https://www.stepsonporn.com/pt/categories/datingmystepson-com/ Thu 30 Apr 2026 16:01:42 +0200 https://www.stepsonporn.com/pt/video/258/it-started-in-the-jacuzzi-s2-e4/
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. ]]> Tue 11 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/258/it-started-in-the-jacuzzi-s2-e4/ https://www.stepsonporn.com/pt/video/257/playing-my-cards-right-s4-e1/
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 11 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/257/playing-my-cards-right-s4-e1/ https://www.stepsonporn.com/pt/video/255/a-game-of-dare-always-spices-things-up-s4-e4/
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. ]]> Tue 11 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/255/a-game-of-dare-always-spices-things-up-s4-e4/ https://www.stepsonporn.com/pt/video/254/learning-some-new-moves-s4-e2/
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 Rion King trying to impress Crystal Rush, mom to McKenzie. ]]> Tue 11 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/254/learning-some-new-moves-s4-e2/ https://www.stepsonporn.com/pt/video/252/riding-more-than-bicycles-s1-e4/
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. ]]> Tue 11 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/252/riding-more-than-bicycles-s1-e4/ https://www.stepsonporn.com/pt/video/246/pleasure-by-the-pool-s2-e5/
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's 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 they've 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 Shalina's pussy. On her knees, Shalina rocks back to meet Matthew's strokes as she laps at Micky's snatch. Micky gets to enjoy Matthew's charms as she lays on her side with her mouth in Shalina's 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 they'll have to do more s haring in the future. ]]> Tue 11 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/246/pleasure-by-the-pool-s2-e5/ https://www.stepsonporn.com/pt/video/265/her-moms-traditional-technique-s4-e10/
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 Millie Morgan, mom to Sarah. She has set up a date where she gives Parker a palm reading followed by a nice massage out in her backyard.Before the massage, Millie has Parker take his shirt off. To make him feel more comfortable, Millie takes hers off, too. Then Millie insists Parker needs to take his pants off. She can't believe how big that dick is. As Millie takes the excuse to let her hands roam Parker's body, she secretly oils her own tits up and uses them to deliver the massage. As soon as Parker rolls over and she sees his hardon, Millie knows they're gonna fuck. She takes him inside and then lays him down in bed so she can blow that nice fuck stick.Crawling on top of Parker, Millie first presses her clit to his mouth so he can eat her pussy. Then she lowers her hips and goes for a cowgirl ride. When it's Parker's turn to show Millie what he can do, he flips her to her back so he can dive deep. She rolls onto her stomach and gets on her knees for a cowgirl dicking down from behind. Millie finishes them both off by riding Parker in reverse cowgirl until he gluts her with his cum shot. When he says he's not going to date Millie's daughter because he can't get past their lifestyle, Millie shoots back that it's fine because his lifeline is short anyway. ]]> Mon 10 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/265/her-moms-traditional-technique-s4-e10/ https://www.stepsonporn.com/pt/video/263/there-is-no-resisting-her-mom-s4-e7/
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. ]]> Mon 10 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/263/there-is-no-resisting-her-mom-s4-e7/ https://www.stepsonporn.com/pt/video/261/dropping-my-balls-in-her-moms-pocket-s4-e5/
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 Rebecca Volpetti. The date is Alex Charger. Rebecca has prepared a date in her game room where they will play pool. They take shots as they chat, but Rebecca realizes she likes Alex so much that she needs to seduce him.Once Alex has enjoyed a bunch of pool shots against Rebecca's ass and pussy, they agree that they're two consenting adults and that anything can happen while they're on a date. To that end, Rebecca is soon top off with Alex sucking her nipples and palming her pussy beneath her miniskirt. A moment later, Rebecca is on her knees with Alex's dick in her mouth as she enjoys an intense blowjob. Alex gives right back, licking and lapping at Rebecca's clit. Getting to his feet, Alex shoves into that greedy cooch. Rebecca moans at the completion, then stands up and leans forward over the table so Alex can do her from behind. The couple get back on the pool table together so Rebecca can ride in cowgirl. Turning around, Rebecca rides Alex in reverse cowgirl until he pops inside her. Dripping with Alex's creampie, Rebecca gives him permission to date her daughter. ]]> Mon 10 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/261/dropping-my-balls-in-her-moms-pocket-s4-e5/ https://www.stepsonporn.com/pt/video/251/the-milf-youd-want-to-marry-s1-e2/
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 Pristine's, Bunny can't wait to see what Jimmy has to offer as a romantic partner. For this date, Pristine has arranged for the lovebirds to share a romantic boat ride. Bunny puts her goods on display right off the bat with a bikini. Of course Jimmy likes what he sees. As the boat ride goes on, Bunny tries to come on to Jimmy, who seems oblivious to the moves. At the end of the ride, Jimmy continues to ignore Bunny. Fed up with Jimmy's obvious disinterest, Bunny hides part of her necklace and tells Jimmy that she wants to role play that they've been married a while and he has to turn her on. Jimmy goes looking for the necklace, which of course leads her clothes coming off and to Jimmy going in for a pussy feast.The date is finally back on track as Jimmy licks the clit and finger bangs Bunny. He gets a blowjob in return, which leads to the inevitable fucking. Bunny starts them out by riding Jimmy's stiffie while her big boobs brush his face. Turning around, she keeps bouncing in cowgirl. Bunny gets on her knees so that Jimmy can nail her in doggy. As soon as Bunny rolls onto her back, Jimmy dives nice and deep, making her moan one last time. When he pulls out to cover Bunny's smooth twat in cum, then immediately asks if Bunny thinks they could have a threeway. As soon as he says it, he knows that he fucked up. ]]> Mon 10 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/251/the-milf-youd-want-to-marry-s1-e2/ https://www.stepsonporn.com/pt/video/249/turning-up-the-heat-s1-e3/
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. ]]> Mon 10 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/249/turning-up-the-heat-s1-e3/ https://www.stepsonporn.com/pt/video/245/stepmoms-secret-confession-s1-e5/
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 isn't 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 that's been laid out for them, and soon enough things have moved from awkward to flirty.When Pristine learns that Jimmy has fucked every single one of her friends, she asks the producers to stop the date. Eventually she agrees to do a final interview, at which point she admits that she has the hots for Jimmy. Jimmy overhears her but pretends not to when he walks in and cuts the interview short. Frustrated, Pristine pops a tit out for Jimmy to suck. Once she makes the first move, Pristine decides to carry through with the real deal. She starts with a blowjob, then quickly moves on to a titty fuck and more.Jimmy gets just enough time to eat that pussy out before Pristine is all over him. She rides him while her big boobies push against his chest, then turns around for reverse cowgirl. Getting on her knees, Pristine welcomes Jimmy back inside her tight cooch. Once Jimmy and Pristine have enjoyed themselves in missionary, Jimmy explodes all over his stepmom. How could he not pick her as the winner of this wild ride of a dating show? ]]> Mon 10 Feb 2025 00:00:00 +0200 https://www.stepsonporn.com/pt/video/245/stepmoms-secret-confession-s1-e5/