Trans dip stick

Have a 2000 V6 tundra.

Anybody else have trouble checking trans fuild.
The dip stick is hard to insert back in. Have to use two hands and sometimes get stuck about 1/2 way in and wont go in or out. Have to put a lot of force on it to get it back out sometimes.

The dip stick looks like it has two twist in the stick. Is this normal.

Never had a vehicle that even was half this hard to get the dipstick back in.

Any suggestions
thanks