Jennifer Love Hewitt sorted by most recent
  • The Devil and Daniel Webster

    Jennifer Love Hewitt

    Jennifer Love Hewitt seducing a guy as she opens her red leather coat to show him her cleavage in a low cut skimpy black dress and then dropping the coat and walking towards him as she pushes him down into a chair and then bends over climbing on top of him giving us a look down her top as they talk briefly and begin slowly making out. From The Devil and Daniel Webster (AKA Shortcut to Happiness).

  • The Devil and Daniel Webster

    Jennifer Love Hewitt

    Jennifer Love Hewitt sleeping naked on her side as a guy runs his hand along her back and notices a mark just above her butt before she jumps out of bed and puts on a red coat briefly showing a hint of the side of her left breast. From The Devil and Daniel Webster (AKA Shortcut to Happiness).

  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt slowly and passionately kissing a guy in front of a fire place and then removing her shirt showing her cleavage in a strapless bra as she goes back to kissing him while she pulls him on top of her onto the ground and then rolls over on top of him showing the bra and her ass in tight jeans before he unclasps her bra and lets it hang down showing the side of her right breast from the top and bottom all as they continue to make out. From If Only. Updated to higher quality.

    Sexy 0:50 - 54.14 MB - 1920x1080 px July 4th, 2022 @ 2:31 pm Jennifer Love Hewitt - If Only - 4.mp4
  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a very slightly see-through white crop top and white panties that show a hint of her nipples and her ass in a pair of darker black thong panties underneath as she tries to calm a guy down who is panicking and then goes behind a screen and changes while leaning out and holding her breasts before she emerges wearing only a jacket and then surprises him by dropping the jacket to flash him giving us a look at her bare back. From If Only. Updated to higher quality.

    Sexy 1:24 - 104.55 MB - 1920x1080 px July 4th, 2022 @ 2:28 pm Jennifer Love Hewitt - If Only - 3.mp4
  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt seen in silhouette changing behind a screen and then walking out and surprising a guy by opening a jacket to reveal her body in a white lace bra and panties as she lets him check her out for a bit before he picks her up and carries her over to a bed making out with her and then has her sit up giving us a better look at her cleavage. Next, we see her follow him into a bathroom where she jumps up on a sink and wraps her legs around him and then has him carry her over to a shower. Finally, she goes back into the bedroom and lies down on the bed giving us another look at her cleavage. From If Only. Updated to higher quality.

    Sexy 1:41 - 124.79 MB - 1920x1080 px July 4th, 2022 @ 2:25 pm Jennifer Love Hewitt - If Only - 2.mp4
  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a pink and black nightgown with a see-through black lace top and black stars covering her nipples as she lies in bed making out with a guy and talking with him before she jumps up out of bed giving us some more looks at the sides of her breasts while she talks with the guy some more and makes her way across the room. From If Only. Updated to higher quality.

    Sexy 0:31 - 37.41 MB - 1920x1080 px July 4th, 2022 @ 2:22 pm Jennifer Love Hewitt - If Only - 1.mp4
  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing an white top with a see-through lace front as she rushes down the sidewalk with a guy while trying to protect herself from the rain using a jacket before they get into the back of a taxi and then start making out while showing her hard nipples in the wet white top. From If Only. Updated to higher quality.

    Sexy 1:47 - 132.83 MB - 1920x1080 px July 4th, 2022 @ 2:20 pm Jennifer Love Hewitt - If Only - 5.mp4
  • Boy Meets World

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a tight top that shows off her breasts as she talks with a guy in a high school hallway before he pushes her up against the lockers and starts passionately making out with her and kissing her neck before they get interrupted by Danielle Fishel, Trina McGee and some guys when suddenly a phone rings and Jennifer jumps and screams causing her breasts to bounce and jiggle around. The bouncing portion then repeats in slow motion giving us a better look at the jiggling. From Boy Meets World. Updated to higher quality.

    Sexy 1:03 - 14.07 MB - 640x480 px July 1st, 2019 @ 6:14 pm Jennifer Love Hewitt - Boy Meets World - S04E17.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing cleavage in a revealing short pink dress as she squats by a road and rolls out some tire spikes to cause a car accident. She then walks over to the crashed car and talks to a guy for a while before she pushes him out of view when another car approaches and she rolls down a hill after him, flashing her panties. From Heartbreakers.

    Sexy 1:38 - 33.88 MB - 1280x548 px July 12th, 2015 @ 6:26 pm Jennifer Love Hewitt - Heartbreakers - 4.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a low-cut blue tank top that shows nice cleavage along with her tight white jeans as she walks into a hotel room and talks to Sigourney Weaver, who is wearing a robe that shows a bit of her bra underneath. From Heartbreakers.

    Sexy 1:06 - 22.83 MB - 1280x548 px July 12th, 2015 @ 6:24 pm Jennifer Love Hewitt - Heartbreakers - 5.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt jogging up a stairway, causing her cleavage to bounce a bit in her skimpy blue tank top. A guy then opens the door for her and she makes out with him, pulling her tank top off and showing her bra from the side as she lays down on top of him on a sofa in her tight white jeans and blue bra. From Heartbreakers.

    Sexy 1:23 - 28.70 MB - 1280x548 px July 12th, 2015 @ 6:21 pm Jennifer Love Hewitt - Heartbreakers - 6.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a low-cut short grey dress that she uses to show off her legs and butt as she bends over in a guy's office. She then approaches his desk and leans over, giving him a great view of her cleavage in close-up. She then pretends to drop the papers and bends over on the floor, kneeling as the guy then kisses her. She jumps into his arms with her legs wrapped around him, her butt in her panties in view. The guy carries her over to his desk and sits so that she can begin to go down on him. From Heartbreakers.

    Sexy 2:02 - 42.51 MB - 1280x548 px July 10th, 2015 @ 2:36 pm Jennifer Love Hewitt - Heartbreakers - 1.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt in a skimpy pink dress, baring some bouncing cleavage as she walks up to a valet at a car park and distracts him so she can sneak a set of keys and break into a car. From Heartbreakers.

    Sexy 1:30 - 31.32 MB - 1280x548 px July 10th, 2015 @ 2:34 pm Jennifer Love Hewitt - Heartbreakers - 2.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing bouncing breasts and lots of cleavage as she walks into a bar wearing a very short tight pink dress with her bra exposed. She sits down on a table with her cleavage on display as she talks to a guy. She then looks over at a guy, sucking olives seductively off a toothpick before choking on one. Lastly, she shows more of her bra while leaning over and talking on a phone. From Heartbreakers.

    Sexy 3:49 - 79.57 MB - 1280x548 px July 10th, 2015 @ 2:32 pm Jennifer Love Hewitt - Heartbreakers - 3.mp4

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  • The Client List

    Jennifer Love Hewitt

    Jennifer Love Hewitt baring lots of cleavage as she gives a number of guys massages in a short montage sequence until we see one of the guys turn around and handcuff her. From The Client List.

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  • The Client List

    Jennifer Love Hewitt

    Jennifer Love Hewitt in sexy lingerie that shows plenty of cleavage as she dances around a stripper's pole in a guy's office before walking over to his chair and giving him a lap dance for a bit. They are then interrupted by a guy entering the room and Jennifer stands beside the pole as the two guys leave. From The Client List.

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  • The Client List

    Jennifer Love Hewitt

    Jennifer Love Hewitt baring plenty of cleavage in a montage sequence in which she gives a few different guys massages in a few different revealing outfits. She then spends some time with one guy in particular while wearing a grey teddy that shows off her breasts. From The Client List.

    Sexy 1:25 - 29.57 MB - 1280x718 px June 3rd, 2013 @ 7:43 pm Jennifer Love Hewitt - The Client List - S02E12 - 1.mp4

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  • The Client List

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing very low-cut white lace lingerie that shows a lot of cleavage while she leans over a guy on a massage table and rubs down his arms and legs. From The Client List.

    Sexy 0:32 - 11.21 MB - 1280x718 px June 3rd, 2013 @ 7:42 pm Jennifer Love Hewitt - The Client List - S02E12 - 2.mp4

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  • The Client List

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing plenty of cleavage in an orange top that shows the edge of her bra underneath while sitting in a chair at a hair salon. She then stands up and talks to another girl and a police officer before leaving with him. Lastly, we see her sitting in the front seat of his car while still in her cleavage-baring dress. From The Client List.

    Sexy 2:28 - 51.20 MB - 1280x718 px May 22nd, 2013 @ 2:29 pm Jennifer Love Hewitt - The Client List - S02E11.mp4

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Jennifer Love Hewitt sorted by most recent continued
Jennifer Love Hewitt sorted by most recent continued
Jennifer Love Hewitt sorted by most recent continued
Jennifer Love Hewitt sorted by most recent continued
Jennifer Love Hewitt sorted by most recent continued
Jennifer Love Hewitt sorted by most recent continued
  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a white tanktop with the words 'Love Boat' printed across her chest and showing off her sexy stomach as she poses for a photoshoot.

    Sexy 1:42 - 20.41 MB - 320x240 px February 17th, 2004 @ 2:41 pm [email protected]
  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a white tanktop and blue jeans while briefly performing at Wango Tango and then wearing a black top and jeans backstage and turning around giving us a look at her butt from VH1.

    Sexy 0:19 - 4.58 MB - 320x240 px August 29th, 2003 @ 8:48 pm JLH-WT2003-beercaps.mpg
  • Various Sources

    Jennifer Love Hewitt

    A quick clip of a young Jennifer Love Hewitt walking down a runway in green shorts and a green bikini top while holding a basketball.

    Sexy 0:04 - 0.35 MB - 320x240 px May 17th, 2003 @ 11:26 pm jlh-runway.mpeg
  • Tuxedo

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing some great cleavage in a collection of scenes, including one in which she is seen underwater in a pool, possibly showing some nipple. From Tuxedo.

    Sexy 0:39 - 9.34 MB - 320x240 px May 2nd, 2003 @ 7:50 pm JLH-Tuxedo-beercaps.mpeg
  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a black halter top and dancing a bit for the camera while presenting at The Teen Choice Awards.

    Sexy 0:19 - 3.19 MB - 320x240 px January 25th, 2003 @ 7:47 pm jlh-hottie-quickjob.mpg
  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing some lovely cleavage in a bikini in this collection of scenes while hosting a VH1 video countdown. Includes a great scene of her rolling over as her breasts almost pop out. Part 1 of 2.

    Sexy 2:24 - 34.84 MB - 320x240 px November 21st, 2002 @ 4:37 pm JLH11162002-beercaps_a.mpg
  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt in a collection of scenes while hosting a VH1 video countdown. We see her looking very sexy in a couple different bikinis while on the beach. Part 2 of 2.

    Sexy 2:14 - 32.44 MB - 320x240 px November 21st, 2002 @ 4:35 pm JLH11162002-beercaps_b.mpg
  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt seen rolling over on the beach in a bikini in this nice slow-motion extract of another clip. She shows lots of cleavage - watch for a possible nipple slip. From a VH1 video countdown.

    Sexy 0:23 - 5.00 MB - 320x240 px November 21st, 2002 @ 4:31 pm JLH11152002-beercaps.mpg
  • MTV's Making the Video: Barenaked

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a blue shirt and white shorts and removing her top to reveal her back along with a very brief glimpse of the side of her breast as she walks behind a wall in a high resolution clip from MTV's Making the Video: Barenaked.

    Sexy 0:16 - 3.33 MB - 640x480 px July 9th, 2002 @ 10:18 pm [email protected]
  • The Tonight Show with Jay Leno

    Jennifer Love Hewitt

    Jennifer Love Hewitt looking sexy as she walks out in a low-cut dress and leaning over as she sits down. From an appearance on The Tonight Show.

    Sexy 0:27 - 6.38 MB - 320x240 px May 11th, 2002 @ 7:33 pm JLH04272002-beercaps.mpg

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  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a halter top that shows off her nice cleavage as she hosts the 2002 World Music Awards.

  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing lots of jiggling cleavage as she runs on a treadmill wearing a sports bra in this deleted scene. Hi-res DVD capture from Heartbreakers.

    Sexy 0:34 - 7.30 MB - 624x272 px January 17th, 2002 @ 11:01 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    A very nice close-up view of Jennifer Love Hewitt's magnificent cleavage as she bends over to talk to Ray Liotta at his desk. Hi-res DVD capture from Heartbreakers.

    Sexy 0:39 - 9.31 MB - 720x304 px November 29th, 2001 @ 7:22 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt bending down to pick up some papers and having her dress ride up to expose her panties as she jumps into Ray Liotta's arms and kisses him. Hi-res DVD capture from Heartbreakers.

    Sexy 0:53 - 12.76 MB - 720x304 px November 29th, 2001 @ 7:20 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    More of Jennifer Love Hewitt's bouncing cleavage as she walks up to a valet and distracts him in order to steal a set of keys. Hi-res DVD capture from Heartbreakers.

    Sexy 0:48 - 11.52 MB - 720x304 px November 29th, 2001 @ 7:19 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt having her awesome breasts bounce nicely as she walks into a bar wearing a very tight short pink dress that shows a lot of cleavage. Hi-res DVD capture from Heartbreakers.

    Sexy 0:33 - 7.79 MB - 720x304 px November 29th, 2001 @ 7:18 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing some great cleavage as she sits at a table in a short pink dress, then gets up to use the cigarette machine. Hi-res DVD capture from Heartbreakers.

    Sexy 0:49 - 11.40 MB - 720x304 px November 29th, 2001 @ 7:17 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt seductively sucking some olives off a toothpick and then choking on one, all while wearing a great tight pink dress. Hi-res DVD capture from Heartbreakers.

    Sexy 0:48 - 11.21 MB - 720x304 px November 29th, 2001 @ 7:16 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    A nice quick clip of Jennifer Love Hewitt showing her bra from underneath her pink dress as she leans over. Hi-res DVD capture from Heartbreakers.

    Sexy 0:09 - 2.00 MB - 720x304 px November 29th, 2001 @ 7:15 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    More of Jennifer Love Hewitt and her cleavage in her great pink dress as she argues with Jason Lee on a road. Hi-res DVD capture from Heartbreakers.

    Sexy 0:47 - 10.89 MB - 720x304 px November 29th, 2001 @ 7:14 pm [email protected]

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Jennifer Love Hewitt sorted by most recent continued