Chainsaw Repair

Turns out my issues with start and run was a disintigrated fuel line as someone had offered.  I bought one online and literally don't know which end is up. 

My line has the tapers and ridges to lock the line in at the top of the tank (this is slightly off center).  There is a smaller female end with less rubber, and a larger hole with much thicker rubber on the other.  The filter has a larger barb the the carb, so I'm thinking that should dictate how it should be placed. 

I tried pulling up through but am worried about breaking the line (pulls at an angle), and it would make more sense to pull down.  Do you guys lube with anything like WD-40 or even some mix oil?

It is probably a moot point by now as the OP hopefully has the line installed. But for future info, the short end of the line goes in the tank.