Villain here has been playing sort of LAGfishy, something like 40/20/2. I've seen him showdown one hand: He b/c with an OESD in a HU limped pot, then x/c the turn when he missed. The river went x-x and he lost.

I have no problem cbetting this flop into two opponents because I think I'm still ahead most of the time, and I'd like to set up for a second barrel when a J+ turns so I can fold out some pocket pairs.

When he raises in position, the flop is just so dry that I suspect he has air almost always, and when he doesn't he has something like 44-88 and will have a lot of trouble calling a raise. I've been experimenting with making bluffs on super dry flops like this against aggressive players, and I think this is a pretty typical example. Thoughts?

Poker Stars $0.25/$0.50 No Limit Hold'em - 6 players

BB: $38.65
Hero (UTG): $59.25
MP: $38.90
CO: $87.75
BTN: $39.45
SB: $65.70

Pre Flop: ($0.75) Hero is UTG with A K
Hero raises to $1.50, MP calls $1.50, 3 folds, BB calls $1

Flop: ($4.75) 3 9 3 (3 players)
BB checks, Hero bets $3, MP raises to $8.50, BB folds, Hero raises to $22

if he's bluffing then you have him beat. you are not going to get him off of hands that has you beat often enough to make this play.

if you think he's bluffing then you can just call but he has position on you and can continue to barrel you with draws or air which he seems to be capable of so I wouldn't recommend calling. as played fold is the best option by elimination of other lines.

on a different note, I often go for a c/r with AK on dry flops instead of standard CB because by cbetting you are folding most hands you beat and getting called by hands that has you beat. Add to that the hands you beat which will float you or bluff raise you. If called, you can just c/f the turn and you still have 6 outs to improve.

I think it's best to go for a c/r on that flop. I also do it with overpairs sometimes to balance especially that you won't often get value from most hadns you beat and most hands that you have beat and will call will also often bet when you check to.

If you're going to 3-bet, just shove

I agree that c/r would be a much better play in the long run. Simply because a hyper aggro fish will be betting more air against you after you don't c bet the flop. when your check raise works, you are gaining so much more when your check raise works with air. Also, if you start doing this with overpairs on dry boards, he might spazz out and 4 bet you which is a great pay off with your good hands.

Also, I would raise a little more pre UTG because you will be out of position on all rounds and with a fishy player like this I would try to extract as much as possible out of him.

Overall, as the hand was played I feel you will be ahead of his range if he does this play often, worst case scenario he might have a flush draw or maybe some overs himself, you can also shove re raise because if he does call its going to be hard playing out of position if the turn bricks.