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Lisa Ann and Nicolette Shea are two wealthy women who both have a thing for personal trailer Scott Nails. When Scott double books himself with his two hottest clients, he offers them a lesson together - while the girls initially refuse, they decide to challenge each other: whichever woman wins a series of fitness challenges gets to fuck Scott.

Scott is shocked and tries to put a stop to this bet, but the women ignore him and go for it. During their heated workout, Lisa pulls a tricky move, throwing Nicolette off and winning the challenge.

Lisa quickly claims the prize of Scott's dick, but Nicolette isn't backing down that easily! Shy girl, Molly Stewart, gets more than she bargained for when she enters the sauna and catches sexy Lisa Ann masturbating.

The sauna isn't the only think heating up! Lisa is not embarrassed. She invites Molly in to join her, but that's not going to stop her from finishing what she started!

When Lisa continues playing with her wet, pink, pussy, Molly overhears her and can't help but play with her dripping pussy as well.

It doesn't take long before these two beauties realizes that they can be pleasuring each other instead! Lisa Ann's professor husband is away at a conference, and he's asked his graduate student and teaching assistant Kyle Mason to check in on her while he's away.

When Kyle shows up, he catches Lisa poolside wearing far less than expected, but he's even more stunned by her cool, worldly, and seductive demeanor.

A completely unfazed Lisa leads Kyle inside and directs him to the living room, where he nervously waits as she goes to change.

Upon her return, an overt seduction begins, which proves to Kyle that no higher education can supplant the value of real life experience.

Lisa Ann is not a woman you want to fuck with! When she catches her husband, Charles, cheating, she drop him like a hot potato. Charles begs to be taken back but Lisa has already moved on.

He's going to have to prove himself if he wants another chance with the goddess. Lisa teases him with her body and makes him work for it.

Can Charles please his wife and convince her to take him back? You'll have to watch to find out! Lisa Ann prepares for a luxurious evening alone in her powder room, lounging in her chaise longue and applying make-up and perfume in front of her vanity.

But the evening takes an erotic, sensual turn when her lover, Isiah Maxwell, unexpectedly shows up. Isiah immediately starts to massage Lisa's tits, leading to a passionate encounter where all of Lisa's body is oiled, worshiped, and attended to with a hard cock.

Bumbling pool boy Jordi is having a hard time focusing on his tasks with Lisa Ann's boyfriend's daughter teasing him by the water. Following her sensual yoga routine, Lisa watches this insolent behavior unfold from inside the house, and she decides to claim Jordi, and his massive cock, for herself.

Lisa changes into her skimpiest bikini and then struts out into the backyard, where only a shocked and wildly turned on Jordi notices her approach.

Jordi watches as Lisa tosses her boyfriend's daughter into the pool, giving Lisa some alone time with the impressionable and eager pool boy for some oily worshiping of Lisa's perfect tits.

After nearly getting caught by Lisa's boyfriend, Jordi is finally able to pound Lisa's tight wet pussy after they sneak through the house and make it to the bedroom.

For Lisa, Jordi turns out to be the ultimate pool boy toy. After a tough leg workout, Lisa Ann deserves a massage.

She calls the spa and requests they send their top masseur. Markus Dupree arrives, but Lisa isn't impressed.

Markus insists he's a professional and gets to work. While he massages her, she keeps berating him for doing such a poor job.

Lisa requests he puts some back into working out her knots. Her ass is tight and sore from all her exercise.

Markus pours oil over Lisa's leggings and starts rubbing her ass. Lisa isn't satisfied and keeps berating Markus until he can't take it anymore.

Markus tears open Lisa's leggings and sticks a finger in her ass. That gets Lisa's attention. Markus might not be a great masseur, but he sure know how to fuck!

Busty housewife Lisa Ann has a pretty big secret: every time her loving husband heads off to work, she meets up with her boyfriend Isiah to satisfy her addiction to big black cock!

She was on her knees sucking Isiah off when her husband came back home looking for a set of keys and almost caught them red handed!

Isiah hid just in time, keeping barely out of view while he ate Lisa's MILF pussy until she was dripping wet! Finally alone, Lisa sucked and fucked Isiah's big dick and then got a huge load of cum all over her big juicy titties!

Jessy faked being sick to get out of having to go to school, and it totally fooled his new step-mother! Lisa went to work, leaving Jessy free to bone his girlfriend Jade Nile all day long.

Those horny teens got right to it, fucking like horny devils right there in bed. When Lisa showed up out of the blue, surprising him in bed with his dick still rock hard from minutes before.

And Jessy was even more surprised when that sexy Milf made a move on her step-son's cock to jack him off. Things only got wilder when Jade joined them in bed, and Lisa gave that lucky girl a hands-on step-mom lesson in how to suck and fuck like a pro.

When Lisa Ann overhears some amateur slut trying to deepthroat Danny D's monster cock in the women's room, she can't help but stop to listen.

The true fellatio master that she is, Lisa can't handle it when the silly skank says that Danny's cock is too big, and kicks her out so she can have that huge dick all to herself!

Lisa gives Danny a masterful blowjob and then lets him jug fuck her big tits until her pussy is dripping wet. Lisa rides that massive cock all the way to a huge monster cumshot that soaks her from her face all the way down to her pretty MILF pussy!

Now that busty MILF Lisa Ann is ready to rejoin to workforce, her first stop is at a sex therapist's office where she can really put her natural talents to use.

Danger is a little hesitant on account of the long gaps in her resume, but she's determined to show him her qualifications one way or another.

She whips out her big tits and Brick sucks, fondles, and fucks them, worshiping those titties like there's no tomorrow. Lisa sucks his hard cock until Brick can barely take any more, and then pulls her panties aside so Brick can feast on her pink MILF pussy.

He eats her out and then goes balls deep fucking her, pounding that pussy all over his office before finally blowing a huge facial cumshot all over her smiling face.

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