Tip first of items into hole — a tip! (9)

I believe the answer is:

pourboire

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'a tip' is the definition.
(I've seen this before)

'tip first of items into hole' is the wordplay.
'tip' becomes 'pour' (I can't explain this - if you can you should believe this answer much more).
'first of items' becomes 'i' (pst letter of 'items').
'into' means one lot of letters goes inside another.
'hole' becomes 'bore' (hole can mean to bore a hole).
'i' inserted inside 'bore' is 'boire'.
'pour'+'boire'='POURBOIRE'

Can you help me to learn more?

(Other definitions for pourboire that I've seen before include "Gratuity" , "Tip" .)

I've seen this clue in The Times.

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