Ashley is starting a new job as the assistant to a very particular man. He likes everything a very specific way, and if he doesn't get what he wants, there will be hell to pay. When Ashley takes one misstep, she's taken on a ride she'll never forget. Sophia wants to have her first anal experience with someone who knows what they are doing. She found the perfect candidate in her best friend's dad. She knows that he'll be into it if she really pushes him, but she wants to have some fun convincing him. She shoots a video of herself in his room playing with her asshole and sends it to him. After watching, he texts her back and tells her to come over. Kenna is dating an older man who likes anal sex. She is nervous about it and backs out every time they try. He has one of his other girls train her before fucking him. Alice is a troublemaker and addicted to anal sex. Her parents send her to a therapist to deal with the former, but she somehow uses it to quench the latter.