Video Description: Josh Rivers is gifted a new remote control car by his loving stepmom, Richelle Ryan. As he plays with it while they chat, Josh accidentally gets an upskirt peek of his stepmom with the car's built-in camera. He is shocked but becomes mischievous and, when Richelle leaves to busy herself in the kitchen, purposely uses the car to follow after Richelle to get even more upskirt shots of her.But he's not as stealthy as he thinks he is. When Richelle finally catches on, she confronts him... but much to Josh's surprise, she's turned on by his cheekiness!

Video Description: Two separate families arrive at a rental home for a two-week vacation together. Tim Axel Haze is there with his stepparents, Jennifer Rachel Cavalli and Phil Daniel Shar, and his stepbrother, Pete Elias Cash, who is Jennifer's other stepson. Meanwhile, Johnny Mighty Dee is there with his two stepmoms, Kelly Sadie Summers and Kathleen Gogo FukMe.Although the joint family vacation is something they've done multiple times in the past, the three boys in the families feel differently now that they're older, so are majorly bored. That's when the boys get mischievous, coming up with various dares to keep each other entertained, which just happens to mostly involve pranking their stepmoms -- and one unsuspecting pizza girl River Lynn!But then the boys decide they need to take things even farther, making the dares even sexier. This results in Pete having sex with his stepmom Jennifer in an indoor tent -- all while workaholic Phil obliviously works on a computer nearby. Then Johnny ends up secretly teasing his lesbian stepmom Kelly with a remote-controlled vibrating butt plug before tempting her to try dick for the first time! And as if THOSE dares aren't wild enough, Tim -- a shy virgin -- has to have sex with all THREE stepmoms! But is the final dare one dare too far??

Video Description: A stepmom, Lauren Phillips, is called to school to pick up her teen stepson, Elias Cash. She is shocked when the teen's very conservative teacher, Annie King, demands that he is taken home after accidentally dozing off in class and getting a boner. Annie is disgusted by his erection while Lauren thinks she's being way too uptight.As things get tense, Lauren becomes overprotective and challenges Annie's prudish ways, which leads to her jerking off and having sex with her stepson right in front of her to make a point! Annie is stunned but inexplicably aroused, which leads to Lauren taking pity on her and inviting her to join them in a steamy threesome.

Video Description: Wendy Raine is flabbergasted that her brilliant stepson, Elias Cash, isn't hearing back from the various colleges he's applied to. In fact, she takes personal offense to it. Not only is he at the top of his class, but he also does tons for the community and is even valedictorian for his year! When she discovers a hidden stack of acceptance letters in Elias' bedroom, however, she confronts him about it and demands an explanation for this senseless subterfuge. In a surprising turn, Elias admits that he doesn't want to leave home just yet... because he's got the hots for his stepmom! Wendy is flattered and, wanting him to get exactly what he needs to move on from the nest, gives him exactly what he's been craving.

Video Description: A lesbian married couple, Christy Love and Syren De Mer, have been trying to get pregnant using sperm banks but to no avail. At their wit's end, they decide that it may be time to consider another option a live donor. But as they wonder WHO the prime candidate could be, their stepson Josh Rivers passes by, and they have their answer!The two stepmoms convince Josh to be their sperm donor, but when it comes time to choose which stepmom will be the one to receive the sperm, Christy and Syren end up fighting over Josh in a tug-of-war. They quickly stop, and realize that the best way to decide is to have a threesome and let the creampie happen naturally!

Video Description: Lauren Phillips tries on a flight attendant uniform for the first time and models it for her stepson, Josh Rivers, who says she looks great. It is revealed that Lauren is about to start a new job as a flight attendant. Lauren admits that she's feeling a bit nervous about starting her new job. Seeing an opportunity, Josh offers to help by roleplaying as a passenger on a plane so she can practice. Lauren agrees to the idea...A short time later, the roleplay is in progress. Lauren serves Josh some snacks as if he's a passenger. Josh convinces Lauren to touch him a little, so she can practice soothing a nervous passenger. Next, Josh convinces Lauren to act like she's helping a passenger to open a window blind. She leans across him to pretend she's opening the blind, causing her boobs to end up in his face.Josh then suggests that Lauren practice putting a blanket on his lap, which she agrees to. But as she slowly and tenderly places the blanket across his lap, she is shocked as she realizes that he has a boner! Josh admits he thinks Lauren looks hot in her uniform, leading to sex where they imagine joining the mile high club!