Pulling the foreskin back for the first time?

I have never pulled my foreskin I have always been to scared of it getting stuck behind the head. I am able to pull it all the way back with not pain one side slips under the head first and if I pull a lil more the whole foreskin tucks unders the head. But when I do one side first and just let go and leave it there and I try to pull it back over, the foreskin rolls up and it doesnt cover my head again I have to do a jerking motion to unroll to cover it back up. Im not too worry about pulling it back just worried of it being stuck because of how one side of foreskin roll up like that and wasn't able to cover the head completely

When I pull it over the head, how does the foreskin cover the head again does it do it naturally? Do i have to do it myself, if so how?