Olivia Wilde sorted by most recent
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I Want Your Sex
Olivia Wilde
Olivia Wilde wearing a see-through white tank top that shows the shadow of her pokey nipples underneath as she sits at a table talking to a guy by a food truck and then stands up. From I Want Your Sex.
Sexy 0:49 - 28.59 MB - 1920x1040 px September 6th, 2026 @ 8:07 pm Olivia Wilde - I Want Your Sex - 4.mp4More [+]
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I Want Your Sex
Olivia Wilde
Charli XCX in a t-shirt as she and a guy have sex in bed while he has a fantasy about being chained up with a blindfold on as Olivia Wilde, topless with black pasties over her nipples and a patch over her eye approaches him and reaches down to jerk him off. From I Want Your Sex.
Sexy 2:00 - 141.89 MB - 1920x1040 px September 4th, 2026 @ 8:34 pm Olivia Wilde & Charli XCX - I Want Your Sex.mp4More [+]
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I Want Your Sex
Olivia Wilde
Olivia Wilde wearing a mesh bodysuit and a jacket over her shoulders as she talks in a video displayed on a laptop computer screen. From I Want Your Sex.
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I Want Your Sex
Olivia Wilde
Olivia Wilde sitting on a couch next to a guy and talking to him as he fantasizes about her being topless. From I Want Your Sex.
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I Want Your Sex
Olivia Wilde
Olivia Wilde wearing some sexy lingerie in a bedroom as we see her in a see-through red bra, black thong panties, a red garter belt and stockings. She holds a pair of handcuffs which she puts on a guy as Chase Sui Wonders, showing cleavage in a blue bra, lies back on the bed. The guy then watches as Olivia climbs on top of Chase and pulls her skirt down to reveal her pink panties. Olivia then makes out with Chase a bit and Olivia stuffs a pair of panties into the guy's mouth to keep him quiet. Olivia then returns to kissing Chase and just begins to go down on her before the guy interrupts. Olivia then hands Chase a strap-on dildo and makes out with the guy before the threesome falls apart and Olivia sits up in bed smoking a cigarette. From I Want Your Sex.
3:33 - 262.97 MB - 1920x1040 px
September 2nd, 2026 @ 8:57 pm
Olivia Wilde & Chase Sui Wonders - I Want Your Sex.mp4
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I Want Your Sex
Olivia Wilde
Olivia Wilde pulling open her shirt and revealing a see-through red lace bra with her nipples visible underneath. She runs her hands over her chest in a guy's fantasy as he imagines her then hiking up her skirt and climbing into his lap to have sex on a couch. From I Want Your Sex.
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I Want Your Sex
Olivia Wilde
Olivia Wilde floating naked face-down in a swimming pool before a guy quickly jumps in and pulls her out. We then see more breasts from Olivia as she lies on her back on the patio by the pool as the guy administers CPR and then runs off. From I Want Your Sex.
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Third Person
Olivia Wilde
Olivia Wilde pulling her sweater off to reveal a bra briefly as she prepares to take a shower. From Third Person.
Sexy 0:02 - 1.31 MB - 1920x1080 px October 15th, 2020 @ 7:32 pm Olivia Wilde - Third Person - 4 - Open Matte.mp4More [+]
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Third Person
Olivia Wilde
Olivia Wilde getting out of bed and pulling her shirt off at the same time as she walks into a bathroom, flashing her right breast from the side as she goes topless. We then see her standing in a guy's hotel room doorway and dropping her bath robe to the floor, first giving us a good look at her bare butt from behind. She then bends down and gathers the robe up before handing to the guy, standing naked with her breasts in view before the guy shuts the door on her. The guy then slides a key under the door and Olivia runs naked down the hallway to an elevator before taking the stairs. We continue to see her naked as she dashes through another hallway and into her room, where she flashes her left breast again getting into bed. From Third Person. Updated to higher quality, including footage from an open matte version that shows more nudity, most notably revealing her nipples when she is standing at the door that are not visible in the theatrical aspect ratio.
1:55 - 61.19 MB - 1920x1080 px
October 13th, 2020 @ 10:13 am
Olivia Wilde - Third Person - 3 - Open Matte.mp4
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Third Person
Olivia Wilde
Olivia Wilde changing clothes in the back seat of a car as the driver watches her in the rear-view mirror. First she changes out of a grey bra into a sexier one, showing some cleavage and shaking her breasts a bit as she adjusts the second bra. We then see some of her panties as she begins to pull off her pants. From Third Person. Updated to higher quality.
Sexy 0:19 - 12.13 MB - 1920x814 px October 13th, 2020 @ 10:12 am Olivia Wilde - Third Person - 1.mp4More [+]
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Third Person
Olivia Wilde
Olivia Wilde being carried over a guy's shoulder into a hotel room where he lays her down on a bed and removes her shirt. Olivia shows cleavage in her bra as the guy climbs on top of her and they have sex. Near the end of the scene, Olivia's left nipple peeks out from her bra. From Third Person. Updated to higher quality.
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Third Person
Olivia Wilde
Olivia Wilde sitting up naked in bed, holding a sheet to her chest. As she then stands up, her bare butt is reflected in a mirror beside the bed. From Third Person. Updated to higher quality.
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Alpha Dog
Olivia Wilde
Olivia Wilde of House and Vinyl fame stripping off her top and bra to reveal her breasts as she kneels on a hotel bed and then having him suck on her nipple and pull her pants off before she gets up naked and pulls the covers off of the bed and gets under them while talking with him and still showing her breasts and then goes down on him for a while all as he starts to trip out until finally she comes back out and lies down next to him giving us a long clear look at her breasts while she smokes a cigarette and he wanders around the room getting dressed and talking with her some more. From Alpha Dog. Updated to higher quality.
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Vinyl
Olivia Wilde
Olivia Wilde in a thin tank top and panties as she takes nude photographs of a guy in bed, showing pokey nipples at times as she snaps pictures from different angles and talks to the guy at the same time. After they finish, Olivia sits down on the bed and then leans over to kiss the guy. From Vinyl.
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Vinyl
Olivia Wilde
Olivia Wilde wearing a nightie in a bathroom as a guy looks in at her and she turns around to walk out, showing pokey nipples. She talks the guy for a bit and they hug before he gets angry and walks away, leaving Olivia behind. From Vinyl.
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Vinyl
Olivia Wilde
Olivia Wilde pulling her dress off over her head to go topless, then removing her panties as well to stand naked, showing a merkin between her legs. She then walks over to a bed and sits down, showing her butt from the side before she takes a seat. We then see plenty more of her breasts as she sits on the edge of the bed and an artist helps to pose her. From Vinyl.
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Vinyl
Olivia Wilde
Olivia Wilde lying in bed with a guy while wrapped in a towel, and then having the guy roll her onto her back, her left nipple peeking out from the towel. The guy then kisses her and slides the towel down to expose her breast fully before slipping his hand down toward her inner thigh. From Vinyl.
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Vinyl
Olivia Wilde
Olivia Wilde making out with a guy in a club bathroom and then leaning over the sink counter as the guy has sex with her from behind standing up, Olivia looking at her reflection in the mirror. From Vinyl.
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Meadowland
Olivia Wilde
Olivia Wilde vigorously riding a guy in bed, bouncing on top of him as we see her bare butt as she grinds against him. After they finish, we see Olivia in her bra and panties sitting on the edge of the bed for a bit before getting dressed. From Meadowland.
Olivia Wilde sorted by most recent continued
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The Lazarus Effect
Olivia Wilde
Olivia Wilde lying on her back in a black bra as a guy attempts to revive her and then picks her up and places her on a table. From The Lazarus Effect.
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Better Living Through Chemistry
Olivia Wilde
Rush star Olivia Wilde wearing a bra and panties with an open sweater over her shoulders as she gets out of bed and stands near the foot while talking to a guy and smoking a cigarette. She then shows some cleavage as she begins to crawl across the bed toward the guy. From Better Living Through Chemistry.
Sexy 1:11 - 24.75 MB - 1280x528 px March 27th, 2014 @ 8:03 pm Olivia Wilde - Better Living Through Chemistry.mp4 -
The Incredible Burt Wonderstone
Olivia Wilde
Olivia Wilde talking with some guys as a woman rips open her black top and removes it to reveal a white bra and then Olivia covering herself with her arms as she talks some more until finally they put a silver dress on her. From The Incredible Burt Wonderstone.
Sexy 0:22 - 7.49 MB - 1280x536 px October 4th, 2013 @ 3:42 pm Olivia Wilde - The Incredible Burt Wonderstone.mp4More [+]
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Drinking Buddies
Olivia Wilde
TRON: Legacy star Olivia Wilde making out with a guy on a couch as he pulls her shirt over her head, revealing her black bra. The guy then leaves the room to fetch a book and Olivia sits on the sofa in her bra for a bit. We then see Olivia bending over beside a bed as she begins to get dressed, wearing her bra and panties while talking to the guy. From Drinking Buddies.
Sexy 1:58 - 40.96 MB - 1280x542 px July 27th, 2013 @ 2:06 pm Olivia Wilde - Drinking Buddies - 1.mp4 -
Drinking Buddies
Olivia Wilde
Olivia Wilde in a black bikini at a beach a she runs into the waves with a couple guys and tosses a football around with them while standing waist-deep in the water. She then walks back up the beach with one of the guys. From Drinking Buddies.
Sexy 0:44 - 15.20 MB - 1280x542 px July 27th, 2013 @ 2:05 pm Olivia Wilde - Drinking Buddies - 2.mp4 -
Drinking Buddies
Olivia Wilde
Olivia Wilde standing up beside a fire on a beach at night, dropping off her sweater as a guy watches her undress. She then peels her shirt off and we see her bare breasts as she begins to walk away in her shorts while topless. She slides the shorts down to reveal some thong panties before removing those too in the distance as she runs naked into the darkness to go skinny-dipping. From Drinking Buddies.
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The Tonight Show with Jay Leno
Olivia Wilde
Olivia Wilde leaning forward in her chair to talk with a guy giving us a look at her cleavage. From The Tonight Show with Jay Leno.
Sexy 0:13 - 4.47 MB - 1280x720 px April 27th, 2013 @ 4:05 pm Olivia Wilde - The Tonight Show with Jay Leno - 2013-03-12.mp4More [+]
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Deadfall
Olivia Wilde
Olivia Wilde hanging upside down in an overturned car, showing lots of cleavage in her dress as a guy opens the door and looks in on her. From Deadfall.
Sexy 0:11 - 3.92 MB - 1280x540 px November 27th, 2012 @ 9:38 am Olivia Wilde - Deadfall - HD VOD - 1.mp4 -
Deadfall
Olivia Wilde
Olivia Wilde showing cleavage in a silver dress as she bends over with the dress hiked up to her waist, revealing her panties, as she pulls on a pair of jeans in the falling snow. From Deadfall.
Sexy 0:11 - 3.91 MB - 1280x540 px November 27th, 2012 @ 9:36 am Olivia Wilde - Deadfall - HD VOD - 2.mp4 -
Deadfall
Olivia Wilde
Olivia Wilde making out with a guy as they begin to undress each other, Olivia keeping her sparkly dress on as she ends up on the floor on her back as the guy lies on top of her and they have sex. From Deadfall.
Sexy 1:43 - 35.66 MB - 1280x540 px November 24th, 2012 @ 11:35 pm Olivia Wilde - Deadfall - HD VOD - 3.mp4 -
Deadfall
Olivia Wilde
Olivia Wilde in a matching bra and panties combo as she stands in a bathroom and talks on a cell phone in her underwear, showing some cleavage. From Deadfall.
Sexy 0:49 - 17.02 MB - 1280x540 px November 24th, 2012 @ 11:34 pm Olivia Wilde - Deadfall - HD VOD - 4.mp4 -
Deadfall
Olivia Wilde
Olivia Wilde making out with a guy and having sex with him while naked in his lap, showing her breasts as she rides him on the corner of a bed. From Deadfall.
0:45 - 15.58 MB - 1280x540 px
November 24th, 2012 @ 11:30 pm
Olivia Wilde - Deadfall - HD VOD - 5.mp4
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Butter
Olivia Wilde
Olivia Wilde stepping on stage at a strip club wearing thigh-high boots, tiny silver shorts and a red bra with a lace top over it. As Olivia mounts the pole, she sheds the top to expose her bra fully before sliding back down and spreading her legs as a guy watches. She crawls over to him, lifting one leg up in the air. She then joins the guy at his chair, giving him a lap dance while showing cleavage in her red bra and getting tips from the guy before leaning in to kiss him. From Butter. Updated to higher quality.
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Butter
Olivia Wilde
Olivia Wilde in a bra and very skimpy shorts as she briefly dances at a strip club, pushing her hips out to one side as a guy prepares to put a dollar bill in her waistline. From Butter. Updated to higher quality.
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Butter
Olivia Wilde
Ashley Greene lying on her back and moaning as off-camera, Olivia Wilde goes down on her. Olivia then moves up and talks to Ashley before making out with her in this lesbian scene. From Butter. Updated to higher quality.
Sexy 0:46 - 15.85 MB - 1280x544 px November 15th, 2012 @ 4:35 pm Olivia Wilde & Ashley Greene - Butter - 1.mp4 -
Butter
Olivia Wilde
Olivia Wilde and Ashley Greene making out until Olivia pulls away and Ashley begins to laugh in this closing credits outtake. From Butter. Updated to higher quality.
Sexy 0:06 - 1.91 MB - 1280x544 px November 15th, 2012 @ 4:34 pm Olivia Wilde & Ashley Greene - Butter - 2.mp4 -
House M.D.
Olivia Wilde
Olivia Wilde (left) and Jaclyn Jonet (right) standing in a hospital lobby as they lesbian kiss each other while a guy watches them from a distance. From House M.D..
Sexy 0:08 - 2.67 MB - 1280x720 px June 3rd, 2012 @ 11:59 pm Olivia Wilde & Jaclyn Jonet - House MD - S08E03.mp4More [+]
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The Change-Up
Olivia Wilde
Olivia Wilde standing in front of a guy who is sitting on a couch and pulling down her jeans to reveal her butt in a thong. She then climbs into the guy's lap, taking her wet shirt off to expose her bra as well while we get some more looks at her panties from behind. The guy then peels her bra off and places his hands on her breasts. While a nipple is visible a few times in this scene, it is unfortunately computer generated (like all the other nudity in this movie). From The Change-Up.
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The Death and Life of Bobby Z
Olivia Wilde
Olivia Wilde showing some cleavage in a black bustier when she removes her robe and climbs into bed with a guy, leaning over him to kiss him as he lays back. From The Death and Life of Bobby Z.
Sexy 0:31 - 10.58 MB - 1280x544 px November 20th, 2010 @ 3:51 pm Olivia Wilde - The Death and Life of Bobby Z - 1.mp4 -
The Death and Life of Bobby Z
Olivia Wilde
Olivia Wilde kneeling at the foot of a bed, her hands tied to the bedposts while topless. We see part of her left breast from behind and the side as a guy walks around and talks to her. From The Death and Life of Bobby Z.
Sexy 0:22 - 7.64 MB - 1280x544 px November 20th, 2010 @ 3:50 pm Olivia Wilde - The Death and Life of Bobby Z - 2.mp4
Olivia Wilde sorted by most recent continued
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House M.D.
Olivia Wilde
Olivia Wilde staring into the camera as an unknown woman in a black bra approaches her from behind and starts kissing her shoulder and neck before Olivia turns towards her and begins passionately lesbian kissing her. Hi-res DVD capture from House.
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House M.D.
Olivia Wilde
Olivia Wilde seen out of focus at first and then close up passionately lesbian kissing Angela Gots as they make out and take off their clothes to reveal Olivia in a bra and Angela in a sports bra with hard nipples. Hi-res DVD capture from House.
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House M.D.
Olivia Wilde
Olivia Wilde (left) leaning over on a hospital bed and lesbian kissing Angela Gots (right). Hi-res DVD capture from House.
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House M.D.
Olivia Wilde
Olivia Wilde lying next to Angela Gots who is topless and on her stomach and then getting up and putting on a shirt and walking across a room before running back over to Angela on the floor and kneeling down showing the side of her ass. Hi-res DVD capture from House.
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Bickford Shmeckler's Cool Ideas
Olivia Wilde
Olivia Wilde of The Black Donnellys and House M.D. fame making out with a guy in a doorway and dropping her white toga to reveal the side of her right breast a couple of times as they kiss before she pauses to show him a book and then pushes him away and closes the door. Hi-res DVD capture from Bickford Shmeckler's Cool Ideas.
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Bickford Shmeckler's Cool Ideas
Olivia Wilde
Olivia Wilde of House fame wearing a white togo with no bra and a hard right nipple as she waits in front of a dorm room door until a guy walks out and looks her over and she kisses him. Hi-res DVD capture from Bickford Shmeckler's Cool Ideas.
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The O.C.
Olivia Wilde
Olivia Wilde and Mischa Barton sneaking some lesbian kissing in while Melinda Clarke isn't looking from The O.C.
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Skin
Olivia Wilde
Olivia Wilde running down a beach with a guy causing her breasts to bounce all over the place from Skin.
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Skin
Olivia Wilde
Olivia Wilde showing some slight cleavage as she swims in a pool with a guy before getting out and standing while talking to some guys in a wet white top from Skin.
