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StepSiblingsCaught.com Episodes - Season: 20
Aggressive Stepsister Wants Sex - S20:E1

Aggressive Stepsister Wants Sex - S20:E1

Ever since Molly Little and Juan Loco became stepsiblings, Molly has gone out of her way to flirt with Juan while simultaneously taunting him. Today, she has decided to up her game by waltzing into the room and sitting herself down in Juan's lap. While she's straddling her stepbrother's hips, Molly begins shooting off her mouth asking him things like whether he asked for a microscope for Christmas so he can see his dick better. When Molly sees that Juan is getting upset, she gets even more aggressive, claiming he's mad because he wants her pussy but he's not going to get it. She lifts her shirt to show her boobs while suggesting that maybe her titties will make Juan's dick grow. Eventually, though, Molly gets sick of her game and takes off to her bedroom. Later, Molly contrives the perfect setup to get herself laid. She begins by laying in bed and masturbating with her fingertips. Eventually, she grabs a vibrating toy and shoves it deep. Molly isn't quiet about what she's doing, either; instead, she moans about how her stepbrother is making her cum. Juan eventually passes by Molly's door and can't help but overhear what's going on. He knocks, and Molly tells him he can come in and that she's decent. That, of course, probes to be a lie when Juan enters the room and finds Molly with her legs wide open and a toy buried inside her twat. She once again taunts Juan about his micro dick, but this time Juan is ready to take the bait. He tells Molly that he's sick of her being such a bitch and then takes the vibrator out and replaces it with his cock. Getting the D doesn't just automatically make Molly nicer to Juan. She keeps on making fun of him even as she blows his stiffie and then hops on top to ride him in reverse cowgirl. Getting on her hands and knees, Molly keeps shit talking Juan over her shoulder even as her breathy moans bely how much she's enjoying herself. Rolling onto her back, Molly opens herself up for Juan to keep up his pussy pounding, until her twat is pulsing in delight. When Juan pulls out and pops a big load of cum into Molly's open mouth, she can't help smiling in satisfaction that she has finally gotten what she wanted all along: the chance to fuck her stepbrother.
9.02 1226 15 Apr 15, 2022
A New Whore - S20:E2

A New Whore - S20:E2

Kinsley Kane and her stepbrother Apollo Banks are having an argument about who gets to wear the costume for a popular villain. Apollo wants to have a movie marathon with his friends, while Kinsley wants to have her own party where she and her friends look cute for their online presences. Just as the costume snaps and breaks, Kinsley's friend Quinn Wilde walks in. The girls leave to go change into other costumes that Kinsley has as a Plan B. As they change, Quinn admits that she finds Apollo hot. Kinsley refuses to agree to that, but she does agree to help Quinn tease him with their sexy outfits to get back at him for ruining their plans. Quinn offers to make Apollo feel real good in the biblical way if he lets them have their party, too. When Apollo seems amenable to that, Quinn makes good on her promise by pulling his hardon from his jeans and sucking it down. Her big naturals make a beautiful cleavage shot as she sucks and deep throats Apollo's stiffie. It turns out that Apollo isn't the only one turned on; Kinsley can't help but masturbate to the sight of her friend blowing her stepbro. When Apollo asks Kinsley if she's into it, Quinn goes over to deliver some deep kisses. The girls return to the cock for a double BJ. Kinsley is the first to get to enjoy Apollo's cock as she gets on her knees for some doggy style fun. Quinn makes sure her BFF is enjoying herself, then lays down with her thighs spread out so Kinsley can eat her out as she's getting fucked. Quinn finally gets to enjoy some hardcore fun as Apollo takes a seat and pulls her down in reverse cowgirl with Kinsley rubbing her clit. Turning around, Quinn shoves her tits in Apollo's face as Kinsley kneads her ass to the rhythm of her stiffie ride. Kinsley lays back and spreads her thighs to invite Apollo back inside. He gives her just what she wants, finishing himself off with a creampie to boot. Just as they're all coming down, Apollo's dad walks in on the trio.
8.88 755 12 May 3, 2022
How Far Can You Shoot Your Load Stepbrother - S20:E3

How Far Can You Shoot Your Load Stepbrother - S20:E3

Molly Little and her friend Khloe Kapri discuss everything. Today, they're in Molly's bedroom chatting about how much they like it when guys blow their load across various distances. Longer is obviously better. Molly's stepbrother, Jay Romero, walks in at just the wrong time to hear the girls talking about five feet. He mistakes that they want a dick that's five feet long, which just makes the girls ridicule him. Later, Khloe and Molly decide to play with Jay. They approach him with a cup of lemonade and tell Jay that if he can shoot his load five feet to hit the glass then Molly will let him fuck her. Jay agrees, so Khloe gets on her knees to measure out five feet and then jerk Jay off. He hits the mark all over Molly's face. True to her word, Molly joins Khloe sucking Jay's cock and balls. Hopping onto the couch, Molly peels her clothes off and spreads her thighs for Jay to sink into that hot little pussy. Khloe isn't satisfied just watching the show. She wants some of the D for herself and Molly is happy to share. Getting on her hands and knees, Khloe takes it in doggy as she eats Molly out. Then Jay takes a seat so Khloe can ride the fuck stick in reverse cowgirl. Molly wants to get some doggy style action, so she gets on her hands and knees to mirror Khloe's spot in the middle. That's enough to bring Jay to the edge. The girls get Jay off for the second time that afternoon, this time with another handie until he gives it to them in a facial that leaves both girls sticky but sated.
8.86 985 17 May 9, 2022
Fuck And Make Up - S20:E4

Fuck And Make Up - S20:E4

Aria Valencia and her stepbrother Nathan Bronson have been fighting nonstop since their parents got married. The newlyweds are sick of it. They decide to lock Aria and Nathan in a room and refuse to let them out until they figure out how to exist without arguing. At first Nathan and Aria hang out in their own corners of the room, but eventually Aria decides that she's bored. The only thing that will make it better is for Nathan to strop off all her clothes and fuck her. Nathan tries to deny that he's attracted to his stepsister, but Aria claims she knows how he looks at her and she refuses to be dissuaded. Nathan eventually does as he's told. The way the stepsibs still feel about each other is obvious in their rough handling of each other, but that doesn't stop them from taking some pleasure in their encounter. Nathan goes from some light breath play to palming Aria's tits. Then he pushes her panties aside and just shoves those fingers right into her greedy twat to find her nice and wet for their encounter. Flipping Aria onto her hands and knees, Nathan drives home in doggy. He grabs her by the neck to bring her up, then traps her arms behind her back to keep her pinned as he pistons in and out of that tight twat. Aria is here for it, moaning and squealing as Nathan gives her what she wants. When Aria rolls onto her back and spreads her thighs, Nathan gives her the full D. They take a break so Aria can deep throat Nathan in a 69. Moving on to Aria riding Nathan, she puts all her disdain into taking that big dick nice and hard. One more round on her back and then Aria strokes the cum right into her mouth as she brings Nathan off. It turns out these stepsiblings don't have to like each other to have fun together.
8.51 674 15 May 22, 2022
Making My Stepsister Cum - S20:E5

Making My Stepsister Cum - S20:E5

Serina Gomez and Jenny Wild are new stepsisters learning how to live together. One of the hiccups in that is that they both find the other wildly attractive. Serina has just finished laying some clothes out on her bed to decide what she'd like to change into when Jenny knocks on her door. Wearing just a bra and panties, Jenny is just too yummy a sight for Serina to ignore. The girls make small talk about the clothes for a bit, but soon enough their talk turns sexual. The girls wind up naked in bed together. As they lock eyes, they each slide their hands all over their tight bodies, feeling up their tits and then sliding them lower to their stomachs. It's not long before both Jenny and Serina are enjoying some mutual masturbation. That's not enough to quench their thirst, though. Tugging Jenny close to settle into her arms, Serena reaches down to rub her stepsister's clit. When that's not quite enough, Serena gets on her knees between Jenny's thighs to drink down her pussy juices. Turning the tables on her stepsis, Jenny gets Serena on her hands and knees so she can finger bang her twat. She goes on to eat Jenny out, before rolling her onto her shoulders so she can go town with those magic fingers. In return for Serina's dedication to her pleasure, Jenny pulls her stepsister onto her chest so she can lay back while still feasting on Serina's fuck hole. That's nearly enough, but the girls need one last orgasm apiece. They achieve it by pushing their twats together for some girl on girl tribbing that leaves them both moaning in absolute delight.
7.69 334 10 Jun 8, 2022
I Hope Your Penis Has A Good Fathers Day - S20:E6

I Hope Your Penis Has A Good Fathers Day - S20:E6

Scarlet Skies has her friend Ryan Reid over on Father's Day. Scarlet has made her stepdad, Damon Dice, a card. Damon is touched as he opens it. Ryan steps forward and tells Damon that she has also made him a Father's Day card. This one, however, is quite inappropriate, as it contains a dick and says that Ryan hopes Damon and his penis have a really nice Father's Day. Ryan says out loud that she wishes that she had a stepdad like Damon. When Damon awkwardly leaves, Scarlet wants to know what the hell her friend is doing. Ryan points out that she can fuck Damon and Scarlet can't. Scarlet wants to know why not, which leads Ryan to realize that Scarlet has a family sex fetish. That's okay because Ryan has an older guy fetish. The girls can work with that. They find Damon on the couch in the living room and take turns asking him increasingly sexual questions in an attempt to one up each other and seduce Damon first. Once both of their titties are out, the girls argue over who gets to suck Damon's dick before ultimately sharing their treat. The competition continues to escalate the situation from guzzling the D to Scarlet peeling off her panties and sinking down onto stepdaddy's dong. Still Scarlet's BFF, Ryan is happy enough to support her friend's weight and rub her clit as she bounces away. Ryan gets a turn on Damon's hardon next as she rides him in cowgirl just like Scarlet did. Ryan keeps on taking that pussy pounding as she lays on her back, now with the added bonus of Scarlet riding her mouth. Getting on her hands and knees, Scarlet tells Damon she wants him to cum on her ass. He can do that! First, though, he fucks his stepdaughter in doggy as she eats Ryan out. Dredging her fingers through the salty treat, Ryan shares with Scarlet as the girls wish Damon a happy Father's Day.
9.01 798 12 Jun 13, 2022
My Stepsister Loves My Dick - S20:E7

My Stepsister Loves My Dick - S20:E7

Haley Spades has made up a chart of the sizes of all the dicks she's tried. She's on a quest to figure out the best size, as she explains to her friend Jazmin Luv. Haley's stepbrother, Juan Loco, comes in as the girls are discussing. They tell him this is a project for school and that it's based off real life, which is the best type of project. Juan asks why there are no dicks in the six-to-seven-inch category, and Haley tells him that she hasn't had any. When Juan implies that he falls into that range, Jazmin offers to measure him. Juan is weirded out and leaves. The girls decide to come up with a way to measure Juan's cock. Haley tries to apologize, saying she didn't mean to make him uncomfortable and that she loves him and his dick just the way they are. When Juan doesn't immediately hug her back, Haley asks if he wants her to prove it. Overriding Juan's weak objections, Haley pops his hardon out and begins sucking it. Jazmin is watching from the doorway and tries to call Haley on her choices by claiming she was joking about sucking Juan's dick. Haley rolls onto her back and peels off her panties to say she wants to see if it will fit in her pussy, too. At first, Jazmin is put off by watching the stepsiblings to at it, but she quickly realizes that she finds it really hot. Eventually Juan brings Haley off, and Jazmin announces she wants to suck Haley's girl goo off Juan's dick. The girls work together, delivering a joint BJ that just gets Juan raring to go again. This time Jazmin hops onto the cock and rides in cowgirl as Haley rubs her clit. Getting on her back, Jazmin continues to take Juan between her thighs as Haley climbs on top to enjoy riding her BFF's tongue. Haley gets another go with Juan when she gets on her hands and knees, which gets her off and brings Juan to the brink of cumming. He pulls out just in time to bust a nut all over Haley's ass, giving Jazmin a treat to lick from her fingertips and then share with her friend.
9.04 687 12 Jun 26, 2022
You Got Cum On My Sandwich - S20:E8

You Got Cum On My Sandwich - S20:E8

Kyler Quinn and her stepbrother David Lee don't really get along. They can't stop sniping at each other in really rude ways. Today, Kyler grabs the cereal from David as he's pouring it and keeps it for herself. When David dares talk a back, Kyler throws cereal at him and then dumps the whole bowl over his head. Later, Kyler is making a sandwich when David tries to get her to talk to him. She gives him the silent treatment, which just spurs David on to greater heights. Getting to his knees, he bends Kyler over, tugs her miniskirt up and her thong down, and licks her pussy. Returning to his feet, David pops Kyler's tits out to jiggle as she continues to ignore him. Kyler maintains her bored persona as David bends her forward and slides into her from behind. Putting his stepsis's leg on the counter, David keeps on pounding that puss. Kyler lets David adjust her so she's sitting on the counter, but she refuses to give in and show signs of enjoying herself. Even as she drops down to a crouch and lets David face fuck her, Kyler remains impassive. A mouthful of cum is Kyler's reward for putting up with her stepbrother's horniness.
8.45 734 37 Jul 26, 2022
Stepbrothers Dirty Thoughts - S20:E9

Stepbrothers Dirty Thoughts - S20:E9

Marina Gold is doing laundry and she goes to her stepbrother, Raul Costa's room to see if he has anything for her. Raul is such a pig that he has dirty clothes all over the place. Marina lectures him, but watching his hot stepsis bend over in her booty shorts is worth it to him. In fact, Raul follows Marina to the laundry room so he can keep on admiring that big booty. Later, Raul joins Marina where she's eating popcorn on the couch. Seeing that she's still wearing those tight shorts, he throws popcorn towards her feet and insists that she pick it up. Then he asks Marina to grab a drink off the table. She catches him staring at her ass and goes off on him. When Raul tries to reach out and take a handful of the booty, Marina tells him to do that on his own time. She keeps her high and mighty attitude right up until she spots how big Raul's dick is. Then it turns into a game of "I'll show your mine if you show me yours." Well of course looking leads to touching. Marina can't keep her hands or mouth off Raul's hardon! Once Raul is done licking her glistening slit, Marina sits him down and climbs aboard in cowgirl. Raul flips Marina onto her back to go deep, then puts her on her knees to do her in doggy. Pulling out, he pops all over Marina's lovely bottom to leave her covered in his hot sticky love.
8.84 449 11 Aug 17, 2022
Stepsister Teaches Me About The Birds And Bees - S20:E10

Stepsister Teaches Me About The Birds And Bees - S20:E10

Aria Valencia is ready to play tutor to her stepbrother, Oliver Flynn. Dressed in a smart sexy outfit complete with a miniskirt, chunky heels, and thick glasses, Aria dresses the way she thinks a teacher would. Oliver is confused why his stepsis is trying to teach him about sex, which causes some friction between the stepsiblings. Eventually he agrees to let her practice on him, but he gets even more of a hands on show than he bargained for. Aria tries to have Oliver pull his penis out, but he refuses. She says she'll go first. Pulling her shirt down, she explains that these are boobs. Aria's miniskirt hits the ground next so that Oliver can see what a vagina looks like. Oliver stares at his stepsister, bemused, as she instructs him to take his cock out so she can show him how impregnation works. Next thing he knows, he has Aria riding his hardon in her tight little fuck hole. Laying Aria down on the bed, Oliver shows her how a real man likes to fuck. She takes his pussy pounding, then goes ahead and blows him as he watches. Oliver finds he really likes watching his stepsis suck him off while wearing those glasses. She climbs back aboard for a reverse cowgirl ride, then drops to her hands and knees so Oliver can bang her from behind as he anchors himself with his big hands on her shoulders. Oliver's strokes get harder and faster as he pounds his stepsis right into the bed. Sated, Aria goes back to work sucking and stroking Oliver's fuck stick until her rewards her for her impromptu lesson with a mouthful of cum to enjoy.
9.1 917 17 Aug 28, 2022
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