How close are we to being PT and whats the next step?

married06

My DS is almost 26 months. He was pooped trained by 18 months and that was purely by accident, but I went with it. I started pee training him 5 days ago. We went straight to underwear. Here's where we are at now: He is accident free if I take him every so often and tell him to go. If I let him be and wait for him to tell me, he will start to grab himself. I will ask if he needs to go, he will say no. If I let him be again he will tell himself out of nowhere "no no pee pee underwear". I will ask if he needs to go, he will say no. If I let him be after that he will pee a small amount in his underwear and he says, "oh no! wet". We will go to the bathroom and he will finish on the potty. I talk about how he was wet and he needs to tell me before so he doesn't get a wet spot on his underear. He looks at me like he could care less.

So should I continue with taking him every so often or should I keep waiting for him to tell me? I want him to learn to tell me to go, like he does with poop but I am not sure what's the best way to go about it from here.