jQuery on('toggle') possible?

Try using only the toggle.

$('#clickme').toggle(
    function(){alert('click 1');},
     function(){alert('click 2');}
);

As it is, it doesn't do anything on the first click because it's only attaching the event handler at that point.

EDIT:

I didn't fully read the post. My bad.

$('body').on('click', '#clickme', function()
{
    var state = $(this).data('state');


    switch(state){
        case 1 :
        case undefined : alert('click 1'); $(this).data('state', 2); break;
        case 2 : alert('click 2'); $(this).data('state', 1); break;
    }
});