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Well he naturally goes outside when I take him out. But for the rest of the evening, I'm in my room and he's in his area... he begs to get out of it, I let him out a play a little, I get back to my work and turn around to see him peeing on something
Him wanting out might be an indicator that he has to go pee and wants to go out. When he begs to come out, take him directly outside. If he pees outside, treat/praise him like crazy then take him back inside for some play time. Immediately after play time, take him outside again.

Sometimes dogs get confused by pee pads and they can't differentiate between "it's okay to go on this place, but not that place". And when they're young, even if they've learned not to pee in your house, they might still pee if you take them to someone else's house - they only know not to pee where you've taught him not to. It can take time for them to figure it out.

How often does he go? Take note of this and make sure you're taking him out well before that time period is up.
 
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