The title says it all. This weekend I'll get to pop my friends butt cherry. He's 29 and has never had a dick in his ass, although its been attempted once before(not by me.) He told me it hurt and has not tried it since. I'd love nothing more than for him to love getting fucked and want more. I'm an experienced top but taking a "rear end virginity" is special and I'd be lying if I said I wasn't nervous. Anyway, I'm looking for your magical tricks and tips or any other advice you feel like giving!