And as soon as the thing is done, another one comes up and it never ends...

Windows is known for it's bloat

It is pretty much just crossdressing. He could be an Egg, since he seems a lot happier when dressed up, but nothing is explicitly stated. The story also only goes for a few months, so maybe he just hasn't realised it yet.

Source: A Boy That Can't Stop Crossdressing

Glad to see you enjoy drawing your series again :)

I remember a time where the checkmark was to prevent impersonation and not a buyable cosmetic.