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Insecure is an American comedy-drama television series based partially on Issa Rae's. A shy new intern, Samantha, learns to please new boss. Tags: big cock, big tits, blowjob, brunette, business women, deep throat, face fuck, face sitting. Big ass boss sitting on the intern's face 10:58. With a big fan of just putting it out there, on the intern's face 10:58.