https://www.xporntv.com/categories/datingmystepson-com/ Sat 25 Apr 2026 08:18:48 +0200 https://www.xporntv.com/videos/367157/show-me-that-youre-good-enough-s5-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 milf is Talia Mint, who has planned a massage to see how potential date Sam Bourne looks without all those clothes in the way.At first, everything is on the level as Talia uses a towel to protect Sam's modesty during his massage. Things get hotter as Sam's boner becomes evident while he's on his back. Talia reaches down to cup it, then ditches the towel and goes full vixen on him. Next thing Sam knows, his potential date's mom is naked and massaging his dick.Climbing on top of Sam, Talia sinks down on that fine man meat to ride him right in the living room. Then she sucks her own juices from his hardon while in a 69 where she sees how Sam is with his mouth. Talia goes for a reverse cowgirl ride next, then takes things down a notch as she and Sam fuck while spooning. When Talia gets on her knees, Sam is there to do her in doggy. As they wind down in missionary, Talia realizes that Sam is more her speed than her daughter's. ]]> Wed 11 Feb 2026 09:13:06 +0200 https://www.xporntv.com/videos/367157/show-me-that-youre-good-enough-s5-e4/ https://www.xporntv.com/videos/362462/i-have-to-have-her-s5-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 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. ]]> Fri 30 Jan 2026 02:12:06 +0200 https://www.xporntv.com/videos/362462/i-have-to-have-her-s5-e3/ https://www.xporntv.com/videos/362454/i-didnt-see-this-cumming-s5-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 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. ]]> Fri 30 Jan 2026 02:03:07 +0200 https://www.xporntv.com/videos/362454/i-didnt-see-this-cumming-s5-e2/ https://www.xporntv.com/videos/356519/i-have-to-have-her-s3-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 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. ]]> Tue 06 Jan 2026 13:55:06 +0200 https://www.xporntv.com/videos/356519/i-have-to-have-her-s3-e5/ https://www.xporntv.com/videos/320801/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. ]]> Wed 15 Oct 2025 22:38:05 +0200 https://www.xporntv.com/videos/320801/i-didnt-see-this-cumming/ https://www.xporntv.com/videos/307145/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. ]]> Mon 22 Sep 2025 11:47:07 +0200 https://www.xporntv.com/videos/307145/country-milf-is-too-much-to-handle-s5-e1/ https://www.xporntv.com/videos/289797/country-milf-is-too-much-to-handle-s1-e6/
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 30 May 2025 00:25:05 +0200 https://www.xporntv.com/videos/289797/country-milf-is-too-much-to-handle-s1-e6/ https://www.xporntv.com/videos/247978/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 29 Jan 2025 13:01:11 +0200 https://www.xporntv.com/videos/247978/her-moms-traditional-technique-s4-e10/ https://www.xporntv.com/videos/245060/showing-her-mom-my-best-moves-s4-e9/
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 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. ]]> Fri 17 Jan 2025 12:55:17 +0200 https://www.xporntv.com/videos/245060/showing-her-mom-my-best-moves-s4-e9/ https://www.xporntv.com/videos/243074/her-mom-took-me-for-a-test-drive-s4-e8/
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. ]]> Thu 09 Jan 2025 12:12:10 +0200 https://www.xporntv.com/videos/243074/her-mom-took-me-for-a-test-drive-s4-e8/ https://www.xporntv.com/videos/233028/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 25 Nov 2024 12:00:15 +0200 https://www.xporntv.com/videos/233028/there-is-no-resisting-her-mom-s4-e7/ https://www.xporntv.com/videos/232061/there-is-no-resisting-her-mom-s5-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 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. ]]> Wed 20 Nov 2024 11:39:11 +0200 https://www.xporntv.com/videos/232061/there-is-no-resisting-her-mom-s5-e2/