In a nutshell, there is a speed sensor on the input and output of the tranny. The TCM does a little math for the gear you are in, and if the input and output don't match, it limps. That is the "falling out of gear" you are seeing. What is happening is the clutches are slipping, and you are ripping them apart - a little at a time.
Either modify your tune (engine and tranny) to keep it out of 5th at WOT and full power, or lock out 5th before hammering it. Soon it won't hold 5th at stock power levels if you keep limping it.