Leelee Sobieski sorted by most popular
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L'Idole
Leelee Sobieski
Leelee Sobieski riding a guy while they have sex on the floor as the guy reaches up her dress and then sits up to embrace her. Hi-res DVD capture from L'Idole.
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L'Idole
Leelee Sobieski
Leelee Sobieski wrapped in a towel as she leans over to kiss a guy, and then they stand up together and he turns her around so he can begin to have sex with her from behind as she leans over. Hi-res DVD capture from L'Idole.
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Uprising
Leelee Sobieski
Leelee Sobieski getting undressed in front of a guy, ending up completely nude - her arm partially covering her large breasts and her hand between her legs. Hi-res DVD capture from Uprising.
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L'Idole
Leelee Sobieski
Leelee Sobieski seen naked from the side as she stands in front of a mirror and brushes her hair, showing her bare butt and breasts. She is then seen sitting down on the side of a bed from behind, still nude as she dries her hair. She then changes clothes with the help of a guy. Hi-res DVD capture from L'Idole.
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Hercules
Leelee Sobieski
Leelee Sobieski giving us a long look at her bare back and numerous looks at the sides of her breasts as well as occasional glimpses of pasties over her hard nipples as she bathes in a pond by a waterfall while talking with a guy on the shore before another guy shows up and then they toss her a bow an arrow that she aims at a boar until finally she gets out of the water and hops on to a deer and rides off holding on to the side. From Hercules. Upgraded to a higher quality and longer version containing more looks at her breasts.
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The Glass House
Leelee Sobieski
Leelee Sobieski looking sexy in a bikini as she swims in a pool and then gets out and stands dripping wet. Hi-res DVD capture from The Glass House.
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In a Dark Place
Leelee Sobieski
Leelee Sobieski and Tara Fitzgerald lesbian kissing each other while Tara undoes Leelee's shirt, and then moves down to kiss her left breast, which we see in a bra. Hi-res DVD capture from In a Dark Place.
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Branded
Leelee Sobieski
Leelee Sobieski climbing into a guy's lap in the front seat of a car and having sex with him, her suit jacket open to reveal her bra and nice cleavage, which the guy kisses before she begins to ride him. From Branded.
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Walk All Over Me
Leelee Sobieski
Leelee Sobieski dancing in a tight-fitting jacket that shows lots of cleavage and a skimpy skirt. A guy interrupts her, and she spills a drink on her chest - leading her to wash the outfit. As she does the laundry, we see her wearing a bustier and panties, her breasts practically spilling out of her top as she shows some stunning cleavage. Good quality capture from Walk All Over Me.
Sexy 1:59 - 28.14 MB - 720x400 px April 20th, 2008 @ 11:57 pm Leelee Sobieski - Walk All Over Me - 1.mpgMore [+]
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Eyes Wide Shut
Leelee Sobieski
A young Leelee Sobieski in a bra and panties as she emerges from behind a couch and then runs out into a hallway, hiding herself behind a guy as another guy yells. Leelee then steps from behind her guy to give us a better look at her underwear before turning away. From Eyes Wide Shut. Updated to higher quality.
Sexy 1:06 - 62.75 MB - 1472x1080 px December 1st, 2025 @ 10:41 pm Leelee Sobieski - Eyes Wide Shut.mp4More [+]
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The Glass House
Leelee Sobieski
Leelee Sobieski showing some very nice cleavage as she lays in bed on her side and her breasts squeeze together. Hi-res DVD capture from The Glass House.
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A Soldier's Daughter Never Cries
Leelee Sobieski
Leelee standing in front of a mirror wearing a bra and checking herself out. From A Soldier's Daughter Never Cries.
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In a Dark Place
Leelee Sobieski
Leelee Sobieski showing some nice cleavage in a flowery bath robe that shows a good portion of her breasts as she first picks out some clothes to wear, and then is seen standing in a window, again showing cleavage in the robe. Hi-res DVD capture from In a Dark Place.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski sitting in front of of a computer as she watches Denise Richards have sex with a guy in black lingerie and then imagining herself in Denise's place giving us some look at her breasts with her hands over her nipples as she fantasizes about having sex with the guy on the computer. Hi-res DVD capture from Finding Bliss.
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Night Train
Leelee Sobieski
Leelee Sobieski undressing in a train car cabin, stripping down to her bra and showing some cleavage as she talks to a guy and then kisses him. We then see Leelee lying on the bed, barely covered by some sheets as a couple other guys open her cabin door and wake her up. Hi-res DVD capture from Night Train.
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Joy Ride
Leelee Sobieski
Leelee Sobieski sitting in front of a window while wearing a pink tanktop with hard nipples as she looks up at a guy and says something. Hi-res DVD capture from Joy Ride.
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L'Idole
Leelee Sobieski
Leelee Sobieski showing some pokey nipples as she stands beside a window in a sweater with no bra underneath, talking to a guy who is behind her. Hi-res DVD capture from L'Idole.
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Wild On...
Leelee Sobieski
Leelee Sobieski wearing a pink tanktop with no bra looking a bit pokey from E!'s Wild On.
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In a Dark Place
Leelee Sobieski
Leelee Sobieski removing her bath robe and turning away from the camera, showing part of her breasts from the side and back when she turns to the window while topless. Hi-res DVD capture from In a Dark Place.
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Leelee Sobieski sorted by most popular continued
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Branded
Leelee Sobieski
Leelee Sobieski and a guy watching as an unidentified girl changes shirts in the car next to them in traffic, showing her white bra. Leelee then follows suit by pulling her panties off from under her skirt and then unbuttoning her shirt, showing cleavage in a white tank top that reveals part of her bra, too. From Branded.
Sexy 1:16 - 26.51 MB - 1280x544 px October 18th, 2012 @ 7:40 pm Leelee Sobieski & Unknown - Branded.mp4 -
Branded
Leelee Sobieski
Leelee Sobieski showing nice cleavage in a black dress with a plunging neckline, watching a guy dance and then falling back on a bed as she makes out with him. From Branded.
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Joy Ride
Leelee Sobieski
Leelee Sobieski walking with a guy while wearing a pink tanktop with a puffy right nipple as the camera pans up her body. Hi-res DVD capture from Joy Ride.
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Uprising
Leelee Sobieski
Leelee Sobieski getting undressed in front of a guy, ending up completely nude - her arm partially covering her large breasts and her hand between her legs. From Uprising.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski showing a lot of the top of her breasts as she whips a bridal veil off in an extended version of her scene from the main film. Hi-res DVD capture of the special features from Finding Bliss.
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Joy Ride
Leelee Sobieski
Leelee Sobieski lying on a bed in a blue tanktop and brown panties as she talks on the phone with a guy. Hi-res DVD capture from Joy Ride.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski rising up in slow motion and throwing a bridal veil back showing a lot of the top of her large breasts as she simulates having sex. Hi-res DVD capture from Finding Bliss.
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Walk All Over Me
Leelee Sobieski
Leelee Sobieski doing her makeup in a bathroom in a cleavage-showing outfit. She then shows some bouncing breasts as she strides out of the room. Good quality capture from Walk All Over Me.
Sexy 0:24 - 5.68 MB - 720x400 px April 21st, 2008 @ 6:09 pm Leelee Sobieski - Walk All Over Me - 2.mpgMore [+]
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Walk All Over Me
Leelee Sobieski
Leelee Sobieski entering a guy's apartment in dominatrix gear, showing cleavage as she allows the guy to kiss her foot and then leads him around on a leash before another guy interrupts them. Good quality capture from Walk All Over Me.
Sexy 2:56 - 41.40 MB - 720x400 px April 21st, 2008 @ 6:08 pm Leelee Sobieski - Walk All Over Me - 3.mpgMore [+]
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Joy Ride
Leelee Sobieski
Leelee Sobieski lying on a bed wearing a blue tanktop with hard nipples as she talks to herself and then sitting up and drinking while talking some more. Hi-res DVD capture from Joy Ride.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski standing in front of a bathroom mirror checking out her stomach and then pulling her shirt up further and look at her breasts in a purple bra before finally pulling her shirt back down. Hi-res DVD capture from Finding Bliss.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski seen walking across the stage in fishnet stockings and high heels and then having the camera pan up to reveal a black bustier split down the middle showing off a lot of cleavage as she walks over to a guy and talks with him and the audience. Hi-res DVD capture from Finding Bliss.
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The Glass House
Leelee Sobieski
Leelee Sobieski showing plenty of cleavage in a bikini as she steps into a swimming pool at night and swims back and forth for a few laps. A guy then gives her hand out of the water and she stands dripping wet before he hands her a towel to wrap herself in. From The Glass House.
Sexy 1:31 - 35.40 MB - 1280x720 px July 27th, 2014 @ 2:27 pm Leelee Sobieski - The Glass House - 2.mp4 -
Various Sources
Leelee Sobieski
Leelee Sobieski laying on a bed with her dress lowered showing some nice cleavage and then wearing a black dress against a wall as she poses in various places during a musical montage of a photoshoot.
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Joy Ride
Leelee Sobieski
Leelee Sobieski talking on the phone while wearing an orange shirt with no bra and a hard left nipple. Hi-res DVD capture from Joy Ride.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski wearing a blue tanktop as she has sex with a guy on her back on a bed an extended version of the same scene from the main film. Hi-res DVD capture of the special features from Finding Bliss.
More [+]
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Branded
Leelee Sobieski
Leelee Sobieski kneeling in front of a guy while wearing a bra, showing nice cleavage as she helps the guy shave and then moves up to make out with him. From Branded.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski lying on her back on a bed as a guy starts to have sex with her before it cuts to him rolling off of her leaving her in a blue tanktop with slightly hard nipples. Hi-res DVD capture from Finding Bliss.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski moving on a bed in slow motion in a tanktop with no bra and slightly hard nipples and then seen trying to get out of the bed while in yellow boxer shorts that show off her legs. Hi-res DVD capture from Finding Bliss.
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Entertainment Tonight
Leelee Sobieski
A quick clip of Leelee looking nice doing some modeling. From Entertainment Tonight.
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Leelee Sobieski sorted by most popular continued
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Dangerous Liaisons
Leelee Sobieski
Leelee Sobieski sitting up in bed in a pink bra showing off some impressive cleavage as she listens to a guy talk on the phone and then starts kissing around his face and neck before she takes the phone to have a conversation while now he kisses around her neck and shoulder and lowers her bra strap until finally she hangs up and lies back against him while they alternate between making out and talking. From Dangerous Liaisons (AKA Les liaisons dangereuses).
Sexy 1:46 - 37.16 MB - 1024x576 px December 25th, 2021 @ 2:23 pm Leelee Sobieski - Dangerous Liaisons - 1.mp4More [+]
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The Glass House
Leelee Sobieski
Leelee Sobieski standing in a hallway of a house at night, pulling her shirt over her head to reveal a blue bra. We then get a closer view of her bra as she pauses while beginning to unhook it, Leelee showing some pokey puffy nipples through the bra. From The Glass House.
Sexy 0:33 - 11.44 MB - 1280x720 px July 27th, 2014 @ 2:28 pm Leelee Sobieski - The Glass House - 1.mp4 -
Various Sources
Leelee Sobieski
Leelee Sobieski showing a little bit of cleavage during an awards show.
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Hercules
Leelee Sobieski
Leelee Sobieski running her fingers over a guy's abs and then leaning down showing her cleavage and kissing him before standing up and taking her dress off revealing her left breast from the side and the top of her ass and climbing into bed with him and kissing him again. It then cuts to her getting dressed showing a bit of the tops of her breasts and then her hard nipples under her dress. From Hercules.
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Dangerous Liaisons
Leelee Sobieski
Leelee Sobieski showing some nice cleavage in a wet bikini as she stands on a pier watching a boat go by and then picks up a towel and wraps it around her shoulders before walking towards the camera and adjusting the towel. From Dangerous Liaisons (AKA Les liaisons dangereuses).
Sexy 0:14 - 8.82 MB - 1024x576 px December 25th, 2021 @ 2:22 pm Leelee Sobieski - Dangerous Liaisons - 2.mp4More [+]
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Finding Bliss
Leelee Sobieski
Leelee Sobieski standing in front of a mirror in a low cut red dress with no bra and slightly hard nipples as Donnamarie Recco helps adjust her top. Hi-res DVD capture from Finding Bliss.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski climbing into a spa in white and green panties and a white bra and then sitting in the water talking with a guy for a bit. Hi-res DVD capture from Finding Bliss.
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The Glass House
Leelee Sobieski
Leelee Sobieski lying on her side in bed in a pink tank top, showing some nice cleavage as her breasts squeeze together before she sits up. From The Glass House.
Sexy 0:10 - 3.90 MB - 1280x720 px July 27th, 2014 @ 2:23 pm Leelee Sobieski - The Glass House - 3.mp4 -
Various Sources
Leelee Sobieski
Leelee looking nice during an appearance on a TV awards show.
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88 Minutes
Leelee Sobieski
Leelee Sobieski seen in a highly stylized desaturated scene rushing over to Leah Cairns and lesbian kissing her. From 88 Minutes.
Sexy 0:04 - 1.45 MB - 1280x544 px December 16th, 2015 @ 8:15 pm Leelee Sobieski & Leah Cairns - 88 Minutes.mp4More [+]
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Dangerous Liaisons
Leelee Sobieski
Leelee Sobieski wearing a white lace nightgown that's slightly see-through showing her white panties underneath and a hint of her nipples all as she follows a guy around a bedroom getting progressively more upset until he leaves and she lies down on the bed. From Dangerous Liaisons (AKA Les liaisons dangereuses).
Sexy 0:33 - 15.91 MB - 1024x576 px December 25th, 2021 @ 2:21 pm Leelee Sobieski - Dangerous Liaisons - 3.mp4More [+]
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Finding Bliss
Leelee Sobieski
Leelee Sobieski removing her orange construction vest to reveal a blue hoodie with hard nipples and then walking away and having her butt in red polkadot panties hanging out of the bottom of her hiked up dress. Hi-res DVD capture from Finding Bliss.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski wearing a red dress with hard nipples as she sits in a theater and watches a presentation with several other people. Hi-res DVD capture from Finding Bliss.
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Finding Bliss
Leelee Sobieski
Leelee Sobieski bending over to pick up some stuff in slow motion and having her black thong panties stick out of the top of her jeans. Hi-res DVD capture from Finding Bliss.
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