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Bosses & Secretaries

Maggie Gyllenhaal in Secretary (2002)

It's every professional man's fantasy to have a sexy secretary. Luckily, we can live out that fantasy in the movies and TV shows that have that very thing. This playlist, of course, features the ultimate boss-secretary film Secretary with naked Maggie Gyllenhaal. We also see Rachel Miner in Californication, Monika Ringwald in Intimate Games, a dancing Lee Meredith in The Producers, Nao Eguchi in Zero Woman Returns, Naomi Watts in Undertaking Betty, Dakota Johnson in Fifty Shades of Grey and many more. Take notes and watch these ladies take some dick-tation. 

    Sexy & Nude Celebrity Playlists 1,526

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