Taylor Swift Squad: Anal Night

Disclaimer: This is a work of fiction. I do not know or own Karlie Kloss, Selena Gomez, Cara Delevingne, Martha Hunt, Gigi Hadid, Lily Aldridge, Taylor Swift, or any celebrity for that matter. I do not make any money from the writing of this story.

*

"How much do you love me?" Taylor asked nervously.

"More than I could ever put into words." Karlie replied without hesitation, before frowning, "Why?"

Taylor bit her lip, and then revealed, "I want an all girl gang bang."

"Isn't that just a normal Friday night for us?" Karlie teased.

"Yeah, but..." Taylor leaned in, whispering into Karlie's ear.

"Oh..." Karlie blushed, before giving her girl a look, "Isn't that a bit much, even for you?"

"Yeah..." Taylor confessed, "But you'll give it to me, right?"

Karlie bit her lip, and then for better or for worse nodded, making Taylor hug her tightly.

*

Taylor Swift loved her friends. Which was normal, but what wasn't normal was having sex with your friends, but that was exactly what she had been doing for years now. Mostly one on one, but more and more Taylor was having fun with multiple girls at a time, and because she was the only proud bottom of her infamous squad, inevitably it ended with her getting gang banged by two or three members of that squad, and sometimes even all of them.

It wasn't quite every night, but it was close. Which Taylor loved, but tonight was going to be extra special. Tonight she would fulfil one of her naughtiest fantasies. Oh yes, tonight Taylor Swift was going to get anally gang banged.

One by one her closest friends arrived, namely Selena Gomez, Cara Delevingne, Martha Hunt, Gigi Hadid, and Lily Aldridge. Then of course there was her favourite member of the squad, the woman who barely left her side these days, and help to arrange all of this, her secret girlfriend Karlie Kloss. Taylor had always known she was gay, but around Karlie she was so gay that she just couldn't hide it, and it was becoming a problem as people were beginning to notice.

But Taylor wasn't going to waste the night concentrating on rumours which were right on the money. No, she was going to focus on all the fun they were going to have tonight, each of her friends greeting her with a warm smile, and the kind of squeezed to her butt they would never dare to do in public, but Taylor loved in this moment.

After everyone had arrived and been given a chance to have some liquid courage Karlie spoke up, "Ladies, can I have your attention please? Thank you. Now, we all know why we're here, but just for fun, let's have 'our fearless leader' explain the rules, shall we?"

Which got a chorus of wicked chuckles and murmurings as all eyes turned to Taylor, who blushed and protested, "Well, they're not rules, per se... it's... a favour. Yes, I like that better. Okay, so... if you want to fool around with each other, that's cool. And you can do anything to each other you want. But, for me? I don't want anyone to touch my pussy tonight. No, my... my greedy little ass hole wants all the attention. Fuck, I don't even want anything in my mouth, except a cock that straight from my whore ass, because what I really, really want this to be, is an anal only night! Oh yes, I want you all to run an all night anal train on me, and leave my slutty little shit hole a ruined mess! Gape it as wide as you can! Fucking wreck my butt! Please?"

There was a brief pause as even after everything they had been through it was a shock to see the allegedly sweet and wholesome Taylor Swift say such things, and no one was more surprised than Taylor, with the possible exception of her girlfriend, who was actually the first to recover and then announce with a smirk, "In other words, welcome to Taylor Swift Squad: Anal Night."

Naturally this led to a cheer from the audience, Selena then adding with a grin, "Oh Tay, all you had to do was ask."

"Mmmmmmm yeahhhhhh, we'll wreck your butt all night long." Cara eagerly added, before suggesting, "So, why don't you show us what we'll be working with?"

"Yeah Tay, show us that ass." Selena quickly agreed with a wicked smile.

Only too happy to oblige Taylor turned around, bent over and did her best to twerk her little white booty in the tiny pair of short shorts she was wearing. She might not have the biggest butt, especially not when compared to some of her celebrity friends, and rivals for that matter, but given the response she got from her audience it was fair to say she achieved her goal.

And she got a similar response when Taylor reached behind her and slowly pull those shorts and her underwear down to reveal where she wanted all the attention to be put onto tonight. Better yet Karlie close the distance between them and join the little show Taylor was putting on, namely by smacking that tight little ass as hard as she could, making Taylor cry out with delight.

She let out a similar cry when with practised eased Karlie spread her cheeks with both hands, briefly showing off her plug stretched butt hole to their audience, before grabbing the handle of that plug and beginning to slowly pull it out of her. Of course, Karlie only pulled out to the widest part of the butt-plug, before then pushing it back in as deep as it would go, and then repeating the process, using both Taylor and their audience, for a few long seconds.

Then she let out a cry of betrayal when Karlie pulled that toy all the way out of her ass, and directly into her own mouth instead of Taylor's, moaning with obvious delight as she savoured Taylor's anal juices, which should be rightfully hers. And Karlie knew it, but still she chose to suck the butt-plug fresh from Taylor's ass as loudly and as greedily she possibly could, even looking directly at her girlfriend as she did so.

"Karlie!" Taylor whined, "No fair!"

"Oh please, we all know you're going to be spoiled rotten tonight with all the ass cream you'll be getting." Karlie pointed out unapologetically, and even smacked her girlfriend's ass to punish her for speaking out, before turning her attention back to their audience, "Well, what are you waiting for? Get naked and choose your weapon. Mmmmmmm yeahhhhhhhhh, everyone grab a strap-on and lube them up. It's time to give this needy little anal whore what she so desperately wants. Oh yes, and as for you Taylor, get naked and on that bed. Ohhhhhhhhh yesssssssss, show us that ass we're all eager to fuck. And don't worry baby, I'm going first, so I'll loosen you up."

"Oh yes, loosen me up Karlie! Loosen up my slutty little ass!" Taylor begged shamelessly, while doing as she was told, and then reaching back and spreading her cheeks so her girlfriend could have all the access she could want, "Mmmmmmmmm yesssssssssssss, be the first to fuck my ass, so you can loosen it up for everyone else to use. Ohhhhhhhhh yeahhhhhhhhhh, mmmmmmmm, I want my girlfriend to loosen up my little dyke whore butt so a bunch of girls can fuck it! Oh please, fuck it! Fuck me, mmmmmmmm ooooooooooh Karlie, ass fuck me like the little anal slut I am! Please? Oh please, ooooooooooohhhhhhhhhh Gooooooooooddddddddddd, mmmmmmmm, aaaaaaaaahhhhhhhhhhh fuckkkkkkkkkkkk!"

Karlie chuckled wickedly at her girl's shameless begging, enjoying it for what had to be a full minute, before she finally took pity on her and shoved a cock in her ass. Which wouldn't have qualified as taking pity on most people, but Taylor Swift was easily the biggest anal whore Karlie or anyone else in the squad had ever met.

Something which was easily proven again by the way Taylor's eyes lit up when her ass hole finally began stretching wider, and the loud cry of pleasure that the adorable little butt slut let out as that strap-on slid through that forbidden hole and into her slutty little ass. And then whimpered in disappointment as Karlie paused for a few long seconds, before crying out joyfully again as the ass stuffing continued.

No matter how many toys Taylor took up her butt Karlie would always be gentle with her at first. She knew that some people outside of the squad weren't, and that Taylor swore up and down she preferred that, but Karlie loved this girl with all her heart, and she didn't want to hurt her.

Which was the same reason that she'd never given Taylor more than a gentle spanking, and maybe the occasional rough spank, when she was deeply pounding that slutty little shit hole so hard that her girlfriend probably didn't even feel it. Not really. Besides, the last thing Karlie wanted to do was damage this perfect little fuck hole. Or more accurately, not before Taylor was truly warmed up, which was exactly what she was doing now.

So Karlie ignored Taylor's petulant whining, and continued slowly sliding her strap-on into the other girl's tailpipe. Eventually it also meant ignoring some of the other girls, who were ready for their turn, but most were like Karlie, savouring the beautiful sight of Taylor Swift's slutty little ass hole slowly swallowing inch after inch of big, thick strap-on dick.

Of course, in Karlie's case, she was constantly switching her gaze between that, and the cute little expressions of frustration on Taylor's face, and more importantly the pleasure shining through her eyes. Also sometimes, just through her face, or in her sweet voice, or hell, Taylor's entire body giving away just how much she was loving the gentle treatment just as much as Karlie.

Eventually of course Karlie's cock was fully buried inside of Taylor's ass, and while she again savoured the moment for a few long seconds it was not long before she started pumping her hips back and forth, making the dildo slide in and out of that forbidden hole, meaning she was officially starting to butt fuck her girlfriend. Butt fucking Taylor Swift!

That's what Karlie Kloss was doing, and both women loved it. So did their audience, for the most part, but again they became restless, not that Karlie could blame them, or her favourite little ass whore craving more. Because God forbid that Taylor Swift should be fucked by only one dildo for more than a few minutes.

"Harder! Mmmmmmm, fuck my slutty little ass harder! Please baby, I can take it. You know I can." Taylor whined after just a few minutes of gentle sodomy, "Ooooooooh yeahhhhhhhh pound that little ass hole! Or let someone else do it. Ohhhhhhhhh yessssssss, spit roast me Karlie! I wanna be spit roasted like the whore I am! Please-"

Taylor was cut off when Karlie crashed her lips to hers in one of the most forceful kisses she had ever given her. Which of course led to Taylor kissing back frantically, because kissing Karlie Kloss was one of her favourite things ever, and it was so wonderfully intense to be able to do it while taking it in the butt.

Hell, she was even kind of getting what she wanted, as the kiss was so rough it was almost like Karlie was fucking her mouth with her tongue at one point. Admittedly it didn't provided the anal cream Taylor was always craving, but it was still a wonderful treat, one that she became completely lost in for a few long, blissful minutes. Or however long the kiss lasted, given it was hard for her to tell in her current state.

"Relax baby." Karlie purred eventually when she broke the kiss, "I wanna properly loosen you up, mmmmmmm, and show our friends that they can use you however they want, but you're mine."

Which made Taylor's eyes light up as she eagerly responded, "Oh God yes, mmmmmmmm, show everyone that I'm yours Karlie! Show them I'm your little anal whore! Oooooooooh yeahhhhhhhh, loosen up my butt hole and get it ready to be gang banged. Ohhhhhhhhh fuckkkkkkkkkkk, take that ass! Fuck it good! Oh God Karlie, I love you so much."

"I love you too babe." Karlie beamed happily, before ordering sternly, "Now shut that pretty little mouth of yours. Mmmmmmm yeahhhhhhh, let me concentrate on loosening your butt hole."

Which of course, was the hardest thing for Taylor to do. Take a cock up her ass? No problem. Taking a dick in each of her fuck holes at the same time? Bring it on. Give head to every member of her squad at the same time? Challenging, but something Taylor was getting better and better at the more she practiced it. But actually stay quiet? God, that was almost impossible for her.

She was just a natural talker, and that went double when she was happy, and she was never happier than when getting fucked in the ass, especially by her girlfriend Karlie. And again, this was a special occasion, all the rest of her closest friends just waiting for the chance to have a turn fucking her butt.

To try her best to stay quiet Taylor concentrated on those friends for a while, all of whom were staring at her lustfully and stroking their fake cocks as if they were real. At least partly because they were rubbing edible lubricant into those dicks, but also because apparently, every little movement rubbed the other end of the dildo against the wearer's clit.

Or at least that's what her friends told her, as Taylor had no interest in topping. Also maybe they were just doing it for effect, or just something to do while they were standing around waiting. Which was hot, but it refilled Taylor's desire to get double stuffed, so she quickly returned her full attention to her girlfriend.

Luckily for her Karlie made this easy for her, as she leaned down to start covering Taylor's face in kisses. Which made them both giggle lovingly, until Karlie kissed her way down to Taylor's neck, which made them both moan softly with delight, but particularly Taylor.

In fact, the singer pretty much drowned out the model with the next few sounds out of her mouth, as her eyes fluttered closed and she just concentrated on the gentle, loving kisses and touches she was receiving, while her most private hole was being extremely stretched open and her rectum filled with dick. God, Taylor would never get tired of that sensation, and again, the fact that it was her girlfriend Karlie Kloss doing it to her made it perfect.

Karlie rested her weight on her elbows so she could start sliding her hands over Taylor's body. That involved sliding a hand underneath Taylor a few times, but it wasn't long before she concentrated on playing with those cute little titties of hers, which had gone neglected so far.

It was kind of a shame, but because Taylor was so obsessed with ass play her boobs frequently went ignored, and in moments like this Karlie adored the chance to show them some love. She even ducked her head down as best she could a few times so she could take each of those nipples into her mouth and suck on them. But mostly, she just caressed them with her hands while focusing her lips elsewhere.

Namely Taylor's lips and neck, her inpatient girlfriend now becoming frustrated at this gentle treatment, especially the frequent kissing, even when Karlie slowed down to be gentle and romantic. The same kind of speed she was using on Taylor's ass hole. Which wasn't necessary for a total anal slut like Taylor Swift, and it was obvious her girl was aching for harder treatment given the little whimpers she was letting out, but Karlie also knew she was loving this.

Because they both loved it when the model made gentle love to the singer's butt. And that was what this was, anal loving. Which was so sweet and loving, even their friend seem content with just watching for a while. Of course eventually they spoke up.

"Come on Karlie, we're dying here." Selena whined.

"Yeah, stop hogging that ass." Cara grinned wickedly, giving her friend a knowing look, "She must be loose enough by now."

"Ooooooooooh yessssssss, I'm loose! My slutty little ass hole is loose enough to gang bang!" Taylor moaned dreamily in agreement, before pleading, "Please Karlie, please let someone else have a turn with my butt hole! Mmmmmmm baby, I love everything you're doing to me, and I love being your little anal princess, ohhhhhhhh, but now I want to be everyone's ass whore! Please Karlie? Pass me around like the piece of meat I am! Oh yes, make sure everyone gets a piece of this ass. It's only fair. Mmmmmmm yeahhhhhhhhh, it's why we invited them into our bed. Oh please, mmmmmmmm Karlie, I'm soooooooo ready for it. Oh yes, I'm so ready for everybody to bang my butt!"

Karlie pretended to look thoughtful for a few long seconds, then insisted, "Not yet. You got to do one thing for me first."

"Anything." Taylor promised without hesitation.

Which caused Karlie to smile warmly, and then suddenly flip their positions before ordering, "Ride me to orgasm."

This unsurprisingly had Taylor's eyes lighting up with glee, and then immediately doing as she was told. It took her a moment to establish a rhythm, but soon she was hammering her little ass frantically up and down her top's cock like the happy little anal loving bottom she was.

Which made her perky little tits bounce up and down directly in front of Karlie's face, and the singer let out such musical cries of pure joy, and God, the grateful look on her face as she approached her orgasm. Which almost made Karlie want to let her have it right away. Almost. But she had other plans, namely letting Taylor get so close she could taste it, and then smacking her little ass to get her to stop.

Karlie of course also ordered loudly, "Stop! I didn't give you permission to cum yet. Mmmmmmm, I just wanted you to ride me until I'm good and ready to let you cum. And don't even think about begging for it right now, because if you are good and did that before I would have let you cum, but you were a greedy little ass whore, and now you have to wait for it."

Admittedly this was a really dirty trick, one which Karlie would be definitely asking for forgiveness for later when all their friends had left, and it was just the two of them. However this was a technique Karlie had used before to ensure that Taylor's eventual climax would be that much more powerful, and she was confident that when the time came her girlfriend would thank her for this level of teasing.

Even if it didn't look like it right now, given how much she was whimpering softly, and looked at Karlie with the look of betrayal which broke her heart, and almost had the model giving the singer what she wanted right away. Instead Karlie was able to stay strong, and once again slide her hands over that perfect little body, which was easier now that Taylor was on top of her, slowly bouncing up and down like a good little anal whore.

Taylor knew deep down, this was for her own good, and not only would it provide more pleasure later, but it meant that she got to spent longer with a cock up her ass right now, which was something she lived for. Especially her girlfriend's cock, as it was always special to have that deep within her slutty little butt.

However, in that moment it felt agonising to slow down the speed of the sodomy, and it hurt her soul to know that it had been her girlfriend who was responsible for it. Who actually seem proud of herself for causing her such agony? So initially, when those talented hands started sliding over her body again Taylor didn't exactly welcome it, even when they went from squeezing her bottom to caressing her tits again.

Honestly Taylor didn't really forgive Karlie for her dirty trick until her girlfriend sat up and pressed their lips together in another passionate kiss. Then Taylor pretty much had no choice, because Karlie was like the best kisser ever, and she just couldn't stay mad at her when they were kissing. Besides, what she was feeling right now felt awesome, especially as during this kissing, she was able to speed up the sodomy slightly.

Which wasn't quite as much as it had been before, but it was enough of an edition to satisfy her in that moment, and thankfully even when the kiss was broken Karlie didn't scold her for it. No, she even reached down to grab her butt again and encouraged her to increase the pace even more, while moving her mouth down to her neck to kiss that.