We're trying something different this season on Dating my Stepson. The males need to date the prospective girlfriend's mother before they may pursue their love interests. He'll immediately start dating the daughter if things work out. On this occasion, Juan Loco is attempting to win over Tiffany's mother, Cassie Del Isla. Juan will go on a date with Cassie where she will teach him how to treat a lady. She demonstrates for him how to compose a haiku, prepare chocolate-dipped strawberries, and arrange roses. Cassie notices that Juan is observing her, and she discovers that she enjoys it. They are unable to stop talking to each other by the time they reach the haiku. After a quick kiss, Juan enters for a pussy feast as Cassie takes off her dress to reveal a gorgeous figure in sultry underwear. He gets his balls and dick sucked in exchange. Cassie gets up and bends over the kitchen island, allowing Juan to tackle her from behind. Juan waits his turn behind the bar so Cassie may get on top of him like a cowgirl and ride him till her back arches with pleasure. She climbs off and lays down on her back, allowing Juan to continue their celebration. After giving Cassie a final huge o, he cums on her abdomen. Even when Cassie offers Juan her blessing, Juan believes he will continue to search for another milf.