dick - "fellow, lad, man," 1553, rhyming nickname for "Richard," one of the commonest Eng. names, it has long been a synonym for "fellow," and so most of the slang senses are probably very old, but naturally hard to find in the surviving records. The meaning "penis" is attested from 1891 in British army slang; dickhead "stupid person" is from 1969.
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