Cowboy may hold this girl with nothing on? On the contrary (5)
I believe the answer is:
lasso
'cowboy may hold this' is the definition.
(a cowboy might use a lasso)
'girl with nothing on? on the contrary' is the wordplay.
'girl' becomes 'Sal' (feminine given name).
'with' says to put letters next to each other.
'nothing on?' becomes 'os' (I am not sure about this - if you are sure you should believe this answer much more).
'on the contrary' says the letters should be written in reverse (letters in the opposite or contrary direction).
'sal' after 'os' is 'ossal'.
'ossal' backwards is 'LASSO'.
Can you help me to learn more?
(Other definitions for lasso that I've seen before include "Ling-nosed rope" , "use one for catching cattle" , "Rope for catching livestock" , "Cattle-catching rope" , "Rope for throwing" .)