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Is there really a single source for a phrase like that? It seems dryly is just an adverb, that can be used to describe speech (in a plain way). I don't know if it has any special source any more than using another adverb of choice (eg. he said plainly, he said bluntly etc.).
"Dry" has often been used as a description of a manner of expression:
dry
12. without adornment; plain: dry facts
13. lacking interest or stimulation: a dry book
14. lacking warmth or emotion; cold: a dry greeting
15. (of wit or humour) shrewd and keen in an impersonal, sarcastic, or laconic way
That caught my interest. Looking up the etymology of "dry," I found that there were
dry
O.E. dryge (adj.), drygan (v.), from P.Gmc. *draugiz. Of humor, 1540s; of places prohibiting alcoholic drink, 1870 (but dry feast, one at which no liquor is served, is from late 15c.)
Shrivel is close to being a synonym
In Celtic dry comes from drui which comes from druid or magician.
Although I didn't find any direct etymology of dry in relation to humor or speech, it is pretty easy to synthesize a plausible one.
Dry humor is often deprecating or shriveling to an inflated ego. It is pretty easy to imagine that in a "dry" tavern, the patrons would amuse themselves with reparte, to the point that that type of sober cutting humor became equated with "dry."
Punwise, I like the magician meaning, because there is an element of magic in good dry humor.
I would say that dryly as an adverb is describing something devoid of emotion. So it probably got just picked up over time.
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