Dude, you're killing me... You have the 351 in that right? My dipstick does not twist or spin at all so there might be something going on. Truly when it comes to engines losing oil, there are one of two things, either a leak or you're burning it. If it is a leak, the best way to really find it is to pull the engine as it could be a host of many things, some that are not visible with the engine in the boat. Sounds like you are dealing with a leak though if it is in the bottom of the bilge. Other possible sources could include but are not limited to, where the oil dipstick tube enters the engine, the oild pressure sending unit (mine had a small leak), the drain plug or anything else somebody mentioned.
'86 Comp TS6M
Monster Tower
1,500 lbs Ballast
Riding Hyperlite Boards