Playground Show Big Porn Movies

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Jack’s Playground: Big Tit Show 9

Jack’s Playground: Big Tit Show 9
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Save the best for last!. Jack says dee cups will surely keep you up!.

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Jack’s Playground: Big Tit Show 6

Jack’s Playground: Big Tit Show 6
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Jack’s Playground: Big Tit Show 6. Big tits are more than a handful. They’re two..

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Jack’s Playground: Big Tit Show 5

Jack’s Playground: Big Tit Show 5
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The One and Only. It’s Time For a Titty Smackdown!.

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Jack’s Playground: Big Tit Show 7

Jack’s Playground: Big Tit Show 7
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Jack’s Playground: Big Tit Show 7. Big tits are more than a handful. They’re Two!.

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Jack’s Playground: Big Tit Show 4

Jack’s Playground: Big Tit Show 4
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Jack’s Playground: Big Tit Show 4. Big Tits, Blonde Chicks Perfect Size For Handy Guys!.

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Jack’s Playground: Big Tit Show 3

Jack’s Playground: Big Tit Show 3
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Got D’s? Some More Juice For You To Squeeze!. “Jack is back with another excellent show focusing on girls with impressive D-cups. There are plenty of titty fucking and pussy…

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Jack’s Playground: Big Tit Show 2

Jack’s Playground: Big Tit Show 2
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Oops…Jack Did It Again! More D-Cups Are Waiting For You To Unload On!. This show is full of 2-many delicious babes, 2-many horny humpers, and 2-many big boobies bursting out…

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Jack’s Playground: Big Tit Show

Jack’s Playground: Big Tit Show
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Jack Says, “Big Tits Are More Nutritious!”. Jack’s at it again! In his playground, Jack is busy casting for music videos. The delicious girls will do anything for stardom. Some…

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Jack’s Playground: Big Tit Show 8

Jack’s Playground: Big Tit Show 8
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Jack’s Playground: Big Tit Show 8. Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s…

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Jack’s Playground: Big Ass Show 7

Jack’s Playground: Big Ass Show 7
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A FantASStic Show Are you ready for some extreme bubble bursting butts?

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Jack’s Playground: Big Ass Show 8

Jack’s Playground: Big Ass Show 8
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Teagan Presley & ANAL, does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and they…

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Jack’s Playground: Big Ass Show 6

Jack’s Playground: Big Ass Show 6
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Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Jack finds pleasure deep…

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Jack’s Playground: Big Ass Show

Jack’s Playground: Big Ass Show
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Mega Packed with Juicy Crack “Check out these packs with juicy crack presented by Jack”

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Jack’s Playground: Big Ass Show 2

Jack’s Playground: Big Ass Show 2
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Jack’s busy in his playground casting big-ass babes for leading roles in his yet-to-be-seen music videos. The delicious girls will do ANYTHING for stardom! Some suck, some fuck and some…

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Jack’s Playground: Big Ass Show 3

Jack’s Playground: Big Ass Show 3
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Big, Hot and Kinky! “More Cushin For the Pushin”

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Jack’s Playground: Big Ass Show 4

Jack’s Playground: Big Ass Show 4
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Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Robby finds pleasure deep…

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Jack’s Playground: Big Ass Show 5

Jack’s Playground: Big Ass Show 5
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Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Jack finds pleasure deep…

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Jack’s Playground: Big Ass Show 9

Jack’s Playground: Big Ass Show 9
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Jack’s busy in his playground casting big-ass babes for leading roles in his music videos. This time he gets Alexis Texas and Shyla Stylez to bend over for him. These…

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Jack’s Playground: Big Tit Show 9

Jack’s Playground: Big Tit Show 9
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Save the best for last! Jack says dee cups will surely keep you up!

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TS Playground 27

TS Playground 27
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TS Playground 27 Director Jay Sin spotlights the sexiest trans talent from Brazil and the U.S. in TS Playground 27. Femme but very functional beauties tease the camera with their…

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TS Playground 25

TS Playground 25
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Director Jay Sin, the master of playfully nasty anal pornography, turns his camera toward the exotic world of glamorous T-girls and the kinky dudes that love them: TS Playground 25…

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TS Playground 6

TS Playground 6
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Kinky porn pioneer Jay Sin has won ass-obsessed hearts through an amazing career of documenting extreme rectal perversity with the most anally acrobatic ladies in the game. His explosive she-male…

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Jack’s Leg Show

Jack’s Leg Show
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Got Long Legs? Just Wait Until It Opens! Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming…

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Ghostbusters XXX: A Porn Parody

56 mins.
Ghostbusters XXX: A Porn Parody
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1.5 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.Ghostbusters XXX: A Porn…

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My First Porn 7

My First Porn 7
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An All New Series That Tries Really Hard To Fit In.. The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 7 features…

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6th Annual Tranny Awards: The Winners

2 hrs. 15 mins.
6th Annual Tranny Awards: The Winners
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6th Annual Tranny Awards: The Winners. 6th Annual Tranny Awards: The Winners is directed by Blackula. The performers in this movie won awards at the most recent Tranny Awards in…

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Dogg Piled: Swinger MILF Gangbangs

Dogg Piled: Swinger MILF Gangbangs
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Dogg Piled: Swinger MILF Gangbangs Big butt swing wife MILF, Gracie Playground, was nice enough to show up to her video shoot with her hubby, Brick. Dogg invited over a…

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This Is Definitely Not Ugly Betty: A XXX Tranny Parody

This Is Definitely Not Ugly Betty: A XXX Tranny Parody
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1st Ever T-Girl Adult Parody! Loosely based on the pilot episode of the hit TV show, This Is Definitely Not Ugly Betty: A XXX Tranny Parody starts at the beginning….

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Jesse Jane Image

Jesse Jane Image
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Jesse Jane: Image explores the famous and undeniably sexy image of Digital Playground superstar, Jesse Jane. Her playful fantasies are fulfilled in 4 amazingly provocative scenes. Watch Rick Patrick give…

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Gabriella Fox Foxxxy

Gabriella Fox Foxxxy
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Gabriella Fox Foxxxy Gabriella Fox, Digital Playground’s sultry Latina contract girl, stars in three of six scenes of the must-own “Gabriella Fox: Foxxxy”. The gorgeous starlet loses all her inhibitions…