Geez, I thought since he’s the second born, he’d be easier. Uh…nope.
Boy 2.0 will be 3 in December. His older brother more or less potty trained himself around this age, maybe a few months younger. We’d tried with the Boy 1.0 when he was just 26mos old or so, and it didn’t work, so I decided to ease off the pressure and try again later. Sure enough, when I told him once he was potty trained he could be in Miss Sally’s preschool class, that was IT. He wanted underwear right then, put it on, went pee in the potty, and was DONE. Now, he had accidents and such, but nothing abnormal.
Enter Boy 2.0. In September we decided he was ready to try. He showed all the signs of readiness, so we went to the store and made a big deal of picking out his new underwear (as well as easily removed pants). He put on the underwear and would sit on the potty at regular intervals, but never once actually peed in it. NEV. ER. He went to preschool, and the teachers told us he hadn’t had a single accident (!!!), so we thought…well, there you go. Easy! No. He was holding it all day. He still wouldn’t go on the potty (despite us sitting there with him, despite us running water, despite us making it a game, despite offering stickers and gummies, despite every trick we tried that we read about), and when it became stressful on him I decided let’s scale back, put him back in diapers, and try again in a few months.
Now enter the vexation. He** still won’t pee at preschool**, even in his diaper. He holds it ALL DAY (7:30am-3:30pm). They say as soon as he wakes up from nap, he’s moaning for me and holding himself, and they try to bribe him to pee anywhere–on the potty, in his diaper, just anything to let go. No go. I pick him up, and usually within 20min the flood gates have opened. On Friday, I tried sitting next to him while he was on one of their little kid potties and waiting, trying to encourage him it was okay to let the pee out his penis (I don’t know that he understands the feeling of pressure on his belly is pee, so I went for the literal). He sat dutifully for 5-10min, but no go. He managed to hold it until we got his brother from school, and somewhere on the drive he completely soaked (and soaked through) his diaper. :sigh:
(Incidentally, he doesn’t hold it at home. He had plenty of accidents during the 5-6 days we tried, but we just had him sit on the potty afterwards, cleaned him, and changed him. Now that he’s back in diapers, we change them at regular intervals as he seems to be peeing in them on a normal basis. So, awesome.)
He wants underwear, he likes his new potty (but won’t sit on it!! I can only get him to sit on his brother’s old potty), he’s"taught" his bear to pee on it, and he obviously has control, but has NEVER peed in the potty. With his brother, from about age 24mos, he would sit on the potty–and often pee in it–before bath as part of a nightly ritual, so he had an understanding of letting it go. His brother…NOPE.
He will transition to the 3yros class in January, and they don’t do diapering in there, so uh…yeah. There is that. But it’s 4mos from now, so hopefully whatever this is will be past by then.
Something seems to be stressing him psychologically, or maybe it’s just the stubborn streak genetically programmed into him, but I don’t want the poor little guy holding it for 8 hours at a time. 
Any ideas and tips on how we can help him let go?