Dear qtoo1, what you are telling is most males have the problem , is the foreskin's opening is very narrow of some people and in non erect state is goes back with little effort but after erection as penile girth increases hence from the narrow opening of prepuce it is very difficult and painful for glans
to come out . and the ring again squeezes the glans or shaft--- gives pain ----- the best solution to this is circumcission or / or a dorsal cut to foreskin. consult a general surgeon
he will decide the best for you.