off the strip and groomed her to work as a companion. After one hot lesbian training session with Richelle, Alexis isn't sure she's ready to service clients yet. But that's where the dolled up ladies are heading, to meet the ridiculously rich Kayla Kayden for a lesbian threesome. Kayla warmly welcomes Richelle and Alexis into her luxurious home and promptly begins to fawn over her brand new sex toy. The bombshell client asks Richelle for permission to play with Alexis' big boobs. She pulls them out of her dress and devours her nipples before kissing her deeply on the mouth. Then Kayla undresses Alexis and removes her sexy heels. She puts one dainty foot in her mouth and rubs her pussy into a frenzy with the other. Alexis lets it happen, although she finds her client's fetishes strange. Kayla takes off her top unleashing her huge pair of boulders. Alexis suckles them while Richelle strips naked. Kayla gets super excited when she hears it's Alexis' first time on the job. Kayla grabs a mouthful of tits and smacks their round asses in celebration. She asks Alexis to lick her armpit while she masturbates her pussy. Then she reciprocates on Alexis' armpit. Then Alexis leans back against Richelle while Kayla laps at her pussy, loosening her up till she cums in her mouth. Kayla asks if she can lick Alexis' asshole next, but Alexis hasn't had that done before. Richelle talks her into it, and once she acquiesces, Alexis can't believe how good Kayla's tongue feels in her booty. Kayla lies down on her tummy and takes an ass licking from Alexis in return. Richelle touches Kayla's quivering pussy at the same time and makes her cum. Kayla takes a turn with Richelle, feasting on her MILF ass and pussy alongside Alexis. The lesbian companions doubleteam the client's hairless pussy, rubbing one out with their manicured fingers. Then Kayla licks another cum out of Alexis' pussy before Alexis sits on Richelle's face while Kayla gorges on the MILF's pussy. Alexis tribs Richelle's pussy while Kayla rides Richelle's face, ending in a three way orgasm!
Kayla Kayden
Blonde, Brunette, Big Tits, Girl on Girl, Hardcore, Threesome, Rim Job
Pics: 70
Name: 87123.zip
Resolution: 1920x1280
Size: 81 Mb
Format: jpg

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My Husband Brought Home His Mistress #06

Amanda Blow, Jenna Ashley, Tommy Pistol
Hardcore, Natural tits, Big Tits, Deepthroat, Threesome, Blowjob, Big Dick
Pics: 598
Name: 55375.zip
Resolution: 1920x1280
Size: 518 Mb
Format: jpg

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Mommy Will Protect You

Scarlett Sage storms into the living room crying embracing her stepmom Cherie De Ville. When Cherie asks her what happened she tells her that her boyfriend cheated on her and that all the kids at school are mean to her. Cherie promises her that she'll protect her as she brings her closer. Scarlett can't stop crying so Cherie pulls out her tits and tells her to lie down on her lap as she sucks them. It always calmed her down in the past and should do the trick today. Sure enough, as she sucks on her breast she calms down. Cherie takes off Scarlett's shirt and assures her everything is going to be alright. She removes her dress and motions Scarlett to continue sucking on her tits. Cherie then lays her down and removes Scarlett's shorts, remarking how cute her panties are. When she takes them off, Cherie dives right into Scarlett's pussy, sucking on her clit. As she moans, she cums in her mother's mouth. Cherie starts fingering her daughter making sure to get her off again. When Scarlett decides to returns the favor, she rams her fingers deep inside Cherie's pussy, making her cum all over the living room couch. The girls 69 and trib as Cherie fucks her daughter's pussy with her breast. When Cherie finally climbs on her daughter again, she grinds her pussy on hers and makes her cum over and over again.
Cherie DeVille, Scarlett Sage
Blonde, Big Tits, Girl on Girl, Member Fantasy, Hardcore, Fingering, MILF & Mature
Pics: 37
Name: 93277.zip
Resolution: 1280x1920
Size: 7 Mb
Format: jpg

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Jana Defi - Vol. 21 - Set 2

32G Jana Defi!

Do we need to say anything else? ;-)

This is the second half of her stellar studio photo shoot and we can't stop collectively drooling on our keyboards here, so we'll just leave it right here and quit while we are ahead!
Jana Defi
MILF
Pics: 26
Name: jana-defi-vol-21-set-2_1280.zip
Resolution: 1280x853
Size: 3 Mb
Format: jpg

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Lana Kendrick - Vol. 6 - BTS - Set 1

Even though it technically just started, for some reason we are really enjoying summer more than ever this year, and so we have decided to keep up with the summer-themed photo sets and videos for as long as we can and what better way to carry on that theme than with all-natural 32GG Lana Kendrick of the upcoming LanaKendrick.Com getting her big tits soaped up and using them to wash a (very lucky) car while wearing a Baywatch-style one-piece bathing suit?

 

This ins the first behind-the-scenes set from Lana on this shoot and it pretty much has it all: a sexy babe with big boobs, a rockin' bathing suit that shows off those tits, plenty of soap and warm sudsy water...  Lana is like a summer time dream come true!
Lana Kendrick
MILF
Pics: 33
Name: lana-kendrick-vol-6-bts-set-1_1280.zip
Resolution: 1280x853
Size: 7 Mb
Format: jpg

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September Carrino - Vol. 1 - Set 1

Okay, so last year many of you will remember that we celebrated our annual April anniversary by debuting our big model surprise at the beginning of the month, and it came in the form of Denise Milani's PinupGlam/PinupFiles amazing debut. Well this year we decided to follow the old showbiz rule and "save the best for last" and in this case "best" is the operative word. PinupFiles.Com and PinupGlam.Com are incredibly proud to close out our 10th Anniversary celebration with a huge bang by presenting the simply astonishing, all-natural 28DDD/28F September Carrino as our latest and greatest new model. September is one of those incredibly rare ladies who just has the look and aura of a superstar and in her debut photo set, she does not disappoint, trust us. We loved having her shoot with us and can't be more excited about her big debut, so please join us in welcoming this fantastic lady to the PinupFiles/PinupGlam family -- we really hope you all like her. You're going to see a lot more of this amazing gal very soon, and when you do see her on the covers of national magazines soon, just remember where you saw her first!
September Carrino
MILF
Pics: 24
Name: september-carrino-vol-1-set-1_1280.zip
Resolution: 1280x856
Size: 4 Mb
Format: jpg

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Ana Rica - Vol. 2 - Behind-The-Scenes - Set 1 - Christmasy big boobs from Ana!

How about some more big boobs to add to your Christmas wish list?  So far we have had a lot of incredible wish-inducing big bust babes on our pages this entire month long, but we certainly are not done yet!  That's because 34H Ana Rica is here and she is rockin' all around your Christmas tree with her huge tits and unbridled sex appeal.  This is another smoking hot photo set from a smoking hot babe who will blow your huge boobs mind this holiday season!
Ana Rica
MILF
Pics: 30
Name: ana-rica-vol-2-behind-the-scenes-set-1-christmasy-big-boobs-from-ana-_1280.zip
Resolution: 1280x856
Size: 5 Mb
Format: jpg

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Desiree-Elyda Villalobos - Vol. 1 - Set 1 - 34G Desiree's big boobs debut in a holiday green corset!

It's December and it is not only time for the holidays, but time to start unwrapping some fantastic new holiday gifts and this year we definitely have a new vision of loveliness in festive green to make the season that much more joyous. As you all know, we always celebrate the addition of a fantastic new busty model to our incredible roster of amazing ladies and this month is no exception as we proudly bring you the lovely and talented and oh-so-sexy 32G Desiree-Elyda Villalobos in a fabulous holiday green corset! Desiree is a true natural beauty with all-natural big boobs and terrific curves and a gorgeous face and irresistible eyes that you simply can't tear your own eyes away from. When we first saw photos of Desiree we were absolutely smitten and once you see this new debut photo set from her, you will be too! Please join us in welcoming her
Desiree Elyda Villalobos
MILF
Pics: 29
Name: desiree-elyda-villalobos-vol-1-set-1-34g-desirees-big-boobs-debut-in-a-holiday-green-corset-_1280.zip
Resolution: 1280x824
Size: 5 Mb
Format: jpg

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Demmi Blaze - Vol. 1 - Set 1

Even though we have already started it in our hearts and minds, the official start of summer is not quite here but is only a few days away and we are here to welcome it as soon as it arrives...

In fact, SCREW IT!  Can we just say that summer starts right now?  Because we have an AWESOME new Busty Pinup Girl debuting here today on our pages at PinupFiles and she is the perfect start to summer!

Yes, she is beautiful, cute, sexy, cool, fun and has absolutely HUGE all-natural breasts...

So please join us in welcoming the lovely 32J Demmi Blaze!

Demmi is a bright new talent and she was so much fun to work with and her enthusiasm shows in every single shot.  She is defintiely the real deal when it comes to sexy girl-next-door babes with astounding all-natural big boobs.

This is Demmi's first photo set and she shines in each one, and there is plenty more to come so please give her a warm welcome!
Demmi Blaze
MILF
Pics: 24
Name: demmi-blaze-vol-1-set-1-2_1280.zip
Resolution: 1280x853
Size: 4 Mb
Format: jpg

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AVN 2015 - featuring Hitomi Tanaka

So we thought we would go for a bit of a change-up this time around and instead of a new HD video for our mid-week update, we thought we would go for a new set of photos instead... and from a convention no less!  

But this is no ordinary set of convention shots... these are from this year's 2015 AVN convention in Las Vegas, and feature one of the most amazing all-natural big boobs marvels of all-time: the incredible 32N Hitomi Tanaka!

When you hear the term "slim and stacked" you usually think of a gal like Hitomi, except she takes that term to a whole new level, and then some.  Seeing her in this tiny pink bikini top, with her huge natural boobs bulging out of it on all sides, was enough to convince us, but we wanted to share her with you all and get your feedback as well.

She is a legend in her home country of Japan and since we really don't have any Japanese models here at PinupFiles -- something many of you have been begging us to change (and we hear you, trust us) -- we thought it might be nice to include some shots we snapped while we were there and see what you all think.  

So what DO you think?  Would you all like to see Hitomi some day here at PinupFiles in her full blown glory?  Let us know!  

MILF
Pics: 23
Name: avn-2015-featuring-hitomi-tanka_1280.zip
Resolution: 1280x853
Size: 3 Mb
Format: jpg

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Samanta Lily - Vol. 4 - Set 1

Welcome to Wendesday everyone!

We are well into summer, and we feel it is only appropriate that we go along with the summer heat with another sexy bikini shoot from one of our stellar big bust babes...

And so 32JJ Samanta Lily is here to answer the call!

Samanta is amazing, as always, and she looks SO good in this bikini... 

And we're just going to leave it at that. ;-)
Samanta Lily
MILF
Pics: 21
Name: samanta-lily-vol-4-set-1_1280.zip
Resolution: 1280x853
Size: 4 Mb
Format: jpg

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Satinee Capona - Vol. 1 - Set 1 - A fresh face with huge boobs!

Every once in a while, something new and rare and amazing comes along and it's like capturing lightning in a bottle and when you're talking about that in terms of incredibly hot big busted glamour babes, then it becomes even more exciting.  Well, today we have exactly that as we proudly present a incredibly sexy new busty babe who is all of 19 years old and has perfectly round and huge all-natural G-cup breasts, as well as one of the most rocking curvy bodies you will ever seen and a gorgeous face and gleaming eyes that will melt your big boob-loving heart.  Pinup gang and fans of big boob ladies everywhere, we happily present to you the lovely and curvaliciously sexy 34G Satinee Capona!  Satinee (pronounced sa-TEEN) is another blistering hot addition to our already stellar model roster here at Pinup and she brings her huge and firm big tits to the cameras for the very first time today in this super sexy Halloween-themed outfit and she knocks it out the park!  This is actually Satine's first shoot EVER and she works it like a seasoned pro, her amazing charisma shining through in each and every shot.  Please join us in welcoming this extremely hot brand new big bust babe!
Satinee Capona
MILF
Pics: 34
Name: satinee-capona-vol-1-set-1-a-fresh-face-with-huge-boobs-_1280.zip
Resolution: 855x1280
Size: 6 Mb
Format: jpg

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Denise Milani - Vol. 4 - Set 1

Is there a better way to kick off your weekend and celebrate the impending arrival of Spring and daylight saving time than with a woman as unbelievably sexy as all-natural 32DDD Denise Milani? If there is, send us an email and let us know but in the meantime, Denise is back and better than ever and ready to line you up and rock your world! This new set is a spectacular bra and baby doll boa lingerie combination that will surely make you weak in the knees. Come on in and check out why Denise is one of the most popular models in the world today!
Denise Milani
MILF
Pics: 25
Name: denise-milani-vol-4-set-1_1280.zip
Resolution: 1280x793
Size: 3 Mb
Format: jpg

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Katarina Angel - Vol. 2 - Set 1

We are keeping the holiday goodies coming hard and fast this holiday season, as we crank it up another notch with the lovely and spectacularyl breasted 32F Katarina Angel, who brings her incredible big natural boobs back to our pages in fine form, and putting a bit of a twist on our traditional holiday-themed photo shoots, as she poses for this one in a sexy outfit that's not exactly suited for a fire-side chat, if you know what we mean. ;-)

Katarina's bombshell body and big bodacious boobies are the perfect fit for this stretchy quasi-fishnet top we gave her and putting her it in took things to a whole new level.  Then, once we topped it off with a classic Santa hat, we knew we had an instant classic on our hands.   When you combine it all with Katarina's undeniable sex appeal, you can see why and how this was such a no-brainer, and once she gets those fantastic big tits of her's out of this outfit, your brain will hit a new level, too!
Katarina Angel
MILF
Pics: 34
Name: katarina-angel-vol-2-set-1_1280.zip
Resolution: 1000x800
Size: 6 Mb
Format: jpg

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