This seems like it should be so basic...but....it's not.

In prep for my ride tommorow...I went to check and fill my tires...back tire no problem. Front tire...not so much. I attached the pump to the valve and it seemed instead to remove air from the tire...suffice to say I now have a front tire that is to soft to ride and has less air in it than it started with.

What the h*ll am I doing wrong???