If there's a lot of luck involved, which it sounds like there is, maybe he's just not ready. Lots of kids don't get "that feeling" for a long time - the bladder-brain connection just isn't developed. If he pees 5 minutes after going to the potty, then he's not emptying his bladder enough - just enough is coming out to relieve the pressure but he's not forcing the rest out. Maybe he doesn't know how! It's not his fault. Boys often take longer than girls so be sure you are training him on his schedule, not yours. I was so anxious to be done with diapers, but my son just wasn't ready. You can try pull ups during the day - they're easy to pull down if he has to go or wants to try, but he won't be wearing pee-filled underwear. You can try the other posted suggestions of boxers and bare bottoms, but make sure he isn't pressuring himself for something he is developmentally unable to do. I promise you, he will not go to kindergarten in a diaper! Hang in there!