C.O.
ETA: When you go to your pediatrician for your next well -child check up - ask about his loose stools. My youngest can take about 10 to 20 minutes to empty his bowels as well - he reads while he goes. And I'm sorry, I missed the "he can't get them back on" - have him pull them down to his ankles. My boys do NOT have bowel movements at school anymore. So sorry!!!
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They were learning as soon as they started potty training. When did they master it? Maybe in the 1st or 2nd grade.
We use the Huggies "One And Done" diaper wipes STILL - they are much better than the Lil Frog or Cottonelle wipes. And since yours has loose stools? Diaper wipes are the way to go!
Now, granted mine are now 26, 12 and 10 - but ALL of us (well the 26 year old lives near her dad) use the Huggies One And Done Diaper wipes. I keep the travel package in my purse (and just used them this evening at the Cub Scouts Blue & Gold banquet)....
My 10 year old LOVES to totally undress EVEN NOW when he does his business. We have told him he can't do that anywhere but home.
Try the diaper wipes. I think you will find it easier for him - they are moist - they are bigger and that MIGHT help him.
GOOD LUCK!!