For this trophy you need to perform a
Testicle Assault and a
Nutshot on an
enemy Gang member.
Search around the city for a Gang member (of any of the gangs) (
Must be male) walk up to the enemy and click the

(your character will punch the man in the nuts) do this until they die (Can take 2 hits)
If you do so correctly you should see 'Testicular Manslaughter' appear top right of your screen.
Now search again for another enemy (You've probably gained some notoriety anyway and have some people chasing you) now select your gun (I chose a shotgun) and aim at the man nuts, shoot till he's dead (Usually one shot)
If you do so correctly you should see 'Nut Shot' appear top right of your screen and the trophy will be yours.
Can do the nutshot first if you wishHere's a video to demonstrate.