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StepSiblingsCaught.com Episodes - Season: 19
Dear Diary My Stepbrothers Dick Was So Good - S19:E1

Dear Diary My Stepbrothers Dick Was So Good - S19:E1

Haley Spades has what you might call a tumultuous relationship with her stepbrother, Oliver Flynn. On the one hand, she's a bit obsessed with him. Oliver is super hot, after all. On the other hand, he pisses her off constantly. When Haley gets ticked at Oliver, she finds herself ridiculously turned on. It's all very confusing, so Haley writes in her diary about it. She's just finishing her entry when Oliver comes into her room to complain that she left the cap off the toothpaste. They bicker, and Haley storms off with her diary still on the bed. Curious, Oliver cracks the diary open and starts reading. When he begins to realize how hot Haley is for him, he flashes back to all kinds of previous interactions they've had from the perspective of his sassy stepsis actually getting increasingly horny. When Haley returns to the room and finds Oliver with her diary in his hands, she flips her shit at the violation of her privacy. True to form, she's also terribly turned on. Haley winds up pulling Oliver's pants down to reveal his hardon and then leaning forward on the bed with her mini skirt flipped up so he can fuck her right there to prove he has balls. Oliver doesn't hesitate; pulling Haley's thong down and sinks his dick balls deep into that greedy wet snatch. He's not gentle as he fucks his stepsister, which only stokes Haley's fire hotter. Now that they're committed to getting it on together, they don't waste any time trying each other out in a variety of positions. Oliver gets on his back so Haley can climb aboard that big dick and go for a hell of a ride. She's been dreaming of seeing how that cock tastes so she arranges herself into a 69 that lets her gobble that dick while Oliver makes her squirm and moan. On her back next, Haley hooks and ankle over Oliver's shoulder so he can give it to her nice and deep. He keeps it up to the tune of Haley's moans until she's twitching around him. That brings Oliver to the end of his endurance, so he pulls out and pops all over Haley's stomach to leave her smiling and feeling lots better about her feelings about her stepbro.
9.16 735 6 Nov 27, 2021
Stepsis Likes My Dick Pics - S19:E2

Stepsis Likes My Dick Pics - S19:E2

Juan Loco and his stepsister Lily Larimar are constantly bickering. This time, they're fighting in front of Lily's friend Braylin Bailey because Juan wants to see Lily's cell phone. Eventually Braylin tries to broker a deal by pointing out that Lily has been saying Juan is a really cool stepbrother and Lily should let him look unless she has something to hide. Juan comes back by saying he'll let Lily look at the dick pics on his phone if he can see hers. Still in the middle, Braylin takes Lily's phone and goes through her messages to see that Lily's two biggest fantasies are to be hogtied and to be DP'ed. Lily also wants to get with her stepbrother. Braylin then goes through Juan's phone and finds the promised dick pics. The girls like what they see. The girls decide to do a social media video of Lily getting down to her bra and thong and Juan getting naked. Braylin pops in and offers to help them out, then gets down to her underthings too. Popping their titties out of their bras, the girls lead Juan out of the frame. How could such a hot vid not lead to some hot sex? Juan finds himself on the bed with Lily's mouth wrapped around his dick! Braylin gets in on that action so that together the girls can suck Juan's big one down and do plenty of ball sucking. It's not long before the girls get Juan on his knees so he can sink that nice cock into Lily's twat in doggy as Lily eats her BFF out. Braylin gets to scoot forward and enjoy Juan's dick next as Lily licks and squeezes her titties to make her moan even louder. When Juan lays down again, Lily climbs aboard for a stiffie ride that gets her bouncing happily away. Braylin wants to experience Juan's cock in doggy, and Juan is happy to give it to her. When Juan can't help but pop, he pulls out and takes aim for Lily's open mouth. He manages to hit his stepsister's face and her BFF's ass, giving them both a sticky shower. Lily is all smiles as she leans in to share her mouthful with Bailey in a kiss that has them both grinning and satisfied.
9.14 1298 12 Dec 9, 2021
Poke A Tree With A Dick In It - S19:E3

Poke A Tree With A Dick In It - S19:E3

Kyle Mason has long wanted his stepsister Andi Rose, but this Christmas he's about to see that wishes do come true. Their adventure starts with Andi doing some Christmas crafts at the table. Kyle is creeping on her, as is his usual, but this time Andi is ready for him. She asks him to help with her craft and Kyle comes back saying of course he will on the condition Andi shows him her tits. Andi doesn't think twice; she flashes those lovely boobies in Kyle's direction and then goes back to work. What is Kyle supposed to do besides help his stepsis out and check her out at every opportunity now that he knows what her breasts and tight little nipples look like beneath her shirt? Knowing that something interesting is about to happen, Andi excuses herself to go change into some sexy little jammies. Kyle takes the opportunity to put his dick in the advent calendar he's just created. He gets Andi to open the day he has fucked, then waits for her reaction. Although Andi is shocked and a little bit upset at first, she has to give her stepbro ten points for creativity. Kyle insists on ten licks instead. Andi thinks about it, then decides that's fair. She counts out ten licks of the tip, but then finds that that's not enough. Removing the calendar, Andi takes a big mouthful to suck in a deep throat BJ. Even that isn't enough for this cum hungry coed, so she leads them to the bedroom where she can really suck Kyle down and then have some fun. Laying on the bed with his stepsister's lips wrapped around his hardon is great, but Kyle is even more excited when Andi straddles his hips and sinks down to ride him. Her hands are all over her boobs as she bounces on Kyle's dick. Falling to her side, Andi lets Kyle do some of the work as he spoons her to fuck her from behind. When Andi rolls onto her knees, Kyle gets behind her and delivers the rough doggy style pounding that his stepsis needs. He finishes her off on her back, which leaves Andi responsible for Kyle's pleasure. She's cool to get back on her knees and open wide as she rubs one out for him. Kyle's cum shot hits his stepsister's open mouth and drizzles down to her breasts, giving her a sticky Christmas mess to enjoy.
9.03 683 10 Dec 12, 2021
Stepsister And Her Friends Want Dick For Christmas - S19:E4

Stepsister And Her Friends Want Dick For Christmas - S19:E4

Eliza Ibarra is getting together with her friends Alicia Williams and Jazmin Luv to make gift boxes for charity. The girls have decided to dress in matching festive elf outfits for the occasion. It's just an added bonus that those outfits are sexy as hell. As the girls put the boxes together, they gossip about all the cute guys they're going to meet and how horny they are. When Eliza's stepbrother, Ricky Spanish, joins them, Eliza tries to tell him to go away. Ricky says he'll stay, provoking Jazmin to taunt him that he's only here because he's in love with Eliza. Trying to dispel the awkwardness, Eliza tells Ricky he actually can help by playing Santa for some social media pics. Eventually Ricky agrees to dress in the Santa costume and lets the girls snap photos of him. Jazmin announces that someone should sit on Santa's lap and immediately volunteers, which lets her feel Ricky's hardon. As soon as Eliza has her back turned, Jazmin enlists Alicia's help as they pop that stiffie out to play with. Eliza is initially irritated, but once she sees what a nice cock her stepbro has, her attitude changes. Dropping to her knees with her friends, Eliza joins in the cock play while begging Ricky not to tell her mom. When he indicates that he won't, the trio of sexy elves goes to work on a triple BJ. The girls want to do more than suck that hardon. Jazmin gets the first turn with the D as she gets on her hands and knees and slides her thong aside so Ricky can do her in doggy. Eliza positions herself in front of Jazmin so her friend can lap at her hard nipples and then lean down to eat her out while Alicia takes up the mantle with Eliza's tender titties. On her back and cradled in both her BFFs' arms, Alicia spreads her thighs for Ricky to give her some Christmas cock. Eliza gets Ricky to lie on his back so she can enjoy her stepbro in a cowgirl and reverse cowgirl ride as her friends get on their knees so Ricky can use both hands to rub their pussies. The girls finish their impromptu foursome by sucking Ricky off until he rewards them by blowing his load for all three girls to enjoy.
9.02 1020 12 Dec 18, 2021
My Stepsis Is Extra - S19:E5

My Stepsis Is Extra - S19:E5

Jay Romero's stepsister, Madi Collins, is so extra that it's really holding her back. Jay tries to indulge her, but eventually his patience wears thin. He offers to help Madi stop being extra. Madi accepts, so Jay instructs her to put on a bathing suit and meet him in the shower. Madi's first challenge is when she walks into the bathroom and sees that her stepbrother is naked. Jay patiently explains to her that no one wears a swimsuit in the shower unless they're extra, so Madi agrees to take hers off. She joins Jay in the shower, where he says he's going to start with warm water and then slowly make it colder. Madi wants out ASAP once the water starts cooling off, but Jay tells her she needs to wait until her nipples are extra hard. Madi insists he feel them to see if they're hard enough. With Jay's hands on her tits to make sure she doesn't have to endure any more discomfort than necessary, Madi learns how to master cold water. Next, Jay tells his stepsis that she's going to have learn how to take big cock. That's the only way Madi will learn how to tackle hard things. Madi is nervous, but Jay insists she needs to learn. Eventually Madi agrees, but she can't like it because she's Jay's stepsister. Leaning forward against the shower wall, Madi takes every inch of Jay's big one while agreeing that maybe it is, in fact, okay to like hard things. She also realizes she doesn't care if Jay is her stepbrother; she just wants him to fuck her. They get out of the shower and into bed where Madi climbs on top of Jay and tries him on for size in reverse cowgirl, which gets her feeling nice and hot for more. Climbing off to lick her own juices off Jay's fuck stick, Madi turns around on her hands and knees so that Jay can fuck her from behind. Getting it in doggy makes the horny redhead moan long and loud, which just makes Jay double down on how hard he gets her to take it. He rolls Madi onto her back next and pins her knees up at by her shoulders to open her up nicely. Watching that pussy gobble his dick and knowing his stepsis has even squirted for him is the ultimate aphrodisiac for Jay as he eventually spoons behind Madi to give her one more big O. When Madi has sucked Jay to the brink of cumming and then opened her mouth to take his cum shot like a good girl, Jay pronounces her well on her way to fixing her extraness.
9.1 1292 18 Jan 14, 2022
Stepping In For Stepsisters Boyfriend - S19:E6

Stepping In For Stepsisters Boyfriend - S19:E6

Nikki Nutz comes to tell Ivi Rein that he's leaving for the night, which is music to Ivi's ears because she has a hot date with her boyfriend. She tells Nikki not to come back before 8 so she will have plenty of time to get it on. Once she has sent her message, Ivi runs upstairs to get ready. She peels off her scanty clothing and then blindfolds herself for a kinky good time. Getting comfy on the bed, Ivi waits for her upcoming afternoon of hardcore fun. In all her expectation, Ivi doesn't realize two things: One, that her boyfriend has cancelled on her, and two, that her stepbrother has come home unexpectedly early. When Nikki passes by his stepsister's room and sees her laid out like a gift, his initial reaction is to take embarrassing photos. When Ivi begins begging him to eat her out, though, he gives in and leans forward to tongue her tight pussy. It turns out that Nikki is quite good with his tongue! As Ivi removes her blindfold and turns around to thank the person she thought was her boyfriend, she's in for a big surprise. Once Ivi gets over her initial surprise, she has to admit that Nikki actually did a really good job. She agrees to return the favor. Peeling Nikki's pants off, Ivi learns that her stepbrother is hung. She enjoys sucking him off so much that she can't imagine not fucking him. Getting on her back, Ivi pulls Nikki on top of her to slide home in missionary. Nikki spoons behind Ivi to give it to her from behind next as Ivi goes wild in his arms. Getting on her knees, Ivi moans and squirms as Nikki pounds her in doggy. Ivi shoves Nikki onto his back for a cowgirl ride that leaves her panting and moaning, then gets him on his feet so she can suck and stroke him off to a big O of his own. When Nikki blows his load on Ivi's face, she can't stop smiling and licking at her salty treat. She insists that this will be their little secret.
9.22 894 7 Jan 17, 2022
You Saw Mine Now I Wanna See Yours - S19:E7

You Saw Mine Now I Wanna See Yours - S19:E7

Learning to live with a new stepbrother has been a challenge for Tristan Summers, especially when Chase Arcangel doesn't do a very good job of knocking before he enters closed doors. Today, Tristan was just toweling off from the shower when Chase barged in on her. Chase got a full frontal view, so Tristan insists that he get naked and show her his full frontal, too. Chase isn't having it, so after saying no he leaves. Tristan isn't about to give up so easily. She gets dressed and then walks into Chase's room without knocking, ostensibly to collect laundry. Chase has no warning before Tristan crawls into bed to try to take his pants off. She's still insistent that she should get to see Chase's cock since he saw her boobs and pussy. Eventually, Chase agrees that he will show Tristan his dick if she will touch it. Tristan seems okay with that, so Chase shows her the goods. He's shocked when his hot stepsis actually goes through with her end of the bargain. She insists that Chase needs to fuck her. Chase accuses Tristan of having a breeding fetish. She doesn't deny it as long as it means she gets his cock in that tight pussy. Eventually, Chase relents. Since Tristan is already on her back rubbing her clit to entice Chase, he just shoves it in and even leans forward to squeeze and knead those big boobs. Then Chase gets on his back so he can keep on enjoying Tristan's titties as she rides him in cowgirl. Tristan takes her time, exploring plenty of different angles for her ride before getting on her hands and knees to let Chase do her in doggy. When Tristan rolls onto her back, she begs Chase to blow his load in her meaty twat. Tristan promises not to tell anyone as long as Chase continues to glut her with cum as long as he promises to keep doing her tomorrow, and the next day, and the day after that...
9.26 1523 32 Jan 23, 2022
My Stepbrother Played Me - S19:E8

My Stepbrother Played Me - S19:E8

Juan Loco is worried that his dick is shrinking, so he's been measuring it. Today, he starts calling for his stepsister Ryan Reid to have her measure for him. Again. She tries to tell Juan he needs to cut it out, but Juan insists that he needs to know. When Ryan tells Juan he really needs to get over it. When Juan isn't convinced, Ryan tells him that what they're going to do is get him hard and measure him over the next few hours. Juan claims he can't get hard because it's kind of cold in there, so Ryan pops her titties out and plays with her pierced nipples to help him out. When Juan says he thinks he's ready for his measurement, Ryan is shocked that he is definitely a grower, not a shower. She can't help but be turned on. Later, Ryan reappears for Juan's next dick measurement. This time, she's wearing nothing but a sheer robe and a thong. She claims she lost the measuring tape, so she'll have to use her mouth instead. Juan is super hesitant, but Ryan claims she hasn't had a dick in a really long time and she just needs her stepbrother's. True to her word, Ryan shrugs out of her robe, tugs Juan's hardon out of his pants, and then measures him with a deep throat blowjob that lets her take him in almost to the root. She includes plenty of eager ball sucking, the better to show Juan how serious she is about wanting that dick. Pulling her thong to the side to open herself up, Ryan sinks down onto Juan's dick so he can feel how tight and wet her Latina pussy is. That stiffie ride is hard and fast, the perfect foreplay for a true hardcore romp. When Ryan falls onto her back and opens her legs, Ryan shoves himself back inside. His stepsis is a perfect fit, especially when she's on her hands and knees and thrusting backwards to meet Juan's every stroke in doggy. Once he has made Ryan cum, Juan gets his own reward as she turns around and gobbles his cock until he gives her a mouthful of cum to swallow. When Ryan tells Juan his dick definitely isn't shrinking, he admits that he just likes it when Ryan touches it.
8.78 1080 17 Jan 29, 2022
Caring Stepsister - S19:E9

Caring Stepsister - S19:E9

What would you do if you had a hot new stepbrother like Oliver Flynn? Lily Larimar and her friend Sera Ryder have decided to fuck him. They follow Oliver around the house and tell Oliver a litany of things they want to do with him. As the list grows increasingly sexual, Oliver asks if the girls have a family fetish or something. Lily doesn't say no, but they do leave it for now. Later, though, Lily and Sera corner Oliver once again with a thermometer to take his temperature. He tells them to leave him alone and makes a run for it, but they chase him through the house until they pin him in his bed. Trapped, Oliver tells them he'll open up for the thermometer if they leave him alone. The girls promise, so he complies. They claim he's running a fever and that he's wearing too many clothes. Before Oliver can say anything, they have peeled his pants off and pulled down his briefs to reveal a raging hardon. This is even better than Lily or Sera could have dreamed of! They can't keep their hands from stroking that hot dick. Sera is the first to give in and start licking and sucking at Oliver's cock, but Lily isn't far behind. With two hot girls taking turns deep throating him, how is Oliver supposed to stop now? Lily doesn't give Oliver the chance to change his mind. Hiking up her miniskirt and tugging her panties aside, Lily sinks down on that fine dick while Sera watches hungrily. She rides in cowgirl so Oliver can see that it's his stepsister fucking him, then tags out so Sera can give him a reverse cowgirl stiffie ride. Falling onto her back, Sera spreads her thighs to welcome Oliver back inside to bang her as Lily climbs aboard to ride her eager face. Then Lily takes her turn in the middle on her knees with Oliver doing her in doggy and Sera mewling in delight as Lily eats her out. Sera only moves when Oliver pulls out of Lily with just a few seconds warning before he cums. He nuts all over Lily's ass, then watches as Sera licks Lily clean and snowballs Oliver's load with her BFF.
9.25 1508 13 Feb 22, 2022
Stepsisters Walk Of Shame - S19:E10

Stepsisters Walk Of Shame - S19:E10

Madison Summers has been hooking up with her stepbrother's best friend. Joshua Lewis isn't exactly in the dark. He tries to let Madison know that he knows when he catches her early in the morning doing the walk of shame, but Madison takes the easy way out and claims she has to go to bed. She feels badly about it, though, so later that day she corners Joshua in his room so she can come clean to him. Her idea of an apology is to describe her sexcapades with Joshua's best friend in as much detail as she spreads her thighs and masturbates in Joshua's face. Joshua keeps on trying to cut Madison's strange apology short, but she insists on continuing to the end. Things take a strange turn when she concludes by saying that her fuck fest with Joshua's friend felt really wrong because she's been crushing on Joshua. Surprised, Joshua tries to get Madison to step it back, but she's coming on really hard and she's super hot. When Madison strips down to her thong and tugs her stepbrother's pants down to offer him a blowjob, Joshua's resistance melts away. He's instantly glad he gave in since Madison is a hot freak with her mouth. Since she's already got Joshua on his back, it's simple for Madison to shimmy out of her thong and swing one leg over Josh's hips to straddle him. Sliding down, she fills herself full of her stepbro's cock and starts riding. He's committed to seeing it through when Madison gets on her hands and knees, so he gives it to her nice and hard in doggy. When Madison flips onto her back, Joshua licks her clean of their shared juices and then slams back in to make his stepsister moan. She's so hot that Joshua can't keep from popping, too. Pulling out, he busts a nut all over Madison's belly for her to run her fingers through and sample.
9.11 836 8 Mar 4, 2022
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