I put him on 1010 or JJ when he checked flop, should I have fired on flop ?
After him raising and then rereraising you, you think he has JJ/TT? No way. His flop check screams AA/KK. I could see calling the turn, maybe. On the turn it's likely he doesn't have AA. But the river is a muck, even getting sweet odds. I think normal people check behind JJ/TT here because you've made your hand fairly transparant.

2nd hand: raise pf, wtf? After not raising pf I might just limp/reraise though doubtful against a raise this big. I probably just muck it because I don't like playing fit or fold poker for such a huge bet.