Well, if worst comes to worst, I suggest just getting rid of the old underwear so he has no choice but to go without underwear entirely or to wear the new things until he gets used to them.
To get the elastic less rough and constricting, I'd stretch it with a few hard tugs, and then wash the underwear a couple of times without putting them in the dryer. Basically loosening up the cotton/spandex/polyester(whatever) and the elastic. If he wants support, but the regular underwear ride up, then try boxer briefs, they're longer, so less likely to bunch together when he sits down, but still tight enough for support, and if stretched enough, the spandex feels great. Hope I could help!
Why is my son strange with his underwear?
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Well, if worst comes to worst, I suggest just getting rid of the old underwear so he has no choice but to go without underwear entirely or to wear the new things until he gets used to them.
To get the elastic less rough and constricting, I'd stretch it with a few hard tugs, and then wash the underwear a couple of times without putting them in the dryer. Basically loosening up the cotton/spandex/polyester(whatever) and the elastic. If he wants support, but the regular underwear ride up, then try boxer briefs, they're longer, so less likely to bunch together when he sits down, but still tight enough for support, and if stretched enough, the spandex feels great. Hope I could help!