https://www.thepornstar.com/models/jimmy-michaels/ Thu 02 Jul 2026 12:21:38 +0200 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/ https://www.thepornstar.com/videos/468989/stepson-rails-stepmom-alyssia-seductive-gigi/
Use code FilthyKings for a FREE WEEK of Filthy Kings! Featuring Jimmy Michaels, Gigi Dior, Alyssia Vera ]]> Thu 25 Jun 2026 20:18:20 +0200 https://www.thepornstar.com/videos/468989/stepson-rails-stepmom-alyssia-seductive-gigi/ https://www.thepornstar.com/videos/462578/a-wild-night-with-andie-anderson-andi-avalon-armani-black-cubbi-thompson-danielle-renae-ellie-tay-jade-luv-mandy-waters-savanah-storm-taylor-vixxen-jimmy-michaels-jodie-johnson-johnny-love-juan-loco-kai-jaxon-parker-sims/
Best StepMILFS & Stepson 2024 Compilation ]]> Thu 18 Jun 2026 11:04:17 +0200 https://www.thepornstar.com/videos/462578/a-wild-night-with-andie-anderson-andi-avalon-armani-black-cubbi-thompson-danielle-renae-ellie-tay-jade-luv-mandy-waters-savanah-storm-taylor-vixxen-jimmy-michaels-jodie-johnson-johnny-love-juan-loco-kai-jaxon-parker-sims/ https://www.thepornstar.com/videos/463619/bambi-barton-and-jimmy-michaels-in-a-tense-struggle-for-desire/
Hard times make strong men. Except for Jimmy Michaels, he's weak. And not hard - not yet, anyway. But when his skanky stepsister Bambi Barton is getting changed with her door open, Jimmy snaps a few pics of her juicy tits. Jimmy ain't no dummy! Now off to the bathroom to tug it. Except Jimmy IS a dummy and doesn't lock the door, so naturally Bambi walks in on her stepbrother jerking his meat. To her tits! Jimmy explains he hasn't had sex in a whole year. Bambi feels sorry for him and charitably offers her boobs up to be jerked on. As Jimmy wanks his willy to his stepsister's exposed tits, she feels a pang of pity. How pathetic her stepbrother looks. She decides to jerk & suck her loser stepbrother - somebody has to do it! Jimmy manages to take her to the bedroom and rub on her pussy enough to get her a little wet. Bambi lets her desperate stepbrother slide his cock into her pussy and she's actually mildly impressed as he pounds away at her hole. Until he starts sniffing her pantioes - what a pervert! That doesn't stop this twangy teen from hopping on board and bouncing her fine ass on her stepbro's cock. He even managed to eke an orgasm out of Bambi. She rewarded him by letting him nut in her pussy & boy oh boy did Jimmy ever unleash in there! ]]> Wed 10 Jun 2026 00:46:58 +0200 https://www.thepornstar.com/videos/463619/bambi-barton-and-jimmy-michaels-in-a-tense-struggle-for-desire/ https://www.thepornstar.com/videos/461657/charli-phoenix-and-jimmy-michaels-rush-to-get-ready-for-company/
Sometimes you just wanna rub one out, but guests are coming over & your stepmom is going nuts cleaning! Jimmy Michaels wants to jerk off when his stepmom Charli Phoenix insists on doing his laundry. She pulls the covers off her naked stepson, only to reveal his activities - but she doesn't care! She just wants him to hurry up & cum before the guests arrive. In fact, she's willing to help her ever-tardy stepson. She spits on her hand and begins to jack him off. Jimmy begins to squeeze his stepmom's big, fat titties. Charli begins to lick & suck her stepson's hard cock, to speed up the process, of course. But he STILL hasn't cum. She is impressed with his stamina! Jimmy's stepmom decides that stuffing his dick into her pussy is the best course of action. Charli lets her stepson penetrate her from behind - she is doing this to help him, but she has to admit to herself, she kinda likes it too! He even smacks her big, beautiful ass! Jimmy tells her she is slutty as he fucks multiple orgasms out of his now horny stepmom, while her big boobs bounce around. Finally, Jimmy juices up his stepmom's pretty face with his cum just before the guests arrive! ]]> Fri 05 Jun 2026 04:51:36 +0200 https://www.thepornstar.com/videos/461657/charli-phoenix-and-jimmy-michaels-rush-to-get-ready-for-company/ https://www.thepornstar.com/videos/452774/katie-morgan-and-jimmy-michaels-bring-you-an-unforgettable-show/
Jimmy Michaels dislikes getting ordered around, especially by his stepmom Katie Morgan. To add insult to injury - Katie just lays out by the pool - naked - showing off her big tits and fluffy MILF muff, while he has to do chores.They need to talk! Jimmy approaches his naked stepmother - she can't waltz around without any clothes on!? But why not, she retorts!? It's the human body and it's beautiful! Besides, she is not his real mom. Jimmy confesses he gets...urges. Katie is flattered, but that doesn't solve Jimmy's problem. Katie proposes a solution - her stepson can watch her naked while he jerks off - she thinks it's hot! Jimmy is hesitant, but he can't resist. Neither can his stepmom once she sees her stepson's big, hard cock. She wants to suck it! Katie begins to slurp and slobber all over Jimmy's dick. Jimmy penetrates his stepmom and she starts moaning from his big dick so they move inside. He fucks his stemom's eager hole in doggy while she talks dirty to him. Jimmy ravages his stepmother, making her cum over and over. Once she's been thoroughly fucked - Katie lets her stepson nut all over her hairy muff. ]]> Mon 01 Jun 2026 01:03:09 +0200 https://www.thepornstar.com/videos/452774/katie-morgan-and-jimmy-michaels-bring-you-an-unforgettable-show/ https://www.thepornstar.com/videos/452413/red-eviee-and-jimmy-michaels-give-you-a-double-dose-of-pleasure-in-twin-peeks/
When Red accidentally walks in on her stepbrother Jimmy - she doesn't expect to see what she saw... her stepbro has a big one! She can't help but take a good peek before exiting. Bit Jimmy ain't no dummy though - he is wise to Red's eyes! Later, when Jimmy confronts her about scoping his junk, Red plays dumb. But then something comes over her and she confesses her sin to her stepbrother. Now, Jimmy wants a peek too - fair is fair! Red pulls out her big natural tits and shows them off to Jimmy. Jimmy wants to touch his stepsister's big boobs and she lets him, but she wants to touch him back! It doesn't take long before Red is on her knees sucking off her stepbrother's big dick in the kitchen! They move to the couch and Red bends over for Jimmy, exposing her wet pussy to her stepbrother. Jimmy porks Red from behind while she moans from being stretched out. She rides her stepbro with her greased up pussy, dripping all her juices on him. Jimmy bangs his stepsister out until she cums hard on his cock and then Red lets him dump his load directly in her mouth! ]]> Sun 31 May 2026 23:57:59 +0200 https://www.thepornstar.com/videos/452413/red-eviee-and-jimmy-michaels-give-you-a-double-dose-of-pleasure-in-twin-peeks/ https://www.thepornstar.com/videos/457251/horny-milf-kat-marie-filled-deep-by-stud-s-load/
Use code FilthyKings for a FREE WEEK of Filthy Kings! Featuring Jimmy Michaels, Kat Marie ]]> Fri 29 May 2026 01:26:34 +0200 https://www.thepornstar.com/videos/457251/horny-milf-kat-marie-filled-deep-by-stud-s-load/ https://www.thepornstar.com/videos/453320/dirty-danii-and-jimmy-michaels-risque-bunny-proposition/
When Jimmy Michaels walks into his new stepmom Dirty Danii's room, he's not sure what to expect. She lures him in and tells him that as stepmom and stepson, they should be able to rely on each other. And Danii REALLY needs Jimmy's help. The guy she hired to dress up as the Easter bunny for her party later cancelled at the last minute, but she has the outfit and needs Jimmy to play the role. He's really unsure, but Jimmy humors his stepmom and tries out the bunny costume. Danni thinks her stepson looks perfect and she offers him a deal - wear the costume to the party and she will make him cum! Danni pulls out her big tits and puts her stepson's hands on them. Jimmy squeezes and sucks them and then his stepmom pulls out his cock and starts to blow him. Jimmmy fucks his stepmom in doggy, making her cum quickly. He flips her over and fucks her with his big stiff cock, giving his stepmom another orgasm. Danii rides and twerks all over her stepson's swollen member until he pulls out and nuts in his stepmom's mouth and all over her face. Happy bunny day everyone! ]]> Sat 23 May 2026 09:34:42 +0200 https://www.thepornstar.com/videos/453320/dirty-danii-and-jimmy-michaels-risque-bunny-proposition/ https://www.thepornstar.com/videos/454342/laney-grey-and-jimmy-michaels-get-horny-after-hours/
When Laney Grey gets home after a night out, she is horny. Unsatisfied from her outing, she can only think of getting dicked down. Her stepbrother Jimmy Michaels is lying down in his room, but Laney doesn't care. She has an itch that needs scratching. Laney sneaks into her stepbro's room and quietly tries to arouse him. She tells him she is aching for cock and she wants it now. Jimmy is lazy, but he understands what's on the table. Laney pulls out her stepbrother's cock and begins to suck him, getting him nice & hard for her horny little hole. Laney slides her dripping pussy down her stepbrother's cock and begins to thrust until her legs are shaking from an orgasm. Jimmy pounds Laney's fluffy muff, making his horny stepsister cum repeatedly. Laney lets her stepbrother cum all over her pretty face and then tells her he's going back to bed! ]]> Mon 18 May 2026 23:44:01 +0200 https://www.thepornstar.com/videos/454342/laney-grey-and-jimmy-michaels-get-horny-after-hours/ https://www.thepornstar.com/videos/456480/sydney-paige-and-jimmy-michaels-explore-the-wild-side-of-stepmom-fantasies/
A new stepmom, a new paradigm. Jimmy Michaels is just trying to relax in his room when Sydney Paige - his new stepmother - sits on the edge of his bed to have achat. Not only does she want him to help pay bills, but she's asking for his sperm too! That's right - Jimmy's dad is shooting blanks and Sydney figures if she sources the sauce from the stepson, results will be similar. Jimmy's stepmom asks him to jerk off and shove his cum inside her but he is way too weirded out for that. But after a little more persuading from this hot MILF - Jimmy is jerking off while squeezing her tits. Sydney begins to suck her stepson's stiff cock - to help of course! It doesn't take long before Jimmy is balls deep in his hot blonde stepmom. He pounds her fluffy muff and it creams right up. Jimmy jangles his dick deep inside Sydney until he unleashes a huge nut inside her eager MILF pussy! ]]> Sat 16 May 2026 19:33:01 +0200 https://www.thepornstar.com/videos/456480/sydney-paige-and-jimmy-michaels-explore-the-wild-side-of-stepmom-fantasies/