lollipop/lollygag

A variety of sources agree that “lollipop” seems to come from a dialectical term, “lolly,” meaning “tongue,” with varying degrees of certainty: Webster’s Unabridged Dictionary (from which I note a secondary meaning of lollygag as to indulge in kisses and caresses, to neck); Dictionary of Word Origins, Jordan Almond; Who Put the Butter in Butterfly?, David Feldman; and Horsefeathers & Other Curious Words, Charles Funk.


But Eric Partridge, in Origins -- A Short Etymological Dictionary of Modern English, speculates:

lollipop, lolly. The former = lolly + pop (it into your mouth); and the ? orig dial lolly is prob short for loblolly, a thick broth or gruel, app a rhyming redup on LOB.

and

lob, pollack, lugworm, (now dial) a heavy (and dull) person, something short and thick and heavy, hence, ‘to lob’, to let fall heavily, throw lazily, whence, as in cricket or lawn tennis, a lobbed ball; hence app loblolly (cf LOLL) and looby, a (heavily) awkward, clumsy person, usu male, and lubber (cf LOOBY and the Sw dial lubber), a clumsy fellow, esp seaman, with adj lubberly and cpd landlubber.

A lob, ult echoic, is akin to and perh imm from MLG lobbe, a plump person or, usu, quadruped, cf Fris lob or lobbe, a short hanging lump, e.g. of fat, and Da lub or lubbe, a pollack.

His entry for loll references to lull, sense 2:

lull (v, hence Negligence), lullaby; loll (whence pa, vn lolling), Lollard.
1. ‘To lull’, ME lullen, to hum a tune to , to lull, MD lollen, to mumble or mutter, to doze, L lallare, to sing to sleep (perh for la-la, comforting sounds + -are) and Skt lolati, he moves to and fro, lulita, swinging. Lullaby perh = to lull a child to sleep + a + b’y for baby, but perh = lull + a comforting dissyllable.
2. ME lullen has var lollen, esp in sense ‘to hang loosely, to droop’, whence ‘to loll. MD lollen, to memble, has agent lollaerd, a mumbler, esp as pej Lollaerd, a mumbler of prayers and psalms.

A Dictionary of Slang and Euphemism, Richard Spears, informs that lallygag/lollygag has an older meaning of “to flirt, court, or make love” (mid-1800s), and a more current meaning of “to be idle” (1900s). The same source reveals the slang term, “ladies’ lollipop.” (British, jocular, 1800s).