Shailene Woodley sorted by most popular
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White Bird in a Blizzard
Shailene Woodley
Shailene Woodley making out with a guy as they come in the door of a house, and then seen topless as she pulls her shorts off and then lays back on a bed with the guy. We see her naked body from the side with the guy on top of her as she and the guy have sex. From White Bird in a Blizzard.
1:10 - 24.34 MB - 1280x538 px
September 25th, 2014 @ 8:42 am
Shailene Woodley - White Bird in a Blizzard - 2.mp4
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Endings, Beginnings
Shailene Woodley
Shailene Woodley making out with a guy and ending up topless, Shailene placing the guy's hand up her skirt to finger her. The guy then slides her panties off and leans over to go down on her before having sex, Shailene showing more of her breasts as she ends up on her back on a table. From Endings, Beginnings. Updated to higher quality.
1:36 - 57.33 MB - 1920x806 px
March 7th, 2021 @ 9:20 pm
Shailene Woodley - Endings, Beginnings - 1.mp4
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White Bird in a Blizzard
Shailene Woodley
Shailene Woodley sitting on a couch next to a guy as she lowers her top to reveal both breasts, giving us a longer look at her right breast as her hair falls over her other. She then leans in to kiss the guy. From White Bird in a Blizzard.
0:43 - 14.91 MB - 1280x538 px
September 25th, 2014 @ 8:39 am
Shailene Woodley - White Bird in a Blizzard - 3.mp4
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The Spectacular Now
Shailene Woodley
Shailene Woodley of The Descendants fame sitting on a bed and pulling her shirt off to reveal a bra before leaning over to kiss a guy. They then lay back on a bed and Shailene takes her bra off, showing her left nipple and then her full breast as her hair covers her right nipple and she has sex with the guy, lying underneath him. From The Spectacular Now.
2:56 - 61.05 MB - 1280x536 px
January 6th, 2014 @ 1:27 pm
Shailene Woodley - The Spectacular Now.mp4
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White Bird in a Blizzard
Shailene Woodley
Shailene Woodley standing in a bathroom wrapped in a towel as she looks at herself in the mirror. She then grabs the corners of the towel and pulls them apart to expose her breasts and look at herself topless before she hears someone at the door and quickly covers up. From White Bird in a Blizzard.
0:13 - 4.42 MB - 1280x538 px
September 25th, 2014 @ 8:41 am
Shailene Woodley - White Bird in a Blizzard - 1.mp4
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Snowden
Shailene Woodley
Shailene Woodley rolling over on top of a guy in bed, showing her bare butt from the side as well as her breasts, which have had the nipples digitally blurred out. She then has sex with the guy, riding him as he looks over a laptop across the room. From Snowden.
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White Bird in a Blizzard
Shailene Woodley
Shailene Woodley very briefly showing her right breast when she is caught with a guy on a couch, her red checked shirt pulled up and her jeans partially pulled down until she covers up quickly. From White Bird in a Blizzard.
0:05 - 1.90 MB - 1280x538 px
September 27th, 2014 @ 2:21 pm
Shailene Woodley - White Bird in a Blizzard - 6.mp4
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Endings, Beginnings
Shailene Woodley
Shailene Woodley making out with a guy who then undresses her on the floor, pulling her pants off before she removes her panties. Her shirt then comes off and we see her bra, her nipple peeking out at times as she has sex with the guy while bottomless. We then see a bit more of her right nipple as she lies on her back afterward, her bra pushed up on one side. From Endings, Beginnings. Updated to higher quality.
1:30 - 50.22 MB - 1920x806 px
March 7th, 2021 @ 9:14 pm
Shailene Woodley - Endings, Beginnings - 3.mp4
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Three Women
Shailene Woodley
Shailene Woodley naked in bed with a guy as they have sex with Shailene on her back under him showing her breasts as she arches her back. Afterward, we get a good look at her butt when she lies about on the bed on her stomach, rolling over to again reveal her breasts as well as some fake bush. From Three Women.
1:16 - 30.53 MB - 1920x802 px
December 12th, 2023 @ 9:18 pm
Shailene Woodley - Three Women - S01E05 - 1.mp4
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Big Little Lies
Shailene Woodley
Shailene Woodley first seen running across a beach in a blue dress that is off one shoulder, causing her breast to almost bounce out as she goes in slow motion. We then see her lying face down on a bed with her bare butt visible briefly before a guy covers her up with her dress. Lastly, we see her once more on the beach, this time at dusk. From Big Little Lies.
0:23 - 25.91 MB - 1920x1080 px
March 6th, 2017 @ 11:58 pm
Shailene Woodley - Big Little Lies - S01E03 - 1.mp4
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White Bird in a Blizzard
Shailene Woodley
Shailene Woodley sitting in bed with the sheets pulled around her as Eva Green leans over and tugs on the covers, causing Shailene's right nipple to partially come into view. From White Bird in a Blizzard.
0:13 - 4.60 MB - 1280x538 px
September 25th, 2014 @ 8:36 am
Shailene Woodley - White Bird in a Blizzard - 4.mp4
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The Descendants
Shailene Woodley
Shailene Woodley of The Secret Life of the American Teenager fame sitting on the edge of a swimming pool in a blue bikini, talking on a phone before she slips into the water and swims across the pool. We then see her emerging from the pool and grabbing a towel to dry off. From The Descendants.
Sexy 1:46 - 36.93 MB - 1280x536 px March 11th, 2012 @ 12:24 pm Shailene Woodley - The Descendants.mp4 -
Adrift
Shailene Woodley
Shailene Woodley seen sitting naked on the deck of a boat in the ocean, showing some side boob and the upper portion of her butt. She then lays back, showing bare breasts as it begins to rain on her. From Adrift. Updated to higher quality.
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Endings, Beginnings
Shailene Woodley
Shailene Woodley making out with a g uy in the front seat of a car at night, giving a dimly-lit view of her breasts as she ends up in the guy's lap having sex. From Endings, Beginnings. Updated to higher quality.
0:20 - 10.59 MB - 1920x806 px
March 7th, 2021 @ 9:12 pm
Shailene Woodley - Endings, Beginnings - 4.mp4
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White Bird in a Blizzard
Shailene Woodley
Shailene Woodley briefly showing pokey nipples in a tank top with nothing underneath as she stands next to a mailbox and looks to her side before turning around. From White Bird in a Blizzard.
Sexy 0:03 - 0.88 MB - 1280x538 px September 27th, 2014 @ 2:22 pm Shailene Woodley - White Bird in a Blizzard - 5.mp4More [+]
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Big Little Lies
Shailene Woodley
Shailene Woodley dropping her dress off while walking into the waves at a beach, showing bare butt as she goes naked. From Big Little Lies.
0:09 - 11.33 MB - 1920x1080 px
March 6th, 2017 @ 11:57 pm
Shailene Woodley - Big Little Lies - S01E03 - 2.mp4
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Endings, Beginnings
Shailene Woodley
Shailene Woodley lying on her back with a guy in bed while having sex, offering a shadowy look at her right breast as the guy finishes. The guy then pulls the covers up a bit, but her breast is revealed again as he moves to pick up a towel. From Endings, Beginnings. Updated to higher quality.
0:52 - 22.73 MB - 1920x806 px
March 7th, 2021 @ 9:17 pm
Shailene Woodley - Endings, Beginnings - 2.mp4
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Snowden
Shailene Woodley
Shailene Woodley wearing a purple sports bra and skimpy red shorts as she teaches a pole dancing class while flipping upside down on the pole spreading her legs and showing her ass and then is seen sliding down the pole slowly eventually coming to rest on her stomach all while in a dance studio full of mirrors. From Snowden.
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Three Women
Shailene Woodley
Shailene Woodley sitting up in bed with the covers around her waist and her breasts in view. She then gets out of bed completely naked and moves into a bathroom. There we see her in some pain as she puts her hand between her legs and discovers she is bleeding, Shailene curling up in a ball on the floor and sitting on the toilet before wiping up some of the blood off the floor. From Three Women.
2:05 - 55.26 MB - 1920x802 px
December 14th, 2023 @ 6:17 pm
Shailene Woodley - Three Women - S01E05 - 4.mp4
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Shailene Woodley sorted by most popular continued
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Three Women
Shailene Woodley
Shailene Woodley on her back under a guy while having sex in bed, the covers over him as he lays on top of her. Afterward, we get some occasional looks at her breasts as the guy moves over and she turns on her side to talk to him. From Three Women.
0:50 - 25.35 MB - 1920x802 px
December 14th, 2023 @ 6:19 pm
Shailene Woodley - Three Women - S01E05 - 3.mp4
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Three Women
Shailene Woodley
Shailene Woodley bottomless lying on her side in a van as a guy has sex with her from behind. A bit of (fake) bush comes into view briefly as she moves. Afterward, they realize his condom was left behind inside Shailene, and she tries to retrieve it before getting on all fours and showing cleavage in her bra down her shirt as the guy pulls the condom out from behind. From Three Women.
Sexy 0:55 - 18.73 MB - 1920x802 px December 19th, 2023 @ 9:01 pm Shailene Woodley - Three Women - S01E05 - 2.mp4More [+]
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Robots
Shailene Woodley
Shailene Woodley lying on her back under a guy while having sex in bed, Shailene topless but her breasts blocked from view by his arm. We do get to see a bit when she and the guy come together and she arches her back as the lamp next to them explodes. We then see Shailene and the guy sitting up in darkness, Shailene's breast seen from the side in silhouette with no nipple. From Robots.
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Adrift
Shailene Woodley
Shailene Woodley wearing a blue bathing suit that shows prominent pokey nipples as she walks across some rocks with a guy, takes off her shorts and jumps off into some water below. From Adrift.
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Adrift
Shailene Woodley
Shailene Woodley wearing a soaked yellow tank top that shows her nipples through as she emerges from the hold of a sailboat in stormy water, walking around on the deck and looking around at the damaged boat. From Adrift.
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Robots
Shailene Woodley
Shailene Woodley wearing a plaid skirt and a tight white crop top with her blue bra visible underneath, displaying plenty of cleavage when she walks into a room where she encounters another Shailene Woodley and a guy. She then comes onto the guy, trying to kiss him and pushing him onto a sofa where she climbs into his lap and places his hands on her breasts over her shirt. We then see her crawling around on the floor as she tries to pull the guy's pants off while straddling him until the other Shailene pushes her away. From Robots.
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Three Women
Shailene Woodley
Shailene Woodley lying in a guy's arms on a sofa, naked on top of him as we see side boob and one bare butt cheek. From Three Women.
0:04 - 0.58 MB - 1920x802 px
December 16th, 2023 @ 2:45 pm
Shailene Woodley - Three Women - S01E07.mp4
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