Videos Featuring Jimmy Michaels

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Fucking Skills My Friends Hot Mom
Fucking Skills My Friends Hot Mom
Jimmy is hanging out at his friend's place while his friend is at the gym. That's when his friend's mom Lolly Dames walks in and catches him munching on some cereal. Lolly notices that Jimmy looks kind of down though, so...
Two for Mochi Hussie Pass
Two for Mochi Hussie Pass
Hawaiian cutie Mochi Mona makes her Hussie Pass debut today, and owner Brian OMally tapped our good friend Jimmy Michaels to be his wingman in this split-filled BBG threesome scene! Director Johnny Robins kicks things of...
Kyler and Jimmy Part 3 See Him Fuck
Kyler and Jimmy Part 3 See Him Fuck
Newbie Twenty-one-year-old Little Jimmy Michaels and coed cutie Kyler Quinn shower after fucking. Featuring Kyler Quinn, Jimmy Michaels. From the web series: Kyler Quinn and Jimmy Michaels. Original release date: January...
Sara and Jimmy Part 1 Hussie Pass
Sara and Jimmy Part 1 Hussie Pass
Curvy MILF Sara Jay give newbie Little Jimmy Michaels a rimjob. Featuring Sara Jay, Jimmy Michaels. From the web series: Sara Jay and Jimmy Michaels. Original release date: January 13th, 2021.
Two for Madison Hussie Pass
Two for Madison Hussie Pass
Long-haired Latina cutie Madison Wilde returns to the Hussie Pass set today for her 1st ever on-screen BBG threesome, and we matched her up with our very own Brian OMally and young buck Jimmy Michaels for today's dazzlin...
XXX Ray Glasses Brazzers
XXX Ray Glasses Brazzers
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 notic...
World Whoppers Scene 4 Zero Tolerance
World Whoppers Scene 4 Zero Tolerance
Description not available. Featuring Lily Starfire, Jimmy Michaels. From the film: Natural Whoppers of the World. Original release date: January 27th, 2024.
Brittany and Jimmy Hussie Pass
Brittany and Jimmy Hussie Pass
Forty-seven-year-old Milwaukee MILF superstar Brittany Andrews makes her long awaited Hussie Pass debut today, and of course we just had to pair her up with our very own Twenty-one-year-old boy wonder "Little" Jimmy Mich...
Boffing Sera Devils Film
Boffing Sera Devils Film
Jimmy Michaels has just finished giving his new babysitter, Sera Ryder, the tour of his house. Things have been going swimmingly, and he has full confidence that Sera will do a fine job looking after his progeny. It just...
River and Jimmy Devils Film
River and Jimmy Devils Film
River Lynn is visiting her boyfriend Johnny Palms at his parent's house, the two of them holding hands and walking in the sun. They don't get to see each other much since they both attend different universities, so they'...
Turkey Stuffed My Friends Hot Mom
Turkey Stuffed My Friends Hot Mom
Charli Phoenix has Thanksgiving dinner ready to go, but her son won't be making it. That's a shame, because Charli needed someone to wear the Pilgrim outfit that she picked up. Luckily, her son's friend, Jimmy, stops by ...
Wildest Dream American Daydreams
Wildest Dream American Daydreams
Sydney Paige is trying to wake her stepson, Jimmy, for school. However, Jimmy needs five more minutes to get rid of the raging morning wood he's got. He wouldn't mind if Sydney gave him a hand. Disgusted by the remark, S...
Two for Bianca Hussie Pass
Two for Bianca Hussie Pass
Nipply Twenty-two-year-old "jackrabbit" Bianca Bangs makes her Hussie Pass debut today, and seeing as she's never been with two studs at the same time, we called in James Angel and Jimmy Michaels for this 1st ever BBG th...
MDay Gangbang Brazzers
MDay Gangbang Brazzers
Callie Black is excited to celebrate her first Mother’s Day as a brand-new stepmom. After her husband wakes her up by sucking on her tits, she decides to have some holiday fun by masturbating in bed... only for her new...
Bending Over American Daydreams
Bending Over American Daydreams
Jimmy went to the beach and forgot sunscreen so he's left with the worst sunburn. Chloe Amour comes to the rescue to put some aloe on him. Chloe is like a second mom to him but Jimmy has always seen her as a MILF. Many j...
Special Way My Sisters Hot Friend
Special Way My Sisters Hot Friend
Sexy Asian Phoebe Kalib is moving out, and the only one that was willing to help her out is her friend's brother Jimmy, but he is backing out now. Phoebe doesn't have another plan, so to encourage him, she is willing to ...
Two for Serena Hussie Pass
Two for Serena Hussie Pass
Mississippi newbie Serena Hill makes her Hussie Pass debut today, and she wanted to participate in her 1st ever BBG threesome, so we brought in James Angel and Jimmy Michaels for this unique update. The scene initiates w...
Gangbang Part 1 Brazzers
Gangbang Part 1 Brazzers
Katrina Colt is lapping up the hot loads of Damion Dice and David Lee when her boyfriend, Jimmy Michaels, stumbles in with the hopes of proposing to his pervy partner. Jimmy is pissed and even more so when two more half ...
Richelle and Jimmy Hussie Pass
Richelle and Jimmy Hussie Pass
This special Christmas Day update features uber MILF Richelle Ryan and our very own Little Jimmy Michaels playing the Adults Only version of Elf on the Shelf. Of course, the scene starts with Richelle having to find The ...
Borrow It Nuru Massage
Borrow It Nuru Massage
Kylie Rocket sneaks her boyfriend, Jimmy Michaels, into a private room, making sure to keep things quiet as she does. It turns out that Kylie's parent, Laney Foxxx, won't allow her to bring boys home. Kylie doesn't think...
Kyler and Jimmy Part 4 See Him Fuck
Kyler and Jimmy Part 4 See Him Fuck
Boy Oh Country Boy, do we have a treat for you today! Twenty-one-year-old Nashville newbie Jimmy Michaels makes his See Him Fuck debut today and we swear: we checked the kid's ID... twice! We paired Him up with the lovel...
Sexy Hottie My Sisters Hot Friend
Sexy Hottie My Sisters Hot Friend
Sexy hottie Katie Kinz is very upset with her friend. Katie makes a visit to confront her for messing around with her boyfriend but she is not at home; the only one there is her friend's brother Jimmy. Katie tells Jimmy ...
Stepmom Plays My Pervy Family
Stepmom Plays My Pervy Family
Cinco de Mayo has to be one of the funnest holidays out there. Tacos and 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 pal...
Fuck Your Mom Brazzers
Fuck Your Mom Brazzers
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 gi...
Thirsty Nerdy Brazzers
Thirsty Nerdy Brazzers
Jimmy Michaels, Jovan Jordan, and 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 da...
Sandy and Jimmy Hussie Pass
Sandy and Jimmy Hussie Pass
The lovely Sandy Love makes her Hussie Pass debut today, and seeing as she's a sexy cougar, we just had to bring back our MILF loving friend Jimmy Michaels for this better-late-than-never update! After our director helps...
Hump Park Part 1 Brazzers
Hump Park Part 1 Brazzers
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 Ebo...
Masseur Swap Brazzers
Masseur Swap Brazzers
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 look...
Bodega Bro Brazzers
Bodega Bro Brazzers
Jimmy is just living his life as a convenience store clerk when stunning lesbian couple Jordyn and Gaby waltz into his bodega. He watches them get nasty with each other before Gaby goes out to have a smoke. He thinks he ...
Sara and Jimmy Part 2 Hussie Pass
Sara and Jimmy Part 2 Hussie Pass
Busty blonde MILF Sara Jay sucks and fucks newbie country boy Little Jimmy Michaels. Featuring Sara Jay, Jimmy Michaels. From the web series: Sara Jay and Jimmy Michaels. Original release date: January 13th, 2021.
Leila and Jimmy Hussie Pass
Leila and Jimmy Hussie Pass
Newbie MILF Leila LaRocco makes her Hussie Pass debut today and we paired her up with Little Jimmy Michaels, who's making his monthly appearance here on the site. After we get to know a little about the bikini bodybuilde...
Movie Night Brazzers
Movie Night Brazzers
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 le...
Pussy Snack Brazzers
Pussy Snack Brazzers
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 ...
Hotter MILF Filthy Kings
Hotter MILF Filthy Kings
Description not available. Full title: Who's the Hotter MILF? Let's Find Out. Featuring Gigi Dior, Alyssia Vera, Jimmy Michaels. Original release date: September 21st, 2023.
Plumber Cum Brazzers
Plumber Cum Brazzers
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 is...
Fuck Ranch Brazzers
Fuck Ranch Brazzers
Avery Black and Zoey Sinn have booked a girls-only glamping adventure that turns out to be more trailer park than resort. Regardless, they plan on getting down and dirty in their tent, so they make the best of it and get...
Armani and Jimmy Hussie Pass
Armani and Jimmy Hussie Pass
Latina cougar Armani Black makes her 1st appearance on the Hussie Pass set today, and as we do with most MILFs, we paired her up with Little Jimmy Michaels for today's anal MILF update. After director Johnny Robins condu...
Safe to Say Brazzers
Safe to Say Brazzers
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 ...
Your Manager Brazzers
Your Manager Brazzers
Sexy blonde shoplifter Mellanie goes to a clothing store with stealing on her mind. After she harasses the cashier, security guard Air Thugger monitors the situation, catching Mellanie's eye. She flashes him her juicy ti...
Young Neighbor Dirty Wives Club
Young Neighbor Dirty Wives Club
Athena Anderson's husband has his work trip extended. That's too bad, cause Athena has been in the mood for some cock. She decides that she can't wait a few more days and has her neighbor come over to give her a hand...a...
Forget the Pie Filthy Kings
Forget the Pie Filthy Kings
Description not available. Featuring CeCe Mecta, Jimmy Michaels. Original release date: November 23rd, 2023.
Lolly and Jimmy Hussie Pass
Lolly and Jimmy Hussie Pass
Unique big booty MILF Lolly Dames (FKA Unicorn Lollipop) makes her return to Hussie Pass this week, and as we do with all cougars, we paired her up with young buck Jimmy Michaels for this steamy update. After the Johnny ...
Fuck Friday Part 1 Brazzers
Fuck Friday Part 1 Brazzers
Dirty talking, flashing, and erotic boundaries are crossed when a group of co-workers, Alexia Anders, Dante Colle, and Jimmy Michaels complete to be the first to finish their report by the end of the day. "Work hard, pla...
Trio Smash Brazzers
Trio Smash Brazzers
Petite Chloe Temple is introducing her boyfriend, Jimmy Michaels, to her dad and new stepmom. Jimmy is nervous but Chloe assures him that everything will be fine. At the house, MILF Cherie DeVille has forgotten the coupl...
French Kate Mrs Creampie
French Kate Mrs Creampie
Anissa Kate is trying to sell Jimmy some art, but Jimmy isn't budging. Anissa needs to make the sale so she decides to throw in a bonus. If Jimmy hands over the cash for a pair of vases, then Anissa will let him play wit...
Like Never Brazzers
Like Never Brazzers
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 inste...
Intense Affair My Friends Hot Mom
Intense Affair My Friends Hot Mom
Andie Anderson hasn't had sex in a very long time because her husband won't fuck her anymore. She is in desperate need of some cock and an orgasm! She figures she can get away with fucking Jimmy, her son's friend, becaus...
MILF U Part 3 Brazzers
MILF U Part 3 Brazzers
MILF Ebony Mystique is hungry for dick, but finds herself alone at MILF U. Deciding to take matters into her own hands, she fingers herself on her bed and teases her ass with a butt plug when Jimmy Michaels -- a soon-to-...
Bossy Step Brazzers
Bossy Step Brazzers
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 and demanding service from her new stepbr...
The Turkey Reality Kings
The Turkey Reality Kings
Jimmy Michaels and his Little Humper buddy show up a little early for Thanksgiving dinner. Advoree isn't quite ready yet, but she tells them to make themselves at home... and next thing you know, Jimmy's teabagging the t...
New Maid Brazzers
New Maid Brazzers
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 ...
Neighbor Nympho Brazzers
Neighbor Nympho Brazzers
A "neighborhood watchman" (Jimmy Michaels) receives a call from Christie Stevens, the big-breasted supervisor of a quiet gated community, because a strange disturbance in someone's home has been causing some complaints. ...
Car Squirter Reality Kings
Car Squirter Reality Kings
Blonde teen Krissy Knight gets so horny over her stepmom's new convertible, she just has to rub herself all over it. She video calls her boyfriend Jimmy Michaels, who rushes right over in time to see her squirt in the ca...
Black Friday BFFs
Black Friday BFFs
Suddenly, they get interrupted by a knock on the door, it's Jimmy Michaels with a camcorder telling them he got them on tape stealing all those clothes. To Jimmy's delight, these girls are willing to do the naughtiest th...
Horny Massage My Daughters Hot Friend
Horny Massage My Daughters Hot Friend
Jimmy is a studying masseur and is tired of practicing with all his male friends. Essie, his dad's girlfriend, is willing to lend a helping body for him to get more hours of training. Essie has such a smoking hot bod tha...
Ball Watch Brazzers
Ball Watch Brazzers
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 c...
Desperate Times My Pervy Family
Desperate Times My Pervy Family
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 ti...
Shoe Shop Brazzers
Shoe Shop Brazzers
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...
Gauntlet Brazzers
Gauntlet Brazzers
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 happ...
Level Up Brazzers
Level Up Brazzers
When "Coach" (Jamie Knox) sees Jimmy Michaels eating Annabel Redd's pussy in the bathroom, he determines to (ahem) level up their fuck game. The couple's activities progress to a massage table in another room, underneath...
Big Butt Gaby My Sisters Hot Friend
Big Butt Gaby My Sisters Hot Friend
Gaby was going to a party with her bestie, but instead, she got stuck with her bestie's brother Jimmy and teaches him the perfect recipe for Guacamole and hot Latina sex! Featuring Gaby Ortega, Jimmy Michaels. Original r...
Mom Ass Brazzers
Mom Ass Brazzers
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...
Lucky Dirtbag My Pervy Family
Lucky Dirtbag My Pervy Family
When your own son is trash-talking you to his stepmother on St.Paddy's, you know something is off. Jessie listens to Jimmy's concerns but tells him she doesn't want to give up on his dad just yet. But Jessie comes back l...
Jimmy Weiner Hussie Pass
Jimmy Weiner Hussie Pass
Milwaukee MILF superstar Brittany Andrews makes her long awaited Hussie Pass debut today, and of course we just had to pair her up with our very own 21-year-old boy wonder "Little" Jimmy Michaels for this great scene tha...
Room with a Cock 2 Mommy Got Boobs
Room with a Cock 2 Mommy Got Boobs
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 especia...
Sharing is Caring from My Pervy Family
Sharing is Caring from My Pervy Family
Description not available. Featuring Vivianne De Silva, Jimmy Michaels, Peter Fitzwell. Original release date: July 22nd, 2023.
Dunking Brazzers
Dunking Brazzers
Lesbian couple Rosalyn and Arietta excitedly await their friends Damion and Jimmy's arrival so they can catch up and shoot some hoops together. Arietta can't help but be turned on by Damion's massive bulge -- leading to ...
Hubby Cock Brazzers
Hubby Cock Brazzers
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...
Pump and Hump Brazzers
Pump and Hump Brazzers
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 r...
Relieving Tent Brazzers
Relieving Tent Brazzers
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 r...
Twice His Age Hussie Pass
Twice His Age Hussie Pass
We just had to bring the lovely Sara Jay right back so that we could pair her up with newbie 21-year-old Jimmy Michaels for what turned out to be on helluva scene! After we chat a bit with our stars, Sara Jay shows Jimmy...
Happy Ending Reality Kings
Happy Ending Reality Kings
Masseur Jimmy Michaels's professionalism is put to the test when hot influencer Jordyn Falls and her friend show up. Jordyn takes her tits out right in front of him, and her friend oils up Jordyn's booty and tells him to...
Feed Me Brazzers
Feed Me Brazzers
Charli Phoenix is ass up, bent over making the bed as her husband gets ready to leave for work. Little does hubby know the minute he exits Charli's got a hot date with the enormous dildo she's tucked into the sheets, and...
Big Barista Brazzers
Big Barista Brazzers
Jimmy Michaels heads into a coffee shop for a quick caffeine fix, but finds more than he bargained for. The barista, Ashlyn Peaks, is smoking hot and has huge tits. Jimmy lays on the charm and Ashlyn is DTF. Once Ashlyn ...
Hard Stroke Brazzers
Hard Stroke Brazzers
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...
Kyler and Jimmy Part 1 See Him Fuck
Kyler and Jimmy Part 1 See Him Fuck
Coed Kyler Quinn sucks off country boy Little Jimmy Michaels. Featuring Kyler Quinn, Jimmy Michaels. From the web series: Kyler Quinn and Jimmy Michaels. Original release date: January 14th, 2021.
Drone Peeper Brazzers
Drone Peeper Brazzers
Gem Jewels wants to go out clubbing, but her boyfriend isn't having it. After he insists that she stay home, Gem takes the opportunity to overtly tease Jimmy Michaels, her boyfriend's son and a college dude who is sudden...
Step Domme Brazzers
Step Domme Brazzers
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 ...
Suffocate You Hussie Pass
Suffocate You Hussie Pass
MILF megastar Jennifer White is back again, and we just had to pair the sexy cougar up with our blushing 21-year-old stud Jimmy Michaels for this week's Hussie Pass update. After the Johnny Robins interview portion of th...
Creepy Creamer Filthy Kings
Creepy Creamer Filthy Kings
Description not available. Featuring Jimmy Michaels. Original release date: June 24th, 2023.
Annoying Stepmom My Pervy Family
Annoying Stepmom My Pervy Family
Description not available. Featuring Wendy Raine, Jimmy Michaels. Original release date: April 8th, 2023.
Cute Jill My Sisters Hot Friend
Cute Jill My Sisters Hot Friend
Jill Taylor stops by for some school help from her friend's brother Jimmy. Jimmy is really tired of helping out his sister's friends without getting anything for it. So he offers to tutor her for an entire year if she do...
Country Boy See Him Fuck
Country Boy See Him Fuck
Boy oh Country Boy -- Do we have a treat for you today! 21-year-old Nashville newbie Jimmy Michaels makes his See Him Fuck debut today and we swear: we checked the kid's ID... twice! We paired Him up with the lovely Kyle...
Jimmys V Card Bang Bus
Jimmys V Card Bang Bus
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 h...
MILF Off Brazzers
MILF Off Brazzers
Cherie and Bunny, both MILFs with perfect tits, haven’t fucked for months. On top of that, Bunny has snapped Cherie’s fave sex toy in half! They argue until Jimmy, the plumber, arrives. Both MILFs grab Jimmy, wanting...
Aussie Barbie Brazzers
Aussie Barbie Brazzers
Barbie is strong, sexy, and hungry for cock! When her boyfriend isn’t able to satiate her appetite (even after fucking her twice in one day), Jimmy Michaels and Max Fills decide to try their luck at satisfying her. Bar...
Sexy Xxlayna My Sisters Hot Friend
Sexy Xxlayna My Sisters Hot Friend
Latina babe Xxlayna Marie is at her friend's to watch a movie since the day is so cold and rainy. It seems that even with blankets on, she cannot get warm enough so she asks Jimmy to lay with her and maybe his hard cock ...
Pervert Step Son Bang Bros
Pervert Step Son Bang Bros
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 o...
Stepmom Needs Me My Pervy Family
Stepmom Needs Me My Pervy Family
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 sh...
It is Important My Pervy Family
It is Important My Pervy Family
Being a stepmom isn't easy and 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 hea...
Moving Day MILF Brazzers
Moving Day MILF Brazzers
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 ...
Coach Peepers Brazzers
Coach Peepers Brazzers
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 t...
Spying on Him Brazzers
Spying on Him Brazzers
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 sho...
Their Interiors Brazzers
Their Interiors Brazzers
Jimmy and his pal Johnny are playing craps like a coupla neighborhood toughs when the interior designer Jimmy's stepsister hired shows up to their house. Jimmy instantly falls in lust with stylish new sexpot Jennifer, wh...
Glaze of Glory Brazzers
Glaze of Glory Brazzers
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...
The Lookalike Brazzers
The Lookalike Brazzers
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...
Stepmom Motivation Filthy Kings
Stepmom Motivation Filthy Kings
Being in school is hard, especially when you're 19. Sometimes you just want to take the day off, watch some TV and relax. My stepmom Kitten Latenight doesn't really agree with me. She says my grades are too low and I'm f...
Finding Her Toy Brazzers
Finding Her Toy Brazzers
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 som...
Her Software Brazzers
Her Software Brazzers
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: bi...
Good Tongue Hussie Pass
Good Tongue Hussie Pass
In honor of Jimmy Michaels' return, we brought in none other than stacked MILF megastar Joslyn James for her first ever Hussie Pass appearance. Featuring Joslyn James, Jimmy Michaels. Original release date: June 11th, 20...
Little Quickie My Pervy Family
Little Quickie My Pervy Family
Description not available. Featuring Jimmy Michaels. Original release date: July 8th, 2023.
Pussy Sandwich Brazzers
Pussy Sandwich Brazzers
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 t...
Another Gamer Reality Kings
Another Gamer Reality Kings
Jimmy Michaels gets a little insecure when he learns his hot blonde gamer gf Aria Banks has been playing online with another guy every night. He shows his girl there are some things he can do better, like eating her puss...
Pervy Pranker Reality Kings
Pervy Pranker Reality Kings
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...
Cure All Brazzers
Cure All Brazzers
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...
Pillow Humpers Brazzers
Pillow Humpers Brazzers
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 decid...
The Mover Brazzers
The Mover Brazzers
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 t...
Waffle Cum Brazzers
Waffle Cum Brazzers
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, ...
Helping Hand My Pervy Family
Helping Hand My Pervy Family
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 t...
Hard Drive Brazzers
Hard Drive Brazzers
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 sh...
A Surprise Brazzers
A Surprise Brazzers
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 he...
Cozy Cock Brazzers
Cozy Cock Brazzers
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, landin...
Our Thing Brazzers
Our Thing Brazzers
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...
Grocery Dick Reality Kings
Grocery Dick Reality Kings
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...
Fuckliness Brazzers
Fuckliness Brazzers
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 wa...
Titty Tutorial Brazzers
Titty Tutorial Brazzers
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 Michael...
Sexting Her Brazzers
Sexting Her Brazzers
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 appealin...
So Much Love Hussie Pass
So Much Love Hussie Pass
The lovely Sandy Love makes her Hussie Pass debut today and seeing as she's a sexy cougar, we just had to bring back our MILF loving friend Jimmy Michaels for this better-late-than-never update! After our director helps ...

 

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