H1: If he does it with AA,QQ,AKs,AKo, you have 33.7% equity against this range Pot odds are 32% so it is a very slim call. If he has any AQ it's a fold because your equity drops to 27.7%. So if you have the slightest doubt that he may have AQ, just fold.
Why are you 3 betting AK pre against a 8/6 UTG raise? He's not folding many better hands and he's folding all his worse hands. I'd flat and wake up if I hit an A or K. Plus the button is there too, so there is a good chance that you will have to play a 3 bet pot OOP without a made hand on the flop. I also think your preflop 3b sizing is too small, would make it like 0.8. As played, I'd bet more on this wet flop, close to pot. Then it would be more of a call when he shoves with AA,QQ,AKs,AKo, because of all the dead money.
H2: I think he has more pocket pairs in his flatting range because it's pretty much correct to set mine in position in this spot. Again,bet more on this wet flop, close to pot. Not sure he folds AK on the flop with two overs and a gutshot. After that his line is a bit bizarre for a 14/11, but maybe he takes chances on the flop and slowplays a set then slowplays his boat on the turn. Difficult to see a 14/11 chasing a straight draw or overs all the way with JJ or AK here but you never know. You can't b/f river, if you bet anything you are committed so you might as well get it in if you're going to bet anything. I don't think it's good to bet here, as he never folds a better hand and he never calls with a worse hand. As played, He should be bluffing >25% of the time for this to be a call.
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