https://fapgoat.com/sites/datingmystepson/ Tue 27 Oct 2026 11:09:07 +0200 https://fapgoat.com/video/3672/micky-muffin-i-aced-her-hole/
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Micky Muffin is going on a date with Alex Charger. They're going golfing, although Micky doesn't know anything about it. Alex is fine with showing Micky the ropes, especially as Micky shows off her thong when she leans forward in her cute miniskirt. Things are going great until Micky accidentally hits Alex in the dick with her golf club. That cuts the date short as Micky leads Alex inside. Alex coaxes Micky into massaging his cock because he claims it helps him feel better. She offers to kiss his booboo, which is all the excuse she needs to stroke and suck Alex down. Peeling off her thong, Micky goes ahead and spears herself on Alex's hardon to ride him. There's no question about their chemistry as Alex pushes Micky onto her back and bangs her, then gets her on her knees and pulls her hair in doggy. Shifting to reverse cowgirl, Micky rides Alex for all she's worth until he aces her hole with a big fat creampie that helps him forget all about his injury. ]]> Wed 14 Oct 2026 19:12:00 +0200 https://fapgoat.com/video/3672/micky-muffin-i-aced-her-hole/ https://fapgoat.com/video/3627/sophia-locke-my-stepmom-is-the-perfect-date/
This season on Dating my Stepson, stepmoms are throwing their stepsons a bone by hooking them up with their single friends. Today's milf is Sophia Locke, who is also Arin Jones's stepmom. She just doesn't think any of her friends are going to love Arin the way she thinks he deserves. Sophia has put together Arin's perfect date, a floor picnic with all of his favorite foods and a jacket for his favorite team. Sophia goes to change into a slutty cheerleader costume that makes it clear she's going to go all the way with him. Kneeling behind Arin, Sophia massages his shoulders. Then she kneels in Arin's lap and pops her big tits out right in front of his face. Arin is putty in Sophia's hands as she gets on her knees beside him to suck his dick. Since Arin is still seated on the floor, it's so simple for Sophia to straddle him again, this time guiding his cock into her twat as she rides him. She moves to the couch so Arin can eat her pussy and then dick her down in doggy. Back on top, Sophia rides her stepson in reverse cowgirl with those juicy tatas bouncing. Arin finishes his stepmilf off as she lays on her back, and then he pulls out to pop on Sophia's bosom. ]]> Fri 09 Oct 2026 19:46:00 +0200 https://fapgoat.com/video/3627/sophia-locke-my-stepmom-is-the-perfect-date/ https://fapgoat.com/video/3664/shalina-devine-candlelit-romance/
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Alex Charger and Shalina Devine are enjoying a candlelit dinner date. It's 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 can't 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 Alex's pants. Once she lays hands on that hard dick, she can't stop from sucking and stroking. Shalina's 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 Alex's 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 ]]> Tue 06 Oct 2026 19:46:00 +0200 https://fapgoat.com/video/3664/shalina-devine-candlelit-romance/ https://fapgoat.com/video/3658/pristine-edge-playing-my-cards-right/
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's date is Jayden Marcos trying to impress Pristine Edge, mom to Rachel. Pristine deals cards to Jayden, but eventually the date turns into strip poker. Things start getting spicy as Pristine's luck turns sour, although Pristine tries to remind herself that they're 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 Pristine's 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 he's ready to pop. She gives Jayden a handie until he blows on her stomach, and they both bask in the afterglow of a good fuck. ]]> Tue 29 Sep 2026 15:50:00 +0200 https://fapgoat.com/video/3658/pristine-edge-playing-my-cards-right/ https://fapgoat.com/video/3670/micky-muffin-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 today's 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. There's 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 Micky's 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. It's 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. Micky's reverse cowgirl stiffie ride milks the cum right out of Matthew in a creampie that seals their affection for each other. ]]> Thu 24 Sep 2026 15:17:00 +0200 https://fapgoat.com/video/3670/micky-muffin-it-started-in-the-jacuzzi/ https://fapgoat.com/video/3653/cassie-del-isla-putting-in-the-effort/
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's 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 can't 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 she's 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 he'll keep looking for another milf. ]]> Fri 11 Sep 2026 20:53:00 +0200 https://fapgoat.com/video/3653/cassie-del-isla-putting-in-the-effort/ https://fapgoat.com/video/3625/cory-chase-an-exercise-in-seduction/
Cory Chase is going on a date with his stepmom, Cory Chase, but he doesn't know it beforehand. He's surprised when Cory is the one who wants to do a workout session with him. This horny milf is divorcing her deadbeat husband and feels like the soon to be former stepson is fair game for her needs. The date begins with Cory wearing tight fitting clothes as she leads Enzo on a workout to test his stamina. Despite his boner, Enzo does his best. It helps that Cory is constantly putting him into positions that are increasingly sexual. By the time Cory finally stops teasing Enzo, he can't wait to get his tongue on her pussy and eat her out. Getting his dick sucked by his stepmom is one of the best moments of Enzo's life to date. Of course, having Cory with her big titties and hairy twat riding him immediately tops Enzo's list of top moments. After she enjoys herself in reverse cowgirl, Cory gets on her knees so her stepson can fuck her from behind. When Cory rolls over so that Enzo can enjoy her big tatas, he watches those enhanced bazongas bounce as he bones her. Pulling out, Enzo pops on said boobs. He and Cory are still seeing each other as of this taping. ]]> Thu 10 Sep 2026 11:22:00 +0200 https://fapgoat.com/video/3625/cory-chase-an-exercise-in-seduction/ https://fapgoat.com/video/3687/sarah-taylor-massage-and-more/
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, Sarah Taylor is the lucky lady who gets to date Jimmy first. The date that Pristine has arranged is a couple's massage. When Sarah comes out in her robe, she finds Jimmy trying to cover his hardon up and tells him not to bother. She's seen everything since she has a son his age. Things are going well right up until Jimmy rolls over at the end of the massage with a massive stiffie, only to lock eyes with his stepmom who was checking on the date. Trying to recover the magic Sarah makes a move by joining Jimmy on his massage table and locking lips with him as she grinds against his dick. Moving lower on the table, Sarah takes that nice erection in her mouth to stroke and suck. Mounting Jimmy, Sarah rides him in cowgirl with long strokes of her hips. Then she gets to her feet so Jimmy can love on her from behind. He presses her onto the table on her belly, diving nice and deep. Turning onto her back, Sarah spreads out for Jimmy to give her a grand finale before he pulls out and cums on her landing strip twat. As she basks in the afterglow, Sarah asks Jimmy to remember her. ]]> Tue 08 Sep 2026 17:31:00 +0200 https://fapgoat.com/video/3687/sarah-taylor-massage-and-more/ https://fapgoat.com/video/3634/shalina-devine-i-didnt-see-this-cumming/
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's milf is Shalina Devine, who could not be hotter or hornier. She's ready to take on Nikki Nutz, who's been looking for love. Shalina has decided to play a game with Nikki that breaks the rules of the show, but that's fine because she loves to date younger guys. Blindfolded, Nikki is supposed to guess what Shalina puts in his hand. She's quick to drop her top so that Nikki is grabbing her boobs. As soon as the blindfold comes off, Nikki dives face first into Shalina's pussy. In return he earns himself a BJ that rocks his world. Shalina has Nikki seated on his lap and riding his ding dong before he knows it. She gets on her side while Nikki spoons behind her and keeps her pussy party going. Getting to her knees, Shalina leans forward and thrusts back as Nikki pounds her. She ends up back on Nikki's stiffie as she rides in reverse cowgirl until he gives her a creampie. Nikki has passed the milf test, but Shalina wants to keep him for herself. ]]> Tue 08 Sep 2026 16:24:00 +0200 https://fapgoat.com/video/3634/shalina-devine-i-didnt-see-this-cumming/ https://fapgoat.com/video/3645/texas-patti-there-is-no-resisting-her-mom/
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's 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. Their game reveals that Alex wants to take care of Texas’s daughter but he’d also fuck the hell out of her for a first date. Alex can feel the connection between himself and Texas, and finds that he’s less interested in her daughter than in her. They come together with a kiss that turns into Alex eating Texas’s pussy. She pops those big naturals out for Alex to enjoy, then crawls forward to suck her new lover’s dick. On her back, Texas watches with hungry eyes as Alex shoves into her landing strip snatch. They spoon together and keep on fucking. Then Texas gets on her knees for Alex to show her how he does it doggy style. They finish with Texas on top, first riding in cowgirl and then turning around to pump a creampie out of Alex in reverse cowgirl. Texas gives permission to fuck (or date) her daughter. ]]> Thu 03 Sep 2026 20:53:00 +0200 https://fapgoat.com/video/3645/texas-patti-there-is-no-resisting-her-mom/ https://fapgoat.com/video/3643/cherry-kiss-her-mom-took-me-for-a-test-drive/
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's 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. ]]> Wed 02 Sep 2026 11:22:00 +0200 https://fapgoat.com/video/3643/cherry-kiss-her-mom-took-me-for-a-test-drive/ https://fapgoat.com/video/3651/shalina-devine-a-game-of-dare-always-spices-things-up/
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's 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 he's 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 he's eating that juicy pussy. Since Shalina is already on her back it's 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, there's no stopping her until she's 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 from Alex. ]]> Sat 29 Aug 2026 17:31:00 +0200 https://fapgoat.com/video/3651/shalina-devine-a-game-of-dare-always-spices-things-up/