Going on vacation with a girlfriend is always exciting, especially when it is a cruise. Unless your wicked step-mother slips a chastity device over your dick the night before! Sam wakes up in total shock when he sees the little piece of pink plastic on his cock. Penny laughs in his face when Sam confronts her and asks for the key. She just starts to torment his caged junk and vulnerable butt crack with wedgies to show how little she cares about his demands or his potential humiliation. While Penny dangles Sam by his undies, she teases him about his girlfriend not even missing his little coc...

Going on vacation with a girlfriend is always exciting, especially when it is a cruise. Unless your wicked step-mother slips a chastity device over your dick the night before! Sam wakes up in total shock when he sees the little piece of pink plastic on his cock. Penny laughs in his face when Sam confronts her and asks for the key. She just starts to torment his caged junk and vulnerable butt crack with wedgies to show how little she cares about his demands or his potential humiliation. While Penny dangles Sam by his undies, she teases him about his girlfriend not even missing his little cock and about finally learning to eat pussy correctly.

Penny decides to give him a little lesson on that subject before his chastity cruise. Luckily, Sam's wedgie makes a great leash for Penny to hold while she sits back and enjoys a little step-mom worship.