'askingly' originates from English, formed from the verb 'ask' with the addition of the gerundive/participle suffix '-ing' and the adverbial suffix '-ly'.

'ask' changed from Old English 'āscian' / 'ascian' to Middle English 'asken' and eventually the modern English 'ask'; the adverb 'askingly' is a later productive formation from 'ask' + '-ing' + '-ly'.

Initially, 'ask' meant 'to request or seek information'; over time this core meaning remained, and 'askingly' developed to describe the manner of asking (a pleading or questioning way).