One interesting possible answer to this question can be drawn from a reference in one of the original line of Star Trek novels (which, albeit generally considered non-canon, where often written by people close to the original productions and may give some insight into original plans that were dropped, etc).
In this case, the novel is The Galactic Whirlpool by David Gerrold, which includes a section explaining that "Tiberius" is not part of Kirk's given name, but instead is a nickname that was given to him by one of his Academy instructors and which he later officially adopted in order to remind himself of that instructor's lessons.
If this is accepted as true, then it leaves open the possibility that "R" was the initial of an original middle name that he dropped when adopting the nickname.