I'm not of much help here BUT wanted add a little story ... When my nephew was about the same age i didn't know how to towel dry him down there after his bath ... interesting enough he told me i wasn't doing it like his Mum and dried himself ... i was amazed at how open he was about it ... and if anything i felt embarrassed that i didn't know how to go about it properly when i am the adult ... but he clearly knew how to look after himself there (obviously with the previous guidelines of his parents help) ...
I think Alan is so right in that your DS needs to explore and in hindsight then learn from you and/or DH at some point in how to clean, etc ...
we havent focused on penile cleaning because its only the skin that was moving previously so he can clean that easily by him self but once he can fully retract the skin then i guess that is when we will tell him he has to make sure its done.
also with the head will it be tender for a while while he is slowly retracting the foreskin back?
(we dont use soaps so not concerned about chemical harshness on the new skin)
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