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1590s, from Spanish bobo "stupid person, slow bird" (used of various ungainly seabirds), probably from Latin balbus "stammering," from an imitative root (see barbarian).
Booby prize is by 1883: an object of little value given to the loser of a game; booby trap is 1850, originally a schoolboy prank; the more lethal sense developed during World War I.
At the end of every session the dominie had the satirical custom of presenting his tawse as a "booby-prize" to some idle or stupid lout whom he picked out as meriting this distinction so that next time they met he might start fresh and fair with new pair for a new set of classes. [Ascott R. Hope, "Dumps," "Young England" magazine, 1883]
A woman's breast
[late 1600s+; perhaps ultimately fr Latin puppa, literally ''little girl,'' which in child language became ''breast''; whence Old French pope, popel, ''breast,'' German dialect Bubbi, and so on]