from Autumn in New York (2000)
 
from Sex and Death 101 (2007)
 
from Dracula (1992)

  • 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.

    0:26 - 5.65 MB - 704x400 px August 21st, 2001 @ 2:59 pm [email protected]

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from E!

  • 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!.

    Sexy 0:22 - 3.50 MB - 320x240 px April 15th, 2003 @ 10:46 pm WinonaRyder-Boobs.mpeg

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from MTV Movie Awards

  • 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.

    Sexy 0:54 - 8.76 MB - 352x240 px June 16th, 2002 @ 11:22 pm [email protected]

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from Celebrity (1998)
 
from The Ten (2007)

  • 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.

    Sexy 1:08 - 23.61 MB - 1280x708 px January 15th, 2010 @ 2:32 pm Winona Ryder - The Ten.mp4
 
from Boys (1996)

  • 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.

    Sexy 0:35 - 34.00 MB - 1916x1036 px April 10th, 2018 @ 8:15 am Winona Ryder - Boys.mp4
 
from The Iceman (2012)

  • 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.

    Sexy 0:31 - 10.62 MB - 1280x720 px August 30th, 2013 @ 7:22 pm Winona Ryder - The Iceman.mp4

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from The Last Word (2008)

  • 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.

    Sexy 1:53 - 26.80 MB - 720x304 px February 22nd, 2009 @ 2:40 pm [email protected]
 
from Stranger Things (2016)