Why would his first thought when being robbed at gunpoint to say please r*pe my sister instead? This is messed up. I'd seriously never want to see his face again if it were me. If people robbing at gunpoint thought he was being scummy af then seriously come on... If you decide to remain in contact with him please for the love of all that is good in the world never. Ever. Go anywhere with him again especially alone. People at stores (certainly here in the UK at least) are told if someone comes in to rob a store regardless of whether they have a weapon or not, remain calm hand over everything they ask for and press the panic button at first opportunity where you won't get hurt. You don't beg, you don't plead, you don't refuse. You hand money over and let them take it. I'm mind blown by your situation. Also I'm so sorry this happened to you and I'm glad you're safe. Lost items is better than being physically harmed.