Oh, NoahsMommy. I know what you are going through. My (now) 8 year old is an indoor only cat, but would absolutely love to go outdoors. He was at one time a outdoor kitty, but it has been a long time. The problem is we live quite close to a busy street.
He is constantly trying to dash out the door whenever he gets a chance- BAD KITTY! We go to great lengths to keep him in for his own saftey.
The good thing is that after about a month or so, he quit crying to go out. He has not ever stopped trying to however. He still manages to give me 'that look' , which still makes me feel guilty sometimes.

In all honesty, I would probably let both my cats go outside if we lived somewhere away from traffic. But we don't, so inside he stays!

Good luck with whatever you decide.