Olivia Wilde sorted by length

  • 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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  • 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.

    3:06 - 64.54 MB - 1280x720 px March 20th, 2016 @ 8:54 pm Olivia Wilde - Vinyl - S01E06 - 1.mp4

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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.

    2:21 - 153.58 MB - 1920x818 px January 11th, 2018 @ 3:11 pm Olivia Wilde - Alpha Dog.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.

    Sexy 2:11 - 45.53 MB - 1280x544 px November 15th, 2012 @ 4:36 pm Olivia Wilde - Butter - 1.mp4

  • 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.

    Sexy 2:10 - 45.42 MB - 1280x718 px April 11th, 2016 @ 2:32 pm Olivia Wilde - Vinyl - S01E09.mp4

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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.mp4

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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

  • 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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  • 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.

    1:54 - 39.79 MB - 1280x720 px February 29th, 2016 @ 1:18 pm Olivia Wilde - Vinyl - S01E03.mp4

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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.

    Sexy 1:45 - 36.59 MB - 1280x720 px March 22nd, 2016 @ 1:03 pm Olivia Wilde - Vinyl - S01E06 - 2.mp4

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  • 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

  • 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.

    1:35 - 32.64 MB - 1280x532 px October 23rd, 2015 @ 1:45 pm Olivia Wilde - Meadowland.mp4

  • 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.

    Sexy 1:25 - 29.33 MB - 1280x528 px October 27th, 2011 @ 10:25 am Olivia Wilde - The Change-Up.mp4

  • 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

  • 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.

    1:11 - 44.49 MB - 1920x1040 px September 2nd, 2026 @ 8:52 pm Olivia Wilde - I Want Your Sex - 3.mp4

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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.

    Sexy 0:51 - 17.74 MB - 1280x720 px February 29th, 2016 @ 1:14 pm Olivia Wilde - Vinyl - S01E02.mp4

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  • 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

  • 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.mp4

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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.

    0:49 - 30.21 MB - 1920x814 px October 13th, 2020 @ 10:08 am Olivia Wilde - Third Person - 2.mp4

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Olivia Wilde sorted by length continued
Olivia Wilde sorted by length continued