https://www.thepornstar.com/models/jimmy-michaels/ Mon 17 Aug 2026 01:55:55 +0200 https://www.thepornstar.com/videos/457860/cubbi-thompson-and-jimmy-michaels-discover-a-horny-stepmom-s-wild-solution/
Cubbi Thimpson is a little self-conscious - she married Jimmy Michaels dad and the age gap is getting to her. Cubbi asks her stepson Jimmy if she has let herself go or maybe if she looks different from when they met - she wants to know what's wrong with her!? Jimmy looks his stepmom up & down - her big tits are bursting out of her bikini top and her smooth legs look sexy. Cubbi has an idea - if her stepson can give her some good sex, she will feel fulfilled! Jimmy thinks it's a little disrespectful to his dad, but his stepmom's boobs are so big, juicy & pierced! Jimmy can't help but play with her fat knockers and his stepmother even wants to suck his cock - right there in the pool! Jimmy begins to bang his stepmother from behind while gripping onto her tits, but they get worried his dad will be home soon so they move to Jimmy's bedroom. Jimmy pounds away at his stepmom's eager pussy, stretching her out and making her orgasm all over his cock. Cubbi can't help but cum all over her stepson's hard dick multiple times as he thrusts in & out of her. Once his stepmom is satisfied, she lets Jimmy cum all over her face & in her mouth! ]]> Sun 09 Aug 2026 08:55:40 +0200 https://www.thepornstar.com/videos/457860/cubbi-thompson-and-jimmy-michaels-discover-a-horny-stepmom-s-wild-solution/ https://www.thepornstar.com/videos/454518/armani-black-and-jimmy-michaels-can-t-resist-just-a-quickie/
Jimmy Michaels is a pervert and everyone knows it. So when he tries to feel up his stepmother Armani Black, she's not particularly shocked. What is surprising though, is that Armani secretly likes it! It makes her wet when Jimmy calls her 'Mommy' and rudely takes his cock out in the kitchen and tugs it in front of her. What a bad boy! She can't help but touch her dripping MILF pussy. Her husband is in the shower - he takes long showers. Maybe... just a quickie? Aramni wants her stepson's young, hard dick in her mouth, she sucks him right there in the kitchen. Her mature pussy is soaked from blowing Jimmy. She takes her stepson to the living room and slides down his meat with her greased up hole. Armani twerks all over Jimmy and then lets him hit it from the back. Jimmy pounds his stepmom to an intense orgasm as her big pierced tittties bounce with each thrust. Armani takes her stepson's load in her mouth just as she hears her husband getting out of the shower, narrowly avoiding being caught! ]]> Sat 08 Aug 2026 19:39:49 +0200 https://www.thepornstar.com/videos/454518/armani-black-and-jimmy-michaels-can-t-resist-just-a-quickie/ https://www.thepornstar.com/videos/472000/hot-blonde-milf-stepmother-sydney-paige-wants-to-get-her-stepsons-seeds/
Hot blonde MILF stepmother Sydney Paige with big boobs wants to get pregnant but her hubby is shooting blanks so she visits her stepson to get his seeds She asks him to jerk off and she offers helping hands and her soaking wet pussy too ]]> Wed 05 Aug 2026 03:39:59 +0200 https://www.thepornstar.com/videos/472000/hot-blonde-milf-stepmother-sydney-paige-wants-to-get-her-stepsons-seeds/ https://www.thepornstar.com/videos/451124/wet-tease-leads-to-dick-delivery/
]]> Tue 28 Jul 2026 13:12:33 +0200 https://www.thepornstar.com/videos/451124/wet-tease-leads-to-dick-delivery/ https://www.thepornstar.com/videos/458369/laura-bentley-and-jimmy-michaels-exchange-secrets-in-a-steamy-showdown/
Just a peek, right? Can't hurt, right!!? That's what Jimmy Michaels thinks when he watches his hot stepmom Laura Bentley in the shower. But what happens when she finds out? She wants to talk... oh no!! She is NOT going to tell Jimmy's father. But, she wants a peek at his junk - fair is fair! Laura is impressed with her stepson's cock. She takes off her robe and lets Jimmy remove her underwear. Jimmy goes down on his stepmom, eating her warm, wet pussy. Laura gets horny from getting licked by her stepson and tells him she wants to fuck. Jimmy shoves his hard cock in his stepmother and begins to thrust inside her eager hole. Laura's pussy creams up as her stepson bangs away at it, making her have an intense orgasm. Laura rewards her stepson by taking him deep in her throat. She rides her stepson hard and cums again before letting Jimmy dump his load right in her mouth! ]]> Wed 22 Jul 2026 18:47:45 +0200 https://www.thepornstar.com/videos/458369/laura-bentley-and-jimmy-michaels-exchange-secrets-in-a-steamy-showdown/ https://www.thepornstar.com/videos/459123/anissa-kate-and-jimmy-michaels-discuss-dad-s-important-advice/
Being a stepmom isn't easy & Anissa Kate really wants to have a healthy relationship with her new stepson Jimmy Michaels. Jimmy has always been a little stand-offish with her so she decides to confront him. When he heads to the bathroom during their conversation, Anissa gets a gander on his phone only to find steamy pictures of herself in his gallery! She knows how important it is to Jimmy's father that they get along, so she decides to fulfill Jimmy's stepmom fantasy. Anissa shows off her big, perfect tits and lets Jimmy squeeze & fondle them. Then Anissa sucks her stepson's already stiff cock before climbing on top and sliding it into her hot MILF pussy. Jimmy pounds his stepmom hard, fucking her to multiple orgasms as she moans in pleasure. Her big tits and tight pussy were on display while she wriggled & jiggled on her stepson's hard meat. After Jimmy got his stepmom off, she sucked the cum right out of his balls and into her mouth and even swallowed it all! ]]> Tue 21 Jul 2026 15:50:09 +0200 https://www.thepornstar.com/videos/459123/anissa-kate-and-jimmy-michaels-discuss-dad-s-important-advice/ https://www.thepornstar.com/videos/464450/wendy-raine-and-jimmy-michaels-the-ultimate-stepmom-vs-milf-showdown/
]]> Mon 20 Jul 2026 09:28:41 +0200 https://www.thepornstar.com/videos/464450/wendy-raine-and-jimmy-michaels-the-ultimate-stepmom-vs-milf-showdown/ https://www.thepornstar.com/videos/460536/selina-bentz-s-taboo-tryst-with-brother-s-friend/
]]> Mon 13 Jul 2026 23:07:46 +0200 https://www.thepornstar.com/videos/460536/selina-bentz-s-taboo-tryst-with-brother-s-friend/ https://www.thepornstar.com/videos/457867/haley-spades-and-jimmy-michaels-share-a-steamy-moment-of-first-dibs/
Dibs! A pretty common way amongst stepsiblings to call front seats, best views or even prime beds or bedrooms. Haley Spades is just too fast for her stepbrother Jimmy Michaels on their family vacation and calls dibs on the nice bed - leaving Jimmy a nasty old couch or crappy bunk. Jimmy at least gets to shower first but he takes forever and Haley isn't having it. She walks in on her stepbrother and catches him jerking off! Haley offers to finish him, if it'll speed things up and free the shower. Jimmy is surprised but accepts the offer and Haley begins to jerk her stepbro's big boner right there in the bathroom. She pulls her tits out to help him a bit and even drops to her knees to suck her stepbrother's cock. But Haley gets horny and tells her stepbrother they should go to the bed together. Jimmy eats his horny little stepsister's pussy and then thrusts into her from behind. Haley is impressed with her stepbro's big dick as he pounds away at her tight little pussy. Haley rides her stepbro, twerking her little butt all over his cock. Jimmy fucks his stepsister real good, making her cum repeatedly on his stiff knob. He finishes by nutting all over Haley's face - she excitedly runs to get her turn in the shower now! ]]> Fri 10 Jul 2026 10:27:08 +0200 https://www.thepornstar.com/videos/457867/haley-spades-and-jimmy-michaels-share-a-steamy-moment-of-first-dibs/ https://www.thepornstar.com/videos/451161/charlotte-rayn-and-jimmy-michaels-discover-the-rewards-of-academic-success/
My hot stepmom has been getting calls from my school about my declining grades. I should care, but I more focused on getting pussy in college like a normal person. Unlike a normal person, my stepmom teases me with her juicy tits, but when I try to grab them she facepalms me! She tries to motivate me to improve my grades, a little studying - a lot of tits! I go back to her after I've asborbed some college crap and try again, she shows me her beautiful ass but that's STILL all I get for now. If this keeps up, I might actually learn something. Finally, after like 3 hours of studying, my stepmom decides to reward my hard work by sucking my hard cock. I turn around and slam her MILF pussy from behind while I watch her big tits knock together - it reminded me of a physics problem I was working on earlier. What's happening to me!? Anyway, I kept pounding my hot stepmom and made her orgasm for all her sexy troubles & then unloaded all over her myself. I'm definitely getting better grades this semester! ]]> Wed 08 Jul 2026 17:50:12 +0200 https://www.thepornstar.com/videos/451161/charlotte-rayn-and-jimmy-michaels-discover-the-rewards-of-academic-success/ https://www.thepornstar.com/videos/453893/busty-cece-mecta-slammed-deep-by-jimmy-michaels/
Use code FilthyKings for a FREE WEEK of Filthy Kings! Featuring Jimmy Michaels, CeCe Mecta ]]> Sat 27 Jun 2026 21:38:11 +0200 https://www.thepornstar.com/videos/453893/busty-cece-mecta-slammed-deep-by-jimmy-michaels/ https://www.thepornstar.com/videos/464295/callie-brooks-and-jimmy-michaels-have-fun-with-my-maraca-in-a-steamy-scene/
Cinco de Mayo has to be one of the funnest holidays out there. Tacos & music - what's not to love! But some people get a tad TOO excited, if that's even possible. When uber-MILF Callie Brooks comes home to see her pale gringo stepson, Jimmy Michaels, decked out in a sombrero & rocking the maracas - she is a little concerned. But Jimmy assures her he's been given a pass by his Mexican buddy Julio from college. Checks out, right?? Convinced, Callie can't help but get into the infectious spirit of the festivities as she dances it up with her stepson. But all that bumpin' & grindin' with his hot stepmom gets Jimmy poking through his poncho! Callie is feeling frisky so she shakes & jerks her stepson's stiff maraca. Jimmy goes wild with Callie's jiggly tits & phat ass, shakin' & slappin' them to his heart's content. His stepmom throws it back on his hard cock, her amazing ass twerking it up on Jimmy's dick. Jimmy makes Callie cum mucho hard as he slams her perfect pussy. Finally, Jimmy celebrates the date by unloading in his stepmom's face. Happy Cinqo De Mayo, amigos! ]]> Fri 26 Jun 2026 23:12:34 +0200 https://www.thepornstar.com/videos/464295/callie-brooks-and-jimmy-michaels-have-fun-with-my-maraca-in-a-steamy-scene/