Jack And Jill (2001)

Starring: Serenity, Stephanie Swift, Annie Sprinkle, Devinn Lane, Sydnee Steele, Nikita Denise, Joel Lawrence, Dillion Day, Ian Daniels.
Meet Jill. An intelligent, beautiful woman who has a problem, she can’t seem to find “Mr. Right”. Jill compensates for her lack of “companionship” by fucking every guy that catches her fancy, but still feels a void in her heart that she can’t get rid of. What was missing in her life and why couldn’t she find it? Meet Jack, Jill’s roommate. Jack has a dilemma of his own, he just broke up with his girlfriend and can’t seem to get over her and move on. Jack spends many nights jerking off to a picture of his ex-girlfriend, fantasizing about them getting back together and “living happily ever after.” Jack misses his ex, but begins to wonder if they were really that happy together or was it just the nasty, kinky sex that he missed? What Jack & Jill soon discover, is that sometimes what you need in love and life has been right in front of you all along…if you just stop and open your heart, you might just stumble upon love.

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