Hanging yourself heads up

AT heads up. Blinds 500-1000 (not real money!). I'm on the button and I raise it to 3000. He calls. Flop was K93 rainbow. I bet it decently until it got scary and then bet it some more to try to blow the other guy off the river. I think I did the right thing (he was 3/8 to have paired his hand and had some odds to have a better hand preflop but the betting told me he didn't have a better hand, so I was right to bet the flop) and lost, so I'm cool with that. He did the wrong thing and won. He hit the K and coldcalled my bet. Look, what does he think I have? I've bet a decent amount so I'm representing a hand. What am I telling him I have? I raised preflop from the button, which I can check if I'm hoping just to hit the flop. So I probably have something. I didn't go massive either, which he could read as a bluff-raise to blow him off the pot. (Because if you're on 500-1000 blinds, you call it from the small blind and the button raises you 5000 or 6000, he probably has bobbins! If he has a good hand, he won't want to scare you away from the pot.) He has to put me on a pair or high cards. KK is unlikely, of course, but AK is definitely in my range; AA, KQ, KJ, KT, K9 all have him beat. He beats Qx, Jx, which I might have raised preflop with, and lower pairs. But any of these latter hands I'm likely just to check the flop. I'm an aggressive player but if I'm sitting on Qx or Jx on this flop, I'm not going to bet against the overcard! (The gutshot is a bit more than five to one against, not good odds when the pot is paying a bit less, but close to it.) If I had a small pair, I'd be likely to check it if I missed the flop. I think he needs to raise me. If I have a small pair or a draw and call the bet, I'm taking my cards too far. If I have a big hand and reraise, he has an easy fold. If I have nothing much and I'm trying to steal it or I bet the gutshot, raising makes the bluff more expensive and ruins my odds for the gutshot. If I fold, he wins without further risk. KK is not a great hand. Okay, he's hit the flop, but he has a poor kicker (an 8). A backdoor flush is a possible out and so are backdoor straights for Qx and Jx. My hand, AQ and AJ are all in my range and each have three outs. (If he knew I had Ax, he would right simply to call. He should lay me the odds to hit my outs because the pot is nowhere near big enough for me to call a raise and it would be a mistake to do so.) A raise would give him information. Say I bet 2000 on the flop (which I think was what I did). He raises another 2000 and what happens? If I fold, he wins my preflop raise and my bet painlessly. If I call him, he knows he is beat and he can save himself the more than 2000 he would be betting on the turn and the river. I could have checked into him at the flop. But I think AT is a good hand, probably winning. Either outcome after a check isn't good: if he checks behind, I have no information about his hand; if he bets a decent amount, I have to decide whether he has hit the K or is trying to scare me off the pot. I can in the latter case bluff-reraise but it's an expensive way to find out he has the K! The turn is not scary. A 5. I bet out again, another 2000. There's no flush possible because we have all four suits on the board. And if I was betting a gutshot on the flop, I now don't have the odds. Why am I betting? Simply, I do not put him on a K. I have him on Ax, Qx, Jx hoping to get lucky or the bluff. I think he should have raised a K and I think he will call bets with Broadway cards with his big stack. But I'm not happy that he has called. It tells me he has the K (or a slowplayed AA). Why? With the blank turn, the bet is representing a hand. He called the flop and didn't raise, so unless he has a 5, I could check into him and expect a check behind. With no hand, he has to think I'd take the free card. I am representing having Kx and putting in a value bet. I figure, I can and will fold to a raise, but he should be folding most hands. What would he call the flop bet and the turn bet with? If he had been hanging in with a Q or a J, he is now drawing close to dead (Q5, Q9, Q3, J5, J9, J3 all have three outs each against the K, but my PF raise would suggest to you that KQ and KJ are possible for me, which slightly devalues the outs). So they're gone. He could have 95, 93 or 53. They all beat me, of course. 93 would probably have merited a raise at the flop though and 53 would probably merit one here. It's only getting beat by KK of my possible range of hands. If he has Ax, he'll again be drawing to three outs on the river and must fold here. Look, he's not a thinking player. He won't have worked all that out, but he knows he's fucked if he has been hanging in with a Q or a J, that's all, and he should be able to see that he's probably fucked with Ax. He doesn't have any draws and I'm sure to call a bluff. (I have quite a bit of my stack in now so I'm hardly going to throw away a pair of Ks to a bluff.) I am semibluffing, of course, because I do not have a hand. I know I am behind any king at this point but his range of hands after the flop was in my view about 50/50. Half the time he'd have a K, the other half he'd have Ax, Qx, Jx or fuck all. Bets are worth making from the small stack if you have an edge, and I considered I had it. But when he called it, my heart sank. The river was another blank. I actually forget what it was, maybe a 2 or a 4, so any draw was a complete suckout. Something like that. What do you do in this spot? It's tough. What I wanted to do was fold. I was sure I was beaten. If I check, he should not bet because he will be opening himself up to the check-raise, which will show him he is beaten, and I will fold to a bet if I don't have it. So he would just check behind and shows down for the money. If I bet the same decent amount, I am throwing money away. If he called it on the turn, he'll almost certainly call it again on the river. The river wasn't scary; no reason to feel I had hit anything. Checking or betting a small amount makes me a sure loser. I've bet enough into this pot to leave me on a respirator if I lose it. He'll have eight times my money and I'll be facing the music if I check, a bigger lead if I bet. I could go all-in. But in his shoes, I'd consider an all-in bet a bluff. I think that's an easy read of the action. So I bet 5000. It says unambiguously, I have it and you're going to pay me if you have Kx. It's saying, I want you to be fool enough to call with your dominated K and pay me off. It's a bluff. I don't want him to call. I want him to think that giving me another 5000 will make me not far short of even but keeping it will leave him healthily the big stack. I want him to fold it away and think that he made a great laydown. He has no read that I will bluff. I haven't been caught in one all night. I played tight early on and raised good hands (in one case I reraised fairly large from late position with KQs and then called the all-in bet from another guy who had 66 -- a bad bet from him, I'd say, because I'm always going to call you if I've put money in, and he paid me when I hit the flop; so he'd seen that I would play big hands aggressively). I stole some blinds with nothing at all but he doesn't know that. My preflop raise was healthy, reflecting the edge I had (AT wins about 60-40 head's up) and maybe a bit more (enough that I could definitely have had a hand like AK or KQ). I had bet decent amounts, given my short stack. I wonder, did he even think about what I had? I don't think so. I think he called it because he was big stack and thought he could afford it. I think laying it down would be a good play with no read that I might bluff. In his seat, I'd be putting me on a better hand. Still, I learn more lessons. I went a lot better with more aggressive play heads up. And thinking back over it, I'm sure that he should have put in a raise on the flop. I am finding it harder to learn from my mistake. I'm sure I made one at the turn but I haven't worked out whether I should have checked or bet more. I'm thinking I should have gone more but I'm not sure why. Ah well. Three live games, three times in the money. You don't have to get them all right if you're at least getting paid a little.