IDK
the stick enters the 727 pan at a pretty shallow angle, so I kindof agree with what TB is saying, especially with regard to the fluid having traveled up the pipe, and when you insert the stick, you are simply sliding it through the fluid that is stuck there. That's been happening to me for years too.
What I have done in the past is to bend the tip of the stick down, at something like 15 to 20 degrees,about 3 inches from the end. Then the bend slides down the tube,and the graduated portion enters the oil near vertical, and not touching the sides nor sliding through the oil. That has worked for me.It might take a couple of tries to get the bend just right.
I also agree with the other part of TBs post