Former bailiff concerned about first female (5)
I believe the answer is:
reeve
'former bailiff' is the definition.
'concerned about first female' is the wordplay.
'concerned about' becomes 're' (regarding).
'first' says to put letters next to each other.
'female' becomes 'eve' (Eve is an example**).
're'+'eve'='REEVE'
(Other definitions for reeve that I've seen before include "Old judge" , "Saxon magistrate" , "Pass the end of a rope through the bailiff" , "Old English magistrate or bailiff" , "Anglo-Saxon magistrate - female bird - pass (a rope) through a hole" .)