I would like to know more about the idiom "like pulling teeth". For example, does anyone know its origin and first usage?
The earliest quotation of the phrase like pulling teeth in the OED is 19th century:
1836 Knickerbocker Sept. 306 And for this service to the sons, what did I get from the sires? The pittance of a few dollars, which came like pulling so many teeth.
I found an earlier example from 1831 published in the Foreign Missionary Register of The American Baptist Missionary Magazine (Vol. 12, October 1832, No. 10), in the 23rd October 1831 entry of Mr. Judson's Journal:
When any person is known to be considering the new religion, all his relations and acquaintance — rise en masse; so that to get a new convert is like pulling out the eye-tooth of a live tiger.
The verb pull has been used to mean extract (a tooth) since at least the 17th century:
1626 First & Best Part Scoggins Iests (new ed.) 39 If you pull any of my neighbours teeth after such sort as you haue done.I will pull out all the teeth in your head.