The heyday of the construction, which was employed by John Lyly, Euphues His England (1580), the poem Willobie His Avisa (1594), in the travel accounts under the title Purchas His Pilgrimes (1602), Ben Jonson's Sejanus His Fall (1603) or John Donne's Ignatius His Conclave (1611), was the late 16th and early 17th century.
[1] For example, in 1622, the Holy Roman Emperor's ambassador in London "ran at tilt in the Prince his company with Lord Montjoy".
Although a small number of examples were produced by earlier scholars to show that the "his" genitive can be traced back to Old English, Allen examines every putative example of the "his" genitive that has been presented from Old English and finds them all to be subject to other possible analyses.
As George Oliver Curme puts it, "The s-genitive was doubtless felt by many as a contraction of the his-genitive, which strengthened the tendency to place an apostrophe before the genitive endings" (as an indication of an elided "his").
[5] The "his" genitive was not limited to masculine singular nouns in Middle English, but was is also found with feminine gender and plural number.
An "agreeing" pronominal genitive is also present in other Germanic languages, but it died out quickly in English.
Therefore, it is likely that people were already saying "his" after a masculine noun in later Middle English by hypercorrection, and the "his" genitive may therefore have been an orthographic anomaly.
In Early Modern English, however, the genitive marker was clearly a pronoun that agreed with the possessor.