No. You should never do that. Condoms are designed in such a way that you should roll them onto your penis. It should not be fully unrolled as it might affect the condom's efficacy. If may also be frustrating to put the entire condom over your organ and then shortening it to fit the size of the organ. Remember, condoms are made in sizes longer than usual male size.
So, when you have unrolled it completely, it may become too clumsy to handle. It is not made to fit exactly to your organ size. So, unrolling the condom over your stiff organ and pushing it down to the maximum is what is recommended and that is the practical way to enjoy sex with a condom on.