How bad was this play?

Daniel JDaniel J Red Chipper Posts: 11 ✭✭
It's 2/5 live and the table just opened up. The first orbit just finished and there is a straddle and the UTG+1 called and I raised from UTG+2 with JcJs. It folds around to UTG+1 and he reraises to 110. I am the effective stack size with $500 and I call. There is 232 in the pot taking into the account the rake. Villain is a good player who occasionally plays 5/10, plays tight but definitely can be aggressive and can make the occasional play.

The board is Ad9c6h and he checks.

Although the A is great for his range I figure I could get the last combo of JJ, QQ, and KK to fold to a flop and turn bet.
Since this was a three bet pot I bet smaller. I bet 75 into the 232 pot expecting a call. I figure I can fire again on most turns. He calls.

The turn is the 9d.

Sticking with my plan, I bet 100 leaving almost 200 behind in an attempt to look like I'm going all in on the river. He thinks for a little and then puts me all in. I pretend to think about it for a bit, I'm definitely done with this hand since there is absolutely nothing that I am beating at this point and fold.

My questions:
Should I have just checked back the flop?
If I am going to bet the flop, how much?
Should I fire again on the turn?
If so, how much?


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