Jimmy Michaels [ Total 22 galleries]

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Summer Hart is frustrated that her stepson Jimmy Michaels is constantly tearing his clothes up. She lectures him about how he needs to learns some life skills. Jimmy tries to defuse the situation by giving Summer a back rub, but she storms out of the room when she realizes that Jimmy is staring down her cleavage.Later that day, Jimmy wanders into the kitchen with his dick hanging out of the hole Summer refused to fix. She pops her huge boobs out and asks what Jimmy is going to do about it. He responds by going to town squeezing those jugs and suckling the nipples. Summer gives him a handie while he's busy going to town on her tits. Eventually she asks Jimmy if he wants to fuck, which is an enthusiastic yes!They relocate to the couch so that Summer can enjoy having her pussy eaten before Jimmy sticks it in. She lets him bang her in missionary, then pushes him onto his back so she can go to work. After sucking her own goo from the D, Summer straddles her stepson and rides him as her big titties bounce. Summer is clearly loving every moment of it as she gets on her knees and takes a doggy style delight. When she has had her fill, Summer gets Jimmy off with a titty fuck until he blows, covering her chest in his sticky love. Runtime: 2:39 Added: 2023-04-07
Jessica Ryan is doing laundry when her stepson Jimmy Michaels comes in to ask her a question. He confesses that he is interested in his hot teacher while also fondling Jessica's thongs. Eventually, Jessica realizes that Jimmy really has a thing for older women and their panties. When Jimmy asks Jessica to share a secret to make him feel better, she admits she wants a guy to cum on her panties for her.Later, Jessica is masturbating with her own thong when Jimmy knocks on the door. He asks to see his stepmom's panties and she hesitates before agreeing. Jimmy can see how wet Jessica's panties are, and she admits she was thinking about their previous conversation. She invites Jimmy to make her fantasies come true. Popping those big jugs out, Jessica spreads her thighs so Jimmy can touch her pussy and then rub his dick against her panties.Sliding Jessica's thong aside, Jimmy shoves his dick into her tight twat before he eats her out. Stepmommy takes charge, riding Jimmy in cowgirl. Jessica sucks their combined juices from Jimmy's dick and then gets to her feet so her stepson can take her from behind. Pulling out, Jimmy busts a nut into Jessica's thong and then watches as she pulls it up to cover her pussy in jizz. Runtime: 3:02 Added: 2025-03-05
Jimmy Michaels is shy and not particularly socially adept. He knows that he wants to go to the school dance, but he doesn't have a date and doesn't care to go alone. When his stepmom, Maggie Green, discovers that Jimmy isn't intending to go, she decides to take matters into her own hands. Busty Maggie gets Jimmy up off the couch and says that she'll measure him for a suit so he looks quite handsome. The only catch is that Jimmy has to strip down to his boxer briefs so she can measure the fit appropriately.When Jimmy obeys his stepmommy's admonition to take off most of his clothes, it becomes painfully clear that he has a big boner. Maggie tries to measure around it, but eventually she can't take it anymore. She pulls Jimmy's briefs down to start stroking him off. Then Maggie shoves him back against the wall and pops her big jugs out so that he can suckle mama's huge tits. Now that Maggie has begun to help Jimmy out, she won't quit until he has gotten his rocks off, with her help of course. She guides him to the bed, where she lays Jimmy down and goes to town sucking and stroking him off. Then she lays down and invites Jimmy to have his way with mom.Even as he's sliding on home, Jimmy can't believe he's getting his dick wet in his stepmom's twat! He curls up behind Maggie to spoon with her. Then Jimmy rolls onto his back so that Maggie can climb on top and ride him like her personal steed. Jimmy gets a crack at Maggie's snatch again as he gets his stepmom on her hands and knees to take her in doggy. Rounding out their educational lovemaking, Maggie flips onto her back and lets Jimmy take her home one last time in missionary. When she's had enough pleasure, Maggie gets on her knees to suck Jimmy off until he pulls out of her mouth to nut all over her face in a cum shot that drips down her massive boobs and leaves them both feeling great. Runtime: 2:42 Added: 2021-01-11
admin added Runtime: 1:49 Added: 2024-01-10
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Crystal Clark is in it to win it. She's already into younger guys, so Jimmy is right up her alley. She can't wait to drain Jimmy's balls as she fucks him right.Today's date is a romantic tandem bike ride with the ultra sexual Crystal. She pulls out all the stops, taking every opportunity to run her hands all over Jimmy's body. When the bike ride ends, Crystal offers to do some stretches with Jimmy that are merely foreplay to getting off. Jimmy can take a hint as he drops to his knees and eats the milf out from behind. Jimmy lays Crystal down on the yoga mat to enjoy the pussy buffet, then takes his own turn on his back so Crystal can go to town sucking the D down before shifting into a 69.Since Crystal is already on top of Jimmy, she keeps the party going by sliding her trimmed muff down to take him all the way inside. Her stiffie ride is just the beginning; Crystal gets on her back once again so that Jimmy can slam into her. On her knees, she takes a doggy style pussy pounding that leaves her twat twitching in delight. Crystal has just enough time to get on her back before Jimmy blows his load all over her face and tits in exactly the happy ending she was hoping for. Runtime: 2:13 Added: 2023-09-27
Sarah Taylor and Katrina Colt are hanging out with their stepsons, Jimmy Michaels and Ricky Spanish. Sarah plays a video game with Jimmy while Katrina chills with Ricky. When Sarah pulls out Jimmy's stiffie to stroke it, Ricky wants the same treatment from his stepmom. Instead, Katrina sends Ricky over to the couch where their neighbors are getting busy with each other to learn how families get along. As Ricky goes to the couch, Katrina storms out.When Katrina walks back in, she finds Sarah with one hand on each of the boys' dicks. Sarah tells Katrina that this is how she and Jimmy get along, then suggests that they fuck each other's stepsons. When Katrina seems cautiously open to that, the ladies split their attention with Katrina delivering a handie to Jimmy and Sarah sucking Ricky off. Sarah eventually leans back and spreads her thighs to invite Ricky inside.That's all it takes to kick off a foursome. Getting on her knees, Katrina blows Jimmy and then lets him do her in doggy. While Katrina is taking her pussy pounding, she licks and slurps Ricky's stiffie alongside Katrina. Then the ladies swap partners so that they can each bounce away on their stepsons in reverse cowgirl. Sarah turns around and rides Jimmy in cowgirl as Katrina falls to her back to let Ricky slam back into her. When Jimmy pulls out to nut on his stepmom's ass, Ricky follows his new friend's lead and blows his load on Katrina's stomach. Katrina happily agrees that Sarah has the right idea when it comes to getting along well with her stepson. Runtime: 2:37 Added: 2023-07-13
Armani Black loves to dress nice and sexy. Showing off her big bazongas is priority number one for any outfit this milf puts on. Knowing that she's about to meet her fiance's parents, she pours herself into a sexy black dress and then out to where her soon-to-be stepson Jimmy Michaels is sitting to get his opinion. Jimmy tells her that it may be too sexy for his grandmother's taste, so Armani goes to change.The next day, Armani is wearing a sheer lace top that can barely constrain her breasts and a short little miniskirt. Jimmy walks in to see her doing the dishes and agrees to help. Anything to get closer to those titties. When Jimmy learns that Armani is going to a tutoring position dressed like that, he protests. Offering Jimmy a sexy little smile, she offers to tutor him. Before he knows it, he has his Armani on her knees in front of him, sucking and stroking him while offering him a position as her boy toy.Armani gets her wish as Jimmy bends her over the counter and slides her miniskirt up so he can fuck her right there. He fondles her pierced nipples and jiggles those jugs as he bangs her from behind. Then Armani gets Jimmy to lay down on the countertop so she can ride him in reverse cowgirl. Her boy toy loves those jiggling tits in his face when she turns around. Taking Jimmy's stiffie on her back, Armani squeals and moans as she reaches her peak. A hot minute later, Jimmy pulls out to blow on her stomach. They bask in the afterglow as Jimmy realizes his life is going to be a lot more fun with a new stepmom. Runtime: 3:47 Added: 2023-05-10
Jimmy Michaels and Jay Romero listen at the door to see if Jimmy's stepmom, Jessica Ryan, is camming. They open the door to check and realize that Jessica is indeed giving Internet strangers a taste of her goods. The phone glitches, prompting Jimmy and Jay to knock on the door and invite themselves in for a closer look at the goods before she ushers them out.The next day, Jessica catches the guys as they come to her bedroom door and asks if they have any ideas. When Jimmy shows his stepmilf an outfit, she agrees and changes into it for them. Calling the guys in, Jessica has Jay hold the camera and film her as she strikes provocative poses on the bed. Jessica's miniskirt hikes up to show her hairy pussy, but she claims her fans really like to watch her get eaten out by one guy while sucking another guy off. Michael gets the cooch while Jay takes the BJ.On her side, Jessica takes Jay's cock in her pussy while stroking and sucking her stepson. Jimmy lays prone on the bed while Jessica rides in reverse cowgirl while she slurps her juices from Jay's fuck stick. Then she turns around and rides in cowgirl so Jimmy can knead her ass and tits. Falling back onto her side, Jessica spreads her thighs for Jimmy while guzzling Jay's dick until Jay and Jimmy both nut for the camera. As Jessica lounges like a satisfied cat, she tells them they should join her at the same time next week. Runtime: 2:59 Added: 2024-07-31
Gigi Dior is trying to repair a problem with the cabinet when her stepson, Jimmy Michaels, comes to ask what's going on. She tells him she's going to have to call a repairman because nothing around there works. Then Gigi orders Jimmy to stay in his room because she doesn't want him in the way. Jimmy sees his stepmommy decked out in a robe as she leads the repairman into the living room and realizes that Gigi is cheating with him.Gigi sees Jimmy watching her and she's turned on as hell. Corning Jimmy in his room, Gigi tells him he can fix something of hers. He can even record it to watch when he goes away to college. Jimmy is very much in favor of this plan, especially when his sexy stepmilf lets him fondle her giant jugs and then gets on her knees to suck his dick.It's simple for Gigi to shift her position so she can straddle Jimmy's hips and take him all the way inside. Shifting to doggy, she watches over her shoulder as Jimmy shoves back home and dicks her down. Gigi falls onto her side with Jimmy still pumping her full of the D. Rolling onto her back, Gigi moans as Jimmy brings her off and then follows up with a creampie. In the afterglow, Gigi reminds Jimmy he can never show that tape to his dad. Runtime: 2:19 Added: 2025-03-06
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Cassie Del Isla will be cooking dinner with Jimmy. Normally Cassie dates older men, but she is making an exception to see how things are with Jimmy. They work together to make a pizza, where Cassie gets increasingly flirty.When Jimmy mentions to Cassie that he likes to date younger women, Cassie realizes that she's going to have to try even harder to get his attention. She claims to have something on her shirt. When Cassie returns wearing just her white lacy lingerie and high heels, Jimmy knows he's about to have a very good time. Sure enough, Cassie hops on the counter and invites Jimmy to eat her smooth bare pussy. In return, she shows him just how well and older woman can suck cock.They come together for the first time with Cassie on a stool that puts her coochie at perfect pussy pounding height. Climbing onto the counter, Jimmy lays down so Cassie can ride the D. She climbs off and stands, putting one foot on a stool to open herself up to a dicking down from behind. As their lovemaking concludes, Cassie gets back on her knees to offer Jimmy a very happy ending all over her face. Runtime: 5:33 Added: 2023-09-26
Blaire Johnson wasn't expecting to have feelings about her stepson Jimmy Michaels spreading his wings and leaving the next, but it turns out she really does. Jimmy approaches Blaire one day while she's ironing and asks for her help. He wants to look at apartments, which sends a stab of jealousy through Blaire. It gets even worse when Jimmy chats about bringing girls back to his place.Later that evening, Blaire comes to Jimmy's room wearing sheer lingerie and a robe. She suggests that he just stay home. If he does as she asks, Blaire offers to let Jimmy fuck her any time he wants. Jimmy wasn't expecting that, but as Blaire lets the robe slide from her shoulders he's instantly a fan of this idea. His hardon is obvious, giving Blaire something nice and big to suck down.Keeping her promise with a smile, Blaire kneels in bed so Jimmy can enjoy the way her ass jiggles before he slides in from behind. Then she lays Jimmy down to ride him in reverse cowgirl. Jimmy licks his stepmilf's pussy, then shoves back home as she lays there on her back with an ankle linked over his shoulder to open herself up nice and wide. At Blaire's urging, Jimmy nuts deep inside for a creampie that seals their deal for him to stay. Runtime: 2:36 Added: 2024-04-04
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Sarah Taylor is the lucky lady who gets to date Jimmy first. The date that Pristine has arranged is a couple's massage.When Sarah comes out in her robe, she finds Jimmy trying to cover his hardon up and tells him not to bother. She's seen everything since she has a son his age. Things are going well right up until Jimmy rolls over at the end of the massage with a massive stiffie, only to lock eyes with his stepmom who was checking on the date. Trying to recover the magic Sarah makes a move by joining Jimmy on his massage table and locking lips with him as she grinds against his dick.Moving lower on the table, Sarah takes that nice erection in her mouth to stroke and suck. Mounting Jimmy, Sarah rides him in cowgirl with long strokes of her hips. Then she gets to her feet so Jimmy can love on her from behind. He presses her onto the table on her belly, diving nice and deep. Turning onto her back, Sarah spreads out for Jimmy to give her a grand finale before he pulls out and cums on her landing strip twat. As she basks in the afterglow, Sarah asks Jimmy to remember her. Runtime: 5:35 Added: 2023-09-13
admin added Runtime: 2:49 Added: 2024-08-07
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Bunny Madison is ready for her date with Jimmy. A college friend of Pristine's, Bunny can't wait to see what Jimmy has to offer as a romantic partner. For this date, Pristine has arranged for the lovebirds to share a romantic boat ride. Bunny puts her goods on display right off the bat with a bikini. Of course Jimmy likes what he sees. As the boat ride goes on, Bunny tries to come on to Jimmy, who seems oblivious to the moves. At the end of the ride, Jimmy continues to ignore Bunny. Fed up with Jimmy's obvious disinterest, Bunny hides part of her necklace and tells Jimmy that she wants to role play that they've been married a while and he has to turn her on. Jimmy goes looking for the necklace, which of course leads her clothes coming off and to Jimmy going in for a pussy feast.The date is finally back on track as Jimmy licks the clit and finger bangs Bunny. He gets a blowjob in return, which leads to the inevitable fucking. Bunny starts them out by riding Jimmy's stiffie while her big boobs brush his face. Turning around, she keeps bouncing in cowgirl. Bunny gets on her knees so that Jimmy can nail her in doggy. As soon as Bunny rolls onto her back, Jimmy dives nice and deep, making her moan one last time. When he pulls out to cover Bunny's smooth twat in cum, then immediately asks if Bunny thinks they could have a threeway. As soon as he says it, he knows that he fucked up. Runtime: 3:53 Added: 2023-09-25
Sweet Sophia is making lemonade for the neighborhood blook party when her stepson Jimmy Michaels wanders in. They chat about Sweet Sophia's secret ingredient, and she claims that it's strawberries and cum. When Jimmy chokes on the lemonade, Sweet Sophia tells him she's kidding about the cum.Later, Sweet Sophia is on her knees trying to fix the hole in her lemonade stand sign when Jimmy comes in. Thinking he's alone, Jimmy whips his dick out to blow his load in the lemonade without knowing his stepmilf is watching him and getting hot and bothered. When Sweet Sophia can't quite hold the moan, she's rewarded by Jimmy sticking his dick through the glory hole for a handy that turns into a full on BJ.The glory hole continues to come in clutch as Sweet Sophia gets her pussy pounded from behind. When she finally comes out, Sweet Sophia rides her way to a good time on the D. Turning around, she gives Jimmy a reverse cowgirl ride so he can enjoy that ass before she hops onto the lemonade stand. Spreading her thighs, Sweet Sophia invites Jimmy to creampie her. In the afterglow, she comments that they'll need to do it again because her lemonade is still missing the secret ingredient. Runtime: 3:48 Added: 2025-07-02
admin added Runtime: 2:36 Added: 2023-07-12
Someone comes to the door and Jimmy Michaels is surprised when his stepmom Alison Rey fluffs her tits and then tries to smooth Jimmy's hair down before going to the door. She flirts with the guy at the door right in front of Jimmy. When Jimmy tries to call her on it, Alison assures Jimmy that it's perfectly natural and that he just doesn't know about the birds and the bees.Later that day, Jimmy comes to tell Alison that he's going to a friend's house. First, though, Alison insists they need to talk about his urges. She offers to let Jimmy be a safe outlet for those urges so he can work through them before he finds himself with a girl and not knowing what he should do. First Alison has her stepson stroke her boobs and then his own cock. Alison likes that dick very much, so she decides to suck it.One thing leads to another and of course Jimmy wants more when his stepmommy wants it. Peeling off the rest of her clothes, Alison crawls on top of Jimmy and shows him how a real woman rides in cowgirl. Then she gets on her knees so he can practice fucking in doggy. Rolling to her back, Alison moans and squeals encouragement to Jimmy until he gets her off. A moment later he pulls out and blows his load all over his stepmom's boobs. Licking cum from her fingertips, Alison tells Jimmy that now he can go out. Runtime: 2:51 Added: 2025-08-08
Armani Black and Mandy Waters are hanging out as they complain about how much their stepsons eat. Mandy complains her stepson Parker Amrbose is also going through an awful lot of tissues and toilet paper with all the masturbating. Armani confesses that she solved that problem by just letting her stepson Jimmy Michaels cum inside her. Mandy loves the idea, but she has no idea how to go about it. Armani cheerfully tells her friend she's got her back.Leading Mandy to where the boys are watching TV, Armani bounces over to sit beside Parker while Mandy takes a seat beside Jimmy. Armani announces that they're going to show Mandy how they handle Jimmy's cum at home. Next thing Parker knows, Armani is sucking him off while Mandy follows suit with Jimmy.There's more in store for these two stepmilfs than just blowjobs. They each mount the other's s tepson to ride in cowgirl, then turn around for some reverse cowgirl action. Then the ladies get on their knees so that Parker can plow Mandy in doggy while Armani gets the same from Jimmy. Slapping their stepmoms' asses, the guys bring themselves to the brink. When Parker is ready to cum, Armani gives him a deep throat blowjob until he pops in her mouth so she can snowball the treat with Armani. Jimmy does the same for Armani, giving his stepmom a mouthful of cum to return the favor. Runtime: 2:18 Added: 2023-08-10
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Jimmy learns that his final date is Pristine herself. Pristine isn't happy about the producers putting her in this situation, but she and Jimmy decide to make the best of it. They agree to sit down to the very nice dinner that's been laid out for them, and soon enough things have moved from awkward to flirty.When Pristine learns that Jimmy has fucked every single one of her friends, she asks the producers to stop the date. Eventually she agrees to do a final interview, at which point she admits that she has the hots for Jimmy. Jimmy overhears her but pretends not to when he walks in and cuts the interview short. Frustrated, Pristine pops a tit out for Jimmy to suck. Once she makes the first move, Pristine decides to carry through with the real deal. She starts with a blowjob, then quickly moves on to a titty fuck and more.Jimmy gets just enough time to eat that pussy out before Pristine is all over him. She rides him while her big boobies push against his chest, then turns around for reverse cowgirl. Getting on her knees, Pristine welcomes Jimmy back inside her tight cooch. Once Jimmy and Pristine have enjoyed themselves in missionary, Jimmy explodes all over his stepmom. How could he not pick her as the winner of this wild ride of a dating show? Runtime: 1:49 Added: 2023-09-28
Jennifer White is a stepmom now. Since Mother's Day is coming up, she begins making a list of things she wants from her stepson Jimmy Michaels. Jimmy's dad is out of town, so Jennifer tells her stepson that she figures she can celebrate together with him.Later, Jimmy calls Jennifer into his room. He has a card and most of the gifts Jennifer wished for. He also has nothing on at all besides a cute little knit hat on his dick. Jennifer is in an awkward spot. She doesn't want to hurt Jimmy's feelings, so she offers to jerk him off. Once Jennifer begins stroking his dick, though, she finds that she wants to fuck her stepson more than she ever would have realized.Soon her handie turns into a blowjob. That turns into a titty fuck. Now that Jennifer has broken her own boundary, there's nothing stopping her from getting naked and climbing onto Spikey's stiffie. She rides him in cowgirl, then in reverse cowgirl. Those big titties bouncing keep Spikey nice and hard as his stunning stepmommy rides him. Getting on her side, Jennifer lifts one leg so Spikey can eat her pussy and then fuck her in spooning until she's moaning. Pulling out, he cums on Jennifer's muff for a real Mother's Day treat. Runtime: 3:28 Added: 2023-05-04
Jimmy Michaels has a crush on Alexis Malone, his friend's mom. Alexis is hot as hell, so it's no surprise she has attracted his attention. Alexis tries to shut Jimmy down, moving away from him, but he continues to look for excuses to put his hands on her.When Jimmy walks in on her in some sexy lingerie, Alexis has had enough. She tells him she's not his mommy and inquires whether he'll go away if she fucks him. Jimmy can get with that picture, so Alexis pops her big boobs out and hikes up her miniskirt to shove Jimmy's face between her thighs.At Alexis's encouragement, Jimmy shoves it in and fucks her hard enough to make those boobies jiggle. He lets her ride him in cowgirl, then climb off to suck her juices from his fuck stick before riding him again. On her knees, Alexis takes a doggy style pussy pounding that leads to some spooning sex. He cums all over Alexis's landing strip twat before being kicked out. Runtime: 1:45 Added: 2023-04-20
Pristine Edge and Sophia Locke have just returned from shopping. They see their stepsons, Jimmy Michaels and Juan Loco playing video games. Grabbing the controls, the ladies tell the guys that they'll never attract ladies like that. Exchanging knowing looks, the ladies go to change into sexy tennis dresses.The guys immediately agree to play tennis when they lay eyes on their stepmoms, but they suck at it. When the ladies begin berating them about not being able to take charge, Juan snaps and grabs Sophia's tits. Pristine cajoles Jimmy into giving her the same treatment, then tells her friend to take care of her stepson. The ladies lift their miniskirts so the guys can learn some pussy eating skills.Swapping so they're each taking on their own stepson, Sophia and Pristine each show off their BJ skills. Then Pristine gets on her knees for Jimmy to do her in doggy while Sophia rides Juan in reverse cowgirl. Pristine goes back to Juan so she can take his dick on her back while Sophia gets her own doggy dicking down from Jimmy. Switching once again, Sophia rides Juan in cowgirl as Pristine rides Jimmy in reverse cowgirl. The girls each get on their backs and spread their thighs so Juan can do Pristine and Sophia can take a pounding from Jimmy until both guys pull out to blow their loads. Runtime: 3:09 Added: 2024-06-27

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