Cassandra Cain heads over to her date's house with the intention to fuck, but as she goes to make her move and starts pulling Toby Springs's pants down as he pleads her not to she ends up seeing that he is locked in a chastity device. Humiliated and embarrassed Toby starts to explain that he just wanted to try it out and didn't realize she was going to want to fuck on the first date. Out of nowhere Cassandra demands for the keys and lets this loser know that she actually has made guys where chastity devices before and now she will do the same to him. She begins making fun of him and taunting him about his position. Toby keeps trying to beg for the keys back and apologizing for not knowing that she wanted to fuck, but Cassandra just keeps making fun of him. She starts flicking the cage that his pathetic dick is locked in and soon begins to have even more fun. Cassandra begins to play with her ginormous tits and starts caressing his inner thigh making him get hard and cry in agony. Just when Toby Springs is completely humiliated and his ego destroyed, she goes to explain that because he pretty much lied and didn't tell her about his pathetic dick being locked up she now is going to punish and humiliate him even more.