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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. Runtime: 3:11 Added: 2025-05-29 Tags: mini skirt brunette milf
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. Runtime: 2:57 Added: 2024-01-25 Tags: blonde milf landing strip pussy
Ellie Murphy loves St. Patrick's Day. She comes in and pinches her stepson, Tyler Cruise's, butt because he's not wearing green. Tyler has questions about faeries, so he starts asking his stepmom. Ellie tells Tyler that they'll fuck him and steal his cum for a big juicy creampie.Later, Tyler has put on a green bowtie to prevent himself from getting pinched, but that still wouldn't prevent a faerie from pinching his cum. When Ellie leaves the bedroom dressed as a faerie, Tyler immediately understands what she wants. He's so eager to take his stepmom into his lap to palm her tits as she pops his hardon out for some good suck. When Ellie lays with her thighs spread out, Tyler dives in to eat her sweet twat.Getting comfy on the couch, Tyler holds his dick steady while Ellie climbs aboard to ride him. He rolls Ellie to her back to dick her down, then spoons behind her to continue her pussy party. On her knees, Ellie enjoys a doggy style pussy pounding and then sighs in contentment as Tyler delivers a luck o' the Irish creampie. Runtime: 1:23 Added: 2026-03-14 Tags: shaved pussy milf girl-boy
Jessica Ryan is doing laundry when her stepson Jimmy Michaels comes in to ask her a question. He confesses that he is interested in his hot teacher while also fondling Jessica's thongs. Eventually, Jessica realizes that Jimmy really has a thing for older women and their panties. When Jimmy asks Jessica to share a secret to make him feel better, she admits she wants a guy to cum on her panties for her.Later, Jessica is masturbating with her own thong when Jimmy knocks on the door. He asks to see his stepmom's panties and she hesitates before agreeing. Jimmy can see how wet Jessica's panties are, and she admits she was thinking about their previous conversation. She invites Jimmy to make her fantasies come true. Popping those big jugs out, Jessica spreads her thighs so Jimmy can touch her pussy and then rub his dick against her panties.Sliding Jessica's thong aside, Jimmy shoves his dick into her tight twat before he eats her out. Stepmommy takes charge, riding Jimmy in cowgirl. Jessica sucks their combined juices from Jimmy's dick and then gets to her feet so her stepson can take her from behind. Pulling out, Jimmy busts a nut into Jessica's thong and then watches as she pulls it up to cover her pussy in jizz. Runtime: 3:02 Added: 2025-03-05 Tags: hairy pussy panties brunette
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. Runtime: 1:59 Added: 2024-03-29 Tags: blonde european milf
Ashley Tee is forgetful and stressed for an upcoming meeting. Her stepson Enzo East helps her get her things together and she gives him a grateful smile before taking off. Ashley is in such a rush to go that she doesn't notice she dropped her diary, which Enzo picks up and reads. He can't believe what a slut his stepmom was back in the day!When Ashley comes home, she finds her stepson clutching her diary. They chat as Enzo asks questions about his stepmom's sexcipades. That gets Ashley thinking about how much fun she had, so later she puts on just a robe and goes to her stepson's room. There, she tells him she's going to all about how she used to fuck. She starts by straddling Enzo's hips as she lets her robe fall away. Then she peels the covers back to unveil his hardon and blow him.Returning to her earlier position astride Enzo's hips, Ashley slides her bald twat onto his fuck stick to ride him in cowgirl. She turns around and keeps her pussy party going in reverse cowgirl. Ashley needs more, so she gets on her knees for Enzo to do her in doggy. Then she rolls onto her back for one more bald pussy pounding as Enzo works his way up to pulling out and nutting all over her stomach. Runtime: 1:00 Added: 2025-09-06 Tags: fair skin masturbation mini skirt
Shay Sights is dressed as an 80s fitness instructor. She's waiting for Zane Walker, a football player that she's coaching. When Zane arrives, she keeps smacking his butt until he questions it. That lets her turn around and insist that Zane slaps her ass. She keeps him doing it again and again until she's satisfied with the action.Turning back to face Zane, Shay whips those big sweater puppies out and informs Zane that she's not his mommy. She wants a hot workout, and that's going to begin with Zane squeezing her tits. Zane does as he's told and then watches in shock as Shay falls onto the couch and rips the crotch right out of her own leggings. With a blatant invitation to stick it in, Zane can't possibly say no.Cock loving Shay isn't satisfied with just one position. She gets on her knees to enjoy her football hunk in doggy. Then she slurps him down in a blowjob before climbing on top to ride Zane in reverse cowgirl. Shay still wants more, so she falls to her side and lets Zane bang her as they spoon together. That's all Zane can take as he pulls out to pop on Shay's stomach. Licking her fingertips clean of cum, Shay smiles as Zane thanks her for the workout. Runtime: 1:52 Added: 2023-05-18 Tags: black hair fair skin shaved pussy
Captain Brandi Love isn't about to take any shit from anyone, especially not from Juan Loco or Ricky Spanish. She knows the boys are friends, so she questions whether they can work well together. Furthermore, she notes that Ricky has been working there for a year and still needs additional training in dealing with the highly dominant and extremely sexual ladies who make up the majority of their clientele. The boys need to be ready for any situation. Abruptly walking forward, Captain Love grabs Ricky's dick and asks if his cock is hard for her. When Ricky says yes, she tells him he's not allowed to ever fraternize with the clients.Later, Captain Love is lecturing the boys on safety when Ricky grabs a buoy and pretends to fuck it. Brandi notices and tells him that if he wants to fuck the buoy, he should pull his dick out and just fuck the buoy. Turning to Juan, Brandi asks if he likes watching his friend bang the buoy even as she's stroking him off. Then she asks Juan if he'd like a blowjob. Ricky tries to run off, but Captain Love wants him to sit there and watch. Getting up from her crouched BJ position, Brandi instructs Juan to have a seat so she can peel off her panties and ride his dick.Insisting this is still part of training so the boys can learn how to take control, Captain Love orders Ricky to whip it out. Finding him nice and hard for her, she lets him see her tits as long as he strokes himself off. When Brandi decides Ricky can have a turn banging her, she gets on her hands and knees so he can do her in doggy as she sucks Juan off. Juan gets another go with Brandi's velvet glove as she sits on the table with her thighs spread wide open. That position lets Ricky stand above her so she can stroke and suck his fuck stick. That keeps Ricky nice and primed for Brandi to ride him in cowgirl. As she leans forward to blow Juan, her tits smush right into Ricky's face. Dropping to her knees with one cock in either hand, Brandi sucks and blows and strokes until both Ricky and Juan have given her a mouthful of cum. When Ricky compliments Juan on how well he did on his first day, Brandi tells him that it's his first and last day because they're both fired. Runtime: 3:08 Added: 2022-06-10 Tags: high heels bras panties
Sophia Locke is so pleased to get a mother's day gift from her stepson Parker Ambrose. He also gave her a pearl necklace and booked them in for a dinner since his dad's out of town. As Parker is helping Sophia put the necklace on, it breaks and spills pearls all over the place including down her shirt. Parker freaks out and tries to help Sophia get the pearls, but ends up with his hands down her shirt.As Parker is finishing up getting ready for dinner, Sophia comes in looking fine as fuck. Parker tells her the plan and mentions giving her a new pearl necklace. Sophia begins questioning him what kind of necklace, and eventually admits that what she really wants is a creampie but she'll settle for some cum pearls.Taking Parker to the couch, Sophia spreads her thighs to teach him how to eat pussy. She sucks his dick in return, then climbs on top to ride her stepson in cowgirl. Next up is some doggy dicking as Parker admires Sophia's big ass from behind. Sophia rolls onto her back so her stepson can get her off, then sits up so he can give her the pearl necklace she really wanted for mother's day. Runtime: 1:43 Added: 2025-05-02 Tags: big boobs shaved pussy redhead
It's a bit awkward for Koda Monroe, but she has to confront her new stepson Leo Valentino about something her daughter said. She claims her daughter told her that Leo showed her his penis. Leo sets the story straight, explaining that his stepsister admired his penis like a snake without any provocation.Koda takes off to consult with her daughter, then returns and pulls Leo's pants down. It is like a snake and Koda wants to touch it. Leo is okay with that, and in return she offers her stepson her big titties and a taste of her milfy pussy. Then, Koda drops to her knees to suck Leo's dick nice and deep.There's no question: Koda has got to get that cock inside her. She gets on her knees for some doggy dicking down and then climbs on top of Leo so she can ride the D in cowgirl. When Koda gets on her back, Leo eats her pussy and then shoves his long one back inside. Finally sated, Koda slurps the D until Leo gives her his cum shot. Runtime: 1:48 Added: 2026-01-03 Tags: big boobs high heels mini skirt
India Summer has kindly agreed to answer fan questions for Moms Teach Sex. This busty mom contemplates how many miles of dicks she has taken during her years as a porn star, and then reminisces about how much her enjoyment of participating in the Moms Teach Sex series has evolved. You'll love hearing India's honest tips for being good in bed, her preferences for porn to watch will definitely surprise you! Runtime: 1:03 Added: 2015-08-28 Tags: black hair bras panties
Nick Ross has a hot stepmom in Kristy Black. She comes home with a bunch of shopping bags and mentions to Nick that she wants to look her best so she can breed. Going to her bedroom, Kristy changes into her new lingerie and then calls Nick in.After asking some very pointed questions about what Nick would do to his girlfriend if he walked in and found her like this, Kristy pulls him in for a deep kiss. She has Nick do everything he just described, starting with suckling Kristi's hard nipples and having her suck his big dick. After sucking down Nick's hardon and lapping at his balls, Kristy climbs aboard to get that nice hardon into her tight twat.Turning around for reverse cowgirl, Kristy keeps on bouncing as Nick smacks her bubble butt. Falling to her side, Kristin lifts one leg so Nick can spoon behind her and shove back home. On her knees, Kristy enjoys a doggy style pussy pounding. When he's ready to blow, Nick flips Kristy onto her back so he can dive deep and fill her to the brim with his cum shot. Runtime: 2:04 Added: 2025-12-10 Tags: high heels shaved pussy bras
Robby Echo and his new stepmom Kate Dee are just getting to know each other. Over ice cream, Kate starts asking Robby questions about himself. Each of Robby's answers is flattering to Kate, who's really digging it. When Kate asks Robby his favorite outfit that he's seen her in, he pushes the envelope by saying that it was when he walked into the bathroom last week and saw her in a towel. That prompts Kate to ask Robby his favorite fantasy, which is revealed to be getting fucked by a hot milf who tucks him in. Now that Kate has confirmed that Robby is flirting with her, Robby turns the tables and begins asking her questions. She tells Robby that her favorite fantasy is him watching her getting fucked, not by his dad but by a stranger. That's not really Robby's thing, so Kate tells him her second favorite fantasy is straight up him fucking her. When Robby hesitates, Kate accidentally on purpose drips some ice cream on her big boobs. Dredging her fingers through the sweet cream, she licks it up before leaving Robby to it. From then on, there's some serious sexual tension between stepmom and stepson. Any time they come together, Kate is wearing something hot as hell that shows off her cleavage. Things keep ramping up until Robby tries to confront her about it. Instead of taking the conversation seriously, Kate offers to show Robby her tits. She pops them out and puts Robby's hands on them, then offers to fuck him and tuck him into bed.Pushing Robby backwards, Kate climbs on top of him and makes good on her promise. She kicks it off with a blowie that proves she's unparalleled with her mouth. Once she's done sucking and teasing Robby's dick with her big naturals, Kate climbs aboard to ride her stepson in reverse cowgirl. Getting on her hands and knees, Kat squeals in delight as Robby enters her from behind and gives it to her in doggy. Kate has already gotten off, but there's always room for more orgasms as she rolls onto her back and spreads herself wide open for Robby to kneel between her thighs and take her to pleasure town one more time. When Robby is on the verge of popping, Kate lays back and urges him to cover those knockers with his big load so she can rub it all into her boobs before tucking Robby in as promised. Runtime: 3:52 Added: 2022-03-31 Tags: big boobs fair skin shaved pussy
Jason goes to his stepmom Ivy Ireland to ask a question. He wants to know why hot girls are boring. Ivy points out that this wasn't what she meant when she told Jason he could come to her with anything, and besides, she's a great lay.Surprised, Jason questions Ivy about how slutty she really is. She reminisces about how wild she was during her college days, so Jason asks her to prove it by showing her tits. Ivy tells Jason that he'll have to see for himself as she offers her shirt for him to untie. Jason does as he's told, freeing his slutty stepmom's titties. Soon, Ivy has gone for the D to suck Jason off before suggesting they go to the bedroom.Another round of cock sucking and Ivy climbs on top for a reverse cowgirl ride. The big booty milf turns around so her stepson can admire her lovely landing strip as she keeps on riding in cowgirl. Getting on her knees, Ivy urges Jason to dick her down before she rolls onto her back so her stepson can pull out to cum on her tan lines. Jason understands now that he doesn't need to look outside the home for some good fuck. Runtime: 1:55 Added: 2024-09-06 Tags: brunette milf landing strip pussy
Max Fills and his stepmom Cherry kiss are in the midst of some semi-questionable study activities that are still clothes on. Max spills coffee on himself, and when Cherry notices he's made a mess. She asks if Max needs more coffee, but he declines. Cherry does want coffee, but no cream or sugar. She wants creampie.Once that's out, Cherry stops pretending she doesn't want her stepson to fuck her to the finish line. She crawls across the couch and pulls his hardon out, dipping her head for some good suck. Cherry's BJ gets Max nice and comfy with the idea of fucking his stepmommy and glutting her with his baby batter.Climbing onto Max's lap, Cherry rides him in reverse cowgirl and then cowgirl. She's insatiable, rolling onto her back to give Max her pussy for another round. When Cherry gets on her knees and has her miniskirt up around her waist, Max can't get enough of pounding that cooch. That ass really does it for him as he delivers the much desired creampie to his horny stepmilf. Runtime: 2:21 Added: 2024-10-30 Tags: mini skirt shaved pussy panties
Crystal Clark isn't shy about strutting around the house in her sheer thong and bra even while her stepson Anthony Pierce and his friend Nick Strokes are around. When she goes back to put her dress on she realizes she needs help zipping it up. When Crystal asks the boys, they go off into their own little fantasy world for a moment. Then they admit they're asking girls about what they like through AMAs. Crystal offers to give the guys an AMA once she's ready for date night.Sitting between her stepson and his friend on the couch, Crystal answers their questions. She also encourages them to touch her all over. With their fantasies coming true, neither Anthony nor Nick is about to question their good fortune. They keep peppering Crystal with increasingly sexual requests as they palm her pussy, give her sweet kisses, and then suckle her titties. Soon, Anthony and Nick are sampling Crystal's pussy juices before they experience handjobs from a mature lady.Getting on her knees, Crystal demonstrates a nice BJ for Anthony as Nick pulls her thong down to fuck her in doggy. Then Crystal gets on her back to let Anthony get his dick wet as Nick enjoys some good suck. Crystal demonstrates her reverse cowgirl skills up to a squirting orgasm for Nick while slurping her juices from Anthony. Then she lets Anthony give it to her on her back until he pulls out to nut on her muff. Moments later, Nick succumbs to Crystal's handjob to give her a nice pearl necklace. Runtime: 3:33 Added: 2024-08-22 Tags: high heels mini skirt puffy nipples
Antonia Sainz just needs to have a creampie to start her day, every single day. Otherwise, she's cranky as can be. She takes her anger out on her stepson, Charlie Dean, who is all too cheerful in the mornings. In fact, after picking a fight with Charlie, Antonia stomps away and leaves him wondering what her problem is.The next morning, Antonia is still in a bad mood but she's at least open to talking it through when Charlie tries questioning her. They come to the conclusion that since Antonia needs cum dripping into her panties all day and Charlie masturbates daily, they can make this work. Things get real when Antonia pops her tits out for Charlie to love on, then has him eat her out for breakfast. Next, she gives him a titty fuck and blows him with every evidence of pleasure.Getting to her feet, Antonia leans forward and lets Charlie come up behind her and dick her down the way she loves. Sitting on the table puts Antonia's pussy at the perfect height for her stepson to keep their passion up. Taking a seat in the chair, Charlie pulls Antonia on top of him. His stepmilf rides him in reverse cowgirl and then returns to her feet so Charlie can dive nice and deep. They wind down with Antonia back on the table, one calf hooked over Charlie's shoulder to open her up to his promised creampie. Runtime: 1:40 Added: 2025-10-03 Tags: redhead big areolas european

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