Well, if I masturbate now, I roll it over and pull it back up again - its quite a nice sensation actually - couldn't do that before.
It keeps the foreskin supple and doesn't let it go back to its old shape ( thats the problem with stretching, when you're young, its still quite elastic ).
A condom won't actually help that much, becuase if it rolls back and its too tight, you'll get blood circulation problems - the condom will make that even more pronounced.
If it doesn't roll back, then it will just feel a bit odd/painful because of the way the condom tugs on the penis - in my experience anyway.
I just didn't have sex for the first 4 months of my relationship, kept it to 'other' activities. It soon stretched out.