https://www.transhero.com/sites/dating-my-stepson/ Tue 14 Jul 2026 06:20:30 +0200 https://www.transhero.com/videos/315041/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 03 Jul 2026 19:05:22 +0200 https://www.transhero.com/videos/315041/country-milf-is-too-much-to-handle-s1-e6/ https://www.transhero.com/videos/278816/the-most-ridicilous-stepfamily-video-ever-with-stepmom-cory-chase/
The most ridicilous stepfamily video ever with stepmom Cory Chase who wanted her stepson to creampie his girlfriend to cancel out stepdads cum as she just busted them fucking! He had to hurry up and she gave him a helping hand! ]]> Wed 18 Mar 2026 13:58:34 +0200 https://www.transhero.com/videos/278816/the-most-ridicilous-stepfamily-video-ever-with-stepmom-cory-chase/ https://www.transhero.com/videos/165009/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. ]]> Wed 18 Mar 2026 06:12:48 +0200 https://www.transhero.com/videos/165009/a-game-of-dare-always-spices-things-up-s4-e4/ https://www.transhero.com/videos/292911/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! ]]> Sat 14 Mar 2026 19:29:14 +0200 https://www.transhero.com/videos/292911/stepmom-milf-anya-olsen-gave-her-two-stepsons-upskirt-shots/ https://www.transhero.com/videos/347278/gigantic-boobs-milf-stepmom-educates-stepson-in-a-very-weird-way/
Gigantic boobs MILF stepmom is a curvy latina Lexi Luna who educates her stepson in a very weird way by making him suffer right in front of her! She exposes her huge tits and touches herself which really got him going! ]]> Thu 12 Mar 2026 09:48:32 +0200 https://www.transhero.com/videos/347278/gigantic-boobs-milf-stepmom-educates-stepson-in-a-very-weird-way/ https://www.transhero.com/videos/184754/huge-boobs-stepmom-milfs-baking-2-pies-for-their-lovely-stepsons/
Huge boobs stepmom MILF babes Rachael Cavalli and Daisy Fuentes baking two pies for their lovely stepsons and one thing lead to another! The surprized stepsons had no idea what was happening right there but did not mind at all fucking both step moms! ]]> Thu 12 Mar 2026 02:39:18 +0200 https://www.transhero.com/videos/184754/huge-boobs-stepmom-milfs-baking-2-pies-for-their-lovely-stepsons/ https://www.transhero.com/videos/399167/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. ]]> Wed 11 Mar 2026 02:38:42 +0200 https://www.transhero.com/videos/399167/there-is-no-resisting-her-mom-texas-patti/ https://www.transhero.com/videos/299458/hot-milf-stepmom-plays-stepson-his-sex-doll-after-he-got-the-hint/
Hot MILF stepmom Crystal Rush plays stepson his sex doll after he got the hint that she wanted to be it for him! His step mom was just amazingly sexy in lingerie with these big fake tits on her! He had no problem driving his huge cock inside of her! ]]> Sat 07 Mar 2026 18:00:27 +0200 https://www.transhero.com/videos/299458/hot-milf-stepmom-plays-stepson-his-sex-doll-after-he-got-the-hint/ https://www.transhero.com/videos/260491/stepson-walks-in-on-huge-boobs-stepmom-milf-in-the-shower/
Stepson walks in on huge boobs stepmom MILF Josephine Jackson in the shower and was amazed by her all natural big tits and she let him touch them! Soon after that she was sucking and riding on his big cock in this family taboo porn video! ]]> Thu 05 Mar 2026 10:12:53 +0200 https://www.transhero.com/videos/260491/stepson-walks-in-on-huge-boobs-stepmom-milf-in-the-shower/ https://www.transhero.com/videos/196661/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! ]]> Sat 28 Feb 2026 07:39:41 +0200 https://www.transhero.com/videos/196661/huge-tits-milf-stepmom-andi-avalon-proves-stepson-she-isnt-boring/ https://www.transhero.com/videos/245570/turning-up-the-heat-cassie-del-isla/
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. ]]> Fri 27 Feb 2026 15:49:55 +0200 https://www.transhero.com/videos/245570/turning-up-the-heat-cassie-del-isla/ https://www.transhero.com/videos/185799/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! ]]> Sun 22 Feb 2026 05:36:44 +0200 https://www.transhero.com/videos/185799/free-use-present-for-xmas-from-his-sexy-milf-stepmom-annie-king/