Exegesis:

ho huios sou houtos ‘this son of yours,’ contrasting with emoi in v. 29. houtos here with obvious contempt, as shown by what follows.

ho kataphagōn sou ton bion meta pornōn ‘who has devoured your possessions with prostitutes.’ katesthiō means here ‘to destroy,’ ‘to consume,’ ‘to eat up.’ For bios cf. on 8.43; here it is used hyperbolically since the younger son spent only his part of his father’s possessions.

pornē ‘prostitute,’ ‘harlot.’

Translation:

One may have to change the sentence structure, e.g. ‘this son of yours has devoured … with harlots; but when (or, as soon as) he (emphatic) came, you killed….’

Devoured. A verb meaning ‘to eat up’ can sometimes be used in the metaphorical sense required here, e.g. in Sranan Tongo; where that is not the case one may say, ‘to spend all,’ ‘to waste,’ ‘to squander’ (see v. 13).

Harlots. Some idiomatic expressions used are, “women of the street” (An American Translation), ‘single (woman) of the-state/government’ (Kituba), ‘women who live like dogs’ (Kaqchikel), ‘ten pence women’ (Uab Meto), ‘bad women’ (Thai 1976, Trukese, Pohnpeian), ‘lustful/debauched women’ (Toraja-Sa’dan, Yao), ‘ones-who-walk’ (Medumba). Often a generic term is used, e.g. “his women” (New English Bible), les femmes (Bible de Jérusalem, similarly Tae’ 1933), in this context the mere plural being enough to give the word a clearly pejorative meaning. Cf. also on “sinner” in 7.37.

Quoted with permission from Reiling, J. and Swellengrebel, J.L. A Handbook on the Gospel of Luke. (UBS Handbook Series). New York: UBS, 1971. For this and other handbooks for translators see here . Make sure to also consult the Handbook on the Gospel of Mark for parallel or similar verses.