https://www.rainblow.xxx/sites/dating-my-stepson/ Wed 15 Apr 2026 08:02:22 +0200 https://www.rainblow.xxx/videos/304488/showing-her-mom-my-best-moves-bunny-madison/
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. ]]> Sat 14 Mar 2026 14:18:22 +0200 https://www.rainblow.xxx/videos/304488/showing-her-mom-my-best-moves-bunny-madison/ https://www.rainblow.xxx/videos/334695/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. ]]> Sat 14 Mar 2026 02:10:45 +0200 https://www.rainblow.xxx/videos/334695/there-is-no-resisting-her-mom-texas-patti/ https://www.rainblow.xxx/videos/317809/dating-my-stepson-pleasured-by-the-pool-micky-muffin-and-shalina-devine/
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. ]]> Wed 11 Mar 2026 08:51:40 +0200 https://www.rainblow.xxx/videos/317809/dating-my-stepson-pleasured-by-the-pool-micky-muffin-and-shalina-devine/ https://www.rainblow.xxx/videos/133340/stepmum-s-secret-confession-pristine-edge/
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? ]]> Tue 10 Mar 2026 03:58:20 +0200 https://www.rainblow.xxx/videos/133340/stepmum-s-secret-confession-pristine-edge/ https://www.rainblow.xxx/videos/360856/dating-my-stepson-playing-my-cards-right-pristine-edge/
This season on Dating my Stepson, Jayden Marcos is taking a new spin towards finding love. She has decided to go on a date with the potential girlfriend's mom. If it works out, he'll date the daughter right on the spot. Today's date is with 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. ]]> Mon 09 Mar 2026 14:17:43 +0200 https://www.rainblow.xxx/videos/360856/dating-my-stepson-playing-my-cards-right-pristine-edge/ https://www.rainblow.xxx/videos/306329/the-mommy-you-d-want-to-marry-bunny-madison/
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 07 Mar 2026 01:22:57 +0200 https://www.rainblow.xxx/videos/306329/the-mommy-you-d-want-to-marry-bunny-madison/ https://www.rainblow.xxx/videos/231530/dating-my-stepson-filled-up-before-dinner-shalina-devine/
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. ]]> Mon 23 Feb 2026 20:55:52 +0200 https://www.rainblow.xxx/videos/231530/dating-my-stepson-filled-up-before-dinner-shalina-devine/ https://www.rainblow.xxx/videos/301633/micky-muffin-is-having-a-picnic-with-her-stepson/
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. ]]> Sat 21 Feb 2026 08:33:18 +0200 https://www.rainblow.xxx/videos/301633/micky-muffin-is-having-a-picnic-with-her-stepson/ https://www.rainblow.xxx/videos/265283/dating-my-stepson-going-overboard-on-her-pussy-kira-queen/
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. ]]> Thu 19 Feb 2026 21:17:58 +0200 https://www.rainblow.xxx/videos/265283/dating-my-stepson-going-overboard-on-her-pussy-kira-queen/ https://www.rainblow.xxx/videos/406993/having-sex-with-her-mom-before-dating-the-potential-gf-crystal-rush/
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. ]]> Thu 19 Feb 2026 17:56:26 +0200 https://www.rainblow.xxx/videos/406993/having-sex-with-her-mom-before-dating-the-potential-gf-crystal-rush/ https://www.rainblow.xxx/videos/310148/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 17 Feb 2026 12:41:06 +0200 https://www.rainblow.xxx/videos/310148/her-mom-took-me-for-a-test-drive-cherry-kiss/ https://www.rainblow.xxx/videos/311877/her-stepmom-s-traditional-technique-millie-morgan/
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 16 Feb 2026 15:08:41 +0200 https://www.rainblow.xxx/videos/311877/her-stepmom-s-traditional-technique-millie-morgan/