early 14c., "an artist's fine brush of camel hair," from Old French pincel "artist's paintbrush" (13c., Modern French pinceau), from Latin penicillus "painter's brush, hair-pencil," literally "little tail," diminutive of peniculus "brush," itself a diminutive of penis "tail" (see penis). Small brushes formerly were used for writing before modern lead or chalk pencils; meaning "graphite writing implement" apparently evolved late 16c. Derogatory slang pencil-pusher "office worker" is from 1881; pencil neck "weak person" first recorded 1973.
1530s, "to mark or sketch with a pencil-brush," from pencil (n.). In reference to lead pencils from 1760s. Related: Penciled; penciling. To pencil (something) in "arrange tentatively" is attested from 1942.
To make a tentative arrangement: Why don't I pencil in an appointment for next Thurday? (1940s+)
To work out details; study: Let me pencil this idea for a while (1990s+)