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Is there anyone out there who doesn't love a cowgirl? Jaime Hammer makes a boot-kicking return to PinupGlam in a brand new set of unpublished photos. Jaime takes the cowgirl thing to sexy extremes with her boots, jeans and tie-back shirt.

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2 amazing hot ass sleek euro babes in jeans get fucked hard in these hot group sex bisex double anal cumshot adventures in these hot pics

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"""All my friends see me as just one of the guys,"" Michelle Lin told us. ""But at the same time, I'm just a regular girl. I could be in a T-shirt and jeans hanging out with the boys one day, and be a total glam girl the?"

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Monica has big tits but they aren't just big, they are AMAZINGLY big and firm and supple and perfectly shaped... and they just don't get much better than this. Sarah dons this super sexy black and white lace bra and tight blue jeans.

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II you're looking to buy real estate in Florida, have we got the agent for you.... Even if you're not looking to buy, you'll want to get a private showing of any house with this week's Cyber Girl, Jeanette Marie. Jea?

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She's hot, busty, has that irresistible goth look combined with classic pinup beauty! Yes, 32GG Dahlia Dark is back in another smokin' hot set of photos, her big boobs popping out of her trim black corset and skin tight jeans.

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12ภาพ

"""I don't want people to think I'm just another dumb blonde,"" says actress-singer - and now Playmate - Jean Manson. ""So far, in my films, I've been cast in roles like that, but someday I'm going to change my screen im?"

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Blonde Jeannette and brunette Zafira have a clash of the titties!

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A blonde wearing jeans fucked hardcore in her tight ass

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Mary Jean fucks her boss on lunch break and then can not find her bra so she fucks him again.

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Tight jeans hot ass latina gets her red hair pussy fucked and creamed in these hot club fucking reality pics

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HI! You got to see what kind of lingerie I had on underneath my tight jeans. Now you get to see whats under the lingerie! BOOBS! I like dressing myself up in sexy undies for you all, but I LOVE taking it off for you! ;) XOXO -- Monica

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Sexy girls having sex in high definition videos is the key idea of this exciting website leading you through the HD sex world where only nude hot sexy ladies who recently turned eighteen years old get indulged in very hard sex with crazy deep throat followed by anal porno and dick thrusts inside the nude teenage pussy. Absolute teen sex must-see!

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12ภาพ

Playboy.com is on set with Jeannie Santiago to shoot her exclusive pictorial. Get to know more about Jeannie Santiago by watching our behind the scenes footage and the complete nude version available exclusively on P?

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12ภาพ

Raven Bay is making sure to stay groomed for her boyfriend by shaving her naughty bits, but she's doing so out on the veranda. Her boyfriend's son catches her and decides to confront her about it, but Raven knows that in reality it's turning him on. She can see his boner popping out through his jeans, so she throws him a bone and invites him to shave her pussy for her. As soon as he's done she let's him take a crack at stuffing her freshly shaved pussy with his cock. He obliges as he does have to relieve his boner...and they both promise not to tell daddy about their naughty experience together.

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12ภาพ

Playboy.com is on set with Jeannie Santiago to shoot her exclusive pictorial. Get to know more about Jeannie Santiago by watching our behind the scenes footage and the complete nude version available exclusively on P?

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Naughty teenage hooker working a tourist for extra money

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This hot little babe jean has the sweetest face and ass watch her lil pussy get slammed in these pics

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12ภาพ

"""I'm not very involved with politics or civil rights,"" says Jean Bell. ""I just try to get along."" For Miss October, though, getting along - these days, as a model - happens to include cracking a few long-standing rac?"

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12ภาพ

"Playmate of the Year Sara Jean Underwood wasn't shopping for talent when she walked into Bebe in Beverly Hills, but in 26-year-old sales specialist Ida (pronounced ""EE-duh"") Ljungqvist she spotted a must-have item. S?"

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12ภาพ

Seth is helping move in some of Alexa's belongings when she gets a text from her boyfriend. Her boyfriend tells this sexy dame that it's over because her vagina is ugly! Since Seth and Alexa have been long times friends she asks him to take a look at her pussy because she needs to know and doesn't have anything to compare it to. He's skeptical at first because his sister could come up at any time but, she pleads with him to look at it and to confirm that it doesn't look like roast beef. He finally agrees and Alexa drops her shorts and slides back her pink laced panties. Seth says it looks fine and Alexa is relived. She starts to unbutton Seth's jeans and he stops her. Alexa says she is going through a hard time and Seth said her pussy looks fine. So, taking Seth's cock in her mouth and pussy will cheer her up!

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12ภาพ

Playboy.com is on set with Elizabeth Jean to shoot her exclusive pictorial. Get to know more about Elizabeth Jean by watching our behind the scenes footage and the complete nude version available exclusively on Playb?

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LaTasha is one of those models who was such a wonderful surprise to work with: funny, charming, hot as can be. Here she brings the sexy in this awesome green tie-top and super-tight jeans that is sure to knock your socks off. :-)

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12ภาพ

Morena Corwin, in Chicago to finish her Playmate shoot, was wearing faded blue jeans and a black leather motorcycle jacket over a skintight black ribbed sweater when we met her for coffee. As we strolled along Chicag?

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12ภาพ

"Jeannette may be down to earth, but she's on a mission and knows exactly what she wants from life. ""one day I want to be married and have a family so I can settle down. But now I want to pursue my acting and modeling?"

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15ภาพ

Mariah has a big meaty ass and shows it off in short skirts or tight jeans wherever she goes. This fuck bunny loves feeling a man's warm cum inside any of her holes. She believes a satisfied man will stay and never cheat. Her guy has no complaints!

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12ภาพ

NATURE GIRL October's woodland nymph likes nature au naturel Nature-loving (and clearly loved by nature) Jean Cannon's natural habitat is any reasonably shady glen, except when she's water-skiing, showing her pr?

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12ภาพ

Michele Drake stands near the shore line of Venice Beach in California, her faded jeans rolled up to her knees, her long blonde hair rising gently with the breeze, her bright-red Hawaiian shirt fluttering against her?

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12ภาพ

Playboy.com is on set with Jeannie Santiago to shoot her exclusive pictorial. Get to know more about Jeannie Santiago by watching our behind the scenes footage and the complete nude version available exclusively on P?

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15ภาพ

Teen chick enjoying his solid schlong in her tight muff

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12ภาพ

Marilyn Monroe, au naturel, appeared in our first issue. Now, years later, actress Misty Rowe, who played the Marilyn character inGoodbye, Norma Jean, follows suit (birthday, that is). From November 1976?

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Busty brunette babe in jeans showing her classy body parts

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Cute teenage prostitute gets dirty with a French tourist

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12ภาพ

Mary Jean fucks her boss on lunch break and then can not find her bra so she fucks him again.

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15ภาพ

Monica Mendez slides out of her blue jeans

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12ภาพ

Raven Bay is making sure to stay groomed for her boyfriend by shaving her naughty bits, but she's doing so out on the veranda. Her boyfriend's son catches her and decides to confront her about it, but Raven knows that in reality it's turning him on. She can see his boner popping out through his jeans, so she throws him a bone and invites him to shave her pussy for her. As soon as he's done she let's him take a crack at stuffing her freshly shaved pussy with his cock. He obliges as he does have to relieve his boner...and they both promise not to tell daddy about their naughty experience together.

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15ภาพ

We simply couldn't wait to get the lovely and talented and supremely blessed 36DDD Maggie Green in a plunging neckline red checkered stretch top and a pair of jean shorts to allow her to show off her Farmer's Daughter best.

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12ภาพ

Playboy.com is on set with Jeannie Santiago to shoot her exclusive pictorial. Get to know more about Jeannie Santiago by watching our behind the scenes footage and the complete nude version available exclusively on P?

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12ภาพ

"""I love dressing in tight jeans, tiny top and leather jacket with boots - and grasping onto a hot Harley guy"".?"

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12ภาพ

Malena and adriana are extremely hot and horny as malena pulls off adrianas jeans and takes care of her dripping wet pussy so the action goes back and forth as the girls explore each others hidden desires

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Hey Guys! I thought that I would share a sexy photo set with you all. Jeans and lingerie are one of my many fetishes and I love to put them on and take them off. I hope you enjoy this set? OXOXOXOOX -- Monica

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Sweetie loves to drink her boyfriends sticky cum hardcore

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Jill Madison makes her PinupFiles debut in a stretch fishnet top, a simple jean skirt and one of our favorite accessories, a pair of stretchy suspenders! The sight of a pair of suspenders stretched over a pair of big tits is always a good look.

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12ภาพ

When told to do what she likes and whatever comes natural she grabs tylers jeans and pulls them down so stacey shows she means business as she sucks cock like a pro and some doggy style shows off her sweet ass

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Jeannie Lou Granny Blowjob - See Mom Suck

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Vintage porn star Jeannie Pepper sucking and getting fucked

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12ภาพ

Seth is helping move in some of Alexa's belongings when she gets a text from her boyfriend. Her boyfriend tells this sexy dame that it's over because her vagina is ugly! Since Seth and Alexa have been long times friends she asks him to take a look at her pussy because she needs to know and doesn't have anything to compare it to. He's skeptical at first because his sister could come up at any time but, she pleads with him to look at it and to confirm that it doesn't look like roast beef. He finally agrees and Alexa drops her shorts and slides back her pink laced panties. Seth says it looks fine and Alexa is relived. She starts to unbutton Seth's jeans and he stops her. Alexa says she is going through a hard time and Seth said her pussy looks fine. So, taking Seth's cock in her mouth and pussy will cheer her up!

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12ภาพ

Playboy.com is on set with Holly Jean to shoot her exclusive pictorial. Get to know more about Holly Jean by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Plus.?

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15ภาพ

HI! So in the first part of this sexy shoot you got to see what kind of lingerie I had on underneath my tight jeans. Now you get to see whats under the lingerie! BOOBS! I like dressing myself up in sexy undies for you all! ;) XOXO -- Monica

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12ภาพ

Super hot ass short mini skirt babe gets her tight box pounded hard after trying on some hot tight jeans in these hot banging pics

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A horny chap jizzing in her adorable opened teenage mouth

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A cumloving sweetie screwed hard by her horny boyfriend

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Megan strips out of her tight jeans and skimpy tank to show off that rock hard ass and perfect tits!

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12ภาพ

Amazing babe gets nailed hard in the jeans store after walking in her amazing ass and mini skirt

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Amazing mega hot black thick ass jeana gets her jeans bad ass biker pussy drilled hard in these hot cumfaced reality fuck pics

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12ภาพ

Playboy Plus is on set with Jeanette Marie to shoot her exclusive pictorial. Get to know more about Jeanette Marie by watching our behind the scenes footage and the complete nude version available exclusively on Play?

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Alexis started with a great blowjob the minute she walked in the door. Then Preston peeled her jeans off to reveal her big bubble butt.

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12ภาพ

Searching for that rare combination of stunning beauty and low maintenance? Look no further than Nikki, a ?T-shirt-and-jeans kind of girl? who feels her sexiest when she?s comfortable, not dressed up in lingerie. Her?

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12ภาพ

CJ Jean works at a sperm bank and when she catches donor Brick Danger relieving himself in the wrong room she makes sure to point him in the right direction. It seems like Brick needs a hand with something else. He can't seem to get off. CJ, being the friendly customer service person that she is, makes sure to give him a hand, and her mouth, and her pussy. She makes sure to squeeze every last drop of sperm out of Brick. To bad he missed the cup and had it land on her face. Looks like he's going to have to try again.

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15ภาพ

Hey! I am SOOOO excited to share these photos with you! They were some of the first shots taken for my site, and my favorite! I love wearing Blue jeans, so I thought I would strip out of them for you all! I cant wait to show the video. OXOX -- Monica

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12ภาพ

"""I'm no cookie-cutter,"" declares Shera Bechard. ""If there's a bandwagon, I'm not on it."" Indeed, it is impossible to categorize our Miss November, a French Canadian beauty who likes to chill in jeans and a tank top a?"

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12ภาพ

Last month, we were loaded with French Canadian Cyber Girls. This month starts with a more European feel as we welcome our first Swedish Cyber Girl of the Week, Jeanette Rundgren. This spectacular Swede may not be as?

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12ภาพ

Those of you with eagle eyes and elephant memories will recognize Pamela Jean Bryant as one of the coeds featured in our September 1977 pictorial Girls of the Big Ten. She almost didn't make it: The story of h?

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15ภาพ

Experimenting teens Jeanine and Monika having hot teen sex

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12ภาพ

CJ Jean works at a sperm bank and when she catches donor Brick Danger relieving himself in the wrong room she makes sure to point him in the right direction. It seems like Brick needs a hand with something else. He can't seem to get off. CJ, being the friendly customer service person that she is, makes sure to give him a hand, and her mouth, and her pussy. She makes sure to squeeze every last drop of sperm out of Brick. To bad he missed the cup and had it land on her face. Looks like he's going to have to try again.

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17ภาพ

Jean has supermodel looks, a rocking body and an insatiable sex drive!

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15ภาพ

Monica Mendez in tan bra and blue jeans

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12ภาพ

"When the Los Gatos High School newspaper asked students where they wanted to be in ten years, Carrie Jean Yazel, class of '88, answered, ""In the pages of Playboy."" Seven years ahead of schedule, Miss May comes to u?"

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12ภาพ

Golden girl Sara Jean Underwood was your overwhelming choice. Your votes helped Sara become Playmate of the Year. ?It blows me away that people would take time out of their day to vote for me,? she says, flashing tha?

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