Although specially admitted to Lincoln’s Inn during his father’s readership, Fleming declined to take up a career in the legal profession, preferring the life of a country gentleman. He was returned for Southampton at a by-election ahead of the second session of the first Stuart Parliament as replacement for his father when the latter became a judge. On 10 Feb. 1606 he was added to the committee to examine the charter of the Spanish Company, of which his father was a member.
Fleming accompanied his brother on a Continental tour in 1615, and during his absence Southampton corporation, hearing rumours of a forthcoming Parliament, decided to offer a seat to Sir Thomas Lake I*.
