Unable to free transform more than once

When I press ctrl + T I can transform the layer/ make it bigger by dragging one point but then if I try to pull again to adjust again it's not doing anything. I'm having to press enter every time to then do the same thing. It's impossible to transform something if the free transform box changes shape once i press ctrl + T. 

Im sure this is probably an easy fix but I cant find anything online and no contact to ask, if someone could please help would be very grateful 🙂