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Blonde Ambition
Jessica Simpson
Jessica Simpson in a sexy beer wench outfit that shows off her cleavage as she stands in a building lobby and greets some guys who walk in. After she talks to them for a while, we see Jessica serving some beers and then sitting at a table at a restaurant, still in the same outfit. From Blonde Ambition.
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Blonde Ambition
Penelope Ann Miller
Penelope Ann Miller lying on her stomach on a massage table wearing a red bra, showing cleavage as she props herself up to talk to Jessica Simpson, who comes into the room and kneels down next to her. From Blonde Ambition.
Sexy 1:01 - 52.63 MB - 1920x1040 px July 20th, 2017 @ 9:28 pm Penelope Ann Miller - Blonde Ambition.mp4More [+]
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That '70s Show
Jessica Simpson
Jessica Simpson sitting at a table in a restaurant wearing a low cut purple top with no bra and hard nipples as she makes out with a guy before Laura Prepon walks up in a blue swimsuit with hard nipples and talks with them for a while. From That '70s Show.
Sexy 1:07 - 23.38 MB - 1280x720 px March 31st, 2015 @ 6:52 pm Jessica Simpson & Laura Prepon - That 70s Show - S05E01 - 1.mp4More [+]
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That '70s Show
Jessica Simpson
Jessica Simpson wearing a blue dress with hard nipples as she stands at a school dance talking with a guy while getting upset with him before finally walking away. From That '70s Show.
Sexy 0:32 - 10.97 MB - 1280x720 px February 14th, 2015 @ 6:11 pm Jessica Simpson - That 70s Show - S05E14.mp4More [+]
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That '70s Show
Jessica Simpson
Jessica Simpson wearing a low cut bikini top under an opened pink wrap and showing some impressive cleavage as she sits on a beach talking with a guy for a while until finally she bends over while getting up and then pours a bucket of water over her body all while Laura Prepon watches. From That '70s Show.
Sexy 1:07 - 23.45 MB - 1280x720 px February 3rd, 2015 @ 9:52 pm Jessica Simpson & Laura Prepon - That 70s Show - S05E01 - 2.mp4More [+]
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That '70s Show
Jessica Simpson
Jessica Simpson sitting in a restaurant showing some nice cleavage in a bikini top under her opened pink shirt all while she talks with Laura Prepon and some guys. From That '70s Show.
Sexy 0:25 - 8.57 MB - 1280x720 px December 23rd, 2014 @ 3:32 pm Jessica Simpson & Laura Prepon - That 70s Show - S05E01 - 3.mp4More [+]
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That '70s Show
Jessica Simpson
Jessica Simpson wearing a blue teddy as she sits on a couch talking with Laura Prepon (purple) and Mila Kunis (pink) and then giving us an upskirt look at her blue panties as she adjusts her position before they grab pillows and start having a pillow fight as feathers fly everywhere. From That '70s Show.
Sexy 0:39 - 13.73 MB - 1280x720 px December 17th, 2014 @ 6:45 pm Jessica Simpson, Laura Prepon & Mila Kunis - That 70s Show - S05E13 - 1.mp4More [+]
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That '70s Show
Jessica Simpson
Jessica Simpson in a restaurant telling a guy she wants to do something wet and dirty with him before it cuts to them making sandcastles on a beach all while she's wearing bikini bottoms and a loose opened shirt with a bikini top underneath that shows her cleavage as they talk. From That '70s Show.
Sexy 0:55 - 19.13 MB - 1280x720 px December 9th, 2014 @ 7:35 pm Jessica Simpson - That 70s Show - S05E01.mp4More [+]
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That '70s Show
Jessica Simpson
Jessica Simpson wearing a white dress as she sits on the couch board with Mila Kunis (left) and Laura Prepon (center) before getting up to leave and bending over showing some cleavage and then being brought back into a room by a guy who then talks to them all. From That '70s Show.
Sexy 0:24 - 8.18 MB - 1280x720 px December 7th, 2014 @ 8:53 pm Jessica Simpson, Laura Prepon & Mila Kunis - That 70s Show - S05E13 - 2.mp4More [+]
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Employee of the Month
Jessica Simpson
Jessica Simpson walking in a fantasy slow motion through a store in a blue top with hard nipples as her large breasts bounce a bit all while some guys watch her. From Employee of the Month.
Sexy 0:17 - 5.75 MB - 1280x688 px December 8th, 2012 @ 5:18 pm Jessica Simpson - Employee of the Month - 1.mp4More [+]
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Employee of the Month
Jessica Simpson
Jessica Simpson sitting on some store shelves high up in a row talking with a guy while showing off some very impressive cleavage in a low cut blue dress until the guy turns the lights off and they sit in the dark talking a bit more. From Employee of the Month.
Sexy 0:59 - 20.43 MB - 1280x688 px December 8th, 2012 @ 5:16 pm Jessica Simpson - Employee of the Month - 8.mp4More [+]
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Employee of the Month
Jessica Simpson
Jessica Simpson standing on a porch talking with a guy while wearing a low cut dress that shows her cleavage until finally he awkwardly kisses her and sucks on her bottom lip as she pulls away and then goes into the house and closes the door. From Employee of the Month.
Sexy 0:36 - 12.37 MB - 1280x688 px December 6th, 2012 @ 5:10 pm Jessica Simpson - Employee of the Month - 4.mp4More [+]
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Employee of the Month
Jessica Simpson
Jessica Simpson sitting at a table in a blue dress that shows off her cleavage as she talks with a guy before the camera pulls back and up. From Employee of the Month.
Sexy 0:15 - 5.24 MB - 1280x688 px December 6th, 2012 @ 5:09 pm Jessica Simpson - Employee of the Month - 5.mp4More [+]
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Employee of the Month
Jessica Simpson
Jessica Simpson showing off some very nice cleavage in a low cut white dress as she sits in a restaurant booth with a guy while he looks around for his wallet and talks with her. From Employee of the Month.
Sexy 0:34 - 11.66 MB - 1280x688 px December 4th, 2012 @ 4:48 pm Jessica Simpson - Employee of the Month - 3.mp4More [+]
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Employee of the Month
Jessica Simpson
Jessica Simpson wearing a low cut blue dress that shows off her cleavage as she stands on the roof of a building with a guy as they hit golf balls out into the parking lot. From Employee of the Month.
Sexy 0:41 - 14.23 MB - 1280x688 px December 4th, 2012 @ 4:47 pm Jessica Simpson - Employee of the Month - 7.mp4More [+]
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Employee of the Month
Jessica Simpson
Jessica Simpson wearing a low cut lavender shirt that shows off her cleavage as she talks with a guy while at a cash register before walking over to where some people are cheering. From Employee of the Month.
Sexy 0:26 - 9.13 MB - 1280x688 px December 2nd, 2012 @ 6:59 pm Jessica Simpson - Employee of the Month - 2.mp4More [+]
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Employee of the Month
Jessica Simpson
Jessica Simpson sitting on a couch eating popcorn and watching a movie with a guy while wearing a blue dress that shows a lot of cleavage all as the camera pulls back to reveal they're in the middle of a store. From Employee of the Month.
Sexy 0:10 - 3.38 MB - 1280x688 px December 2nd, 2012 @ 6:56 pm Jessica Simpson - Employee of the Month - 6.mp4More [+]
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The Dukes of Hazzard
Jessica Simpson
Jessica Simpson bending over in a pair of Daisy Duke shorts and a red bikini top as she tries to get a couple police officers to help her with her car. From The Dukes of Hazzard.
Sexy 0:32 - 11.15 MB - 1280x528 px April 1st, 2011 @ 11:39 am Jessica Simpson - The Dukes of Hazzard - 1.mp4More [+]
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The Dukes of Hazzard
Jessica Simpson
Jessica Simpson showing some stunning cleavage as she approaches a guy at his desk while in a pink bikini, and then bends far over to give him a good look at her breasts. From The Dukes of Hazzard.
Sexy 0:37 - 12.93 MB - 1280x528 px April 1st, 2011 @ 11:38 am Jessica Simpson - The Dukes of Hazzard - 2.mp4More [+]
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Jessica Simpson: Reality Tour Live
Jessica Simpson
Jessica Simpson wearing a pink dress that shows lots of cleavage, squeezing her breasts and almost causing them to spill over the top of the dress as she sings a song on stage at a concert. After the song, she stops to adjust her top and talk about it before beginning to perform again. Good quality HDTV capture from Jessica Simpson: Reality Tour Live.
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Various Sources
Jessica Simpson
Jessica Simpson being filmed by a personal video camera on a stage wearing an extremely tight red outfit that shows off an very large camel toe that gets zoomed in on repeatedly by the cameraman as some guys cheer and watch while she talks to the audience.
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Extra
Jessica Simpson
Jessica Simpson wearing a low cut white dress that shows some cleavage as she poses for photographers and then talks with a guy from Extra.
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2006 ALMA Awards
Jessica Simpson
Jessica Simpson wearing a strapless orange dress and showing off a lot of cleavage as she presents at the 2006 ALMA Awards.
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Access Hollywood
Jessica Simpson
Jessica Simpson wearing a low cut green dress that shows off some nice cleavage as she poses for photographers on the red carpet and talks with a guy briefly from Access Hollywood.
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The Dukes of Hazzard
Jessica Simpson
Jessica Simpson showing some stunning cleavage as she approaches a guy at his desk while in a pink bikini, and then bends far over to give him a good look at her breasts. Hi-res DVD capture from The Dukes of Hazzard.
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The Dukes of Hazzard
Jessica Simpson
Jessica Simpson bending over in a pair of Daisy Duke shorts and a red bikini top as she tries to get a couple police officers to help her with her car. Hi-res DVD capture from The Dukes of Hazzard.
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The Dukes of Hazzard
Jessica Simpson
Jessica Simpson seen in a sexy pink bikini as she bends over the General Lee while washing the car during part of her These Boots are Made For Walkin' music video. Hi-res DVD capture from the extras of The Dukes of Hazzard.
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2005 MTV Video Music Awards
Jessica Simpson
Jessica Simpson wearing a beige top and briefly bending over and showing some cleavage before her sister Ashlee Simpson and herself go to the mic stand to present at the 2005 MTV Video Music Awards.
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The Dukes of Hazzard
Jessica Simpson
Jessica Simpson giving us some nice looks at her ass in a pink bikini with slightly hard nipples as she washes a car in a behind the scenes look at her These Boots Are Made For Walking music video from The Dukes of Hazzard film as seen on MTV's Making the Video.
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Access Hollywood
Jessica Simpson
Jessica Simpson seen wearing a pink bikini in a couple brief clips from her upcoming movie The Dukes of Hazzard and then seen wearing very short jean shorts and a red bikini top in some behind the scenes footage from Access Hollywood.
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