Can you give us pics? Do you know if it is presta valve or schrader? I have to give my presta valve a tap, because sometimes it sticks. Is there a fastener you tighten on the hose before pumping? If I turn it the wrong way, air doesn't go in the tire (just fills up the hose). I also pulled out a stem before mastering this simple task.
Floor pumps do make a huge difference--maybe check garage sales or Craigs list for one.
Keep asking for help--don't give up
"Well-behaved women seldom make history." --Laurel Thatcher Ulrich
'09 Trek WSD 2.1 with a Brooks B-68 saddle
'11 Trek WSD Madone 5.2 with Brooks B-17