https://www.429men.com/sites/dating-my-stepson/ Tue 14 Apr 2026 22:12:32 +0200 https://www.429men.com/videos/318187/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. ]]> Thu 26 Feb 2026 01:46:13 +0200 https://www.429men.com/videos/318187/country-milf-is-too-much-to-handle-s1-e6/ https://www.429men.com/videos/396416/free-use-present-for-xmas-from-his-sexy-milf-stepmom-annie-king/
Free use present for Xmas from his sexy MILF stepmom Annie King Stepson could do anything he pleases with her as she wanted to be bread as well! This way they both got what they wanted for Christmas and it was amazingly hot to watch them do it like this! ]]> Wed 25 Feb 2026 22:18:30 +0200 https://www.429men.com/videos/396416/free-use-present-for-xmas-from-his-sexy-milf-stepmom-annie-king/ https://www.429men.com/videos/233961/her-mom-took-me-for-a-test-drive-cherry-kiss/
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. ]]> Tue 24 Feb 2026 02:30:29 +0200 https://www.429men.com/videos/233961/her-mom-took-me-for-a-test-drive-cherry-kiss/ https://www.429men.com/videos/272715/dating-my-stepson-kira-queen-s-casino-night-with-stepson/
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 must face off with her stepson, Matthew Meier. They are to enjoy a casino night together, even though they can't seem to stop telling each other how much they hate one another. Matthew doesn't take it well when Kira beats him, and she slaps him to stop him from continuing to yell. The next moment, the two of them are making out.Once the two begin their kissing, they can't keep their hands off one another. The dealer makes his way out of the room, leaving Matthew and Kira to make their way over to the couch. Matthew eats his stepmilf out and then watches with hot eyes as Kira returns the favor by blowing him. Soon enough, Kira rolls onto her back and spreads her thighs to welcome Matthew inside.They begin in missionary with Kira on her back, but soon their passion heats up to even greater levels. Kira gets on her side so her stepson can slide deep inside as they spoon together. Then she gets on her knees so Matthew can really give it to her in doggy. When Matthew lies down on his back, Kira dominates him first in cowgirl and then in reverse cowgirl. That final position is all Matthew can take; he gluts his stepmom with a creampie that leaves them both breathless. ]]> Sat 21 Feb 2026 22:54:47 +0200 https://www.429men.com/videos/272715/dating-my-stepson-kira-queen-s-casino-night-with-stepson/ https://www.429men.com/videos/288525/huge-tits-milf-stepmom-andi-avalon-proves-stepson-she-isnt-boring/
Huge tits MILF stepmom Andi Avalon proves to her big cock stepson she is not boring at all by sucking and riding his big dick while he recorded everything on his camera! This big boobs blonde cougar was about to go out with her friends allegedly! ]]> Fri 20 Feb 2026 12:33:33 +0200 https://www.429men.com/videos/288525/huge-tits-milf-stepmom-andi-avalon-proves-stepson-she-isnt-boring/ https://www.429men.com/videos/330770/italian-stepmom-milf-rebecca-volpetti-once-was-stepsons-crush/
Italian stepmom MILF Rebecca Volpetti once was stepsons crush and when she called him stepson when she came home one day the truth came out! She admitted she also used to have a crush on him and then this happened between them! ]]> Thu 19 Feb 2026 07:34:07 +0200 https://www.429men.com/videos/330770/italian-stepmom-milf-rebecca-volpetti-once-was-stepsons-crush/ https://www.429men.com/videos/414239/i-didnt-see-this-cumming-shalina-devine/
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 17 Feb 2026 11:21:30 +0200 https://www.429men.com/videos/414239/i-didnt-see-this-cumming-shalina-devine/ https://www.429men.com/videos/274728/mature-stepmom-on-a-date-with-a-guy-who-wanted-her-stepdaughter/
Mature stepmom Texas Patti on a date with guy Alex Charger who wanted to date her teen stepdaughter but had to meet her step mom first to see if there was any type of connection between them and oh dear there definitely was! ]]> Fri 13 Feb 2026 03:24:27 +0200 https://www.429men.com/videos/274728/mature-stepmom-on-a-date-with-a-guy-who-wanted-her-stepdaughter/ https://www.429men.com/videos/290572/stepmom-milf-anya-olsen-gave-her-two-stepsons-upskirt-shots/
Stepmom MILF Anya Olsen gave her two stepsons upskirt shots when cleaning with full intention and then got down on her knees to suck em both off before they take turns fucking her wet cougar pussy in this incredible family taboo threesome! ]]> Thu 12 Feb 2026 19:45:08 +0200 https://www.429men.com/videos/290572/stepmom-milf-anya-olsen-gave-her-two-stepsons-upskirt-shots/ https://www.429men.com/videos/381817/dating-my-stepson-i-creampied-my-stepmom-after-picnic-micky-muffin/
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 12 Feb 2026 04:53:04 +0200 https://www.429men.com/videos/381817/dating-my-stepson-i-creampied-my-stepmom-after-picnic-micky-muffin/ https://www.429men.com/videos/261398/there-is-no-resisting-her-mom-texas-patti/
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. ]]> Fri 06 Feb 2026 21:08:45 +0200 https://www.429men.com/videos/261398/there-is-no-resisting-her-mom-texas-patti/ https://www.429men.com/videos/284059/divorced-stepmom-milf-shalina-devine-is-really-into-guys-now/
Divorced stepmom MILF Shalina Devine is really into guys now and her stepson even brought her a rose at the beginning of their date! That started off perfectly for her and now they were going to cook together She told him she was very good at it! ]]> Thu 05 Feb 2026 17:23:24 +0200 https://www.429men.com/videos/284059/divorced-stepmom-milf-shalina-devine-is-really-into-guys-now/