New York City
I was in the Big Apple for a business trip when I received an unexpected text message. If it wasn't some kind of trick, pop star Taylor Swift was asking me if I wanted to hang out while I was in town. Now I'm not a huge Taylor Swift fan, but I wasn't going to say No until I had at least heard her out. Something about the way she was wording her messages I could tell she wanted to more than 'hang out' with me. Normally I'd be all for hooking up with a cute blonde like Taylor, but her attitude definitely left much to be desired. Anytime I'd seen her on TV she seemed a little stuck up, almost like she thought she was better than everyone else. The fact that she's always writing songs about her exes wasn't helping her case. Several people had also told me that Taylor was also a bit prude. Despite all that, I decided to give her a shot, considering she followed a couple of simple rules.
A hour later I hear a knock on my hotel room door. Sure enough, it's Taylor, almost right on time. I open the door, gesturing to her to come in. "Hi, I'm Cptnstrwrs," I say. "Hi. Obviously I'm Taylor," she laughs. We walk into the living room area of the hotel suite, sitting on the couch next to each other. She has on a denim tank top and matching jean shorts, and ankle highs boots. "So before we do anything else, I just need you to sign this," I say, pointing to a paper on the coffee table in front of the couch. "What's that?" Taylor asks, confused. "It's your normal nondisclosure agreement. I know you like to write songs about the guys you break up with. I don't need any negative publicity if things don't go your way tonight," I say, smirking at her. "What exactly do you think we're going to be doing tonight!?" Taylor exclaims. "Oh don't play dumb with me. If you want anything to happen tonight you need to start being honest with me right now," I reply, giving her the most serious look I can manage. "Alright, alright! Maybe I had ulterior motives for coming here tonight. I thought maybe we could fool around, maybe make out a little bit," Taylor sighes, blushing a dark red. "Well, sign the disclosure and who knows what we might do?" I laugh. "Fine," Taylor sighes, signing the disclosure.
"Now that the paperwork is out of the way, there is one last thing," I say. "And what's that?" Taylor says. "I'm still not sure you're here with the best of intentions, but I'll make a deal with you. Let me invite my friend over. Once he's here, you hook up with him while I watch. After that, I'm all yours for the rest of the night, no strings attached," I say. Taylor's quiet for a moment, the look on her face telling me she's more than a little uncomfortable. "Fine, call your friend. I'll sleep with him, but then he has to leave so we can be alone," Taylor replies softly. I send a quick message to my friend, knowing he was already on his way over anyway. He should be here shortly, but we can save time by getting you ready to go. Take off your top and your shorts," I say, the look on Taylor's face telling me she'd rather not. To my surprise she stands up, sliding the tank top up and off her body. Tossing it to the floor, she goes right to her shorts, unbuckling her belt before she unbuttons her shorts. Slipping them down and off, she kicks them aside, once again blushing. I take a moment to soak in the sight, the world famous Taylor Swift standing a few feet from me in nothing but her white bra and panties.
She jumps as a knock on the door startles her. "Now we get to see how bad you want to get with the Captain," I say. I try not to smile as I walk to the door. Opening the door my friend walks in, Taylor's eyes going wide as she sees him. "What the Hell is he doing here?!" Taylor exclaims. "Well I thought you knew Kanye West was a good friend of mine," I explain as Kanye and I walk over. "If we're being honest, you owe Kanye an apology. Everyone knows your entire feud with Kim Kardashian was because Kanye embarrassed you at that award show all those years ago. If you want to sleep with me, you have to apologize to Kanye first. And I think we both know I mean more than a verbal apology," I say, smirking at her. She stands there trembling, and I can't tell if it's anger or fright. "Alright, let's just get this over with," Taylor says softly. I can't believe how easy it was to break down her initial resistance to the whole situation, but I take it as a good sign, Taylor obviously wanting to fuck me, no matter the cost.
The three of us go into the bedroom. I sit on a chair in the corner and Taylor and Kanye sit on the foot of the bed. "I think Taylor should start by sucking Kanye's cock," I say. "Me too," Kanye agrees. "And no hands, just your mouth," Kanye adds quickly, taking off his pants. Taylor kneels in front of Kanye, slowly pulls his boxers down to his ankles, her eyes going wide once again as she sees his cock for the first time. I watch in awe as she wraps her lips around the head of his cock as she starts to blow Kanye. As she moves her head up and down his shaft I can tell Taylor's done this sort of thing many, many times before. I walk over to the two of them crouching down behind Taylor. Taking the clasp of her bra in my hands, I undo it, slipping the straps of her bra down her arms and shoulders as I slip it off of her. Reaching around I cup a tit in each hand, squeezing Taylor's tits softly as she continues to suck off Kanye. I pinch and roll her nipples between my fingers, making them instantly hard as Taylor moans, the sound muffled by the big, black dick in her mouth. If I had to guess I'd say her tits are a natural C cup, a perfect fit in my hands. As I play with her tits, Kanye puts his hands on either side of Taylor's head. Holding her tightly, he begins sliding her head even faster up and the length of his cock than Taylor had previously been going. I watch him throat fuck Taylor, her eyes watering as Kanye gags her over and over with his cock.
I decide she's had enough for now and signal Kanye to stop. He pulls his cock out of her mouth, Taylor coughing and gasping for air. "That was a good start Taylor but we're just getting started. Lie down on the bed, on your stomach," I say, Taylor obeying. Reaching around her hips I grab the waist of her panties, sliding them off her body. Kanye climbs onto the bed, positioning himself above her slightly. "Did you mean what you said when you told me you'd do anything to fuck me tonight?" I ask Taylor. "Y-yeah..." Taylor replies softly. "So if I said Kanye was about to fuck your ass right now, you're fine with that?" I ask, smirking at her, Taylor nodding. "I need to hear you say it," I say. "Kanye can fuck my ass!" Taylor says loudly, probably louder than she wanted. I watch as Kanye spreads her cheeks, spits on her asshole, then pushing himself inside her, almost all in one motion. "Ugh! Go slow! Please! Go slow!" Taylor whines as Kanye slides deeper and deeper into her toned ass.
To my surprise, Kanye does as she asks, slowly entering her asshole rather than cramming himself in hard and fast. Once he's fully inside, Kanye begins pumping Taylor's ass as I watch, the singer moaning and groaning as she's fucked prone bone. Kanye's so close to her that he might as well be pinning her to the bed, his body just inches from Taylor's. Between the sight of her taking it up the ass and her cries of pleasure, I decide I'm not just going to sit back and do nothing. "Damn Baby! Are you always this loud when you're getting fucked? Open up," I snap at her, Taylor reluctantly opening her mouth wide. I quickly drop my pants, already fully hard from seeing the biggest prude in Hollywood getting fucked in the ass, and slide my cock down her throat. If you had told me a few hours ago that I'd be spit roasting Taylor Swift with Kanye West tonight I would have called you crazy. After just a few minutes of being double teamed, the last of Taylor's resistance melts away, the singer pretty much going limp between us. If this is how a blowjob from Taylor feels when she's barely putting in any effort, than a normal blowjob must be amazing, a testament to Taylor's dick sucking skills. I feel myself getting bored as my balls slap against Taylor's face for what feels like the hundredth time and I decide to do something about it.
Pulling my cock out of Taylor's mouth, I get Kanye's attention. "Hey man, lift her up. I think it's time our friend here gets a reward for being so agreeable tonight," I say with a grin. Without pulling out of Taylor's ass, Kanye puts his arms under her legs, lifting Taylor up into the air facing me, spreading her legs open in the process. "Do you trust me?" I ask Taylor. "Uh-huh," she groans back, nodding slowly. I walk towards the two of them, cock in hand. Once I'm inches from them, I push my cock into Taylor's pussy, surprised by how wet she is. "Ugghhh! Oh fuck! I've never had two cocks inside me before!" Taylor whines. "Please! I'm sure your boyfriend passed you around the locker room after he won the Superbowl!" Kanye laughs as we double penetrate Taylor in midair. He has his hands under her thighs as I put hands under her knees, helping Kanye slide Taylor up and down on our cocks. She looks dazed and confused as we toss her around like a rag doll, using her tight holes to pleasure ourselves. Deciding she's had enough, I nod to Kanye, who pulls out of her ass.
I lay Taylor down gently on the bed, face up as I pull out of her. Kanye walks over, cock in hand, jerking himself hard and fast. Using his other hand, he turns Taylor's head to face him. Just as he's about to cum, Kanye pushes his cock down Taylor's throat, cumming in her mouth. She's so out of it at this point that Taylor swallows shot after shot of Kanye's cum without a word. Finally finishing Kanye pulls out of her mouth, grinning at the blonde singer. "I guess she's not so bad after all! Taylor, I accept your apology," Kanye laughs as he starts to get dressed. I walk him to the door of the hotel room. "That was awesome bro! Give me a call if you ever want to do something like this again," Kanye says as he walks out the door. "Count on it," I reply, closing the door behind him. I hear a muffled cry from the bedroom and I walk back there as quick as I can.
As I enter the bedroom I see Taylor forcing herself up into a sitting position. "Hey! Don't forget what you said! You promised me that if I hooked up with your friend that you'd fuck me!" Taylor says, a groggy look on her face. "Are you serious?! You're exhausted. You were barely able to sit up right now," I laugh. "It doesn't matter. Just because I'm the tired one doesn't mean that YOU can't still fuck ME," Taylor says, dragging herself to the center of the bed. She falls onto her back, spreading her legs wide. "Please don't make me beg Captain!" Taylor whines, gently rubbing her clit. "I need this," she says. With a sigh I climb onto the bed. "Fine, but it's going to be quick. I wasn't planning on tag teaming you with Kanye back there," I say as I climb on top of her. Pushing myself into her pussy, I fuck her as hard and fast as I can, the bed shaking violently as we fuck. "Oh yeah! Don't stop Captain! You feel so fucking good inside me!" Taylor growls, getting a second wind. "I know I do! Your pussy is so tight, but that's fine. That just means I'll have stretch that prude pussy out, show you what it feels like to get fucked by a real man!" I laugh, pounding her even faster. She doesn't last long, Taylor letting out a loud shriek as she climaxes. "Oh God! I'm cumming! I'm cumming all over your cock! Thank you Captain!" Taylor wails incoherently as she cums.
Her screams of pleasure and the feel of her pussy spasming wildly against my cock is the last straw. I cum inside, and I cum HARD. "Oh my God! It's so warm! Your cum is filling me up!" Taylor groans as trails of cum leak out of her and down her thighs. I hold her hard by the hips, waiting until I feel myself finishing cumming before I pull out of her, a string of cum falling onto her clean shaved crotch. I go into the bathroom and clean myself off, bringing Taylor back a towel. "Here, clean yourself up," I say, tossing her the towel. "I need you out of her in the next ten minutes," I say, gathering up her clothes and bringing them to her. "What? You mean to tell me you're just going to fuck me and then kick me out?!" Taylor exclaims. "I sure am. This was a one night stand, and you were lucky to get it. And don't forget, you can't tell anyone or else you'll be hearing from my lawyer," I say with a smirk. "I never should of signed that non disclosure agreement," Taylor sighes as I walk her to the door. "Yeah you're probably right. But you did, and even if you hadn't, it's not like anyone would've believed that you got fucked by Cptnstrwrs. Most people think you're a stuck up prude," I laugh, closing the door behind her.
I hear her mumbling to herself as she walks towards the elevator but I ignore Taylor. Right now it's more important that I get to bed and get some sleep, especially after I check my phone. The same number that's been calling me for the last couple of months left me a few voicemails while I was busy with Taylor. I feel bad that I've ignored her this long. Sending a quick apology text, I hop into bed, my phone quickly buzzing as I get a reply to my text. As I read it I let out a groan. I pray I fall asleep quickly, knowing that if J-Lo is coming over first thing tomorrow morning then I'm going to need all the rest I can get tonight...
To be continued soon in Captain's Log - J-Lo
Topic: Captain's Log - Taylor Swift (Read 186 times)