https://familyporn.tv/sites/datingmystepson/ Sun 05 Apr 2026 23:53:21 +0200 https://familyporn.tv/videos/filled-up-before-dinner-s3-e1/
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Sam Bourne and Shalina Devine are having their date cooking dinner together. Sam arrives with a rose, which instantly pleases Shalina. They get busy, and it turns out that they work well together with their clothes on. All Shalina can think of is seeing if they work as well together with their clothes on the ground.Taking her chance, Shalina pours water onto Sam accidentally-on-purpose. It's of course on her to help him clean off. Dropping to her knees, she tugs Sam's pants down until his stiffie pops free. She wants to suck it, but first she daubs it with whipped cream to give them both a little treat as she gets down to the business of her BJ.Dinner is forgotten as Shalina gets in a chair and spreads her thighs for Sam to eat her pussy. Getting to his feet, Sam sinks balls deep into that velvet glove. They make good use of the chair, with Shalina on her back and then her side, winding up on her knees. Giving the chair over to Sam, Shalina sucks their juices from his hardon and then rides him in reverse cowgirl until he's close. Turning around, she goes for a ride in cowgirl until he delivers a creampie that's way more satisfying than any meal could ever be. ]]> Sat 28 Feb 2026 14:44:13 +0200 https://familyporn.tv/videos/filled-up-before-dinner-s3-e1/ https://familyporn.tv/videos/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. ]]> Sat 28 Feb 2026 02:48:18 +0200 https://familyporn.tv/videos/learning-some-new-moves-s4-e2/ https://familyporn.tv/videos/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. ]]> Sat 28 Feb 2026 02:19:04 +0200 https://familyporn.tv/videos/the-milf-youd-want-to-marry-s1-e2/ https://familyporn.tv/videos/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. ]]> Fri 27 Feb 2026 14:44:14 +0200 https://familyporn.tv/videos/a-game-of-dare-always-spices-things-up-s4-e4/ https://familyporn.tv/videos/i-aced-her-hole-s2-e3/
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. ]]> Thu 26 Feb 2026 18:54:21 +0200 https://familyporn.tv/videos/i-aced-her-hole-s2-e3/ https://familyporn.tv/videos/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. ]]> Thu 26 Feb 2026 13:28:08 +0200 https://familyporn.tv/videos/playing-my-cards-right-s4-e1/ https://familyporn.tv/videos/going-overboard-on-her-pussy-s2-e2/
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Kira Queen is paired up with Sam Bourne. Kira still lives with her stepson, so she's 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 he's 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. ]]> Mon 23 Feb 2026 18:32:44 +0200 https://familyporn.tv/videos/going-overboard-on-her-pussy-s2-e2/ https://familyporn.tv/videos/country-milf-is-too-much-to-handle-s5-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 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. ]]> Fri 20 Feb 2026 19:03:52 +0200 https://familyporn.tv/videos/country-milf-is-too-much-to-handle-s5-e1/ https://familyporn.tv/videos/coming-clean-s3-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 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. There's 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 inside her. ]]> Thu 19 Feb 2026 08:12:28 +0200 https://familyporn.tv/videos/coming-clean-s3-e4/ https://familyporn.tv/videos/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. ]]> Wed 18 Feb 2026 21:12:05 +0200 https://familyporn.tv/videos/her-moms-traditional-technique-s4-e10/ https://familyporn.tv/videos/putting-in-the-effort-s4-e3/
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. ]]> Tue 17 Feb 2026 15:35:27 +0200 https://familyporn.tv/videos/putting-in-the-effort-s4-e3/ https://familyporn.tv/videos/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. ]]> Mon 16 Feb 2026 14:44:10 +0200 https://familyporn.tv/videos/pleasure-by-the-pool-s2-e5/