Transitioning to Underwear.......

I know exactly what you are talking about. My oldest (son) was the same why... he had to be naked waist down for along time. He knew he couldn't potty on floor or furniture or he would be in trouble but going in his clothes was ok he thought. It was a very long process. But it was over the summer and we lived in Georgia at the time so the weather was not an issue.
I used regular underwear with him with those plastic covers that went over them. That way he could feel wet but not make a mess. They do not absorb like a pull up but keep wetness inside so less mess for you.
It was along time ago (He will be 11 end of month) so details are fuzzy but eventually he got it. We started potty trainind right after his birthday in Feb (the naked thing didn't start until warm weather) and was completely done before we moved back to Ohio in September.
With the girls I put them in the undies with those covers just in case and set a time to take them potty very often throughout the day. With all kinds of fun and different rewards when they were sucessful. I didn't wait until they told me they had to go until they started just going on their own before the timer went off. Once I got a good idea about how often they really needed to go the timer got longer and longer apart to see what they would do.
Hope this helps :)

We had the same problem with our son as well. We found that putting his shorts on without underwear (!) or boxers really helped until he was able to know with real underwear on.
Good Luck!

How does he react after he has an accident in his pants (not a diaper)? If he doesn't like the way it feels, then just keep him in underwear (and pants if needed) all the time. Eventually he will get tired of feeling wet & dirty & having to change his pants!

You could also have him help rinse the underwear. Again, depends on how he reacts to this. My daughter didn't mind cleaning hers! LOL So it wasn't a good incentive for her haha

You could try taking him shopping for his underwear, letting him pick some out. When you put them on make a big deal of saying, "Keep your undies dry. Don't get Mickey Mouse wet." Or whatever character is on them. This worked for my daughter 2 1/2. This was part of a 3 day potty training program we did. She went through it almost 2 months ago and she will still say things like, "Mommy, Dora doesn't like to get wet" or "No potty on Dora!" It helps for you to remind him also to keep his undies dry.
Hope that helps!

I think the age is importatnt, I tried with my son around 2 and again around 2.5 but he showed no interest so I just left it. Around 3 we tried again and I found what you did the best, just left him nakes around the house and stayed home for the weekend. But he was in daycare Mon-Fri, I told them there what we were doing and they said put him in underwear for school and send lots of clean clothes, he may have accidents but we don't mind if you don't and sometimes it helps them learn. Within a few weeks he had it mastered. For a long time after he still had accidents (pee only) at nap time and night time and he turns 5 next week and I still put him in the sleep pants but the accidents are rare. From what I have read it does take boys longer than girls. Be patient and good luck, he'll get there:-)

My son was about 3 1/2 when he potty trained himself. I waited until he showed signs that he knew when he had to go. If your son is still having accidents maybe he's not ready yet. The first time my son went to the bathroom by himself I put him into underwear that day. I got into the habit of bringing a change of clothes wherever we went and I had a portable potty that I took with us when we were out and about.

By waiting for him to know his signals we didn't do the reward thing. He only had 2 accidents and that was when he was VERY preoccupied and didn't want to stop what he was doing.

I think it's more about them knowing their own body signals. I felt like that wasn't something I could teach my son. Only he would know and be able to figure it out! For some kids that might be at 2 for others at 4. If you can let him lead on this, when he's ready, he will let you know! :)

Good luck!

My boy just turned 2 and is doing great (wearing no underwear) (no reminders) but forgets to pull down his underwear. I don't know what to do either but work with him about pulling them down.