Create a playlist and let this script divide up your poms. (more info on pomodoro work focus technique: http://workawesome.com/productivity/pomodoro )

Pomodoro MediaPlayer.ahk

#NoEnv 
#SingleInstance ignore
SendMode Input

playPauseKey = {Control down}{Alt down}{Home}{Alt up}{Control up} 
workPeriod  := 25 * 60 * 1000
breakPeriod  := 5  * 60 * 1000
pomsBeforeLongBreak := 4

Pomodoro:
	Loop, %pomsBeforeLongBreak% {
		msgbox, Back to work!
		Send, %playPauseKey%
		Sleep, %workPeriod%
		if (A_Index < pomsBeforeLongBreak) {
			m = Short break
			s = %breakPeriod%
		}
		else {
			m = Long break 
			s = %workPeriod%
		}
		msgbox, %m% (%A_Index% / %pomsBeforeLongBreak%)
		Send, %playPauseKey%
		Sleep, %s%
	}
Gosub, Pomodoro

You can compile this into an exe with AutoHotkey.