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YumTheeBoss,Jimmy Michaels in 'Brazzers' - Shoe Shop Til Dick Drops (Brazzers Exxtra)

Yum Thee Boss and her man stumble into a seemingly empty shoe store to do a lil shopping. Little do they know, the foot fetishist salesman, Jimmy Michaels, is watching behind a gloryhole wall while they browse. Yum's man doesn't get her hard-on for heels and takes a hike to let her peruse the shoes. It doesn't take long for Yum to discover a nice hard cock in a pair of strappy sandals looking like it'll fit just right. Yum rocks that cock 'til all the shoes drop and eventually drags Jimmy out from behind the wall to finish the fuck the right way.

Released : September 21st, 2022
Tags : Slim, American Man, Blond Hair, Short Hair, Storeclerk, Big Dick, Big Ass, Bubble Butt, Tattoo, Athletic, Black, Brunette, Bald Pussy, Innie Pussy, Big Tits, Enhanced, Sex, Cumshot Clean-Up, Facial, Glory Hole, Sneaky, Blowjob, Face Fuck, Spanking, Indoors, Store, 18-24, Cheating, Couples Fantasies, Interracial, Work Fantasies, Cowgirl, Doggystyle, Doggystyle - Standing, Missionary, Side Fuck, Top Ad, 4k

Ella Hughes in 'Good Boy'
Eva Angelina in 'Camera Cums In Handy'
Ella Hughes in 'Good Boy'

Pictures from YumTheeBoss,Jimmy Michaels in 'Brazzers' Shoe Shop Til Dick Drops

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More 'Brazzers' scenes from YumTheeBoss,Jimmy Michaels

Kimmy Kimm in 'Fucking My GF's Tall Lookalike Roomie'

Kimmy Kimm - Fucking My GF's Tall Lookalike Roomie

Kimmy Kim takes her new BF Jimmy Michaels over to her place for some casual fucking... but this gets interrupted by Kimmy's taller lookalike roomie Kimora Quin, who teases the couple and flirts with Jimmy. Jimmy tries to be faithful, but a classic case of lookalike confusion leads him to get a blowjob and sex from Kimora. Kimmy catches the cheating couple, but instead of starting a fight, she decides to make it a steamy threesome!

Cherie Deville in 'I Wanna Fuck Your Mom'

Cherie Deville - I Wanna Fuck Your Mom

Cherie Deville's son Dave's pop punk band goes viral with their latest track 'I Wanna Fuck Your Mom', and Cherie's not too happy about being the presumed titular MILF…or is she? After sending Dave to his room, she gives the rest of the band members (Diego Perez, Jimmy Michaels and Juan Loco) a scolding - but she's got more than just that to give them! She wants to know if they truly wanna fuck her, and if they're up to the task! After Jimmy proves himself worthy, Diego and Juan Loco join for a foursome, with Cherie's pussy and mouth taking on all their young hard cocks!

Jayla Page in 'The Plumber's Cumming'

Jayla Page - The Plumber's Cumming

Curvy cutie Jayla Page isn't getting any attention from her pencil neck husband, so she reacts logically by sabotaging her pipes and calling over a pair of plumbers. Plumbers, immy Michaels and Will Pounder, solve the issue quickly and are rewarded by Jayla squirting all over them. Jayla then lures then men into her shower for a double blowjob and steamy threesome. All right under her husband's nose!

Hot Ass Hollywood in 'This Thing of Ours'

Hot Ass Hollywood - This Thing of Ours

Connie Perignon and Hot Ass Hollywood are in the living room relaxing, gaming, and scrolling on their phones. But when Jimmy Michaels comes to the fridge looking for a snack, he catches a glimpse of Connie's sweet, tight pussy. Jimmy can't help himself and starts jerking off behind the unsuspecting women. Finally, tattooed Connie and big-titted Hot Ass Hollywood catch the little pervert and put him to work! Jimmy thinks he's living out a real-life fantasy, but the women are less impressed, fucking Jimmy as they scroll on their phones and continue to play video games. Jimmy better bring his A-game because, although eager to cum, these two thicc goddess are hard to impress!

Bella Rolland in 'The Gauntlet'

Bella Rolland - The Gauntlet

Summer Col is a shy hottie with a new man, Jimmy Michaels, who she hasn't gotten to home base with yet. Summer wants to impress Jimmy with her sexual openness and doesn't know how. Her pervy roomie, Bella Rolland is happy to teach her a thing or two about being a baddie. After a few pussy poppin' tips, it's time for some buttplug training. Next, Bella has set up a gauntlet of tasks for Summer that leads to some hardcore girl-on-girl sex swing strap-on action. When Jimmy shows up, Summer is primed and ready to get this hardcore threesome rolling.

Amber Alena in 'Spying On Roomie's GF With XXX-Ray Glasses'

Amber Alena - Spying On Roomie's GF With XXX-Ray Glasses

Jimmy Michaels gets a new pair of x-ray specs... just in time for his roommate's girlfriend (the sexy big-titted Amber Alena) to come over. Jimmy puts on his specs and gets to ogle Amber's naked body. Amber quickly notices that Jimmy's perving out on her, but she's pissed at her boyfriend and decides that hopping on Jimmy's cock might not be a bad idea. The two fuck repeatedly, while avoiding being caught by the roommate.

Jordyn Falls in 'Big Titty Tutorial'

Jordyn Falls - Big Titty Tutorial

Gorgeous Jordyn Falls is following along with a DIY shirt tutorial on her laptop. Usually, these tops don't work for Jordyn, as her incredible big tits just pop right out of them! Jordyn calls her roommate, Jimmy Michaels, into the room to help her take some sexy pics for her boyfriend. From the floor, Jimmy has an amazing view right up busty Jordyn's shirt. The video tutorial warned about nip-slips, but Jimmy is about to witness a whole damn tit-slip!

Nadia White in 'My Friend's Mom's Ass'

Nadia White - My Friend's Mom's Ass

Jimmy Michaels goes to visit his friend... only the friend is out running an errand, so Jimmy has to chat with sexy MILF Nadia White for a bit. As Nadia cleans, Jimmy gets a good look at her nice ass, then Nadia lets him have her way with it. Hot anal action ensues!


Erin Everheart in 'Servicing My Bossy New Stepsister'

Erin Everheart - Servicing My Bossy New Stepsister

Jimmy's new older stepsister Erin got injured in a minor fender bender recently. While Jimmy tries to get frisky with his girlfriend Dixie, Erin interrupts them by ringing a bell & demanding service from her new stepbrother. Jimmy is frustrated by Erin's demands, but she keeps his interest as they get increasingly sexual – leading to Jimmy cheating with his new stepsister! Dixie catches on but instead of getting mad, she gets even – and demands to be serviced herself in a hot threesome!

Daya Knight in 'Prankster Gets a Pussy Sandwich'

Daya Knight - Prankster Gets a Pussy Sandwich

Jimmy Michaels is the quintessential perv, running through the public streets and stealing clothing right off women's bodies! Adorable Daya Knight is his next unsuspecting target. Jimmy spies on her before stealing her top and running away with it. Daya's gorgeous natural tits get a breath of fresh air as she runs after the thief. Jimmy takes shelter in a private backyard, where he stumbles upon curvy Dee Williams lounging by the pool. Dee and Jimmy get into some sneaky sex before Jimmy has to hide from Dee's husband! Jimmy doesn't know it yet but waiting inside for him is a very vexed Daya - Dee's new stepdaughter!

Jayla Page in 'Massaging Your Hubby's Cock'

Jayla Page - Massaging Your Hubby's Cock

Important businessman Jimmy Michaels is getting a couple's massage with his prudish wife. Masseuse Jayla Page goes to work on the couple, but her intentions are anything but professional. While wifey is distracted, Jayla seduces and fucks Jimmy, making use of a special gloryhole to avoid detection. Sneaky Jayla is eventually caught, but Jimmy gets his happy ending.

Rosalyn Sphinx in 'Dunkin' On The Neighborhood MILF and Lesbian's 1st Cock'

Rosalyn Sphinx - Dunkin' On The Neighborhood MILF and Lesbian's 1st Cock

Lesbian couple Rosalyn & Arietta excitedly await their friends Damion & Jimmy's arrival so they can catch up & shoot some hoops together. Arietta can't help but be turned on by Damion's massive bulge – leading to her lover catching them & then Rosalyn's first EVER cock in a hot threesome! Meanwhile, stepmom Kate Dee hunts Jimmy for some sexy MILF action…

Hazel Moore in 'Welcome to Humper's Park 1'

Hazel Moore - Welcome to Humper's Park 1

When a new couple moves into the trailer park, they are delighted by the hospitality and generous invitation to Hazel Moore and Diego Perez's party trailer. However, Jimmy Michaels ditches his girlfriend when he sees Ebony Mystique shake her beautiful, round, butt cheeks in the trailer next door. Gorgeous Ebony is looking for fresh meat and Jimmy is just what she needed! Jimmy keeps a rotating feed of Diego and Hazel into Ebony's trailer - it looks like this gang just can't be satiated! However, sneaking around only lasts so long because, when all the players find out what's happening, they opt for a sloppy foursome instead!

Vivianne Desilva in 'Thirsty Stepmom and The Coach's Nerdy Daughter'

Vivianne Desilva - Thirsty Stepmom and The Coach's Nerdy Daughter

Jimmy Michaels, Jovan Jordan & Vivianne DeSilva have just arrived home after a win for the guys' baseball team. Jimmy scopes nerdy Willow Ryder for the first time, but Jovan warns him to stay away from his precious daughter. Willow tempts & teases Jimmy & against his better judgement; he fools around with her. Luckily, single stepmom Vivianne is thirsty for some big cock & keeps Jovan distracted for a while. Everybody manages to get their rocks off, before inevitably – Jovan catches Jimmy fucking his nerdy daughter and is less than pleased!

Syren De Mer in 'Cum on My Waffles, Honey'

Syren De Mer - Cum on My Waffles, Honey

Syren De Mer is working her waitress job, she's bored and the tips are shit. Enter Jimmy Michaels, who just wants a cup of coffee but is about to get a lot more than that! Syren decides to show off her perfect big tits, in hopes of make a few more dollars in tips. Jimmy can't believe his eyes! Syren wants to have a little more fun and crawls onto the counter to twerk for Jimmy. Before they know it, Jimmy has his whole fist inside of Syren's ass as she cries out in pleasure. Jimmy just came in for lunch but he's about to get a whole damn anal snack!

Payton Hall in 'Gilf Makes His Cock Cozy'

Payton Hall - Gilf Makes His Cock Cozy

Payton Hall loves to knit. When Jimmy Michaels, the local handyman, arrives to fix the toilet, Payton pulls the ol' - here's a refreshing glass of lemonade - and then - whoops! She spills it all over his shirt, landing Jimmy in the shower. Payton decides to knit Jimmy a cock cozy as an apology. To get the job done, she creeps into the bathroom and spies his cock size while he's hard and stroking. Jimmy catches her and he's immediately embarrassed. But she assures him there's nothing to be embarrassed about and gifts him the cock cozy with the added touch of her hand, and pussy.


Sophia Leone in 'He's Pumping, She's Humping'

Sophia Leone - He's Pumping, She's Humping

Horny Sophia Leone prays for the days her roommate, Jimmy Michaels, goes to the gym. It means she can watch porn and masturbate as loud as she wants! But when brunette Sophia's phone dies mid-porn, she breaks the house rules and goes looking for it in Jimmy's room. When Jimmy unexpectedly comes home, sneaky Sophia hides in his closet so she won't get busted. Jimmy is about to get the perfect pump at home... just not the kind he expected!

Misty Stone in 'MILF Lesbians Toy With The Mover'

Misty Stone - MILF Lesbians Toy With The Mover

Dominant lesbian couple Brittany Andrews and Misty Stone are moving into a new place and having a pair of movers (including Jimmy Michaels) lug their stuff inside. The couple take a liking to Jimmy and do what they can to tease him throughout the day. When Jimmy's coworker leaves for a bit, Brittany and Misty stick Jimmy under a couch while they sit on it and play with each other. Eventually, the hot couple let Jimmy join them for a threesome.

Armani Black in 'In A Glaze Of Glory'

Armani Black - In A Glaze Of Glory

Armani Black and Summer Col sneak into a public bathroom and take advantage of the privacy by getting down and dirty on the sink counter. They get busted by the janitor who is more interested in busting a nut than giving them a hard time. All the while, Jimmy Michaels is watching from a gloryhole in the bathroom stall. After the janitor cums, the ladies tell him to take a hike and Jimmy ceases the opportunity by sticking his dick through the hole and beckoning the horny babes his way. The ladies take his rock hard cock for a joyride and make a squirty, cummy, threesome mess of the space. Wait till the janitor gets a load of this.

Simone Richards in 'Masseur Sneaks A Glory Hole Pussy Snack'

Simone Richards - Masseur Sneaks A Glory Hole Pussy Snack

It's sexy Simone's birthday. She's in the middle of stripping out of her clothes, revealing her huge boobs and a thick round ass, when her dorky husband sneaks up behind her and cops a feel. Simone doesn't have time for him, her best friend got her a bday masseur and he's on his way! When Jimmy the masseur knocks on her door, Simone slips out her tits, surprising him so much he drops his table on his toe! When Jimmy sets up his table, the husband is confused by the hole in the middle and shoves his head in. While he's stuck, Simone lets Jimmy motorboat her wet tits after he accidentally squirts oil all over them. After Jimmy gets hubby unstuck, he leaves and Jimmy starts rubbing Simone down, enjoying every curve. Simone whips off her towel and touches her pussy, then takes advantage of Jimmy's obvious boner, giving him hot BJ then fucking his brains out on the table! When hubby comes back, Jimmy thinks fast and sticks his head through the massage table hole and eats Simone's pussy, hidden by a towel. Hubby leaves, then Jimmy and Simone get back to oily, intense fucking, leading to Simone giving Jimmy's cock a serious milking until he shoots cum all over her! Hubby busts Jimmy naked on the massage table and chases him out as Simone relaxes, playing with the cum on her tits.

Roxie Sinner in 'Relieving Tent-sion'

Roxie Sinner - Relieving Tent-sion

Sexy Roxie Sinner pays a visit to an old friend's home to catch up. The only problem is that this friend has two annoying college roommates (Jimmy Michaels and Damion Dayski) who've pitched a literal tent in the living room and are generally being obnoxious. Roxie can't help being intrigued by the attention-grabbing guys and winds up fucking them under her friend's nose.

Mini Stallion in 'Bikini-Clad Booties'

Mini Stallion - Bikini-Clad Booties

Mini Stallion and Yum Thee Boss might be quite different when it comes to body shapes - one is a petite cutie and the other a curvy cake - but Mazee loves his women as diverse as they get, especially when they know how to tease a man. It's no surprise that both Mini and Yum sport the bikini with confidence and style. The oil drizzled all over their booties makes it all the more inviting for the horny Mazee, who soons starts pounding the two friends, one after the other. An unforgettable threesome, one might say.

Lola Fae in 'Horny House Sitters: Part 2'

Lola Fae - Horny House Sitters: Part 2

After fucking Lola Fae, Yum Thee Boss heads up to her bedroom to take a nap. However, Juan Loco has scrambled upstairs to clean up yet another mess. As he tries to stuff everything into a closet, Juan ends up hiding in the most obvious of places, leading to Yum discovering him. Despite a long day of travelling and a wild romp with Lola, Yum discovers she has more than enough energy to take every inch of Juan's massive cock, after smothering him with her big tits and ass of course. However, Lola, who was kicked out after some hot lesbian action, sneaks back into the house and ends up joining them for a wild threesome! After warming to her horny house sitters and taking blasts of Lola's squirt and a hot load of Juan's cum, Yum realizes that a mess hardly matters when you can get total sexual satisfaction.

Lola Fae in 'Horny House Sitters: Part 1'

Lola Fae - Horny House Sitters: Part 1

Lola Fae and Juan Loco have been housesitting for Yum Thee Boss, and they've definitely made themselves at home. Whether it's leaving a mess or fucking on every available surface, Lola and Juan have ignored Yum's stern house rules. Just as they're getting ready to fuck on the couch, Lola gets a text from Yum saying that she'll be home in five minutes, not to mention several days early. From there, Lola needs to both hide Juan and clean up a substantial mess. When she fails to do the latter, Yum decides that Lola can serve a different purpose. It turns out that Lola is far better at fucking, scissoring, and squirting than she is keeping house, which ends up sitting quite well with Yum, who warms up to Lola after smothering her with her big tits.


Aubree Valentine in 'Spying On My New Step Brother'

Aubree Valentine - Spying On My New Step Brother

Aubree Valentine's new stepmom is worried her son, Jimmy Michaels, is having sex now that he's in college, so she pays Aubree to snoop around his bedroom and find out. Aubree sneaks into her stepbrother's room and is shocked to discover he's been masturbating to pictures of her, but she can't help but feel a little flattered too... and turned on! She makes herself comfortable and rubs her pussy, until Jimmy walks in on her. Now face to face, and both horny, the sexual tension between the two finally leads to what Jimmy's been hoping for: sex with his new stepsister!

Ryan Keely in 'Watch Where Your Balls Go'

Ryan Keely - Watch Where Your Balls Go

Jimmy Michaels is enjoying a baseball game with his friends when he accidentally throws a ball right through MILF goddess Ryan Keely's bedroom window! Inside, Ryan is enjoying her favorite dildo when the baseball comes crashing through. The poor Jimmy goes to search for the lost baseball but he finds a half-naked and horny Ryan instead. Even though Ryan is pissed at first, she eventually decides to trade in her dildo for a real-life upgrade!

Nina Rivera in 'Sexting My New Stepsis'

Nina Rivera - Sexting My New Stepsis

The ever-horny Nina Rivera is on the computer, having video sex with a stranger. They can't see each other's faces because they both desire privacy, but they do get a good look at the other person's clothing and appealing genitals. They dirty talk and masturbate together, but just when they're both about to cum, Nina's dad calls her down for dinner. Nina has to go downstairs, leaving them both horny and unsatisfied. When she goes to sit down at the table, she notices that her new stepbrother, Jimmy Michaels, is wearing the same shirt as the guy she was video chatting with. The two lusty individuals were just camming with each other! It doesn't take too long before Nina sneakily teases Jimmy under the table, before they both slip upstairs and fuck in Nina's bedroom.

Summer Hart in 'RAMming Her Software'

Summer Hart - RAMming Her Software

Curvy redhead Summer Hart is Jimmy Michael's personalized AI assistant. When Jimmy's date stands him up, Summer comes to life in order to help the poor guy satisfy his needs. She provides him with everything he needs: big boobs, lots of oil, and a tight pussy. But is Summer really just here to please Jimmy, or does she have other plans?

Jessica Ryan in 'A Surprise For His Stepmom'

Jessica Ryan - A Surprise For His Stepmom

Jimmy Michaels is obsessed with his new stepmom, Jessica Ryan. She thinks he's sweet but what he really wants is to fuck her, peeping on her any chance he can get! Jimmy leaves Jessica a gift, which she thinks is from her husband, in the form of a suction cup dildo. She tests it out in the shower, and when she catches Jimmy jerking off to her, she decides to discipline him... and get herself off too!

Quinn Waters in 'Finding My Stepmom's Toy'

Quinn Waters - Finding My Stepmom's Toy

Jimmy Michaels is looking through his dad's room for money, but what he ends up finding is his stepmom's dildo! When the sexy Quinn Waters catches him with it, she dismisses him from the room and then decides to have some fun with her toy. Jimmy sneaks back into the room once Quinn is all wet and gets to put his dick in her sweet pussy. Probably not the family bonding Quinn's husband was hoping for...

Nina Diaz in 'Hard Stroke'

Nina Diaz - Hard Stroke

Nina Diaz likes to play croquet, but she prefers to play with her tits and pussy between strokes. Peeping Jimmy Michaels sneakily turns the sprinklers on, getting Nina's top all wet before she takes him to the bedroom to suck and ride his cock!

Mz Dani in 'Masseur Swap'

Mz Dani - Masseur Swap

Mz Dani is pissed at her husband, who bought her a solo massage for her birthday instead of wanting to do something as a couple. Mz Dani proclaims to her friend on the phone that she's ready to fuck the next guy who looks at her. It looks like her friendly masseur will be the lucky guy, but Jimy Michaels, who was waiting for his own massage, has his own ideas. In the middle of Mz Dani's massage, Jimmy knocks on the door and beats up the masseur, stealing his outfit in the process. Jimmy then continues Mz Dani's massage, eventually transitioning into hot sex, as if he were a natural masseur.


Luna Star in 'Pulled Into A Workout'

Luna Star - Pulled Into A Workout

Jimmy Michaels stumbles upon a workout video tape featuring the one and only Luna Star. Jimmy can't keep his eyes off the bombshell as she stretches out her perfect body, showing off her big tits and fine ass. Seeing how Jimmy's all alone, why not pull out his dick and jerk off along to the video? This video tape, however, is unlike any other, as Luna can not only watch Jimmy stroking his big cock, but also reach out for it, magically pulling Jimmy into the TV set for the fucking of a lifetime! But will Jimmy be able to make it back to his couch afterwards, or will he be stuck there forever? We suppose spending the rest of his days with Luna wouldn't be a bad tradeoff!

Alexis Fawx in 'Step-Domme'

Alexis Fawx - Step-Domme

When stepmom Alexis Fawx has had enough of being treated like a maid by her lazy new stepson Jimmy Michaels, she decides to show him her other side, going through her closet and transforming into a domme in order to put him to work! Wearing a pair of knee-high boots and wielding a flail, Alexis whips Jimmy into cleaning up, but this dominant Milf soon finds herself aroused by his submissive obedience, craving more than just a tidy house - she wants his big cock!

Isis Love in 'Fucking The New Maid'

Isis Love - Fucking The New Maid

Isis Love is a brunette sex pot with big tits and a perfect booty. And Jimmy Michaels is in trouble. When Isis shows up to clean his house, he can't turn a corner without getting a boner and cumming his joggers! Doesn't help that she hates panties and hates bras. Isis doesn't think he should be embarrassed, she's into it and assures Jimmy that it's totally normal to have a rocket in your pocket ready to blast off at any second. In fact, she's impressed by the number of huge loads and lack of refractory period he has. Isis lends Jimmy a helping handjob and shows him how to control his cumming, while sliding in and out of her perfect wet pussy.

Katie Morgan in 'Safe To Say I Fucked Your Stepmom'

Katie Morgan - Safe To Say I Fucked Your Stepmom

Katie Morgan is a hot blonde with a body that won't quit. Her new stepdaughter is not the nicest to her boyfriend, Jimmy Michaels. Jimmy wants to get busy and has got a condom to prove it. But his girlfriend is too busy studying to give a shit about his erection, wrapped or not. Good thing for him Katie, her MILF of a new stepmom, is there. He gets off in a condom watching Katie clean on her hands and knees, sticking her tushy out for the world to see. Jimmy jacks off into a condom and leaves it for Katie to find. Katie can't believe his audacity or his load size. Katie confronts Jimmy and gives his cock a lesson.

Charlotte Rayn in 'Movie Night'

Charlotte Rayn - Movie Night

Charlotte Rayn is enjoying a movie night with her new husband when her new stepson, Jimmy Michaels, tries to butt in and watch alongside them. Jimmy's dad would rather he go clean up the mess in his room, however, and leave them alone. Jimmy's got a few tricks up his sleeve, however, and after the old "vacuum against his cock trick" doesn't help get him some alone time with his hot stepmom, he finds another way to take his dad out of the equation! Let's just say Charlotte's in for a big surprise when she sticks her hand in the bucket of popcorn - and the treat she discovers is too good to pass up!

Osa Lovely in 'Hard Drive, Harder Dick'

Osa Lovely - Hard Drive, Harder Dick

Osa Lovely has a peculiar seduction strategy when it comes to Jimmy Michaels, who just happens to be dating Osa's boyfriend's daughter. After she bakes a majestic laptop made completely of chocolate, Osa pretends that she's having computer troubles. Luckily, Jimmy is tech savvy and eager to make a good impression because he's meeting Osa for the first time. Jimmy, though, can't believe what he's seeing, and tasting, when faced with the infamous "laptop". From there, Osa shows Jimmy that she's far more interested in his hard cock than her hard drive, leading to big tits worship, sneaky sex, a tasty dessert of cum.

Casca Akashova in 'Cleanliness Is Next To Fuckliness'

Casca Akashova - Cleanliness Is Next To Fuckliness

Casca Akashova is a big breasted blonde babe with a real desire for cleanliness. She's a clean freak! She even irons her towels. When she walks in on Jimmy Michaels post cum in his filthy room she's appalled. She just wants him to tidy up but he's too busy playing video games. She decides to take matters into her own hands and tries to clean it for him. Only takes a second for her to end up knuckles deep in his splooge sock. Next, she finds his laptop and dirty search history. She realizes not only is his room dirty, his mind is filthy. Casca decides there's only one way to deal with a dirty perv like him; to fuck and suck him clean.

Cory Chase in 'Pervy Prank Master'

Cory Chase - Pervy Prank Master

Horny MILF Cory Chase has some movers coming over today and she's eager for them to handle more than her boxes. When a pair of movers arrive, including Jimmy Michaels, Cory initially ignores Jimmy in favor of his taller co-worker... but she changes her tune when she finds out that Jimmy is the other employee's supervisor (power is hot!). Cory quickly corners Jimmy, feeling up his cock and letting him play with her tits. Jimmy came to move Cory into a new house, but now he finds himself moving his cock into Cory's nice MILF pussy.


Clara Trinity in 'Coach Peepers Lends A Big Hand'

Clara Trinity - Coach Peepers Lends A Big Hand

Jimmy Michaels is supposed to be training under the watchful eye of his stern football coach, Coach Peepers (Jay Slayher)... but he's a little distracted right now. Jimmy's cute girlfriend Clara Trinity has broken into the fieldhouse, eager to get a taste of Jimmy's dick. Jimmy thinks he's getting away with this, but Coach Peepers has caught on and sneakily spies on the young couple. When the inexperienced Jimmy runs out of breath trying to eat pussy and needs a time out, Coach Peepers tags in to save the day for the disappointed and horny Clara. The coach knows how to drill a woman properly. Eventually, the coach goes into hiding again, allowing Jimmy to finish the job. But will Jimmy be more impressive on his second try?

London Rose in 'A Room With A Cock 2'

London Rose - A Room With A Cock 2

The highlight of London Rose's day is when young stud Jimmy Michaels sneaks past her clueless husband to give her the sexual satisfaction she craves. However, on this particular morning, London's husband is being especially nosy and persistent in his annoying requests and intrusions. London quickly realizes that she needs to redirect her husband's focus if she wants enough alone time with Jimmy to take every inch of his hard cock, so she uses his peculiar obsession with his wardrobe to draw his attention to the mountain of laundry in their bedroom. But before that, London and Jimmy are forced to play a tense version of musical chairs, with Jimmy finding as many creative ways as possible to hide in a small space. Once they get rid of London's husband, the only way to properly celebrate is with intense sex.

Bailey Base in 'Rim Like You Never Rimmed Before'

Bailey Base - Rim Like You Never Rimmed Before

While Jimmy Michaels is stuck cleaning up the mess his roommate (Bailey Base) left in the kitchen, Bailey's being lazy. Bailey's feeling horny, however, and masturbates until she decides to have some fun with Jimmy instead, sneaking up behind him and pulling down his pants for a surprise rimjob! Jimmy tries to continue cleaning but it isn't easy when he's got Bailey's tongue rimming his asshole while she fondles his dick and balls! It doesn't take long before Bailey's giving Jimmy a blowjob and is on all fours, panties to the side while she gets pounded doggystyle on the kitchen floor!

Michelle Anderson in 'Pillow Humpers'

Michelle Anderson - Pillow Humpers

Michelle Anderson has a laugh when she catches Jimmy Michaels humping a pillow, and she pulls out her phone to record the oddly intriguing sight. Not long after, however, curiosity gets the best of Michelle and she decides to give pillow humping a try herself, only for Jimmy to peep on and record her in return. When Michelle catches Jimmy, she serves up some punishment for the peeping perv by sitting on his face until she has her way with his cock!

Lacey London in 'Nurse's Threesome Cures All'

Lacey London - Nurse's Threesome Cures All

Sexy home care nurse Lacey London has her hands full with an aging patient, but what makes matters more complicated is the rivalry between stepsiblings Tori Montana and Jimmy Michaels - who both desperately want to fuck her. As they vie for Lacey's attention, Tori wins out thanks to some trickery, giving her alone time for some hot scissoring and pussy-eating. But when Jimmy stumbles in looking for Lacey, Tori decides on some next level trickery to show her seductive powers over Jimmy, which ultimately culminates in a scorching threesome after a shocking revelation under the blankets. After draining Jimmy's cock of all his cum, it's clear that Lacey has a healing touch.


Scenes from other sites featuring YumTheeBoss,Jimmy Michaels

Maggie Green in 'MILF Confronts Pervert Step Son'

Maggie Green - MILF Confronts Pervert Step Son

Today we have a special one for you guys. Maggie Green is casually walking in her home when she finds her stepson Jimmy jacking off to a Penthouse video. She's tired of him jacking off all the time and leaving the door open, she doesn't want her stepson to grow up a pervert. She catches him one more time jacking off in the living room and couldn't take it anymore. She had to do something about it so to touch her stepson a lesson, she takes out of her boobs and confronts him. He admits that he's a virgin boy and needs help talking to girls. Lucky for him Maggie is the type of stepmom who knows her job is to help out her stepson. She lets him grab and play with her boobs before getting real down and dirty. Watch Maggie Green teach her stepson how to fuck while dominating him with her curvy figure. Watch until the end where Maggie helps her stepson blow a huge load all over her face.

Ava Sinclaire in 'Ava Takes Jimmy's V-Card'

Ava Sinclaire - Ava Takes Jimmy's V-Card

We got a newcomer, Jimmy Michaels, on the bus. This young guy is here to fuck some girls. We find Ava Sinclaire jogging on the streets. We convince her to get in the van. Once inside Jimmy works his magic. He tells Ava he's a virgin! She feels bad for him. So she takes off her top to help the cause. She has giant bouncy tits. Jimmy laches on to her boob. She loves it. She begs to fucked by him. He's more than happy to comply. He fucks her perfect pussy in six different ways. So much for being a virgin. He cums all over her pretty face. Ultimately we decided to leave him behind with her. You can't win them all.