Villain has around 208$ and I cover him.
Ok I'm on CO with [9h], a very LAG (58/38/1.43 after 30 hands) player raises to 5$ on UTG so I reraise him back to 20$ and he just calls the bet.

FLOP: (pot 41$): [4h][9d]

He checks and I check behind him, because he was very aggressive in earlier hands.

TURN: (pot 41$)

Now he bets 22$ and of course I'm planning to raise, but how much? I still don't know how much should I bet/raise when it comes to this kind of situations so I've raised to 55$, what do you think of that, and what should I then make on the river? Should I bet the flop? I usually would bet the flop, but not against this player because he was new to the table and was playing some strange game.