Riding More Than Bicycles - S1:E4
Glasses
Pristine Edge convinces her stepson Jimmy Michaels to date four of her milf acquaintances and one mystery woman. Dating My Stepson's Crystal Clark goes all out to get Jimmy a girlfriend, seizing every opportunity to touch his body. After a romantic tandem bike trip, Crystal offers to take Jimmy for stretches, but he falls to his knees and takes a hint. Crystal takes Jimmy inside with her trimmed muff, and Jimmy runs her over, causing Crystal to twitch with pleasure.
Turning Up The Heat - S1:E3
Boy / Girl
Pristine Edge convinces her stepson Jimmy Michaels to date four of her milf acquaintances and one mystery woman. In this episode of Dating My Stepson, Cassie Del Isla and Jimmy work together to cook a pizza, focusing on flirtatiousness. Jimmy confides in her that he prefers younger women. Cassie invites Jimmy to eat her nude pussy, demonstrating how good an older woman can suck cock. Their passionate exchange ends happily, with Cassie falling back on her knees.
Massage And More - S1:E1
Boy / Girl
In the Dating My Stepson episode, Pristine Edge convinces her stepson Jimmy Michaels to date four of her milf acquaintances and one mystery woman. Sarah Taylor, having a child of the same age, gets to date Jimmy first. After a massage, Jimmy makes eye contact with his stepmother. Sarah locks lips with him, sucks and strokes him, and gives him a hip-swinging cowgirl ride. Jimmy dives in deep, pressing her into the table. Sarah urges him to keep her in mind.