$3/5NLHE. V is an middle-aged non-sophisticated (my read) opponent who bought in originally short and was on his second or third buy-in. History is that I won one of these buy ins from him. I was pretty card dead with tight image,then raised in middle position with Kh5h, he called on the button. Flop came Kx Xh Xh, I c-bet and he called. Turn came a heart. He only had a pot sized bet left so I checked for deception. He shoved, and I called and was good. He was very bewildered by me and bought in again.
Now this hand comes up. I'm in MP with T9 suited, folds to me and I raise to $20. V calls on the button (stack ~$350, I have him covered), rest of the table folds.
$45ish in the pot. Flop comes A72 rainbow. I c-bet $35. He thinks for a while and calls.
Now $115 in the pot. Turn comes a blank 4 rainbow or such. I double-barrel for $100. He thinks for a long time, looks super-pained and then calls. He looks weak and reluctant.
Now $315 in the pot and he has $200 behind. River comes a J.
Would you bluff the river and if so, how much would you bet? Or would you check?