Boy

18 Total pics

But instead of fucking him up! They just fuck him like a rock star! Oh and degrade the shit out of him too! It was a good day for the girls. They fuck the pool boy and some creepy peeper!

Gallery tags: Boy Babe Big cock

16 Total pics

Veronica Avluv was in desperate need for some hardcore pussy pumping. Our boy had her screaming and squirting

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Hardcore

16 Total pics

Bouncy Russian babe Lia Rav with a very sexy bush

Gallery tags: Boy Babe Blowjob

18 Total pics

Blonde hottie with a nice shaved pussy. We were eager to get our boy ramming this chick so we can get to the good stuff.. facials!

Gallery tags: Boy Babe Black

16 Total pics

Beautiful Latina girl gets fucked in her sleep and Asian slut shows pizza boy how much meat she can swallow

Gallery tags: Boy Amateur Asian

12 Total pics

I used to be a real nerd in high school, but I\'ve changed a lot since then. I\'m also worth a lot more money after I sold the company I helped start. Now, I can afford anything I want, and after I found out that one of my old teachers was a porn star I knew I had to have her. I always had a crush on her and would day dream about the things I wanted to do to her. So I have her agent send her to my hotel room. Of course, she doesn\'t recognize me at first, but soon remembers once I put on my old glasses. Tonight, I get to be a bad boy, and my old teacher gets to punish me the way I always wanted her to.

Models on This Gallery: Syren De

Gallery tags: Boy Ass Brunette

16 Total pics

BUT I decided to play a different kind of drinking game this week with my friend Savannah, she brought along her boyfriend and friend and we decided to take shots of cum

Gallery tags: Boy Amateur Babe

12 Total pics

Gorgeous babe Rilynn Rae is searching for money and decides to fuck her boyfriends son.

Models on This Gallery: Rilynn Rae

Gallery tags: Boy American Babe

15 Total pics

Teen babe Natalia Rossi gets her shaved pussy eaten by her mature boyfriend.

Models on This Gallery: Audrianna Angel Natalia Rossi

Gallery tags: Boy Amateur Babe

16 Total pics

Damn boy ... These chicks like to play rough

Models on This Gallery: Alaura Lee

Gallery tags: Boy Anal Ass

15 Total pics

Presley\'s boyfriend submitted this collection of sexy self shot pictures of his girlfriend getting fucked hard

Gallery tags: Boy Amateur Blowjob

12 Total pics

"A bombshell with broadcasting ambitions, Sloan wants to be the voice of your favorite sports team someday, preferably covering football (she\'s a Cowboy\'s fan) or basketball. ""What guy wouldn\'t want to watch sports an?"

Gallery tags: Boy Blowjob Casting

12 Total pics

Playboy: Who do you look up to most in the communications field?
Alyssa: ESPN?s Erin Andrews. Enough said.

Playboy: So you?re into sports. Any in particular?
Alyssa: E?

Gallery tags: Boy Dildo Glamour

12 Total pics

You remember Mary Jo Anders, don\'t you? Well, how could you forget her... Since our Playboy Cyber club exclusive Super Babe pictoiral, Mary Jo has been sen on the pages of Playboy.com/Sports touting our Fantasy Sport?

Gallery tags: Boy Babe Blonde

16 Total pics

Huge black boobs fuck the shit out of this white boy\'s big dick

Models on This Gallery: Silvia Saint

Gallery tags: Boy Big cock Big tits

16 Total pics

You guys may have been making your own dirty homemade porn all along, but something weird is definitely going on. Ever since I put up that last shoot with Rachel and her boyfriend Josh,

Models on This Gallery: Juelz Ventura

Gallery tags: Boy Amateur Brunette

18 Total pics

, well actually a lot more i would think its the ultimate in an upskirt experience check it out boys and girls.....

Models on This Gallery: Silvia Saint

Gallery tags: Boy Amateur Brunette

12 Total pics

"Cyber Girl Audra Lynn gives Canada\'s bratty punks a backstage striptease. How do four snot-nosed punks feel about snapping nudes of a Playboy model? ""It\'s kind of my fantasy,"" Sum 41\'s drummer and resident spaz S?"

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Girl

12 Total pics

"How\'s this for a Playboy fantasy? Imagine this week\'s Cyber Girl, Carrie A. Taylor, and Miss January 2002 Nicole Namin wearing short skirts and riding a mechanical bull. ""It turned out to be woo much fun,"" Carrie tol?"

Gallery tags: Boy Foot fetish Girl

16 Total pics

Sheron Plays With Her Pink In Little White Socks

Gallery tags: Boy Babe Gorgeous

12 Total pics

Zivity: Riding Shotgun Playboy and Zivity.com bring fresh talent to the Cyber Club! Members of both sites voted on the theme for this pictorial, Short Skimpy Skirts. The winning pictorial features model Sharon Marie?

Models on This Gallery: Silvia Saint

Gallery tags: Boy Club Foot fetish

12 Total pics

Bill walks in on his friend\'s girlfriend, Luna Star, passed out in some sexy lingerie. She looks super hot so Bill does what any bro would do and takes some pics of her, but Luna wakes and catches him red handed. She\'s a little upset, but while deleting the pics off of Bill\'s phone she confides in Bill that she thinks that her boyfriend is cheating on her. So she stops being mad at Bill and fucks him in order to get back at her boyfriend.

Models on This Gallery: Luna Star

Gallery tags: Boy Amateur Ass

12 Total pics

Abbey Brooks needs someone to talk to early in the morning so she sneaks into her boyfriend\'s friend\'s room while he sleeps. She confesses to her boyfriend\'s friend that she\'s kind of had enough of her boyfriend. She is young and wants to fuck, but her boyfriend isn\'t always up to it. She needs someone to fulfill her needs. She needs to be fucked really good..that\'s where her boyfriend\'s friend comes into play. She seduces him into fucking her while her boyfriend sleeps in the next room.

Models on This Gallery: Abbey Brooks

Gallery tags: Boy Amateur Blowjob

18 Total pics

Horny club chick jayden gets pounded in the vip room in these orgy pics

Models on This Gallery: Chanel Bryant

Gallery tags: Boy Babe Blowjob

15 Total pics

Hey there...I\'m 22 years old with a passion for power exchange. My BF is cool with me playing with other boys so I\'m looking for a "no drama" playmate that love to give and maybe receive a few spankings!

Gallery tags: Boy Amateur Ass

12 Total pics

Scarlet Red is spending the night at her friend\'s place. Since her friend is busy fucking her boyfriend Scarlet ends up passing out on her friend\'s brother\'s bed. He gets home and finds her sleeping in nothing but her underwear. He convinces her to stay in bed with him. One thing leads to another and they\'re fucking in no time.

Models on This Gallery: Scarlet Red

Gallery tags: Boy Ass Blonde

15 Total pics

Lana is an overstuffed plumper with blonde hair. The chubby cutie likes to play it rough and tough.

Gallery tags: Boy Ass Bbw

15 Total pics

Seriously, I don\'t know if I just don\'t look in the mirror enough or if it\'s just that looking at photos of yourself is just kinda weird anyway, but I saw these and I can\'t believe how big and busty they look. xoxoxo -- September

Models on This Gallery: Samantha Bentley septembercarrino.com

Gallery tags: Boy Amateur Big tits

12 Total pics

"Bonnie has this weird boyfriend named Ralph whose idea of a good time is to hang around shopping centers, where he likes to greet customers - ""Good evening, ma\'am, that\'s a lovely dress you\'re wearing"" - then shake h?"

Models on This Gallery: Alexis Adams

Gallery tags: Boy Ass Glamour

12 Total pics

"""Somehow, I guess my mom knew I was going to be an unusual child,"" Rebekka Armstrong says, ""so she figured she had to give me an unusual first name."" Maybe it was the weird desert climate or the barren landscape of h?"

Models on This Gallery: Ashley Fires

Gallery tags: Boy Amateur Black

30 Total pics

Super hot hard college boys get down and suck eachother off after getting tricked by a hot smoking babe

Gallery tags: Boy Babe Blowjob

16 Total pics

I know this might be weird, but I really like to have my boyfriend cum on my legs and feet.

Models on This Gallery: Missy Martinez

Gallery tags: Boy Amateur American

16 Total pics

Watch Brandie get pseudo-fucked by little virgin boy!

Gallery tags: Boy Amateur Brunette

12 Total pics

Hot blonde parties in the club then gets some cum in her face later

Models on This Gallery: Alana Summers Angel Madrid

Gallery tags: Boy Amateur Blonde

14 Total pics

Smoking hot ass red head gets fucked by her sisters boyfriend in these hot creampie fuck pics

Models on This Gallery: Sindee Jennings

Gallery tags: Boy Ass Creampie

16 Total pics

Sexy young Latina Satine Phoenix spreads her pussy and sucks some dick

Gallery tags: Boy Big cock Blowjob

16 Total pics

Lovely Latina Satine Phoensix gets trampled by massive cumshot and penis

Gallery tags: Boy Ass Big cock

12 Total pics

Layton Benton is a sexy black girl who decides to sleep with her boyfriends son and ride his big cock.

Models on This Gallery: Sindee Jennings Layton Benton

Gallery tags: Boy Ass Big cock

16 Total pics

Latina heart throb Satine works some verga with that latin pussy of hers

Gallery tags: Boy Big cock Glamour

18 Total pics

Latin slut Satine gets fucked and sucks huge black OG Mudbone dick

Gallery tags: Boy Babe Big cock

12 Total pics

Playboy Germany?s Playmate of the Year 2005 Janine Habeck became the second German Playmate to become an American Playmate.?

Models on This Gallery: Silvia Saint

Gallery tags: Boy American Foot fetish

12 Total pics

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

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Glamour

12 Total pics

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

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Glamour

12 Total pics

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

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Glamour

12 Total pics

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

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Glamour

16 Total pics

Smoking hot mini skirt blonde get drilled hard after she just dumped her boyfriend in these hot pics

Models on This Gallery: Amber Sym Kelly Klass

Gallery tags: Boy Blonde Hardcore

11 Total pics

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

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Glamour

12 Total pics

Hot blonde girl sleeps with her boyfriends son so she can get his big dick in her tight wet pussy.

Models on This Gallery: Alexis Ford

Gallery tags: Boy Amateur Babe

12 Total pics

Ashley Anne\'s boyfriend thinks she has an ugly pussy. She wanted to confide in her bff but somehow her bff\'s brother, Kris, came to the rescue instead. Lucky for Ashley, Kris is an expert on pussies and deems hers to be worship-worthy! What a pick-up artist!

Models on This Gallery: Silvia Saint Stacy Silver

Gallery tags: Boy Foot fetish Hardcore

12 Total pics

Hot brunette girl sleeps with her boyfriends son because she is horny and her pussy is wet.

Models on This Gallery: Bella Reese

Gallery tags: Boy Babe Brunette

12 Total pics

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!

Models on This Gallery: Silvia Saint Stacy Silver Alexa Aimes

Gallery tags: Boy Foot fetish Hardcore

14 Total pics

Tara wakes up and fucks her boyfriends son

Models on This Gallery: Tara Lynn

Gallery tags: Boy Babe Dad

16 Total pics

Models on This Gallery: Sindee Jennings

Gallery tags: Boy Ass Creampie

12 Total pics

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!

Models on This Gallery: Silvia Saint Stacy Silver Alexa Aimes

Gallery tags: Boy American Foot fetish

12 Total pics

Emma Starr is at it again and she has her friend, Julia Ann, with her this time. She\'s out to show Julia just how easy it is to seduce a deliveryboy who wants to be a star. She calls up the store, orders herself a bottle of wine, and when the delivery boy gets there she fills his head with dreams of stardom. First she makes him audition for her and Julia, then she makes him get naked and has him lay back as both these hot blonde cougars take turns on his cock.

Models on This Gallery: Julia Ann

Gallery tags: Boy American Blonde

12 Total pics

Skin Diamond has been eyeing the really uptight guy at the bar. So when the guy\'s wife heads to the ladies room, Skin invites him to meet her in the other restroom. Skin is a real dirty girl and wants this guy to fuck her like the dirty girl she is in a dirty bathroom. He protests as he is married, but he sure is tired of that vanilla sex with his wife so he takes a chance to feel how much better dirty sex can be.

Models on This Gallery: Skin Diamond

Gallery tags: Boy Amateur American

12 Total pics

Whitney Westgate caught the bouquet at the wedding, again. She\'s beginning to think it\'s bad luck because she can\'t seem to find a guy. The only guy she\'s interested in is Eric, but he\'s married. Luckily, Eric\'s wife isn\'t at the wedding, so he\'s free to give Whitney what she wants...his hard cock inside her and his hot cum on her face.

Models on This Gallery: Rachel Starr Whitney Westgate

Gallery tags: Boy American Babe

12 Total pics

Scarlet LaVey has her friend\'s boyfriend, Ryan, come over to her salon for a haircut. She has ulterior motives for calling him over though. She always found Ryan hot and she figured if she could get him alone then she can finally make her move on him. She starts by rubbing her huge tits on his head and after that he\'s putty in her hands. She takes Ryan\'s cock throughout her salon and he drops his load on her tits.

Models on This Gallery: Scarlet LaVey

Gallery tags: Boy American Face

12 Total pics

Juelz Ventura finds it odd that her boyfriend forgot his phone. He\'s never apart from it. She decides to look through it to make sure he\'s been getting the text\'s that she sends him. Well, she find that not only is he getting her text, but also text\'s from his best friend\'s girlfriend. Looks like Juelz\'s boyfriend has been cheating on her all along, with his best friend\'s girl of all people. It would be selfish to keep this information to herself, so she calls over her boyfriend\'s best friend, Karlo. Juelz shows Karlo what she found. Karlo can\'t believe that his best friend would fuck him over by fucking his girl. Juelz has a nice way of getting back at their cheating partners. She decides if you can\'t beat them, join them. An eye for an eye, a fuck for a fuck.

Models on This Gallery: Juelz Ventura

Gallery tags: Boy Amateur Dildo

12 Total pics

Alexis Grace comes home and is horny for her friends boyfriend and she seduces him with her big busty tits.

Models on This Gallery: Alexis Grace

Gallery tags: Boy American Ass

12 Total pics

Sexy blonde Tasha Reign is horny and decides to have hot sex with her pool boy who is a perfect stranger to her, but he is hot and has a big cock so she seduces him.

Models on This Gallery: Tasha Reign

Gallery tags: Boy Amateur Big cock

12 Total pics

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

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Glamour

12 Total pics

"The Campbell twins posed briefly for Special Editions before sitting for their Playmate test. ""I have always dreamt of posing for Playboy,"" wrote Jennifer in her data sheet. Natalie echoed that sentiment, adding that?"

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Glamour

12 Total pics

Hot busty blonde is sick of her boyfriend so she seduces his son and gets fucked rough by his thick cock.

Models on This Gallery: Zoe Holiday

Gallery tags: Boy Big tits Blonde

12 Total pics

Fans of Playboy\'s Special Editions will instantly recognize this week\'s Cyber Girl, mesmerizing Texas beauty Mysti Sherwood. What they\'ll miss is her twin, Crysti. The two created quiet a stir with their rub-a-dub-du?

Gallery tags: Boy Foot fetish Girl

12 Total pics

A romantic getaway for Mary must include a canoe, tent, campfire and S\'mores. Finding a mama\'s boy to share her sleeping bag would make her one happy camper.?

Gallery tags: Boy Babe Blonde

15 Total pics

This new set is one of my favorites and it is super sexy because it has all the elements I love in a good set: cool location, sexy outfit, great makeup and hair, and huge giant tits that make your eyes pop out of your head! ;-) LOL. xoxoxo -- Leanne

Models on This Gallery: Leanne Crow

Gallery tags: Boy Amateur Ass

12 Total pics

"Can the daughter of an Illinois turkey farmer find happiness as a Playboy Bunny in San Francisco? ""Definitely,"" says January Playmate Leslie Bianchini, who is precisely that. ""Even though we left the farm and moved t?"

Models on This Gallery: Cindy Dollar Silvia Saint

Gallery tags: Boy Foot fetish Glamour

12 Total pics

Hot Madison Ivy is setting up for a romantic night but then decides to fuck her boyfriends son.

Models on This Gallery: Madison Ivy

Gallery tags: Boy Dad Foot fetish

12 Total pics

Angelica Taylor loves getting attention anywhere she can. She stops by her friend\'s house, when she knows that her friend is out, in order to try to get some attention from her friend\'s boyfriend. Her friend\'s boyfriend isn\'t falling for it. He refuses to acknowledge Angelica and her big tits, but what\'s a man to do when she bust out her tits and rubs them all over his face. Why, he starts sucking on them of course. One can only fight temptation for so long. After he\'s done sucking her tits, he pounds Angelica\'s wet pussy on the couch all before his girlfriend gets home.

Gallery tags: Boy Big tits Blowjob

12 Total pics

Hot Madison Ivy is setting up for a romantic night but then decides to fuck her boyfriends son.

Models on This Gallery: Madison Ivy

Gallery tags: Boy American Babe

16 Total pics

PIano Playing slut gives her boyfriend the fuck of his life!

Models on This Gallery: Monica Mendez

Gallery tags: Boy Amateur Big tits

16 Total pics

Watching the ladies run around in tight spandex shorts drove the boys insane. They say the heck with soccer. Let fuck! Nothing, but ass jiggling going on here

Gallery tags: Boy Ass Big tits

12 Total pics

Welcome to The Smoking Jacket, Playboy?s new safe-for-work site that provides guys with smart and sexy distractions throughout the day. Like Playmate Kimberly Phillips in nothing but a smoking jacket. Not a bad way t?

Models on This Gallery: Kimberly Phillips

Gallery tags: Boy Glamour Gorgeous

16 Total pics

Anyway, time to meet Ashley and Danny. Ashley is a sneaky girlfriend. She\'s always wanted to film her and her boyfriend fucking on video.

Gallery tags: Boy Amateur Brunette

12 Total pics

GIRL WHO WEARS GLASSES librarian Virginia Gordon: special edition in a deluxe binding Playboy has garnered Playmates from many walks of life, but a whiskered old prejudice about the plainness of librarians, as we?

Models on This Gallery: Silvia Saint

Gallery tags: Boy Ass Foot fetish

16 Total pics

Her pig tails, boy shorts and perky tits make her a perfect candidate for Facial Fest. She\'s a little nervous that she wont do a good job,

Gallery tags: Boy Blonde Blowjob

16 Total pics

A prime-time older lady

Gallery tags: Boy Anal Ass

18 Total pics

I love bras, but it?s hard to find one that fits. Sometimes I have to put them through rigorous testing to be sure it?ll hold on to my sweater puppies ;) So watch me push this bra to the limit in my bra tryout video! xoxoxo -- Tessa

Models on This Gallery: Amber Sym

Gallery tags: Boy Big tits Blonde

16 Total pics

Horny girl in leather outdoor fucked by these two cowboys

Models on This Gallery: Silvia Saint

Gallery tags: Boy Amateur Foot fetish

32 Total pics

You remember when your mother said that girl is trouble? Well, she meant these 3! And boy was she right... these 3 hot asses do anything under sun thats short of wrong. Thanks mom!

Gallery tags: Boy Ass Blowjob

18 Total pics

I woke up on this beautiful day, I just had to throw a little get together with some friends and play some Bocce ball. But what fun would it be if we didn\'t torture some boys???

Models on This Gallery: Silvia Saint

Gallery tags: Boy Amateur Beautiful

12 Total pics

Playboy fans remember Ryan as the coed who got kicked out of her sorority for appearing nude in the October 2008 Girls of the Big 10 pictorial. Her life?s been on an upswing ever since, mainly because she feels sexy?

Gallery tags: Boy Big tits Blonde

16 Total pics

A really horny redhead babe fucking a dick in this library

Gallery tags: Boy Amateur Babe

15 Total pics

The beach is always special for Nina because she lost her virginity there. One day her boyfriend took her there at night and under the moonlight he destroyed her cooch and showed her how to swallow cum. It was a magical night!

Models on This Gallery: Silvia Saint

Gallery tags: Boy Amateur Babe

18 Total pics

Milf secretary strips and sucks for the cam

Gallery tags: Boy Amateur Anal

16 Total pics

Secretary in stockings gets laid hardcore

Gallery tags: Boy American Anal

15 Total pics

Husband is tortured, locked in a chastity belt, completely humiliated and butt-fucked from behind in front of wife\'s boyfriend!

Models on This Gallery: Aiden Starr Silvia Saint Danny Wylde

Gallery tags: Boy Domination Foot fetish

12 Total pics

3 hot ass mini skirt milfs pounded hard in their wet bikinis hot ass licking pussy fucking pics

Models on This Gallery: Nicky Angel

Gallery tags: Boy Ass Bikini

12 Total pics

Sexy babe gets tricked into fucking on camera so her boyfriend can get payback fro cheating.

Gallery tags: Boy Amateur American

18 Total pics

This Spanish hottie has the tightest natural little spinner body youve seen. Naturals tits and a nice tight shaved pussy for the long banging! And boy can she take a banging.. but we tore that up!

Gallery tags: Boy Amateur Ass

12 Total pics

Sexy brunette babe and her boyfriend leave nice mess for their landlord.

Gallery tags: Boy Amateur American

15 Total pics

Zazie has to pull out all the stops to get a confession from her suspect. Interrogating makes this fat slut really wet and using her massive mams and giant wet slit, she coaxes more than a confession from her captive.

Gallery tags: Boy Ass Bbw

23 Total pics

Teen slut Dakota Charms jerking cock to squirts semen on the laundry

Gallery tags: Boy Girl Glamour

12 Total pics

This sexy amateur chick is one of those filthy girls who love deep penetration sex and hard anal fucking. This is why this movie is one of the coolest amateur anal videos you\'ve ever seen

Models on This Gallery: Brook Logan

Gallery tags: Boy Anal Blonde

16 Total pics

Hot blonde russian babe plays with her pussy for the camera

Gallery tags: Boy Amateur Babe

12 Total pics

Check out these horny college boys suck and jerk eachother off in these hot dorm room crazy partys

Gallery tags: Boy Blowjob College

13 Total pics

Blonde teen is doing a rimjob outside before she gets facial

Gallery tags: Boy Beautiful Big cock

12 Total pics

Milf with nipple rings and black thong getting banged on a lazyboy

Models on This Gallery: Afrodite Night Nina Kournikova Silvia Saint

Gallery tags: Boy Black Foot fetish

12 Total pics

PLAYBOY\'S GIRL FRIDAY an ad exec\'s private secretary is a pretty hot prospect herself This month, the credit for Playmate discovery goes to a sharp-eyed space salesman on Playboy\'s advertising staff. During a ca?

Gallery tags: Boy Babe Girl

12 Total pics

DanielleRiley-orangecamitopandboyshorts

Gallery tags: Boy Amateur Ass

12 Total pics

"""Why not be a Playboy model?"" Ashley thought when she submitted her photos to our offices. ""You\'re only young once. My best friend said that I should send in my photos, so I did."" Ashley is a budding legal secretary?"

Gallery tags: Boy Glamour Gorgeous

12 Total pics

Little boys, as we all remember from our childhoods, do their best to be the bane of little girls\' lives. One such mischievous young prankster will, however, go down in history as the prime reason Gwendolyn Hajek ref?

Gallery tags: Boy Asian Big tits

15 Total pics

Anya slides into (and then out of) a sexy, frilly polkadot top and tight little red boyshorts and lets her big, amazing 32GG\'s spill out all over, taking time to primp in front of a mirror and giving us TWO ANYA\'S for much of this set!

Models on This Gallery: Anya Zenkova

Gallery tags: Boy Amateur Big tits

12 Total pics

Busty blonde Puma Swede decides to sleep with her friends boyfriend and seduces him with her big tits.

Models on This Gallery: Puma Swede Silvia Saint

Gallery tags: Boy Big tits Blonde

12 Total pics

Stephanie\'s ambition in life is to obtain a bachelor degree in criminal justicce, which she\'s working on at the University of Cincinnati. Until recently she had no idea that she was making history in Playboy and on t?

Gallery tags: Boy Extreme Glamour

12 Total pics

Busty blonde Puma Swede decides to sleep with her friends boyfriend and seduces him with her big tits.

Models on This Gallery: Puma Swede Silvia Saint

Gallery tags: Boy American Big tits

16 Total pics

Hot and horny big tits teen agrees to get fucked for cash while her boyfriend watches and jerks off on her hot pics

Models on This Gallery: Bella Rossi

Gallery tags: Boy Big tits Brunette

12 Total pics

Scarlet comes in and apologizes about being late. As she turns around she sees that it\'s her sister\'s ex-boyfriend Bill. She takes a look at his resume and mentions a qualification that isn\'t listed like how he sexually pleased her sister in bed. Scarlet grabs Bill by the tie and spreads open her legs and asks Bill if he really wants to the job. Who knew a desk job interview could be so physically exhausting.

Models on This Gallery: Scarlet Red

Gallery tags: Boy Brunette Casting

12 Total pics

No idle hands here. When not posing for Playboy, Cyber Girl Carlotta Champagne is known to make handbags, belts, prom dresses and garter belts out of condoms. As seen in Playboy\'s Grapevine (February 2009), Carlotta\'?

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Girl

12 Total pics

Heidi has 20 years of dance training under her belt but describes herself as a bona fide tomboy. She\'s designing her own lingerie line and wants to put her dance skills to work in music videos.?

Models on This Gallery: Silvia Saint

Gallery tags: Boy Foot fetish Glamour

12 Total pics

?So many sex icons got their start with Playboy,? observes this Irish-Spanish model. ?I would love to be a part of that.? Welcome aboard, Krystle! Among the many cool things about her: Deftones is her favorite band,?

Models on This Gallery: Kendra Lust

Gallery tags: Boy Army Black

12 Total pics

Rahyndee James is staying over at her sister\'s house, but she\'s more interested in spending quality time with her sister\'s husband than her sister. She puts on sexy red lingerie and seduces her sister\'s husband. Rahyndee fucks her sister\'s husband as payback for her sister fucking her boyfriend. In this case, revenge isn\'t sweet, it\'s naughty.

Models on This Gallery: Rahyndee James

Gallery tags: Boy Asian Big nipples

12 Total pics

Yurizan Beltran and her boyfriends son are locked in the same room and have hot sex to pass the time.

Models on This Gallery: Alyssa Michelle Silvia Saint Yurizan Beltran

Gallery tags: Boy Ass Dad

12 Total pics

Yurizan Beltran and her boyfriends son are locked in the same room and have hot sex to pass the time.

Models on This Gallery: Alyssa Michelle Silvia Saint Yurizan Beltran

Gallery tags: Boy American Ass

12 Total pics

Presley Hart\'s boyfriend is a little to old to satisfy her anymore. He\'s 60 years old! Presley really misses hard cock inside her, so she decides that the perfect person to fill her is her boyfriend\'s son. He\'s a little reluctant at first, I mean it is his dad\'s girl, but she is HOT! He would be crazy to turn down her request.

Models on This Gallery: Presley Hart

Gallery tags: Boy American Babe

12 Total pics

Eden was willing to suck dick and fuck our hero to get some extra cash she needed and boy did she blow his mind and his load

Gallery tags: Boy Blowjob Brunette

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