Motorcycle tires can sometimes be a pain, especially if the sidewalls are stiff. The best thing I can advise is that you use a ratchet strap if you are having an issue getting them to hold air. You can wrap it around the tire to draw the sides closer towards the rim. Once they start holding air most tires have a maximum pressure and you just don't want to exceed that. You can leave your compressor at whatever the max pressure is but what you want to do is remove the valve core from the valve stem and use your air chuck to compress the tire as quickly as possible. Make sure and use a lot of lube around the edge of both beads, then blast the tire up to the max pressure or until it seats the bead, whichever comes first. Once it's at either and holding air pull the air chuck off and put the valve stem core back in. If the tire bead has not set let it sit for a bit and it will probably pop suddenly, but if it sets and doesn't pop then leave it sitting at max pressure, stand the tire up and use a rubber mallet to gently hit along the top of the tread and it should give enough pressure and vibration to pop the bead all the way on. Once it pops reduce the air pressure to something around 32 to 36 PSI or whatever the bike manual recomends.