For some reason every time I enter my sim card into the first gen it says connect to itunes and it wont let me get past that part to actually use the phone.
Sounds like it's not activated? I don't have an iPhone but I recall that most jailbreaking programs ask if you want to activate the phone 'while your at it'. You may have to re-jailbreak with that option enabled, but I'm no expert so I'm not sure.