pigeon-hole n.

late 14c., pijoun, "a dove, a young dove" (early 13c. as a surname), from Old French pijon, pigeon "young dove" (13c.), probably from Vulgar Latin *pibionem, dissimilation from Late Latin pipionem (nominative pipio) "squab, young chirping bird" (3c.), from pipire "to peep, chirp," a word of imitative origin. As an English word it replaced culver (Old English culufre, from Vulgar Latin *columbra, from Latin columbula) and native dove (n.). 

The meaning "one easily duped, a simpleton to be swindled" is from 1590s (compare gull (n.2)). Pigeon-hearted (1620s) and pigeon-livered (c. 1600) are "timid, easily frightened." A pigeon-pair (by 1800) are twins of the opposite sex (or family consisting of a boy and a girl only), so called because pigeons lay two eggs, normally hatching a male and a female.

Old English hol (adj.) "hollow, concave;" as a noun, "hollow place; cave; orifice; perforation," from Proto-Germanic *hulan (source also of Old Saxon, Old Frisian, Old High German hol, Middle Dutch hool, Old Norse holr, German hohl "hollow," Gothic us-hulon "to hollow out"), from PIE root *kel- (1) "to cover, conceal, save." As an adjective, it has been displaced by hollow, which in Old English was only a noun, meaning "excavated habitation of certain wild animals."

As a contemptuous word for "small dingy lodging or abode" it is attested from 1610s. Meaning "a fix, scrape, mess" is from 1760. Obscene slang use for "vulva" is implied from mid-14c. Golfing hole-in-one is from 1914; as a verbal phrase from 1913. To need (something) like a hole in the head, applied to something useless or detrimental, first recorded 1944 in entertainment publications, probably a translation of a Yiddish expression such as ich darf es vi a loch in kop.