Let me ask you this: Are you tightening the bleeder nipple before or after you let off the brake pedal? Probably a dumb Q on my part...
The way I've always bled brakes is to get a clear, big glass or plastic jar, fill it halfway with brake fluid, attach a hose from the bleeder nipple and run it down into the clear jar of brake fluid, open the bleeder and pump the brakes until there is no air coming out. I quit using the two-man system long ago (one in the cab and one under the truck loosening and retightening the bleeder nipple after every stroke.
Start at the master and then proceed to the nearest wheel.