Massage And More

Massage And More

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


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Learning Some New Moves

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

Candlelit Romance
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Candlelit Romance

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 creampi

Coming Clean
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Coming Clean

Coming Clean This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On todays episode, Micky Muffin is having a picnic with her stepson Sam Bourne. They both confess to the cameras that the week in the house has changed their opinions of each other. They initially agree to go with the flow and not make things awkward, but they get flirty together with the fancy food and find themselves coming together for a deep kiss. Taking things back inside the house, they find that their chemistry has really ignited. Sam pushes Micky onto the couch to pepper her with kisses and eventually finds himself with his face between her thighs. He licks and suckles, then closes his eyes in bliss as Micky returns the favor by blowing him. Theres no question that these two are going to go all the way. Sam eventually seals the deal as he sinks his cock deep inside. When Micky falls to her side with Sam spooned behind her, of course he follows her down to keep on going. Micky gets to her knees so Sam can give her a doggy style pussy pounding. Then she mounts him, enjoying every inch of his nice long dick as she rides in cowgirl. Turning around, Micky keeps on bouncing in reverse cowgirl until Sam cums insi

Pleasure By The Pool
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Pleasure By The Pool

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

Country Milf Is Too Much To Handle
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Country Milf Is Too Much To Handle

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

There Is No Resisting Her Mom
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There Is No Resisting Her Mom

There Is No Resisting Her Mom 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 Texas Patti. Alex Charger is back once again, looking for love in the form of his potential girlfriend’s mom. Patti wants her daughter to meet a guy who’s kinky like her. The date Texas has prepared is a game of Would You Rather that will let her get to know Alex better

Her Mom Took Me For A Test Drive
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Her Mom Took Me For A Test Drive

Her Mom Took Me For A Test Drive 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 Cherry Kiss, mom to Lindsay. Parker Ambrose, the potential suitor, is a bit confused about the show’s premise, but he’s game since the normal dating scene isn’t working out. Once they’ve returned from their dinner date, Cherry tells Parker they aren’t done yet. She wants to make s’mores and then have him for dessert. Coming up behind Parker as he roasts a marshmallow, Cherry wraps her arms around him. She gently maneuvers him back against the counter to kiss her way down his body to pop his hardon out. Assuring Parker that her daughter won’t be home for a while, Cherry goes on to suck him off. Determined to take Parker for a thorough test drive, Cherry gets to her feet and lifts one leg to the kitchen counter so Parker can shove in from behind. Laying Parker on the ground, Cherry licks her own juices from his dick and then mounts him. Cowgirl makes this mommy moan as she rides. Getting on the counter, Cherry opens up for Parker one final time. He pumps Cherry to climax and then enjoys his own orgasm as Cherry kneels in front of him. Now Parker knows he’ll choose Cherry’s daughter

It Started In The Jacuzzi
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It Started In The Jacuzzi

It Started In The Jacuzzi This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On todays episode, Micky Muffin is up for her second date in the series. This time, she and Matthew Meier are getting to know each other in a jacuzzi. Theres nothing stopping them from feeling each other up and eventually coming in to make out. When Micky beckons for Matthew to get out of the water, he follows her obediently to a convenient bedroom. They resume their kisses as Matthew explores Mickys body with his hot hands. Easing her down, he palms her pussy while worshipping her tits. Once Matthew has had a taste of her pussy, Micky needs a taste of his cock. Its only fair. When she has finally removed her bikini, Micky lays on her side as Matthew spoons behind her. Rolling onto her back, she moans as Matthew reenters her. Then he gets on his back so Micky can ride him, first in cowgirl and then in reverse cowgirl after a brief detour into doggy. Mickys reverse cowgirl stiffie ride milks the cum right out of Matthew in a creampie that seals their affection for each other

Showing Her Mom My Best Moves
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Showing Her Mom My Best Moves

Showing Her Mom My Best Moves 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 Bunny Madison, mom to Becky. Bunny has prepared a floor picnic as a date with Parker Ambrose. They begin chatting, and the chemistry between them definitely sparks. They go outside to play a variety of games in Bunny’s magnificent backyard. The longer they play, the hornier Bunny gets. When they play foosball, Bunny tries to distract Parker with her big boobies. Deciding to take Parker and his dick for a test drive is the next natural step for Bunny, who eases Parker onto his back so she can enjoy every inch of his hardon. First she sucks him off, and then Bunny climbs aboard for a ride on that nice stiffie. Parker takes Bunny to the couch to really have his way with her. After enjoying a pussy feast, Parker shoves it back in and bends Bunny nearly in half with his dicking down. Getting to her knees, Bunny watches over her shoulder as Parker gives her one last fuck in doggy right through a creampie. Parker tells Bunny that he’s not interested in her daughter, but he’d do this again with Bunny herself

Going Overboard On Her Pussy
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Going Overboard On Her Pussy

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.

The Milf Youd Want To Marry
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The Milf Youd Want To Marry

The Milf Youd Want To Marry 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, Bunny Madison is ready for her date with Jimmy. A college friend of Pristines, Bunny cant wait to see what Jimmy has to offer as a romantic partner.