have never pumped a tire properly. HELP

[Pedal Wench]

Different pumps "latch" onto the stem in different ways - are you sure you're securing it properly? Some have a lever, some a knob, some twist - make sure you're latching it on.

And, when you unscrew the valve, I hit the valve to release a bit of air - this seems to open up the valve to make that first pump easier.

And finally, some pumps are easier than others. I have to lean all my weight on mine too (and I'm not a very light person!) and I've borrowed pumps that take almost no effort at all.

Edit: Ooops, while I was typing my epic response, Cunninghamair said the same thing, but better!