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1887, Harriet W. Daly, Digging, Squatting, and Pioneering Life in the Northern Territory of South Australia, page 112:
e might be disturbed during the night by an order being given to "go about," and by hearing in the quiet hours of the morning the familiar inquiry of "How's her head?" Mine often ached with the din of the men caulking all day long!
To apply caulking to joints, cracks, or a juncture of different materials.
1829, William Nugent Glascock, Sailors and Saints: Or Matrimonial Manœvres, page 179:
There was the goggle-eyed daughter a blowing the Grampus [throwing a bucket of water upon a person] with the platter-faced planter, whenever he caulked upon deck; […]
1897, Herbert Elliott Hamblen, William Stone Booth, On Many Seas: The Life and Exploits of a Yankee Sailor, page 40:
[…] and as sleep is about the only thing there is for a sailor at sea to get in the way of recreation, he prizes it accordingly and gets all he can. It is technically called "caulking," and a man will brag of having "caulked" the whole four hours of his watch on deck […]