RE:When to use a towel to sit on?

The sooner they get used to using a towel, the less reminding they will need. It will be second nature to them.
You use a towel partly for not getting whatever you are sitting on 'dirty" but you also use it to protect you from others that may not have used a towel.
Also, if you are at an outdoor setting, you have no idea how many birds, squirrels etc have crapped on whatever you plan on sitting on.

Stay Naked!

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