To the best of your knowledge, the guy's actions are waaay more guilty/wrongful than whatever little crap you're female friend might have done, especially b/c of her age. If he has photos, that's a felon like Lehsyrus said. Take it to police and you will win, these kinds of cases where it's a man perpetrator harassing/abusing/blackmailing a chick always works in the favor of the one who has a vagina, it's a stigma of society. One of the leading types of convictions that put male criminals away are sexual.