Los Angeles, California
Derek felt like the luckiest man alive. He had gotten a call from his friend Cptnstrwrs, who offered him a once in a lifetime opportunity. The Captain had been invited to spend the day with Kylie and Kendall Jenner but couldn't due to a work trip. Somehow he'd been able to talk the sisters into letting Derek take his place. The best part was Cptnstrwrs had even hired a driver to take him to and from the Jenners' house, which meant he wouldn't have to watch how much he drank if their private party got a little crazy. The car picked him up a couple hours after lunch and drove him nonstop to the Jenners' mansion in the Hollywood Hills. He wasn't sure if he should ring the doorbell or not when the front door opens, a man who's clearly the girls' butler standing in the doorway. "Master Derek, I presume?" The butler asks. "Yeah , that's me," Derek replies. "Very good sir. Please follow me," The butler says.
The butler leads him out to the pool, Kendall and Kylie laying on a couple of lounge chairs nearby. While Derek normally prefers older women, the sight of these two in their bikinis may change his mind, at least for today. Kendall has a light red bikini that barely covers her smaller, but perky breasts. Her bottom does an excellent job of covering up what it's supposed to cover while still showing off her small, toned ass. Kylie is the complete opposite. She's built more like her older sister, Kim, with her huge tits and her phat, sexy ass. Derek would never say no to either sister, let alone BOTH at the same time. At least, he HOPED that's what was going to happen today as the sisters approached him.
"Hi, you must be Derek. I'm Kylie and this is my sister Kendall," Kylie says, each of them quickly hugging Derek. He could feel Kyle's impressive tits being crushed between their bodies and he wanted nothing more than to take her right then and there, but he decides to play it cool and let the ladies take the lead...at least, for now. "Cptnstrwrs spoke VERY highly of you. Hopefully you'll be just as much...fun as he is!" Kendall purrs, putting a hand on Derek's shoulder as she gives him a sly grin. "Why don't you come swim with us in the pool?" Kylie asks, putting her hand on his other shoulder, giving Derek a similar smile. "I would, but I didn't bring a swimsuit," Derek says, looking back and forth between them. "That's no problem! Just swim without it!" Kylie laughs, unbuckling his belt as Kendall unzips Derek's fly. He watches, speechless as the Jenner sisters pull both his jeans and his boxers down to his ankles. Derek removes his shoes and then kick his pants and boxers to the side, just as Kendall and Kylie pull his shirt up and over his head, leaving him completely naked.
"Oh no! Now we're overdressed!" Kylie giggles. "I guess there's only one thing to do!" Kendall giggles back. Derek watches, amazed, as both women reach behind their heads and untie the strings on the bikini tops, letting them fall to the ground before sliding their bikini bottoms off. The girls take him by the hands, Kendall on his right hand, Kylie on the left and walk him towards the pool. Walking down the steps into the water, they stop once it's shoulder deep for the women, and both sisters are all over Derek in an instant. From either side of him, they take turns, one of them kissing Derek while the other reaches underwater, stroking his cock and fondling his balls. Kylie and Kendall switch several times, finally stopping once Derek is hard enough for them. "Follow us!" Kylie giggles, climbing out of the pool, Kendall following close behind.
They have Derek lie down on a lawn chair next to the pool, Kylie kneeling down between Derek's legs. She pushes her breasts together around his cock and begins to titfuck him. Derek groans as she rubs her huge, warm soft tits up and down his shaft as Kendall climbs onto the chair with him, lowering her hips towards his face. He doesn't hesitate for a second, immediately licking at Kendall's clit and pussy as her sister starts to titfuck him faster. If you asked him earlier today, Derek wouldn't have guessed he'd end up in a situation like this, not that he's complaining though. As hard as it is for Derek to focus, Kendall groans in approval of his technique, Derek grateful that he can please her even though Kylie is distracting him with her tits.
A few more moments pass, Kendall crying out loudly as her thighs close tightly around Derek's head. "Ugghhhh! Fuck Derek! You're going to make me cum! Ugghhhh!" Kendall screeches, cumming hard above him, her body trembling as the pleasure overtakes her. Kylie stops titfucking Derek as Kendall cums, standing up once her sister finishes. Kylie helps Kendall off of the chair, walking her in front of Derek. Kendall kneels down as Kylie takes her sister's previous place on Derek's face. Leaning down, Derek thinks Kylie is about to start sixty nining him. What happens next though is even better.
Kendall and Kylie take turns sucking and licking Derek's cock. Kylie's huge tits crushed against Derek's body as the sister blow him. As great as it is, Derek is still able to focus long enough to eat Kylie out like he did with her sister moments ago. Kylie's pussy tastes similar to Kendall's, but almost a little bit...sweeter? It was hard to pinpont, but when you're eating out a couple of hot sister back to back you just don't care. What Derek DID care about in the moment, though, was getting Kylie to cum sooner rather than later. A few quick final flicks of his tongue and he gets his wish. Kylie, about to cum, clenches her thighs around Derek's head, just like her sister did moments ago before her orgasm overtakes her.
"Oh fuck! He IS good! Ugghhhh! Agghhhh! I've never cum thisbhard before!" Kylie whines as she climaxes. She shakes for several minutes before her orgasm finally subsides, climbing off of Derek, utterly exhausted. Kendall and Derek watch Kylie practically collapse on the chair next to theirs, the curvier Jenner panting and gasping for air. "You're doing great sucking my cock, but let's get to the good stuff!" Derek says, motioning to Kendall to stand up. He stands as well, Kendall quickly taking his place on the chair. She lies down on her back, slowly opening her legs for him, rubbing her clit with one hand as Derek closes the gap between them. Kendall nods at him and he slides his cock inside her, Kendall's pussy still wet from her orgasm. He begins fucking her slow and steady, eager to enjoy every single second of it.
"Ugghhh! He's so fucking deep inside me! His cock is stretching my tight little pussy out!" Kendall moans as Derek picks up speed, the chair gently rocking with his every thrust. Kylie watches from the other chair, rubbing her clit with one hand while using her other hand to play with her big tits. "Fuck! That's so hot! I can't wait for my turn!" Kylie purrs, winking at Derek. He gives Kendall a few final hard, quick thrusts before pulling out of her, turning his attention to her sister. "Get over here and lie down! I'm not just going to lay there and take it like my sister!" Kylie giggles, giving her sister a playful look as Kendall rolls her eyes.
As soon as Derek is on his back, Kylie is all over him, straddling his hips as she guides his cock to her pussy with one hand. Both of them groan softly as Kylie slides herself onto his dick, Derek slipping inside her with no resistance. She rides him hard and fast right from the start, Derek afraid that the chair might break beneath them. He doesn't have to see the look in Kylie's eyes to know the busty brunette is extremely horny right now. Derek quickly grows tired of just watching Kylie's tits bounce around as they fuck, reaching up and grabbing one in each hand. "Aghh! Just like that! Play with my titties while I fuck your big hard cock!" Kylie growls down at him, somehow finding the strength to speed up even more. She slips a hand between them, rubbing her clit as she rides him. Just as Derek feels like he's about to cum, Kylie shrieks loudly. "Ugghhhh! Fuck! I'm cumming again! It was just starting to get good too!" Kylie whines, her pussy quivering tightly around Derek's cock, her walls squeezing it in a deathgrip.
As great as it feels, Derek is relieved when Kylie climbs off of him, the brunette taking his spot on the chair. "Why don't you go back to my sister? I'm definitely going to need a few minutes to recover after that!" Kylie says, grinning at him. Kendall goes to stand as he approaches, but Derek motions to her to stop. "Turn around and bend over!" Derek growls at her. "Oooh!" Kendall and Kylie reply in unison, grinning and giggling at each other. Ignoring them, Derek grabs one of Kendall's asscheeks in each hand, spreading them wide before using his hips to push his cock inside her. Fully balls deep inside her, Derek grabs Kendall by the hips and starts hammering her hard and fast doggystyle. "Oh yeah! Pound my pussy until I can't walk straight!" Kendall growls over her shoulder to him, lust in her eyes. That's all he needs to hear and a second later he's fucking her with every ounce of strength he can muster. He sees Kendall grab the edges of the chair tightly, eyes closed as she enjoys the feel of his cock inside her. As much as he enjoys Kylie's curves, he's enjoying the feel of Kendall's tight pussy as he takes advantage of her slimmer, toned body. Just as he gets a good rhythm going, he feels his cock start to tremble inside her. "Fuck yeah, Baby! Cum inside me! Fill me up with your big hot load!" Kendall wails. Even if that wasn't already his plan, Derek's body betrays him, shooting shot after shot of his cum deep into Kendall's waiting pussy. They both moan softly as thin trails of his cum leak out of her and down Kendall's thighs. Pulling out of her, Derek watches with a grin on his face as Kendall quickly turns around and sits up, licking and sucking his cock clean.
"Hey! Don't forget about me! You better be able to cum again!" Kylie pouts. "I'm sure that won't be a problem!" Derek says, taking Kylie's place on the chair. He stops her as she goes to climb onto his lap again, a confused look on her face. "Turn around!" Derek growls, smacking her ass as she obeys. "I get it. You want to see my big sexy ass while we fuck!" Kylie laughs, sliding herself onto his cock again in the reverse cowgirl position. She's only slide herself up and down on his cock a few times when Kendall walks over, kneeling in front of them. A second or two later Derek feels what can only be Kendall's tongue, moving slowly across his balls as her sister rides his cock. In that moment he knows that this will probably one of, if not, the greatest single moments of his life, fucking not one but two of the Kardashian sisters at the same time.
Thanks to the sisters' teamwork, Derek starts to feel his cock trembling yet again. "Don't fight it Baby! Cum for me! I want MY pussy filled up too! Just like you did with my sister!" Kylie exclaims. He gives her what she wants, pumping what feels like gallons of cum up into Kylie's waiting pussy. "Nooo!" Kylie whines, as just like with Kendall, Derek fills her up quickly, some of the extra cum leaking out and down her legs. No sooner has Kylie pulled herself up and off his cock does Kendall spring into action.
She surprises Derek though. Kendall doesn't go for his cock as he expected, but instead starts licking up the trails of cum running down her sister's thighs. "Holy shit!" Derek exclaims as Kendall dives in facefirst, licking at Kylie's clit and pussy, lapping up as much of his cum as she can get. He knew from Cptnstrwrs that these girls were freaks in the bedroom...or wherever they happened to have sex, but he never thought he'd ever get to see one sister eating out another one. He doesn't care though, considering neither one is related to him, and the fact that they've drained his dick dry is another win for the two of them. He watches in amazement as Kylie and Kendall cumswap his load several times before finally splitting what's left between the two of them before they swallow it down hard.
He gathers up his clothes, dressing quickly as the sisters put their bikinis back on. "Give us your number! We DEFINITELY need to do this again sometime," Kylie says. "Yeah. And next time, we might even be able to get a few of our older sisters to join in! They have a thing for younger men!" Kendall giggles. Which is completely fine with Derek, seeing as how he prefers older women anyway. "Don't keep me waiting for too long!" Derek laughs, giving them his number before heading out the door...
The End for now
Topic: Derek's Pool Party (Kylie and Kendall Jenner) (Read 183 times)