He chose to transgress societal norms and expectations by openly challenging authority.

I'll not transgress this way again.

A synonym of transgress is violate.

Transgress means to disregard the laws or rules and is more often used in a religious sense. 'Transgress him' is not grammatically correct so we would really need to know how you want to use these words in a sentence. Your may mean he does/does not transgress, or he transgresses/has transgressed or will transgress.