Olivia Alaina May sorted by most recent
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May removing her robe to reveal a pink bra and panties and then joining Michelle Maylene and a guy on a bed as they all kiss and remove each other's clothing before the guy goes down on Olivia as Michelle kisses and sucks on her nipples and then has sex with her while she lies on her back until finally Michelle gets on top and has sex riding him fully nude as Olivia lesbian kisses her and kisses him while sitting next to them and touching their bodies all during a threesome. From Co-Ed Confidential.
3:12 - 67.22 MB - 1280x720 px
February 12th, 2016 @ 2:15 pm
Michelle Maylene & Olivia Alaina May - Co-Ed Confidential - S02E08 - 3.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May removing her towel to reveal her fully shaved nude body and then having a guy kiss her breasts and kneel on the ground going down on her before they move to the bedroom where she helps him remove his pants and returns the favor by going down on him until finally they have sex with her up on her knees and him behind her grabbing her breasts. From Co-Ed Confidential.
2:48 - 58.59 MB - 1280x720 px
February 10th, 2016 @ 8:07 pm
Olivia Alaina May - Co-Ed Confidential - S02E08 - 2.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May showing off her fully nude body as she walks down some steps into a pool and then walks around a bit skinny dipping before leaning against the edge talking with a guy until finally she climbs naked out of the water and walks with him towards the house. From Co-Ed Confidential.
0:40 - 17.40 MB - 1280x720 px
February 6th, 2016 @ 7:02 pm
Olivia Alaina May - Co-Ed Confidential - S02E08 - 1.mp4
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Ouija (one)
Olivia Alaina May
Olivia Alaina May of Co-Ed Confidential fame seen through a wet glass door showing her breasts as she takes a shower and washes her hair. From the short film Ouija (one).
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Masters of Sex
Olivia Alaina May
Olivia Alaina May (credited as Olivia May) of Co-Ed Confidential and 18 Year Old Virgin fame seen in black and white in an old time nickelodeon peep show machine as she lies on a couch topless with one hand between her legs and then other running over her breasts. From Masters of Sex. Updated to higher quality.
0:05 - 1.83 MB - 1280x720 px
May 5th, 2015 @ 8:54 pm
Olivia Alaina May - Masters of Sex - S01E09 - BD.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May wearing a turquoise top and panties with a slight cameltoe as Michelle Maylene lowers Olivia's top to reveal her breast and kisses her right nipple before she takes Olivia's panties off and goes down on her while Olivia cries out in French until Michelle stops and asks her if she can even speak the language and Olivia sits up and reassures her by lesbian kissing her. From Co-Ed Confidential.
1:22 - 28.79 MB - 1280x720 px
April 22nd, 2015 @ 4:27 pm
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E07 - 1.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May (right) walking up to Michelle Maylene (left) and lesbian kissing her as they remove their clothes to reveal Olivia's fully shaved body as Michelle rubs her between the legs and plays with her breasts before Olivia sits on the edge of a bed and Michelle kneels on the ground while going down on her until finally Michelle lies on her back on the bed with Olivia on top of her as they continue to lesbian kiss and Olivia rubs Michelle in between the legs. From Co-Ed Confidential.
3:21 - 70.27 MB - 1280x720 px
February 11th, 2015 @ 2:34 pm
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E06 - 1.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May having Michelle Maylene lower her pink top and kiss and feel her breasts and then lesbian kiss each other before Michelle goes down on Olivia giving us some explicit views in between Michelle's legs until finally they sit up on their knees as Michelle rubs herself in between the legs as Olivia puts her hand over Michelle's to help her. From Co-Ed Confidential.
3:25 - 71.60 MB - 1280x720 px
December 5th, 2014 @ 10:19 pm
Michelle Maylene & Olivia Alaina May - Co-Ed Confidential - S02E05 - 2.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May (right) lesbian kissing Michelle Maylene (left) and having Michelle feel her left breast all as they stand on a stage during a rally while a guy talks to the crowd and Hannah Harper watches. From Co-Ed Confidential.
Sexy 0:14 - 4.78 MB - 1280x720 px November 29th, 2014 @ 9:54 pm Olivia Alaina May, Michelle Maylene & Hannah Harper - Co-Ed Confidential - S02E05.mp4More [+]
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May lying topless and in panties on her back as Michelle Maylene kisses her breasts and then removes her panties and goes down on her before Olivia returns the favor by kneeling down between Michelle's legs and going down on her as well eventually giving us an explicit view in between her legs with a bit of a patch covering herself as she climbs back up to lesbian kiss Michelle. From Co-Ed Confidential.
2:39 - 55.34 MB - 1280x720 px
October 30th, 2014 @ 5:27 pm
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E04 - 1.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May (left) falling onto a bed naked with Michelle Maylene (right) and then lesbian kissing her before they lie there nude and talk for a while until finally they get interrupted by a guy and duck under the covers. From Co-Ed Confidential.
0:27 - 9.58 MB - 1280x720 px
October 26th, 2014 @ 5:06 pm
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E04 - 2.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May sitting at a table in a restaurant with her red dress lowered while a guy kisses her breasts and then sitting on the edge of the table while he stands up having sex with her. From Co-Ed Confidential.
0:36 - 12.31 MB - 1280x720 px
August 23rd, 2014 @ 5:24 pm
Olivia Alaina May - Co-Ed Confidential - S02E03.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May and Michelle Maylene in a walk in closet together as Olivia repeatedly removes her clothes revealing her breasts and nude body as Michelle gives her different outfits to try on until all of a sudden Olivia lesbian kisses Michelle briefly and then pauses before going back to kissing her until they get interrupted by someone calling for them. From Co-Ed Confidential.
1:51 - 38.56 MB - 1280x720 px
August 19th, 2014 @ 3:18 pm
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E03 - 2.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May standing fully nude painting as Michelle Maylene stands in the doorway and starts talking with her for a bit before Olivia walks naked over to the bed and sits down with Michelle and talks with her some more. From Co-Ed Confidential.
0:51 - 17.79 MB - 1280x720 px
August 15th, 2014 @ 6:32 pm
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E03 - 1.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May lying on her back in a bed as she pulls her right nipple out of her pink bra as she plays with her breasts and then sliding her hand down her pink panties and rubbing herself all while she arches her back and moans as Michelle Maylene watches from the doorway until finally Olivia finishes and talks briefly with Michelle. From Co-Ed Confidential.
1:37 - 33.55 MB - 1280x720 px
August 7th, 2014 @ 1:06 pm
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E02.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May going down on Aurora Snow who is sitting in an office chair naked showing her breasts and then Olivia sitting on the edge of a desk as Aurora goes down on her and then kisses and licks her nipples before kissing down her body and then lesbian kissing her a bit. From Co-Ed Confidential.
1:50 - 38.07 MB - 1280x720 px
July 6th, 2014 @ 2:32 pm
Olivia Alaina May & Aurora Snow - Co-Ed Confidential - S02E01.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May standing in a foyer as she lowers her dress to reveal her breasts and then removes it all together to reveal her fully nude body and then starts to walk away all as Michelle Maylene and a guy watch. From Co-Ed Confidential.
0:06 - 1.91 MB - 1280x720 px
July 2nd, 2014 @ 2:02 pm
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E01.mp4
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May bending over in a short schoolgirl's skirt to show part of her butt as a guy stares while sitting on a bed. She then pulls her shirt over her head, seen from behind as she climbs into his lap during this fantasy sequence. From 18 Year Old Virgin.
0:33 - 11.57 MB - 1280x720 px
January 23rd, 2013 @ 9:28 pm
Olivia Alaina May - 18 Year Old Virgin - 1.mp4
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May standing bottomless in a bathroom, holding a clipper to her (likely fake) bush as she tries shaving it. We then see plenty of her bare butt as she shuffles around the bathroom when the clipper gets stuck. Lastly, we see her in her bra as Lauren Walsh helps her clean up. From 18 Year Old Virgin.
1:02 - 21.42 MB - 1280x720 px
January 23rd, 2013 @ 9:27 pm
Olivia Alaina May - 18 Year Old Virgin - 2.mp4
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Olivia Alaina May sorted by most recent continued
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May undressing in a bedroom, getting down to her blue panties and bra as she kneels on a bed with a guy. The guy then bends her over the bed and grabs her breasts from behind while pulling her panties down to expose her bare butt. She then flips onto her back and the guy holds her legs up in the air while pressing against her in preparation for having sex with her. From 18 Year Old Virgin.
2:41 - 55.99 MB - 1280x720 px
January 23rd, 2013 @ 9:25 pm
Olivia Alaina May - 18 Year Old Virgin - 3.mp4
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May stumbling upon Crystal Baker, an unknown girl and a guy as they invite Olivia to join them in bed. Crystal and the other girl in red panties start off topless and then Crystal removes her skirt after throwing Olivia onto the bed and kneeling over her face. Olivia then watches as the others begin to get into a threesome in a variety of positions. They end up standing fully nude as the guy has sex with Crystal and Olivia rushes to try to take Crystal's place, pulling her blue panties down to reveal her butt in the process while trying to lose her virginity. From 18 Year Old Virgin.
3:01 - 62.88 MB - 1280x720 px
January 21st, 2013 @ 2:59 pm
Olivia Alaina May & Crystal Baker & Unknown - 18 Year Old Virgin.mp4
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May straddling a guy in bed as he lies on his stomach and she sits on the back of his legs while holding a whip and wearing nothing but a strap-on. We get a nice view of her bare breasts as she talks to the guy and tentatively uses the whip on him. From 18 Year Old Virgin.
1:35 - 32.89 MB - 1280x720 px
January 21st, 2013 @ 2:59 pm
Olivia Alaina May - 18 Year Old Virgin - 4.mp4
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May straddling a guy in bed as he removes her blue bra, revealing her breasts, which he reaches up to squeeze and comments on how nice they are. He then continues to squeeze and suck them for a bit before trying to get Olivia to go down on him. She then collects her things and stumbles out of the room. From 18 Year Old Virgin.
1:00 - 20.75 MB - 1280x720 px
January 21st, 2013 @ 2:58 pm
Olivia Alaina May - 18 Year Old Virgin - 5.mp4
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May naked as she lies underneath a guy outside on some blankets beside a fence. We see her breasts and also her butt from the side as she kisses him and then sits up to face him. From 18 Year Old Virgin.
1:12 - 25.08 MB - 1280x720 px
January 21st, 2013 @ 2:57 pm
Olivia Alaina May - 18 Year Old Virgin - 6.mp4
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Party Down
Olivia Alaina May
Olivia Alaina May doing a striptease at a party as she removes her nurse's uniform to reveal a white bra and white panties with a garter and stockings and then removing her bra to reveal her breasts and dancing around a room and with a guy until finally he passes out and she tries to cover her breasts as another guy runs in to help all while Marilu Henner watches. From Party Down.
0:38 - 13.34 MB - 1280x720 px
February 9th, 2012 @ 9:49 pm
Olivia Alaina May & Marilu Henner - Party Down - S01E03.mp4
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Party Down
Olivia Alaina May
Olivia Alaina May standing in white panties and topless with her hands held up against her breasts as Marilu Henner and some guys try and help a guy who is passed out until finally Jane Lynch kisses the guy and revives him causing Olivia to celebrate by lifting up her bra and finally revealing her breasts. From Party Down.
0:58 - 20.13 MB - 1280x720 px
February 9th, 2012 @ 9:47 pm
Olivia Alaina May, Marilu Henner & Jane Lynch - Party Down - S01E03.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May and Michelle Maylene both completely naked in a threesome sex scene with a guy on a bed, the guy having sex with Olivia first as she kneels on the bed and Michelle touches her breasts and kisses her. Michelle then rides the guy as Olivia kneels beside them and leans over to kiss both the guy and Michelle while also playing with Michelle's breasts. From Co-Ed Confidential.
2:04 - 42.89 MB - 1280x720 px
April 9th, 2010 @ 11:36 am
Olivia Alaina May & Michelle Maylene - Co-Ed Confidential - S02E09.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May having sex with a guy on bed, naked in his lap as she rides him. The guy then lays back and Olivia continues to bounce on top of him while occasionally grabbing her own breast. From Co-Ed Confidential.
1:24 - 29.25 MB - 1280x720 px
March 18th, 2010 @ 12:20 pm
Olivia Alaina May - Co-Ed Confidential - S02E13.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May starting off topless and kneeling on a bed as she makes out with a guy. She then slips her panties off and lays back as the guy gives her oral sex. Next we see her on top, riding the guy and occasionally grabbing her own breasts as she moans loudly. From Co-Ed Confidential.
3:20 - 69.30 MB - 1280x720 px
March 6th, 2010 @ 3:33 pm
Olivia Alaina May - Co-Ed Confidential - S02E11 - 2.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May pulling her green nightie off to sit down on a couch with a guy while wearing just a pair of pink panties. They then make out and the guy goes on Olivia before she rides him while fully nude. They then move behind the couch, where the guy has sex with Olivia from behind as she leans over the back, grabbing her breasts as they bounce. From Co-Ed Confidential.
2:39 - 55.12 MB - 1280x720 px
March 2nd, 2010 @ 6:57 pm
Olivia Alaina May - Co-Ed Confidential - S02E11 - 1.mp4
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Co-Ed Confidential
Olivia Alaina May
Olivia Alaina May lying on her back in bed as a guy slides her pink panties off and she goes fully nude. The guy then goes down on Olivia for a bit before they have sex, Olivia bouncing his lap while occasionally grabbing her own breasts. From Co-Ed Confidential.
2:13 - 46.18 MB - 1280x720 px
February 24th, 2010 @ 11:41 am
Olivia Alaina May - Co-Ed Confidential - S02E10.mp4
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Party Down
Olivia Alaina May
Olivia Alaina May stripping out of a nurse's outfit while entertaining a party, whipping her bra off to reveal her breasts, which she shakes while dancing with a guy. One of the older guys then collapses, and Olivia holds her breasts with her hands while the guy gets revived. They then celebrate, and Olivia goes topless again as she resumes dancing. Good quality HDTV capture from Party Down.
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May bending over in a short schoolgirl's skirt to show part of her butt as a guy stares while sitting on a bed. She then pulls her shirt over her head, seen from behind as she climbs into his lap during this fantasy sequence. Hi-res DVD capture from 18 Year Old Virgin.
More [+]
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May standing bottomless in a bathroom, holding a clipper to her (likely fake) bush as she tries shaving it. We then see plenty of her bare butt as she shuffles around the bathroom when the clipper gets stuck. Lastly, we see her in her bra as Lauren Walsh helps her clean up. Hi-res DVD capture from 18 Year Old Virgin.
More [+]
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May undressing in a bedroom, getting down to her blue panties and bra as she kneels on a bed with a guy. The guy then bends her over the bed and grabs her breasts from behind while pulling her panties down to expose her bare butt. She then flips onto her back and the guy holds her legs up in the air while pressing against her in preparation for having sex with her. Hi-res DVD capture from 18 Year Old Virgin.
More [+]
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May stumbling upon Crystal Baker, an unknown girl and a guy as they invite Olivia to join them in bed. Crystal and the other girl in red panties start off topless and then Crystal removes her skirt after throwing Olivia onto the bed and kneeling over her face. Olivia then watches as the others begin to get into a threesome in a variety of positions. They end up standing fully nude as the guy has sex with Crystal and Olivia rushes to try to take Crystal's place, pulling her blue panties down to reveal her butt in the process while trying to lose her virginity. Hi-res DVD capture from 18 Year Old Virgin.
More [+]
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May straddling a guy in bed as he lies on his stomach and she sits on the back of his legs while holding a whip and wearing nothing but a strap-on. We get a nice view of her bare breasts as she talks to the guy and tentatively uses the whip on him. Hi-res DVD capture from 18 Year Old Virgin.
More [+]
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May straddling a guy in bed as he removes her blue bra, revealing her breasts, which he reaches up to squeeze and comments on how nice they are. He then continues to squeeze and suck them for a bit before trying to get Olivia to go down on him. She then collects her things and stumbles out of the room. Hi-res DVD capture from 18 Year Old Virgin.
More [+]
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18 Year Old Virgin
Olivia Alaina May
Olivia Alaina May naked as she lies underneath a guy outside on some blankets beside a fence. We see her breasts and also her butt from the side as she kisses him and then sits up to face him. Hi-res DVD capture from 18 Year Old Virgin.
More [+]
