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cherry: cherry: [14] Cherry comes ultimately from Greek kerasós ‘cherry tree’, which in Latin became cerasus. This was borrowed into the Germanic languages in prehistoric times, producing, as well as German kirsche, Old English ciris ‘cherry’, which died out in the 11th century. In Vulgar Latin, meanwhile, cerasus had become ceresia, which passed into Old Northern French as cherise (source of modern French cerise). When it was borrowed into English, its -s ending was misinterpreted as indicating plurality, so a ‘new’ singular cherry was created.
sherry: sherry: [16] Various sorts of dryish or sweetened white wine known as sack (etymologically ‘dry wine’) were imported into England in the 16th and 17th centuries. Many came from Spain, and the sort made around Xerez (now Jerez) in southern Spain was called in English (in an approximation to the Spanish pronunciation of Xerez) sherris sack. Before the end of the 16th century this had been reduced to sherry, which in due course came to be applied to the fortified Spanish wine that now goes by that name.
cherry (n.): c. 1300, earlier in surname Chyrimuth (1266, literally "Cherry-mouth"); from Anglo-French cherise, from Old North French cherise (Old French, Modern French cerise, 12c.), from Vulgar Latin *ceresia, from late Greek kerasian "cherry," from Greek kerasos "cherry tree," possibly from a language of Asia Minor. Mistaken in Middle English for a plural and stripped of its -s (compare pea).

Old English had ciris "cherry" from a West Germanic borrowing of the Vulgar Latin word (cognate with German Kirsch), but it died out after the Norman invasion and was replaced by the French word. Meaning "maidenhead, virginity" is from 1889, U.S. slang, from supposed resemblance to the hymen, but perhaps also from the long-time use of cherries as a symbol of the fleeting quality of life's pleasures.
cherry-pick (v.): "to select the very best selfishly," 1959 (implied in cherry-picking), American English ("Billboard"), a pejorative figurative sense,from cherry (n.) + pick (v.). Related: Cherry-picked.
sherry (n.): kind of white wine, c. 1600, mistaken singular from sherris (1530s), from Spanish (vino de) Xeres "(wine from) Xeres," modern Jerez (Roman (urbs) Caesaris) in Spain, near the port of Cadiz, where the wine was made.
wherry (n.): "light, shallow rowboat," mid-15c., of unknown origin.