For My Trouble Maker, My Lovely Son

Thise phrase has several meanings, including the following;

• A tip drill is a basketball practice in which players take turns to tip the ball off the backboard consecutively without the ball touching the ground. After each rebound the player goes to the back of the queue leaving the next player to repeat the drill. The aim of the drill is to develop timing and jumping ability for rebounding.
• This term has also been extended to describe a form of group sex or gang bang, in which a line of men queue to have sex with (usually) one woman.
• Tip Drill is the name of a Nelly song.