Massage And More Jimmy Michaels has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Sarah Taylor is the lucky lady who gets to date Jimmy first. The date that Pristine has arranged is a couples massage

A Game Of Dare Always Spices Things Up This season on Dating my Stepson, were taking a new twist. The guys are looking for love, but they need to date the potential girlfriends mom first. If it works out, hell date the daughter right on the spot. Todays date is Shalina Devine, mom to Amirah. The date is Alex Charger. Shalina wants to make sure Alex chooses Amirah, so she sets him up to play a game of truth or dare. Alex admits that he cheated when he was younger, then tells Shalina his longest relationship was six months. When Shalina chooses dare, Alex tells her to show him how she chops wood. That gives them an excuse to get close together. When they get rained out, Alex sits down to a meal where he has to admit hes vegan. After another round of truth or dare, Shalina lets Alex get busy a different type of meat as she shows off her tits and then her ass. Soon Shalina is sucking Alex off and then hes eating that juicy pussy. Since Shalina is already on her back its simple for Alex to adjust his position to glide home into her greedy twat. From there they spoon together and then Shalina rolls to her side for a doggy style dicking down. When Shalina gets on top, theres no stopping her until shes sated. She rides in cowgirl before turning around and riding in reverse cowgirl until she has milked a creampie and a promise to really consider choosing Amirah fro

Riding More Than Bicycles Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Crystal Clark is in it to win it. Shes already into younger guys, so Jimmy is right up her alley. She cant wait to drain Jimmys balls as she fucks him right

Pleasure By The Pool This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On todays episode, Shalina Devine is supposed to have a date with Matthew Meier. Unfortunately for Shalina, Micky Muffin has other plans. She likes Matthew far too much to let him go easily. After Micky barges in on the date, Matthew and Shalina decide to take off and let Micky have the hot tub. Micky comes to find them, claiming that Shalina forgot her towel. The ladies begin fighting over Matthew, who seems only too pleased to let Shalina suck his cock while Micky pulls her tits out for him to enjoy. When the ladies fight over the blowjob, Matthew just gets even hotter for both of them. Eventually the girls decide that fighting is pointless and they should use Matthew as a toy together. Now that theyve decided to share, the girls treat Matthew as the fuck toy he is to them. Micky gracefully gives Shalina the first go on the D in cowgirl before she lays back to let Matthew do her as she eats Shalinas pussy. On her knees, Shalina rocks back to meet Matthews strokes as she laps at Mickys snatch. Micky gets to enjoy Matthews charms as she lays on her side with her mouth in Shalinas coochie and Matthew spooned behind her. Then Shalina climbs on and rides Matthew hard in reverse cowgirl, milking a creampie out of him that Micky snowballs with her. The two milfs agree theyll have to do more s haring in the

Learning Some New Moves This season on Dating my Stepson, Jayden Marcos is taking a new spin towards finding love. She has decided to go on a date with the potential girlfriends mom. If it works out, hell date the daughter right on the spot. Todays date is with Pristine Edge, mom to Rachel. Pristine deals cards to Jayden, but eventually the date turns into strip poker. Things start getting spicy as Pristines luck turns sour, although Pristine tries to remind herself that theyre here for her daughter. Once her tits are out, though, Pristine gives in to the chemistry between herself and Jayden. She crawls across the table, palms his boner, and makes it clear he can have anything he wants. Once Jayden has sampled Pristines pussy with his tongue, he stands up and shoves it in. Then Pristine crouches in front of him, licking his balls and shaft clean. She gets to her feet and leans forward over the table so Jayden can do her from behind. As they wind down, Pristine sits Jayden down and demonstrates her fitness by fucking him in cowgirl until hes ready to pop. She gives Jayden a handie until he blows on her stomach, and they both bask in the afterglow of a goo

Country Milf Is Too Much To Handle This season on Dating my Stepson, were taking a new twist. The guys are looking for love, but they need to date the potential girlfriends mom first. If it works out, hell date the daughter right on the spot. Todays milf is Silvia Saige, mom to Lilly Mae. A southern country belle, she needs to know if Sage Roux can handle her and her daughter. Sage has a bit of a culture clash with Silvia, but he does his best. Silvia thinks its cute! When Sage tries to barbecue, Silvia makes a comment about having lots of experience with meat. She leads him inside and begins questioning whether he knows how to treat a lady. Sage is going to have to demonstrate that he knows what hes doing to get to Lilly Mae. He begins by licking and sucking Silvias tits, then getting on his knees to eat her pussy. Silvia comes back with a blowjob, then leads Sage to her bedroom. Once Sage is prone in her bed, Silvia climbs on top of him to ride like the cowgirl she is. Turning around, she leans back so her tits are held high as she bounces in reverse cowgirl. Sage dicks Silvia down from behind as hse leans forward in cowgirl, then flips her onto her back so he can make that milf moan with a creampie. While Silvia is cleaning up in the aftermath, Sage confesses to the camera that he wont choose Lilly Mae because he doesnt want to be bossed around. Silvia overhears and kicks Sa

Stepmoms Secret Confession Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Jimmy learns that his final date is Pristine herself. Pristine isnt happy about the producers putting her in this situation, but she and Jimmy decide to make the best of it. They agree to sit down to the very nice dinner thats been laid out for them, and soon enough things have moved from awkward to flirty..

Putting In The Effort This season on Dating my Stepson, were taking a new twist. The guys are looking for love, but they need to date the potential girlfriends mom first. If it works out, hell date the daughter right on the spot. Todays date is Juan Loco trying to impress Cassie Del Isla, mom to Tiffany. Cassie has prepared a date where Juan will learn how to treat a lady. She shows him how to arrange roses, how to make chocolate dipped strawberries, and how to write a haiku. Cassie can tell Juan is checking her out, and she finds that she likes it. By the time they get to the haiku, they cant seem to keep their mouths off each other. After a brief makeout, Cassie peels off her dress to unveil a stunning body with hot lingerie and Juan goes in for a pussy feast. In return, he gets his dick and balls sucked. Getting to her feet, Cassie leans forward over the kitchen island so Juan can do her from behind. Juan takes his turn on the counter so Cassie can mount him in cowgirl and ride him until shes arching her back in delight. Climbing off, she gets on her back so Juan can keep their party going. He gives Cassie one last big O, then cums on her stomach. Although Cassie gives her blessing to Juan, Juan thinks hell keep looking for anothe

Going Overboard On Her Pussy This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On todays episode, Kira Queen is paired up with Sam Bourne. Kira still lives with her stepson, so shes on the show to find a boy toy for herself. Their date is to go on a boat with Sam manning the oars to take them around a nearby lake. When Kira has had enough, Sam brings them back to the dock so they can move the party indoors. Everything is going smoothly until Sam falls into the lake. Kira leads Sam indoors to the closest part of the house, where she begins to undress him so he can warm up. Kneeling in front of Sam, Kira tugs his jeans off and sees that hes packing a really nice cock. Knowing that Sam will heat up even more if she strokes it, Kira gives him a handie. That of course leads to her going back to her knees to suck him down and even pop those big jugs out for a titty fuck. No longer cold, Sam does some pussy exploration with his tongue that gets Kira moaning. Although he could go on feasting like that forever, Sam decides to get his dick wet as he takes Kira right there in that little bunk bed. They go to town in spooning and then Kira turns over so that Sam can keep her party going from behind. Getting Sam onto his back, Kira uses the bunk bed for leverage as she rides in cowgirl and then reverse cowgirl. She keeps up the good work until he fills her to the brim with a creampie, leaving just enough cum dripping down his own hardon for Kira to suck him clean.

Candlelit Romance This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On todays episode, Alex Charger and Shalina Devine are enjoying a candlelit dinner date. Its a bit awkward for the stepmom and stepson to be dining romantically, but they have both been into each other for a long time. Shalina tries to deny the chemistry between them, but she cant keep slapping Alex away. Finally giving in to her urges, Shalina lets Alex kiss her. Their passion is almost animalistic as Shalina gets to her knees and unbuttons Alexs pants. Once she lays hands on that hard dick, she cant stop from sucking and stroking. Shalinas tits are heavy and tender as she uses one hand to feel herself up and even rub her pussy while she continues to blow Alex. Leaning forward, Shalina moans as Alex finally comes into her from behind. She sucks their combined juices off his dick and then lays back so he can give it to her on her back. Climbing onto Alexs lap, Shalina rides him in cowgirl for the intimacy. Turning around, she goes for it in reverse cowgirl until he blows his nut inside her in a hot creampie