Pre-lubing should be clockwise. Think of your distributor rotation as it fires the plugs, 1-8-4-3-6-5-7-2.
Not sure if you have the proper tool, it's not just a matter off cutting off a long screwdriver blade-you need to have the spacer at the lifter valley to lube the lifters and top end. Moroso makes the proper one, about $25 through Summit Racing or Jeg's. People have also reworked an old distributor by pulling the guts. It's that center band that "covers" the lifter valley, and gets oil to the top.
The suggestion of filling the oil filter first is good. I also like to have someone turn the key on (if a light) and/or watch the gauge. If no one is available, I use a big mirror and watch through the windshield.
I also "bump" the engine over 1/3, lube it again, bump 1/3 and lube it again. This ensures all of the lifters and rockers have had plenty of chance to get pressurized oil feed. This may be excessive, but it's a comfort for me. Let it settle a bit and recheck your oil level-it may need topping off. Good luck, and enjoy your first firing!
Rick