Sounds just like my Allen. He insists on being outside (he;s 4 now) and I let him when I'm out with Nicki. He never wanders far (if he wanders 5 feet from the door I'm shocked). I am actually GLAD I let him out because a few times, the others have gotten out and he's kept them herded together til I came to save them. But, Allen gets out daily for rubs on the concrete steps and patio He grazes on grass and comes back in all happy and content. He KNOWS the word "In" and if he ignores me (which is often the case) I lightly nudge his tail - they hate that - and he goes running to the door.

NONE of my other cats get to have this luxury. Then again, none of them are door dashers either.