That friend is the third hand I spoke of. Without the use of them new fangled bleeder values with the spring loaded ball valve inside, how can it be other than a two person job. I suppose you might get the right side done singlehandedly but it's a stretch to get to the left side.
With the lever pumped up (pressured) it should not depress against the grip until the bleeder is opened, unless you're sucking air or the line is full of air and or the reservoir is empty
Pump up the brake lever and hold the pressure on. When the bleeder valve is opened the brake lever will collapse down to the grip. Without taking your hand off the lever at this point have your assistant close the bleeder valve. With the bleeder closed pump vigorously on the brake level to feed more fluid down the line. The lever should quickly regain it's normal position, then hold it again with pressure. Now again open the bleeder and the lever will again collapse against the grip. Without releasing the lever from the grip close the valve again. Repeat...repeat...repeat until no air is spewing out with the fluid. If you use a long enough clear line hose you will see solid fluid in the tube with no interruptions with air pockets.
It sounds as though you have succeeded with the aid of your friend; and it sounds as though you didn't use a proper box end wrench (with the rounding off of the bleeder value). Cresent wrenches and open end wrench have their purposes but this ain't one of them. Safe traveling and don't be a stranger.