Putting In The Effort - S4:E2
Boy / Girl
This season of Dating my Stepson involves men dating the mother of a potential girlfriend before pursuing their love interests. Juan Loco aims to win over Tiffany's mother, Cassie Del Isla, by teaching him how to treat a lady. They engage in a romantic feast, with Cassie revealing her sultry figure and Juan tackling her from behind. Despite Cassie's blessing, Juan believes he will continue searching for another partner.
Do You Want To Watch Me Get Naughty - S2:E5
Bikini
Lana Smalls, missing her college stepbrother, decides to spice up their video call by modeling her sexiest bikinis. When her stepdad, Ken Feels, walks in, she seizes the opportunity to take things to the next level. Lana entices Ken, putting on a show for her stepbrother that includes a sizzling reverse cowgirl ride and more. Don't miss this electrifying performance that pushes boundaries and leaves inhibitions at the door!
I Can Do That For You Stepsis - S3:E5
Boy / Girl
Haley Reed, a caller on Lil Sis, shares her experience with her stepbrother Juan Loco, who used to provide her with lavish meals. However, Juan's girlfriend ended their relationship, and Haley had to give him physical affection. She was led by Alex, who shared her experience with Juan, who confessed his desire to have sex with her. Haley embraced Juan, fucked him, and smothered him. When Juan pulled out, Haley was left with no options. Alex then reveals that a transactional coupling isn't necessary.
A Lesson In Discipline For Stepsis - S3:E4
Boy / Girl
Love coach Alex Coal hosts a hotline on Lil Sis, where Parker Ambrose discusses Lulu Chu's affair with Brooke Barclays. Brooke threatened to alert Parker's father if he found out again. Lulu hasn't taken the situation seriously, and her mother has been playing tricks on him. Parker chastises Lulu with a hard kiss, eating her pussy and having her suck his dick. Lulu cowgirds up to Parker's hardon, giving her a final orgasm before he finishes. Lulu tries to get Parker in trouble by stealing his clothes, but he gets out.
I Can Still Be Your Boyfriend Stepsis - S3:E2
Girl / Girl
Alex Coal hosts a hotline on Lil Sis, discussing the growing intimacy between Lucky Fae and his new stepsister, Haley Spades. They had started making out and getting hot on movie dates. Haley revealed that their parents left them unexpectedly, and Lucky got her pants off to lick and finger bang her. Haley provided a blowout, making the two eager to hook up. Alex ends the call, stating that they have a normal connection and shouldn't let labels stop them.