Let's say Kevin plays for x hours.
Jesse plays for (x/2 + 2) hours.
Their total playing hours are x + (x/2 + 2) = 11.
Combining like terms, we get (3/2)x + 2 = 11.
Subtracting 2 from both sides, we get (3/2)x = 9.
Multiplying both sides by 2/3, we get x = 6.
So Kevin plays for 6 hours and Jesse plays for (6/2 + 2) = 5 hours.
Therefore, the answer is option D.