Words at Play : Words With Remarkable Origins, Vol. 2
Speaking of Sigmund Freud (in "Hysteria"), here's some symbolism he might have appreciated: pencil and penis share a Latin root.
In ancient Rome, a small brush that served as a writing instrument was called the peniculus (literally, "brush," after the diminutive of the Latin penis meaning "tail").
The writing tool turned up in Middle English as pensel, and the modern spelling and meaning of pencil – a cylinder filled with graphite – appeared in the 16th century.
The sense of penis for the male organ arrived in English in the 17th century.
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