Often what bubs do when they are trying to stimulate a let-down, is kind of pull and tug at the nipple. Obviously if you have already fed on that side the let down will not be as forceful, so some babies can get a little pushy!
What happens sometimes with babies is that the initial let-down/feed tires them out, so they might go on for 5-10 mins, then come off (and sometimes have a little sleep). Then they can go back on the same breast and get the remainder of the milk, but it does come out slower. It sounds like you just have an impatient bub on your hands!
I think he would get used to the change quite quickly....the only way to tell if it works is by trying it. HTH!