https://www.transhero.com/models/jimmy-michaels/ Tue 14 Jul 2026 02:26:39 +0200 https://www.transhero.com/videos/274242/essie-got-back-receives-that-happy-ending-massage-from-her-boyfriend-s-horny-son/
]]> Thu 02 Jul 2026 19:55:35 +0200 https://www.transhero.com/videos/274242/essie-got-back-receives-that-happy-ending-massage-from-her-boyfriend-s-horny-son/ https://www.transhero.com/videos/290055/perfect-the-way-you-are/
Ricky is having trouble with girls. He feels like his stature is getting in the way of landing chicks, and his friend Jimmy watches as Ricky lives his life in utter turmoil. Luckily for Jimmy and Ricky, their stepmoms, Annie and Ryan, are cool as fuck, and want to help the boys with their girl troubles. Annie and Ryan teach the guys about picking up chicks and let Ricky and Jimmy practice their lines on them. They want to see how the guys would seduce girls, and Ricky and Jimmy soon find themselves in a risque groove. Things get heated when the milfs put their hands on their stepsons’ cocks. Before anyone knows it, the group is deep in a full-blown fuck sesh. Ricky and Jimmy can’t believe they’re fucking each other’s stepmoms, though things get even wilder when they switch back and fuck their own stepmoms. The lucky studs give the milfs their all until Ryan and Annie milk Jimmy and Ricky’s cocks clean of all their juice. ]]> Sat 27 Jun 2026 16:12:04 +0200 https://www.transhero.com/videos/290055/perfect-the-way-you-are/ https://www.transhero.com/videos/120241/tiny-blonde-molly-little-fucked-hardcore-by-acting-coach/
When petite cutie Molly gets a knock on the door, she discovers that her parents hired acting coach Jimmy Michaels to help her with her auditions. ]]> Sat 20 Jun 2026 18:16:45 +0200 https://www.transhero.com/videos/120241/tiny-blonde-molly-little-fucked-hardcore-by-acting-coach/ https://www.transhero.com/videos/399675/huge-titted-ashlyn-peaks-riding-cock-in-the-grocery-store/
Jimmy Michaels is stocking shelves at the grocery store when one of his Lil Humper buddies points out stacked MILF Ashlyn Peaks and her big melons. Jimmy's all ready for some air humping when he espies Ms. Peaks taking a sneaky tits-out video and decides to show her his big zucchini instead, and she eagerly devours it! The horny pair hide down an aisle for doggystyle fucking, and sneak into the back. Ashlyn wraps her boobs around that cock, then rides Jimmy and takes his load on her tits. ]]> Sat 20 Jun 2026 10:20:50 +0200 https://www.transhero.com/videos/399675/huge-titted-ashlyn-peaks-riding-cock-in-the-grocery-store/ https://www.transhero.com/videos/260286/little-humper-banging-stepmom-s-friend-on-her-bachelorette-party-lilly-hall/
Little Humper Jimmy Michaels tries to crash his new stepmom's bachelorette party and look down her bestie Lilly Hall's top. After he cuts a peephole in the shower curtain and hides behind it, he gets an eyeful of Lilly's tits and sticks his big cock through his homemade gloryhole. Lilly's tempted into a bj but tells him to behave himself... and of course, that's a challenge for any self-respecting Little Humper! Jimmy decides to streak instead, and soon Lilly fucks him in front of her friends. ]]> Tue 16 Jun 2026 22:26:17 +0200 https://www.transhero.com/videos/260286/little-humper-banging-stepmom-s-friend-on-her-bachelorette-party-lilly-hall/ https://www.transhero.com/videos/173300/what-bad-bella-wants-cock-bad-bella/
This Bad Bella scene has a serious social message. Too much time on a smartphone has a negative effect. Here we have Jimmy Michaels hunched over his phone in the bedroom when he should be hunched over Bella and pleasing her pretty pussy. Bella wants attention and she wants to fuck. She's even worn a new sexy dress for the guy. For the first time ever, Bella has to shake a guy out of his smartphone trance and get him to bury his face between her tits where his face belongs. Bella gets her way because no man in his right mind would blow off Bella when she is in need of the boner. Jimmy sucks on her pert nipples and drops his pants. It's a victory for this blonde hottie who can now happily throat his meat and suck on his balls. Bella lies back, her panties to the side, eager for Jimmy to lick her pink taco. After his taste of Bella, she lifts her legs up and tosses her panties away. Now she's going to get the hot beef injection, and for dessert, a load of hot cream on her face and tits. Bella deserves it because she had to straighten his ass out. ]]> Tue 09 Jun 2026 21:46:18 +0200 https://www.transhero.com/videos/173300/what-bad-bella-wants-cock-bad-bella/ https://www.transhero.com/videos/454492/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 03 Jun 2026 23:38:34 +0200 https://www.transhero.com/videos/454492/charlotte-rayn-and-jimmy-michaels-discover-the-rewards-of-academic-success/ https://www.transhero.com/videos/453789/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! ]]> Wed 03 Jun 2026 09:17:25 +0200 https://www.transhero.com/videos/453789/charli-phoenix-and-jimmy-michaels-rush-to-get-ready-for-company/ https://www.transhero.com/videos/453639/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! ]]> Wed 03 Jun 2026 06:04:57 +0200 https://www.transhero.com/videos/453639/red-eviee-and-jimmy-michaels-give-you-a-double-dose-of-pleasure-in-twin-peeks/ https://www.transhero.com/videos/453376/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! ]]> Wed 03 Jun 2026 02:21:21 +0200 https://www.transhero.com/videos/453376/haley-spades-and-jimmy-michaels-share-a-steamy-moment-of-first-dibs/ https://www.transhero.com/videos/452317/busty-cece-mecta-slammed-deep-by-jimmy-michaels/
Use code FilthyKings for a FREE WEEK of Filthy Kings! Featuring Jimmy Michaels, CeCe Mecta ]]> Sat 30 May 2026 20:18:52 +0200 https://www.transhero.com/videos/452317/busty-cece-mecta-slammed-deep-by-jimmy-michaels/ https://www.transhero.com/videos/452838/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. ]]> Thu 21 May 2026 10:27:13 +0200 https://www.transhero.com/videos/452838/katie-morgan-and-jimmy-michaels-bring-you-an-unforgettable-show/