[Masquerade]

I like a small raise with a medium pair, particularly with a deep stack. It inhibits someone else with a medium pair making a raise if you just limp.

After raising pre-flop I'd always make a continuation bet unless I flopped a monster or so badly that I'm not putting any more chips in so I don't like the check-call so much.

Let's take his bet at face value: He's announcing he thinks he has the best hand. No real draw he could be betting so he's got a Jack or a pair. As he called a raise an overpair is unlikely so maybe 77-TT range.

I don't like checking the turn as this is your chance to get him off a better hand if he has 99 or TT. Alternatively you could check-raise the Jack. The turn bet from him doesn't seem too confident. Maybe he's got a Jack and is worried about the kicker or still feels like his pair is good.

River push indicates he thinks he has the best hand or nothing. A jack just takes a showdown here as does a pair. As there's no draw he could've been betting I put him on JT or TT now and fold. I certainly wouldn't be in this spot, or anything near it, with 88.