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Eh, I just like teens as thats the most out of family social phase in their life. If even one of their friends saw him/her diapered, it would be complete humiliation
I'd imagine pretty well, though Toshiro might be nervous about it all with Rangiku probably trying to enve courage him. Although I do have to wonder how long Toshiro was under the elderly woman's care, I don't imagine she's blood related, but it may be likely he could've died as an infant or toddler at the youngest.