Maggie Gyllenhaal sorted by length
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Late Night with Conan O'Brien
Maggie Gyllenhaal
Maggie Gyllenhaal of Mona Lisa Smile fame wearing a white top with no bra and having her breasts jiggle as she laughs and moves around occasionally showing some cleavage as she bends forward or pushes her breasts together from Late Night with Conan O'Brien.
Sexy 6:51 - 66.81 MB - 352x240 px December 29th, 2003 @ 7:06 pm cma-MaggieGyllenhaal@LateNightWithConanO'Brien1.mpgMore [+]
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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 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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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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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 Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal naked as she and a guy have sex in bed, Maggie showing bare breasts while on her back under him. After he finishes, he rolls over next to her and Maggie reaches for a drink. She lays back and shows breasts and a bit of bush. Maggie then slides a hand down between her legs under the sheets and begins to masturbate, rolling over onto her stomach to bring herself to orgasm, shaking as she does so. From The Deuce.
2:34 - 176.44 MB - 1920x1080 px
October 8th, 2017 @ 9:22 pm
Maggie Gyllenhaal - The Deuce - S01E05 - 2.mp4
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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.mp4 -
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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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 Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal leaning back on a desk top as a guy goes down on her while filming a porno, Maggie's left breast free from her see-through bra. The guy then stands up with Maggie's feet over his shoulders as he has sex with her, causing her breast to bounce. After a while, the guy moves away and Maggie remains lying on her back on the desk. From The Deuce.
1:54 - 136.59 MB - 1920x1080 px
October 16th, 2017 @ 9:37 am
Maggie Gyllenhaal - The Deuce - S01E06.mp4
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Happy Endings
Maggie Gyllenhaal
Maggie Gyllenhall first removing her shirt to reveal her bra, and then having sex with a guy on a bed, her right breast briefly visible as she flips over onto her stomach. Hi-res DVD capture from Happy Endings.
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal lying on her back in bed while topless, smoking a cigarette as she looks over at a guy who is next to her and talking to him. After a while, she puts out her cigarette and sits up, getting dressed at the edge of the bed. From The Deuce.
1:40 - 106.07 MB - 1920x1080 px
October 8th, 2017 @ 9:19 pm
Maggie Gyllenhaal - The Deuce - S01E05 - 3.mp4
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The Kindergarten Teacher
Maggie Gyllenhaal
Maggie Gyllenhaal sitting at the edge of a bed and unzipping her dress before unhooking her bra with her back to the camera. She then lays back in bed, turning so that we get a look at her breasts and panties before she rolls over to rest her head on a guy's chest and put her arm around him. From The Kindergarten Teacher.
1:35 - 34.33 MB - 1920x802 px
October 12th, 2018 @ 6:51 pm
Maggie Gyllenhaal - The Kindergarten Teacher - 2.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal showing plenty of cleavage in some sexy blue lingerie as she walks out of a house and down beside a swimming pool, stopping to talk to a couple guys about the script for a porn shoot. Maggie shows plenty of cleavage in her lacy bra. From The Deuce.
Sexy 1:32 - 87.10 MB - 1920x1080 px October 28th, 2019 @ 8:04 pm Maggie Gyllenhaal - The Deuce - S03E08 - 1.mp4More [+]
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Strip Search
Maggie Gyllenhaal
Maggie Gyllenhaal sitting on a stool in a torn-open blue shirt that doesn't quite cover her breasts as a guy yells at her to stand up. We see her bush and bare buns as she walks bottomless over to a wall and spreads her hands against it. She is then seen fully nude as the guy runs his hands down her body, squeezing her breasts as he makes his way down. From Strip Search. Updated to higher quality.
1:29 - 94.82 MB - 1920x1080 px
November 26th, 2020 @ 9:53 pm
Maggie Gyllenhaal - Strip Search - 6.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal lying in bed with a guy while topless, showing her breasts as she and the guy talk and she puts her leg around him as he leans over next to her. After a while, she sits up and places a pillow behind her back. From The Deuce.
1:29 - 107.03 MB - 1920x1080 px
September 24th, 2019 @ 11:03 am
Maggie Gyllenhaal - The Deuce - S03E03 - 2.mp4
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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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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal lying topless on her back, wearing only some white panties a guy kisses up her legs and stomach. Hi-res DVD capture 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.
Maggie Gyllenhaal sorted by length continued
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Strip Search
Maggie Gyllenhaal
Maggie Gyllenhaal standing nude in an interrogation room, showing bare breasts as a guy questions her, shines a light into her open mouth and then flicks her nipples with his fingers. From Strip Search. Updated to higher quality.
1:24 - 85.83 MB - 1920x1080 px
November 26th, 2020 @ 9:58 pm
Maggie Gyllenhaal - Strip Search - 2.mp4
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Strip Search
Maggie Gyllenhaal
Maggie Gyllenhaal sitting on a stool talking to an interrogator, holding her shirt closed with one hand, wearing no bottom so we see a bit of her bush at the bottom of the frame. From Strip Search. From the uncut original broadcast version, this scene is longer than the edited version.
1:23 - 29.12 MB - 1280x720 px
November 30th, 2020 @ 3:13 pm
Maggie Gyllenhaal - Strip Search - 8.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal laying back on a desk wearing some sexy lingerie that shows off sideboob and looks to be a bit see-through with her nipples almost visible underneath as she talks to a guy while a crew prepares a movie set around her. From The Deuce.
Sexy 1:23 - 83.88 MB - 1920x1080 px September 11th, 2018 @ 9:12 pm Maggie Gyllenhaal - The Deuce - S02E01.mp4More [+]
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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 Kindergarten Teacher
Maggie Gyllenhaal
Maggie Gyllenhaal making out with a guy on a sofa while wearing a see-through blue bra, her nipples visible as the guy runs his hand over her bra before she walks into another room to answer a phone call. From The Kindergarten Teacher.
1:20 - 25.86 MB - 1920x802 px
October 14th, 2018 @ 8:14 pm
Maggie Gyllenhaal - The Kindergarten Teacher - 1.mp4
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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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Strip Search
Maggie Gyllenhaal
Maggie Gyllenhaal of The Dark Knight fame having a guy pull open her shirt to reveal a bra underneath. The guy then forces her to strip and she removes the bra first, holding her breasts with her hands as she takes off her skirt to reveal red panties. She then bends over to slip those off, showing her bare butt. Maggie then stands completely naked, showing full-frontal nudity with her breasts and bush in view when she drops her hands by her side. From Strip Search. Updated to higher quality.
1:16 - 89.79 MB - 1920x1080 px
November 26th, 2020 @ 10:00 pm
Maggie Gyllenhaal - Strip Search - 1.mp4
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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. Hi-res DVD capture from Secretary.
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Strip Search
Maggie Gyllenhaal
Maggie Gyllenhaal showing full-frontal nudity as she sits naked on a stool in an interrogation room and a guy sits at a table across from her and asks some questions. We also see her bare butt before the guy approaches her and gives her a shirt to cover up with. Maggie offers a nice view of her breasts again while putting on the shirt. From Strip Search. Updated to higher quality.
1:13 - 85.25 MB - 1920x1080 px
November 26th, 2020 @ 9:55 pm
Maggie Gyllenhaal - Strip Search - 4.mp4
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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
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.
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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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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal pulling up her skirt and putting her hands inside her panties to masturbate to orgasm in a bathroom stall. Hi-res DVD capture from Secretary.
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River of Fundament
Maggie Gyllenhaal
Maggie Gyllenhaal lying in bed as she opens up her nightie to expose her right breast, squeezing her nipple to squirt a bit of milk out. She continues to show her breast as she then rubs a scar on her belly. From River of Fundament.
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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.mp4 -
The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal naked on her stomach on a bed as a guy has sex with her from behind, his hands on her hips. After they finish, the guy leaves the room and Maggie shows more nudity as she sits up. From The Deuce.
0:56 - 57.52 MB - 1920x1080 px
October 22nd, 2017 @ 8:44 pm
Maggie Gyllenhaal - The Deuce - S01E07.mp4
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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.mp4 -
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.
More [+]
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Strip Search
Maggie Gyllenhaal
Maggie Gyllenhaal sitting bottomless on a stool, her butt visible briefly as a guy talks to her. She is wearing a shirt that is torn open in the front so we get a view of her cleavage and some of her right nipple as well. From Strip Search. From the uncut original broadcast version.
Maggie Gyllenhaal sorted by length continued
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal standing against a counter in a kitchen smoking a cigarette while wearing a very see-through thin robe, her right breast visible underneath. From The Deuce.
0:46 - 48.84 MB - 1920x1080 px
September 26th, 2017 @ 8:53 am
Maggie Gyllenhaal - The Deuce - S01E03.mp4
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Secretary
Maggie Gyllenhaal
Maggie Gyllenhaal seen bent over a desk as she pulls down her panties to expose her ass from the side. Hi-res DVD capture from Secretary.
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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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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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Strip Search
Maggie Gyllenhaal
Maggie Gyllenhaal fully nude in an empty interrogation room as she stands by the wall and then begins to trash the place, turning over the tables and chairs while stark naked. We see bare breasts, buns and bush as Maggie knocks things over. From Strip Search. Updated to higher quality.
0:38 - 40.74 MB - 1920x1080 px
November 26th, 2020 @ 9:51 pm
Maggie Gyllenhaal - Strip Search - 7.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal and Alyssa Kempinski both topless kneeling in front of a couple guys on the set of a porn movie, filming a facial scene in which someone shoots fake come on the face of Maggie and Alyssa, both girls showing bare breasts in the process. From The Deuce.
0:38 - 44.20 MB - 1920x1080 px
September 18th, 2017 @ 2:14 pm
Maggie Gyllenhaal & Alyssa Kempinski - The Deuce - S01E02.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal lying on her back with her shirt pulled up to expose her breasts as a guy has sex on top of her. After a bit, he falls down beside her and she sits up, pulling a see-through top on over her breasts. From The Deuce.
0:35 - 40.09 MB - 1920x1080 px
October 8th, 2017 @ 9:26 pm
Maggie Gyllenhaal - The Deuce - S01E05 - 1.mp4
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The Kindergarten Teacher
Maggie Gyllenhaal
Maggie Gyllenhaal seen topless through a gap in the shower curtain as she showers. From The Kindergarten Teacher.
0:34 - 11.86 MB - 1920x802 px
October 12th, 2018 @ 6:47 pm
Maggie Gyllenhaal - The Kindergarten Teacher - 4.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal showing her breasts as she has sex with a guy in bed, topless in his lap as she rides him before he rolls her onto her back to finish. From The Deuce.
0:30 - 35.25 MB - 1920x1080 px
September 24th, 2019 @ 11:05 am
Maggie Gyllenhaal - The Deuce - S03E03 - 1.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal on her back in bed as she and a guy finish having sex. As the guy rolls over next to her. we see her bare butt as she rolls the other way out of bed. She then stands up to pull on some shorts and we see her breasts briefly before she pulls her top down. From The Deuce.
0:29 - 35.68 MB - 1920x1080 px
October 2nd, 2017 @ 9:43 am
Maggie Gyllenhaal - The Deuce - S01E04.mp4
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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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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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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.
More [+]
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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 Kindergarten Teacher
Maggie Gyllenhaal
Maggie Gyllenhaal wearing a see-through blue bra as she stands in front of a mirror in a bedroom looking at her reflection. Her nipples are visible through the sheer blue fabric. From The Kindergarten Teacher.
0:21 - 4.90 MB - 1920x802 px
October 12th, 2018 @ 6:49 pm
Maggie Gyllenhaal - The Kindergarten Teacher - 3.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal sitting on a bed and pulling her top down partially to expose her left breast to a guy briefly. He then watches as she puts one hand down her pants as she tries to entice the guy. From The Deuce.
0:18 - 19.26 MB - 1920x1080 px
October 10th, 2017 @ 2:25 pm
Maggie Gyllenhaal - The Deuce - S01E05 - 4.mp4
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The Deuce
Maggie Gyllenhaal
Maggie Gyllenhaal on her back with her bra pulled down enough to expose both nipples as one guy stands at the edge of a bed and has sex with her, her legs up over his shoulders. Another guy kneels beside her head and jerks off as Maggie films a threesome scene for an adult movie. From The Deuce.
0:18 - 20.11 MB - 1920x1080 px
October 28th, 2019 @ 8:02 pm
Maggie Gyllenhaal - The Deuce - S03E08 - 2.mp4
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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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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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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.
More [+]
Maggie Gyllenhaal sorted by length continued
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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.mp4 -
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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Strip Search
Maggie Gyllenhaal
Maggie Gyllenhaal showing full-frontal nudity and having her breasts bounce a bit as she stands naked in front of an interrogator and then sits down on a stool. From Strip Search. From the uncut original broadcast version.
