Of all fourteen years of being Tim's friend, I have not once seen that expression on his face. Of all fourteen years > Prepositional phrase, adverbial of (being Tim's friend) > Prepositional phrase, adjective, modifying "years". Being is the object (gerund); friend is the object of the verbal (gerund) "being" I have not once seen that expression on his face.
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Grammar GeekA question for other native speakers: Would you not say "IN all the years, I have not seen" rather than "OF all the years..."?I certainly would. I, too, found the original anomalous.