In an attempt to get her stepson Jimmy Michaels a girlfriend, Pristine Edge has persuaded him to date four of her milf acquaintances in addition to one mystery woman. The fortunate Sarah Taylor gets to date Jimmy first in this Dating My Stepson episode. Pristine had scheduled a massage for the two of them on this date. Sarah tells Jimmy not to worry as she emerges in her robe and discovers him attempting to hide his hardon. Having a kid of the same age, she has witnessed everything. Everything is going great until Jimmy, sporting a huge stiffie, lays over at the conclusion of the massage and makes eye contact with his stepmother, who is checking in on the date. Sarah moves to join Jimmy on his massage table and locks lips with him while she grinds against his dick in an attempt to reclaim the enchantment. Sarah slides down the table and uses her lovely erection to suck and stroke. Sarah mounts Jimmy and gives him a long hip-swinging cowgirl ride. Then she stands up so Jimmy can give her a behind-the-back kiss. He dives in deep, pressing her into the table on her stomach. Sarah flips over and lays out for Jimmy to give her a spectacular farewell before he pulls over and gives her a cums on her landing strip twat. Sarah urges Jimmy to keep her in mind while she enjoys the afterglow.