Does it hurt when the hymen breaks? what's the most painful way to lose your virginity?

A little bit, maybe: The hymen isn't like the paper seal on a jar of instant coffee; it's an elastic membrane that has some capacity to bend. Different women report different experiences with first intercourse. But your first time should be wonderful, something you've waited for and planned for. The right man will put you at ease even if it is also his first time. When (if) it happens, may you remember the joy always.