i have only been with one virgin so far and she is my current girlfriend and mother of our child. It is quite some time ago we both lost our virginity together, but from what i can remember is hard work to break in. it needed several session and more force from me than i thought. after some of the first unsuccessful tries i already thought i have to settle with just the tip of my penis in and this is never gonna work. but eventually it worked and still works great.