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Models on This Gallery: Bailey Blue

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Models on This Gallery: Angelina Croft

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Models on This Gallery: Aliz B

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Models on This Gallery: Faye Reagan

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"When you meet Helena Antonaccio for the first time, she has a charmingly modest habit of lowering her eyelashes - a persistent holdover from her bashful teens. ""I was always a shy type,"" she admits, ""but since becomi?"

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Models on This Gallery: Abbey Brooks

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Models on This Gallery: Adelyn Ames

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Capri Cavanni was given the go ahead to experiment with girls in order to spice up her relationship with Johnny. The lucky girl that Capri chose to fuck for the first time is none other than Taylor Whyte. Johnny arrives and finds Capri about to go to town on Taylor and he is upset. Apparently there was a misunderstanding. Johnny was OK with Capri experimenting with other girls as long as he was there to enjoy it as well. Capri see's this as a very easy problem to solve. She has Johnny join in and fuck them both.

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Models on This Gallery: Codi Bryant

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Models on This Gallery: Hailey Comet

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Models on This Gallery: Aarielle Alexis

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Remy accepted Johnny's request for a one on one session for yoga. It's Johnny's first time and he didn't want to be embarrassed if he couldn't keep up with all the others in the class. They start the session with a little stretching because Johnny seem a bit tense. Remy starts to rub all over Johnny's muscular body and couldn't help but notice his bulge in his briefs.. Remy has a better idea for what Johnny needs to relieve the tension in his body and fucking the sexy Remy LaCroix might be the best release he's ever had.

Models on This Gallery: Remy LaCroix

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Models on This Gallery: Bianca Trump

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Models on This Gallery: Tiffany Fallon

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Cybergirl Jenni Lynn comes to you from sunny Los Angeles, California. She?s tall ? 5?9? ? with dark blonde hair, green eyes and a generous bust. She?s a working model, but this is her first time posin

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Models on This Gallery: Abbie Cat

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Models on This Gallery: Candace Brown

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Models on This Gallery: Karlie Montana

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Models on This Gallery: Renata Black

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Models on This Gallery: Alana Evans

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This is Madison first time shooting so we thought we would give her a world premiere by releasing her on the world famous Assparade.com. So come watch this phat ass get her brains fucked out!

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Models on This Gallery: Agnes Black Ali Kat

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We bumped into Kelly Tough for the first time in the kitchen at Playboy Mansion West. She'd stopped by for an orange juice after a daily rehearsal / workout with The Playmates, the Playboy singing group. Kelly's hair?

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Models on This Gallery: Candice Cassidy

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Hello everybody. Today our guest is Miranda Kelly, a hot amateur girl that came to my office because of the newspaper ad, and of course it was her first time on camera.

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Models on This Gallery: Adrienne Coyne

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Models on This Gallery: Kodi Gamble

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Models on This Gallery: Alyson Sykes

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Some moments are so precious that it's a shame not to film them! Luckily, first time sex on camera will never be forgotten 'cause you can watch this beautiful movie over and over again

Models on This Gallery: Ashanti A Kendall Karson

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Gorgeous and curvaceous Carrie Stevens may be one of Playboy's most photographed women, but there are photos of Carrie that can only be seen on Playboy Plus. Here, for the first time, are her original Playboy test sh?

Models on This Gallery: Missy Nicole

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Models on This Gallery: Alana Play

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Models on This Gallery: Charlee Monroe

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India Summer went back to school after not attending for years. I guess you could say that makes her the cougar of the classroom and she's definitely on the prowl. She invites the teacher's aide, Bill, over to her place because she needs help studying. She just gets so distracted in class. School is hard for India, but only because she's too busy thinking about taking Bill's hard cock in her pussy. Once she has Bill alone in her bedroom this cougar pounces on him. Bill will never forget his first time seduced by a cougar.

Models on This Gallery: India Summer

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Models on This Gallery: Andrea Sultisz Chanel Bryant

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Models on This Gallery: Aiden Ashley

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Models on This Gallery: Cinthia Santos Tiffany Fallon

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I like to see the evolution. When she takes her bra off and those natural tatas fall it gives me goose bumps. Watch a first timer get fucked now. Enjoy!

Models on This Gallery: Erica Campbell

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I have a "thing" for older women, so when I saw that Darla Crane was available through the agency, I had to have her. The sexy MILF is perfect with that thick ass and long beautiful hair. She knows how to fuck and take care of a man. This was my first time ever doing anything like this. She helped me out, considered role playing, and I had the night of my life.

Models on This Gallery: Darla Crane

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Models on This Gallery: Natasha Nice

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Models on This Gallery: Angela D'Angelo

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"The first time you meet Melinda Mays, she's likely to smile and say in her soft, husky, little-girl voice, ""Hey."" On the other hand, she might not. Because of pressure from boyfriends who've told her she's too friend?"

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Models on This Gallery: Emily Addison

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