The story of Cimon and Iphigenia is taken from Boccaccio's Decameron. Cimon the son of a nobleman of Cyprus, a handsome young man although coarse and uneducated, fell in love with the maiden Iphigenia and eventually married her. The effects of the marriage were wholly beneficial to his nature transforming him into an accomplished and polished gallant. In Kauffmann's picture Cimon is shown when he first sets eyes on Iphigenia as she lies asleep beside a stream. The Triumph of Venus was a recurrent theme in Italian paintings of the 15th and early 16th Centuries when civic processions, which often celebrated the the triumph of pagan deities, were popular in Italian cities. Kauffmann depicts Venus in a triumphal chariot drawn by Cupid.
The exact early provenance of the pictures remains unclear but is seems likely that they were commissioned by a member of the Brooke family of Runcorn. Lady Victoria Manners mentions 'Two Classical pictures' under an entry for 'Mr. R.M. Brooke, Norton Priory, Runcorn' as recorded in the artist's Italian list (Lady V. Manners, op.cit., p.180). The artist's memorandum of paintings also records a 'life size' portrait of a Thomas Brooke Esq., dressed as a Spaniard in black, together with one of Mr Brooke's wife, attired as a muse, for which payment of 240 Zechini was received (entry dated Rome April, 1795) and in a note on this entry Lady Victoria Manners commented 'This Thomas Brooke would possibly be a member of the family of Brooke of Norton Priory. He was perhaps the Thomas Brooke (b.1760) who married a daughter of Sir Thomas Cunliffe' (Lady V. Manners, op.cit., p.166, note 3).