A man may be out of line to sleep with his stepsister, but sometimes a man has to step out of line.

Checking in With His Stepsister- Ed volunteers to help his stepsister Jessica move into her first apartment, even though it involves a twelve hour drive. In a hurry the morning of the move, Jessica accidentally walks in on her stepbrother in the shower. Aroused by what she sees, she nearly gives into temptation but barely manages to resist. But when they get a late start and end up having to stay together in a motel, the two stepsiblings can no longer deny their love for each other.

Filling in His Stepsister- When Craig's parents receive news that his grandfather may be dying, they ask Craig if he'll stay at the house to avoid leaving his nineteen year old stepsister alone. Each night, Craig takes the call from their mother, then relays the information to his stepsibling. One night, when the news is particularly good, Craig forgets that his sister showers at the same time every night, and he walks in on her naked. That moment is the catalyst for them finally to confess their attraction to each other, and take their relationship to the next level.

His Stepsister's Sext- Ben thought living with his stepsister during college would be a great idea, until he was overcome with jealousy every time she went on a date. Unable to deal with it any longer, he has a talk with Natalie about one of them moving out. As Natalie listens to her stepbrother, she's surprised to find just how much she hates the idea of one of them leaving. The more she thinks about it, the more she realizes she's in love with him. Wanting to profess her feelings but not sure how, she decides to "accidentally" send him a sext and see how he responds.

His Stepsister's Valentine- Craig is excited when his stepsister, who he has a crush on, tells him to set Valentine's Day aside for her. But when the day arrives he is sad to discover she wants him to double date with her boyfriend and her friend Angela. When Sarah realizes what Craig really wanted, she is surprised to discover that she wants it too.

The Stepsister's Secret Stash- Gary could really use a drink after a long week, but he spent all his money. He knows his sister keeps a secret stash in her bedroom, but he can't find it. Bored, he decides to play around on her tablet, only to discover pictures of her in compromising positions. When Michelle walks in and catches him looking, Gary accidentally confesses to finding the photos hot. Turned on, Michelle offers him the opportunity to see the real thing.

His Seductive Stepsister- The prestigious art academy Ben applied to needs additional samples of his work before deciding whether to admit him, and his beautiful stepsister Isabella insists he has no chance if he doesn't submit at least a few nudes. Luckily she's willing to be his model. But when Ben meets her in her bedroom ten minutes later, it is clear she has something on her mind other than being sketched.

Banging His Stepsister- Kyle mocked his friends for their interest in a new app that lets them know which of their online friends want to have sex with them. But back in his room all alone, he decides to give it a try. Not yet ready to actually know which of his friends are interested in him, he selects his stepsister, assuming there is no way she would have selected him. But when an alert pops up on his screen a moment later, he discovers just how wonderfully wrong his assumption was.

His Virginal Stepsister- When his mother finds a condom wrapper in the living room, she's convinced it belongs to Brent's innocent-seeming stepsister Emily. Brent agrees to confront Emily, but he quickly learns the condom actually belongs to Emily's best friend. Emily is saving herself for marriage, but she confesses to her stepbrother she wants to give him something special. With the front door closed, the backdoor is the remaining option.