Winona Ryder sorted by length
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The Last Word
Winona Ryder
Winona Ryder showing some nice cleavage in a slinky black dress as she has a few drinks with a guy in a club, throwing back some shots at the bar before heading to the dance floor, where her breasts bounce a bit while she dances. Hi-res DVD capture from The Last Word.
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The Ten
Winona Ryder
Winona Ryder showing plenty of cleavage in a black bra as she acts like she is having sex with a ventriloquist's dummy, riding him on a motel room bed before they are interrupted by someone bursting into the room. Winona remains in the bra as backs against the wall, and then sits down on the floor. From The Ten.
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Sex and Death 101
Winona Ryder
Winona Ryder showing nice cleavage in a black bustier as she approaches a guy in a hotel room and he slowly backs away from her, out onto the balcony. From Sex and Death 101.
Sexy 0:59 - 20.34 MB - 1280x720 px October 18th, 2009 @ 3:28 pm Winona Ryder - Sex and Death 101 - 1.mp4More [+]
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Autumn in New York
Winona Ryder
Winona Ryder seen having sex with a guy, and her nipple is clearly visible through some glass as she presses up against it at the edge of the frame. Hi-res DVD capture from Autumn in New York.
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MTV Movie Awards
Winona Ryder
Winona Ryder grabbing her breasts and shaking them several times as well as allowing a guy to touch them to make sure they are real while on stage at The 2002 MTV Movie Awards.
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Boys
Winona Ryder
Winona Ryder of Stranger Things fame sitting in the corner of a bathroom as a guy helps her take her shirt off, revealing a black bra. She shows cleavage until the guy covers her up with a shirt, but then we see more when she takes the shirt off in another room. From Boys. Updated to higher quality.
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The Iceman
Winona Ryder
Winona Ryder lying on her side as a guy has sex with her from behind in bed while grabbing her breasts through her nightie. We then get a view of almost her entire left breast as her nightie barely covers it she pauses for a bit before sitting up and pulling her nightie up at the same time. From The Iceman.
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Dracula
Winona Ryder
A slow-motion clip of 3 scenes of Winona Ryder in Dracula: kissing another girl, then running down some stairs with bouncing breasts under her nightgown, and then wearing a see-through nightgown in a backlit scene. Hi-res DVD capture.
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E!
Winona Ryder
Winona Ryder giving a brief speech before bending over and showing a lot of cleavage and then hugging a guy while putting her star on the Hollywood Walk of Fame from E!.
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Sex and Death 101
Winona Ryder
Winona Ryder kneeling topless in bed with a guy, kissing him before they fall over sideways, revealing both of her breasts as she falls. From Sex and Death 101.
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Sex and Death 101
Winona Ryder
Winona Ryder kneeling topless in bed with a guy, kissing him before they fall over sideways, revealing both of her breasts as she falls. Hi-res DVD capture from Sex and Death 101.
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Stranger Things
Winona Ryder
Winona Ryder undressing and revealing some nice cleavage in a bra, as well as giving a view of her panties from the side. Winona then pulls a yellow t-shirt down. From Stranger Things.
Sexy 0:14 - 8.90 MB - 1920x960 px July 1st, 2022 @ 7:04 pm Winona Ryder - Stranger Things - S04E09.mp4More [+]
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Celebrity
Winona Ryder
Winona Ryder reclining in a nice white top that accentuates her breasts as another girl leans over and they kiss. Hi-res DVD capture from Celebrity.
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Autumn in New York
Winona Ryder
Winona Ryder in quick clip in which her nipple is exposed while wearing a nightie in bed. Hi-res DVD capture from Autumn in New York.
