(I decided that seeing as how I've written about all the other Kardashians, I couldn't leave Kendall out. Hopefully other people enjoy it too. Thanks for reading)
New York City
I'd finally gotten to the airport for my flight home. My business trip in New York City was over and all I could think about was getting back to Los Angeles. I even got to the airport hours before my flight was scheduled to take off. Everything changed, however, when I got word that my flight had been cancelled. The next flight wasn't leaving until tomorrow night. To say I was pissed off was an understatement. That's when one of the airport staff pulled me aside to give me an unexpected surprise. They told me that there was someone at the airport who not only owned a private jet, but that the owner was flying to LA and wanted to know if I wanted to go with them. Even though it seemed a little strange, I figured there was no harm in checking it out, especially if the next flight wasn't until tomorrow night.
After getting my luggage I head straight for the gate. As I approach I see that whoever owns the private jet has their own security checkpoint set up. Once the security guards decide I'm good to go I walk to the waiting area, surprised at who I find waiting there. It's Kris Jenner and her daughter Kendall Jenner. Kris notices me immediately, giving me a huge smile, which confuses me since I've never met her before. That's not to say I don't know the rest of her family, having fucked four of her five daughters already. It's kind of funny to me that here she is with the only daughter of hers that I HAVEN'T fucked. She stands up, walking over to me quickly. "Hi Cptnstrwrs! I'm Kris Jenner. It's great to meet you. I'm glad you got my message," Kris says, shaking my hand. "Hi. Your message said something about an offer of some kind? That I could fly back to LA with you if I agreed? What did you have in mind?" I ask. "Well...This is sort of embarrassing, but my daughter Kendall over there doesn't really know a lot of guys. Sure she travels all over the world modelling but since she doesn't have the same...'build' as her sisters, there are some areas she doesn't have experience in," Kris explains, as I realize where this is going. "What do you mean?" I ask, wanting to hear her SAY it. "What I mean is, I'll fly you back to LA if you sleep with Kendall on the way there. You'd be in charge during it all, but I'd be there...supervising things," Kris says with a smirk.
A free ride home AND I get to fuck the last Kardashian sister? Even if her mom is watching, which I admit, is a little weird, how can I say no? "Alright I'm in. Does Kendall know anything about this arrangement?" I ask. "Yeah, it was mostly her idea. She heard about you from her sister Kylie," Kris says, smirking at me again, the look on her face telling me that she knows I fucked Kylie only hours ago. "Well, word does travel fast in this city," I reply, turning a dark red. "Don't worry about it. If I didn't trust you I wouldn't be letting you anywhere near my daughter," Kris replies. "Come on, I'll introduce the two of you," Kris says, walking back towards Kendall. As we approach I get my first real look at Kendall. She's taller than most of her sisters and also thinner, with an average size chest. But the one big difference, or lack there of, is that she has a small, toned ass instead of the normal big, phat ass that her other sisters have. If I had my choice of Kardashians, Kendall wouldn't be my first choice, but like I said, she's the only one I haven't fucked yet so I'm all in.
"Ken-doll, sweetie, this is Cptnstrwrs. He'll be joining us on the way home," Kris says, Kendall giving her a weird look. "He agreed to our...arrangement so I think you two should get acquainted, especially since we're not taking off for a hour," Kris says. "Hi, I'm Cptnstrwrs," I say, shaking the young model's hand. I can tell she's a little nervous which is understandable for a lot of reasons. When you're Cptnstrwrs you get that reaction a lot, and I'm sure knowing that you're mother is going to watch you fuck a stranger doesn't make things any easier. Kendall and I sit and make small talk as Kris talks to the airport staff about the trip home. Finally we board their private jet and I realize only after taking a few steps inside the jet that's it unlike any other plane I've been on before. It's like a small apartment crammed inside a plane with a living room, kitchen, bedroom and bathroom all in the confines of the plane. We put our luggage in the closet in the bedroom, Kendall and I staring at each other awkwardly until Kris intervenes.
"What are you two waiting for? We only have a few hours before we land" Kris says. With a shrug, I pull my shirt up and off, tossing it aside as Kendall's eyes go wide. I reach over and pull her tank top up over her head, throwing it towards my shirt. She's still stunned as I slide her shorts down to her ankles, Kendall kicking them aside. I take a moment, looking her up and down as she stands there in only her bra and panties. True, she's not as curvy as her other sisters but Kendall is still cute in her own ways. "Am I doing the honors or do you want to?" I ask, nodding towards my belt. "Go on Ken-doll!" Kris snaps. Slowly and nervously, Kendall reaches out towards my waist. She fumbles with the belt buckle for several minutes before she gets it undone. Kendall swallows hard as she unbuttons my jeans, pulling the zipper down. I let my jeans fall to my ankles, Kendall's eyes going wide again, no doubt noticing the bulge in my boxers. If she thinks it's big now, then she's going to be in trouble once I'm fully hard and ready to go. Her hands are shaking as she grabs the elastic waist of my boxers and slides them down my legs.
I feel both women's eyes burning into me as I stand there naked in front of them. Sitting on the edge of the bed, I wave Kendall over. "So if I'm going to help you get more experience in the bedroom, then I think the best way to start is for you to suck my cock," I say. "I think I should do it. Or at least get you started for Kendall," Kris says softly, her eyes still glued to my cock. Normally I wouldn't give a woman Kris' age the time of day, but she's not just any older woman, she's the mother of the most amazing cocksuckers called the Kardashians. I mean skills like that have to be passed down from generation to generation right? "Ok, but only for a few minutes. Our agreement was for me and Kendall," I say, knowing Kris will take the bait. "Sure, only for a few minutes," she replies, kneeling down in front of me. "Watch how I do this Ken-doll," Kris says, taking my cock in her hand. Wrapping her lips around the head, Kris begins flicking her tongue on the tip as she bobs her head up and down my shaft. It's surprisingly one of the better blowjobs I've ever gotten, proving that the Kardashian blowjob skills are genetic. Within the first two minutes I'm fully hard, and thanks to Kris slobbering all over my cock, wet enough to fuck Kendall.
"Alright, that's enough. Time for Kendall to get her turn," I say smirking at the young woman. Kris releases my cock, the huge, hard cock pointing at Kendall as she approaches. She kneels down, taking Kris' place in front of me. "Let's make things interesting. You have to blow me without using your hands, only your mouth," I laugh, Kris raising an eyebrow at me. Kendall leans in slowly, mouth wide open, the young model placing her hands on my hips to support herself. Wrapping her lips around the shaft of my cock she begins slowly sliding her head up and down my length, mimicking Kris' technique. "I think we can do even better," I say, putting a hand on either side of Kendall's head. Holding her tight, I pump my hips in and out of her mouth, face fucking Kendall as hard as I can. "Mmmm!" Kendall mumbles, clearly enjoying her current situation, despite the circumstances. I give her a few more good thrusts, deep throating her with my cock, her eyes watering as I hit the back of her throat.
Deciding she's had enough I pull out of her mouth, Kendall coughing and gasping for air. I climb onto the bed, laying on my back in the center of the bed. "Alright baby, let's see what you've got. Get over here and ride my cock until I tell you to stop," I say, smirking at her. She hesitates for a second before taking off her bra and sliding her panties off. I watch as Kendall crawls on all fours across the bed towards me. She swings a leg over my hips before she begins to lower herself towards me, using one hand to guide my cock to her pussy. "Ugh! It's so big!" Kendall groans as she slowly impales herself on my hard cock. Despite being a thinner, smaller girl Kendall is able to fit my cock fully inside her. She starts slow, riding me with long and steady movements, sliding herself up and down my shaft. I feel myself stretching her out as she rides me, Kendall definitely the tightest of all the Kardashians. Still I get bored quickly with her going so slow on top of me.
"Faster! I want to see you cum on that cock!" I snap, smacking her tiny, toned ass. Kendall frowns as my hand slaps her ass but she does as she's told, speeding up quite a bit. "Ugh! Ugghhh! He's so deep inside me!" Kendall wails as she fucks me. "You're doing great Ken-doll! Don't stop now!" Kris says, watching a few feet from the bed. She speeds up again, the bed rocking as we fuck. The look on Kendall's face is so hot, her face contorted in a mix of pain and pleasure, leaning more towards pleasure. "Touch yourself! Rub your clit while you fuck me!" I command her. She obeys, sticking a hand between us and furiously rubbing her clit as she rides me. Normally, I'd let her ride me forever, but I want her to cum so we can change positions. I don't have to wait long, Kendall letting out a shriek after only a minute or two of her clit rubbing. "Oh fuck! I'm cumming! I can't take it anymore!" Kendall cries as she orgasms, her body tensing up as she shakes in pleasure. I put my hands under her arms, the only thing keeping her upright as she finishes climaxing. Once she's done, I gently lay her on the bed next to me, pulling my cock out of her.
"Sweetie! Are you okay?" Kris asks frantically. "Y-yeah. I'm fine," Kendall groans, her voice shaky. Kris' face goes from concerned to aggravated. "You finished way too soon! You have to last longer of you don't want to disappoint your man. I taught you better than that!" Kris exclaims. "She did alright for her first time with the Captain. It's also partially my fault for having her rub her clit while we fucked. But I think it's time we work on building up your endurance," I say, grinning down at Kendall. Putting my hands on her thighs, I gently spread her legs. Without a word, I push myself inside of her. "Ugh! It feels so good inside me!" Kendall moans, still dazed from her orgasm. I wouldn't say I thrusted into her slowly, but I also decided not to go full speed just yet. That doesn't mean I'm planning on going easy on her though, pounding her pussy non-stop for the foreseeable future.
Her moans and groans are so hot that it takes all I have not to blow my load right then and there. I know I need a way to keep her distracted while I do my thing, and I come up with the perfect idea. "Let's also work on your dirty talk in the bedroom. I want you to talk as dirty to me as you want, don't hold back. Beg me not to stop fucking. I want to hear you scream my name as I fuck you," I say, smirking at her, Kris raising an eyebrow at my request as Kendall nods her agreement. She starts immediately as I start pounding her pussy again. "Fuck me Cptnstrwrs! Please don't stop! I need that huge Captain Cock inside me!" Kendall screams. I give her what she wants, hammering into her with each quick, hard thrust, the bed shaking wildly. As we fuck I can feel her body starting to tense up again, Kendall getting close to another orgasm. "Uh-uh! You don't get to cum again unless I let you!" I exclaim, pulling out of her.
I straddle her upper body, sticking my cock in her face. "Why don't you suck on my cock for a little bit? Don't stop until I tell you to," I bark, sliding my cock into her mouth. Despite her obvious exhaustion, Kendall focuses on the task at hand, sucking me off as hard as she can, her eyes locked on mine. "That tastes good doesn't it? I bet you never thought you'd ever get to taste your own juices, huh? You got them all over my cock so now you get to clean it off," I laugh, watching her do her thing. She sucks and sucks, flicking her tongue over every inch of my cock until it's completely clean. I'm surprised at how sad she looks when I pull my cock out of her mouth. "Sit up and get on all fours," I say, grinning down at her.
Kendall does as she's told, quickly and quietly, getting on her hands and knees in the center of the bed. Kneeling behind her, I line my cock up with her pussy. I can't lie, for a split second I want to stick it in her puckered little asshole, but it would be weird if I ass fucked her with her mother watching the whole time. She's still wet enough that I slide right inside her with no resistance. Grabbing her by the hips I start jack hammering into her, Kendall groaning and moaning as I plow her from behind. "I always like saving doggy style for last. It's a good way to let the ladies know that they're my bitch!" I laugh, smacking Kendall's ass as Kris shakes her head, smirking at me. I'll admit, it was weird at first to have someone watching me fuck Kendall, especially when that someone is her mother. But now for some reason, it kind of turns me on. Grabbing her hips even harder, I speed up, Kendall actually whimpering and whining like a dog as I do her dirty. She cums unexpectedly, her pussy quivering tightly around my big, hard cock.
As the last waves of her climax wash over her, I feel my cock tense up. I pull out of her quickly. "Turn around and open your mouth!" I bark, Kendall once again obeying. Cramming my cock down her throat, I grab the back of her head. Holding her head tightly in my hands I pump every last drop of my load down her waiting throat, Kendall swallowing every drop like a champ. I release her head, pulling out of her mouth as Kendall licks her lips. "She did much better than I thought she would. You should be proud of your daughter," I say, smirking at Kris. "I am," she replies, smirking back at me. Looking out the window I can tell that it won't be long before we land. "I think there's still a few things I can teach her, but I need a few weeks. Call me sometime and I'll see when we can do this again," I say. "Alright," Kendall AND Kris say at the same time. As I finish getting dressed I give them one final look. "And who knows, I may even have some time for you too," I say, looking Kris square in the eyes as I walk off the plane...
The End
Topic: Captain's Log - Kendall Jenner (Read 144 times)