https://fapgoat.com/sites/datingmystepson/ Sat 12 Sep 2026 10:01:24 +0200 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/ https://fapgoat.com/video/3628/diana-grace-she-wants-coffee-and-my-cream/
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 Diana Grace, who is BFFs with Gunnar Bishop's stepmom. They're going to have a coffee date where they try different coffees and creams. Both are excited to see where the day leads. The coffee tasting isn't Gunnar's cup of tea, but he perseveres the best he can. When he's served a coffee with ghost pepper in it, Gunnar overheats and peels his shirt off. Diana is happy to match him, popping her boobs out of her dress. From there, it's easy to coax Gunnar into eating her pussy and then showing her what he's got down under. Diana can't wait to get her mouth around that nice cock for a good BJ. Gunnar shows his strength by lifting Diana up and holding her upside down so they can have a vertical 69. Climbing into Gunnar's lap, Diana rides him in cowgirl. Then she lets Gunner push her to her knees so he can do a solid dicking down from behind. Diana enjoys another ride, this time in reverse cowgirl. Then she lets Gunnar bend her nearly in half as he lifts one of her ankles to hook around his neck and open Diana up. Diana finishes Gunnar off by taking his cum shot in her mouth, but it's not enough for Gunnar to want a relationship. ]]> Sat 29 Aug 2026 15:50:00 +0200 https://fapgoat.com/video/3628/diana-grace-she-wants-coffee-and-my-cream/ https://fapgoat.com/video/3683/cassie-del-isla-turning-up-the-heat/
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, Cassie Del Isla will be cooking dinner with Jimmy. Normally Cassie dates older men, but she is making an exception to see how things are with Jimmy. They work together to make a pizza, where Cassie gets increasingly flirty. When Jimmy mentions to Cassie that he likes to date younger women, Cassie realizes that she's going to have to try even harder to get his attention. She claims to have something on her shirt. When Cassie returns wearing just her white lacy lingerie and high heels, Jimmy knows he's about to have a very good time. Sure enough, Cassie hops on the counter and invites Jimmy to eat her smooth bare pussy. In return, she shows him just how well and older woman can suck cock. They come together for the first time with Cassie on a stool that puts her coochie at perfect pussy pounding height. Climbing onto the counter, Jimmy lays down so Cassie can ride the D. She climbs off and stands, putting one foot on a stool to open herself up to a dicking down from behind. As their lovemaking concludes, Cassie gets back on her knees to offer Jimmy a very happy ending all over her face. ]]> Wed 26 Aug 2026 08:34:00 +0200 https://fapgoat.com/video/3683/cassie-del-isla-turning-up-the-heat/ https://fapgoat.com/video/3636/silvia-saige-country-milf-is-too-much-to-handle/
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 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 it's 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 he's doing to get to Lilly Mae. He begins by licking and sucking Silvia's 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 won't choose Lilly Mae because he doesn't want to be bossed around. Silvia overhears and kicks Sage out. ]]> Mon 24 Aug 2026 13:36:00 +0200 https://fapgoat.com/video/3636/silvia-saige-country-milf-is-too-much-to-handle/ https://fapgoat.com/video/3632/sharon-white-i-have-to-have-her/
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 Sharon White, who is newly divorced. She's allegedly looking for someone for her daughter, but if she finds a dude for herself she's not going to argue. Sharon's date today is Sam Bourne, who Sharon immediately thinks is nice, young, and definitely her type. The date itself is going to be Sam teaching Sharon some English. Sam is confused, but Sharon knows this will give her excuses to touch Sam and have him touch her. Their lessons get hands on when Sharon asks Sam to touch her boobs. A hot minute later, Sharon is kissing him and then sucking Sam's dick. There's no language barrier as things get hardcore. After worshipping Sharon's boobs and ass with his mouth and hands, Sam shoves it in in doggy. Then he fucks Sharon as he spoons behind her. When Sharon takes control, she rides her new lover in reverse cowgirl and then cowgirl. Their fuck fest culminates with Sam going to town in Sharon's cooch until she's squirming beneath him. Pulling out, he lets the milf guide his cum shot all over her trimmed snatch. ]]> Sat 22 Aug 2026 09:41:00 +0200 https://fapgoat.com/video/3632/sharon-white-i-have-to-have-her/ https://fapgoat.com/video/3682/crystal-clark-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. She's already into younger guys, so Jimmy is right up her alley. She can't wait to drain Jimmy's balls as she fucks him right. Today's date is a romantic tandem bike ride with the ultra sexual Crystal. She pulls out all the stops, taking every opportunity to run her hands all over Jimmy's body. When the bike ride ends, Crystal offers to do some stretches with Jimmy that are merely foreplay to getting off. Jimmy can take a hint as he drops to his knees and eats the milf out from behind. Jimmy lays Crystal down on the yoga mat to enjoy the pussy buffet, then takes his own turn on his back so Crystal can go to town sucking the D down before shifting into a 69. Since Crystal is already on top of Jimmy, she keeps the party going by sliding her trimmed muff down to take him all the way inside. Her stiffie ride is just the beginning; Crystal gets on her back once again so that Jimmy can slam into her. On her knees, she takes a doggy style pussy pounding that leaves her twat twitching in delight. Crystal has just enough time to get on her back before Jimmy blows his load all over her face and tits in exactly the happy ending she was hoping for. ]]> Wed 19 Aug 2026 08:00:00 +0200 https://fapgoat.com/video/3682/crystal-clark-riding-more-than-bicycles/