trouble inflating tires
Practice with a spare tube outside of the tyre.  You'll see it start to inflate on one or two pumps.

Could it be the pump you're using locks-on the other way?  When its clamped down you should not be able to feel air moving out the end, around the valve.

Possibly your pump is a schrader-only style?  There are wee thread-on adapters that let you use a schrader (car valve) fitting on a presta bike valve.  They also work as caps to protect the valve.