Many people say that the outlining hurts more. The reason for the increased pain in outlining is that a thinner needle is used for the precision of the outline, which causes more pain.
Others say that the filling in is more painful. The needle is thicker and should be less painful, but the area covered is also larger. If you're having a large tattoo done, you may experience more pain as time goes on because your body's endorphins, which cope with pain, will wear off after awhile.
Start with a small tattoo on an area which isn't extremely sensitive and judge the pain of the situation for yourself. Then, if you think you can handle it, move on to something splashier!