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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal sitting on bed beside a guy as she opens up her top to expose her breasts, licking her fingers and tweaking her nipples. The guy then reaches over to squeeze her breasts as she guides his hands and then undoes his pants and pulls out his penis. Maggie then pulls out a condom with her breasts still in view. From The Deuce.
1:10 - 75.40 MB - 1920x1080 px
August 25th, 2017 @ 1:33 pm
Maggie Gyllenhaal - The Deuce - S01E01.mp4
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal sitting down next to a guy as she cries, leaning over to show some great cleavage before the guy reaches his hand down her dress to grab her breast. From Sherrybaby.
Sexy 1:08 - 23.84 MB - 1280x696 px October 11th, 2015 @ 8:22 pm Maggie Gyllenhaal - Sherrybaby - 4.mp4More [+]
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal lowering her dress to reveal her breasts as a guy moves a smoking bowl around her to cleanse her. From Sherrybaby.
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal of The Dark Night fame shown bent over as a guy has sex with her from behind in a basement. We then see her breasts as she sits on a workbench topless and tells the guy that she is shaven and that he should kiss it. She then leans back as he goes down on her and we see more of her breasts. From Sherrybaby.
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal unbuttoning her shirt while standing in front of a guy's desk, pulling her purple bra up to show her breasts to a guy as she tries to get hired for a job. From Sherrybaby.
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal having a guy pull her shirt over her head to expose her breasts as she stands topless, turning around to show her body to the guy. She then lies down on a bed as the guy joins her and begins to kiss her. Maggie is also wearing some red panties that appear to be see-through. From Sherrybaby.
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Sherrybaby
Bridget Barkan
Bridget Barkan showing some generous cleavage and pokey nipples in a wet bathing suit as she gets out of a pool and stands on the side while talking to Maggie Gyllenhaal. From Sherrybaby.
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Frank
Maggie Gyllenhaal
Maggie Gyllenhaal first seen having wild sex with a guy in a hot tub, dunking him under the water as she rides him while wearing a robe that gets all wet. We then see her naked as she sits in the hot tub across from the guy afterward, giving us a slightly murky view of her right breast through the water. From Frank.
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The Honourable Woman
Maggie Gyllenhaal
Maggie Gyllenhaal making out with a guy on a sofa as we see some pokey nipples in her brown shirt. She then slides down to the floor and the guy undresses her, revealing her undergarments after he takes her shirt and pants off. Maggie then lies on her back on the floor with her right nipple popping out of her slip as the guy drips some alcohol into Maggie's mouth and on her body. From The Honourable Woman.
2:06 - 43.79 MB - 1280x720 px
August 8th, 2014 @ 2:32 pm
Maggie Gyllenhaal - The Honourable Woman - S01E06.mp4
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The Honourable Woman
Maggie Gyllenhaal
Maggie Gyllenhaal standing up bottomless with her pants pulled down on one ankle and her shirt only partially covering her bare butt. She then bends over to pull her pants back on, her shirt riding up and exposing more of her butt. From The Honourable Woman.
0:24 - 8.22 MB - 1280x720 px
August 2nd, 2014 @ 5:47 pm
Maggie Gyllenhaal - The Honourable Woman - S01E04.mp4
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The Honourable Woman
Maggie Gyllenhaal
Maggie Gyllenhaal wearing an open shirt that exposes her partially see-through red bra underneath, her pokey nipples on display as she leads a guy into an apartment with her skirt hiked up to show her panties. She then lays down on a couch and the guy makes out with her for a while, first with Maggie on her back and then with Maggie straddling him in his lap. From The Honourable Woman.
Sexy 2:35 - 53.99 MB - 1280x720 px August 2nd, 2014 @ 5:45 pm Maggie Gyllenhaal - The Honourable Woman - S01E02.mp4More [+]
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The Honourable Woman
Maggie Gyllenhaal
Maggie Gyllenhaal pulling her shirt over her head to reveal a see-through brown bra that shows her left nipple. From The Honourable Woman.
0:10 - 3.49 MB - 1280x720 px
July 31st, 2014 @ 11:50 am
Maggie Gyllenhaal - The Honourable Woman - S01E01.mp4
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The Honourable Woman
Maggie Gyllenhaal
Maggie Gyllenhaal sitting on the floor in a bra and panties, the bra slightly see-through to show her left nipple as she begins to talk on a phone while crying. From The Honourable Woman.
Sexy 0:27 - 10.24 MB - 1280x720 px July 19th, 2014 @ 11:42 am Maggie Gyllenhaal - The Honourable Woman - S01E03.mp4More [+]
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Jimmy Kimmel Live
Maggie Gyllenhaal
Maggie Gyllenhaal walking out on stage and then sitting down and talking with a guy all while wearing a low cut black dress with her breasts pushed together showing some impressive cleavage. From Jimmy Kimmel Live. Part 1 of 3.
Sexy 3:15 - 67.57 MB - 1280x720 px June 26th, 2013 @ 3:10 pm Maggie Gyllenhaal - Jimmy Kimmel Live - 2013-06-18 - 1-1.mp4More [+]
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Jimmy Kimmel Live
Maggie Gyllenhaal
Maggie Gyllenhaal talking with a guy while wearing a black dress that shows off her cleavage. From Jimmy Kimmel Live. Part 2 of 3.
Sexy 2:36 - 54.18 MB - 1280x720 px June 26th, 2013 @ 3:07 pm Maggie Gyllenhaal - Jimmy Kimmel Live - 2013-06-18 - 1-2.mp4More [+]
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Jimmy Kimmel Live
Maggie Gyllenhaal
Maggie Gyllenhaal wearing a low cut black dress with her breasts pushed together showing some nice cleavage as she talks with a guy. From Jimmy Kimmel Live. Part 3 of 3.
Sexy 2:51 - 59.34 MB - 1280x720 px June 26th, 2013 @ 3:05 pm Maggie Gyllenhaal - Jimmy Kimmel Live - 2013-06-18 - 1-3.mp4More [+]
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal sitting in a bath tub and lifting herself up to toss a snow globe into a nearby trash bin, most of her right breast and almost her nipple coming into view as she rises up to make the throw. From Secretary.
Sexy 0:11 - 3.96 MB - 1280x720 px September 11th, 2010 @ 2:47 pm Maggie Gyllenhaal - Secretary - 1.mp4More [+]
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal bent over a desk in an office, receiving a spanking from her boss as he stands behind her and first spanks her slowly and then more forcefully. From Secretary.
Sexy 2:25 - 50.39 MB - 1280x720 px September 11th, 2010 @ 2:45 pm Maggie Gyllenhaal - Secretary - 2.mp4More [+]
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal looking at herself in the mirror as she pulls down her stocks and panties to expose one butt cheek, bruised from a spanking. From Secretary.
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal lying on her stomach on a bed, reaching her hand down between her legs to masturbate to orgasm while dreaming about her boss and rolling onto her back. From Secretary.
Sexy 0:54 - 18.77 MB - 1280x720 px September 9th, 2010 @ 10:28 am Maggie Gyllenhaal - Secretary - 4.mp4More [+]
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal pulling her panties down as she leans over a desk, showing her bare butt from the side as a guy stands behind her and then finally walks away. From Secretary.
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal pulling up her skirt and putting her hands inside her panties to masturbate to orgasm in a bathroom stall. From Secretary.
Sexy 0:56 - 19.42 MB - 1280x720 px September 7th, 2010 @ 10:37 am Maggie Gyllenhaal - Secretary - 6.mp4More [+]
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal seen topless taking a bath, and then standing fully nude as a guy dries her off, and then finally lying naked on her back, showing us her breasts and bush. From Secretary.
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal lying topless on her back, wearing only some white panties a guy kisses up her legs and stomach. From Secretary.
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Crazy Heart
Maggie Gyllenhaal
Maggie Gyllenhaal kissing a guy as he slides his hand up her dress and then lays her down on a bed. Her dress is hiked up and we see the guy slide his hand into her panties. We then see Maggie on her back with her dress now off, exposing a purple bra that is see-through enough to show her nipples before the guy leans over to kiss her again. From Crazy Heart.
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal having a guy pull her shirt over her head to expose her breasts as she stands topless, turning around to show her body to the guy. She then lies down on a bed as the guy joins her and begins to kiss her. Maggie is also wearing some red panties that appear to be see-through. Hi-res DVD capture from Sherrybaby.
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal sitting down next to a guy as she cries, leaning over to show some great cleavage before the guy reaches his hand down her dress to grab her breast. Hi-res DVD capture from Sherrybaby.
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal lowering her dress to reveal her breasts as a guy moves a smoking bowl around her to cleanse her. Hi-res DVD capture from Sherrybaby.
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Sherrybaby
Maggie Gyllenhaal
World Trade Center and Stranger than Fiction star Maggie Gyllenhaal shown bent over as a guy has sex with her from behind in a basement. We then see her breasts as she sits on a workbench topless and tells the guy that she is shaven and that he should kiss it. She then leans back as he goes down on her and we see more of her breasts. Hi-res DVD capture from Sherrybaby.
More [+]
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Sherrybaby
Maggie Gyllenhaal
Maggie Gyllenhaal unbuttoning her shirt while standing in front of a guy's desk, pulling her purple bra up to show her breasts to a guy as she tries to get hired for a job. Hi-res DVD capture from Sherrybaby.
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