Your question is in the Audio Systems category - but no matter.
I know nothing much about anything - least of all car engines but I would have thought that if you run a car engine with the dipstick taken out of its hole then the pressure inside the sump will blow oil out of the hole and make a mess.
If oil is coming out with the dipstick in the dipstick hole then the dipstick is defective - or at least the seal around it.
Your question does not make it clear.
Peccavi, July 2011