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Taylor Swift - End Game	By : TheChemist Category: Celebrities - Misc > General Views: 10416 -:- Recommendations : 1 -:- Currently Reading : 2
Disclaimer: This is a work of fiction and didn’t actually occur. I do not know Taylor Swift. Mature themes so must be older than 18. I make no money from this fictional story

Chapter List
- 1-Taylor Swift
- 1
“Thanks for feeding my cats while I’m away,” Taylor spoke as she finished packing her suitcase.
“No trouble,” her friend replied, laying on Taylor’s bed as the pop star bustled about her room. “So you and the boy are going away for a little couple’s retreat? Despite the fact you too are both playing the field.”
Taylor had explained the facts to her friends several times, so she knew she was just being poked and purposefully annoyed. Though both Taylor and the guy in question, Jase, were nothing serious in their relationship, the singer wanted to change that. Though she went through periods where she loved playing the field with many different men, that window was closing and she wanted an exclusive relationship with Jase. However, he was also happy with not being tied down, so it would take a little extra convincing from Taylor to lock him down for good.
“So your plan is to take him to a private island for a weekend of sexual pleasure,” her friend surmised. “I know you got a magical pussy Tay, but your boy is a straight up player. And so are you.”
“I know but he’s the one,” Taylor countered. “And I need to make him see that I’m more than just the hottest girl in his rotation. That I’m his endgame.”
“Solid plan. But one last item. It’s a well known fact that Jase loves him some anal. Like, L-O-V-E anal. And though you are a lot of things, an anal slut ain’t one of them,” the singer’s best friend reminded her. “Sure, you’ve done it once or twice but never enjoyed it. And him overcoming or suppressing a kink like that long term, no chance.”
“Oh I’m aware. Which is why I’ve been practicing and using a tutor,” Taylor mentioned as if it was nothing.
“What?! Practicing?!”
“Yeah. Using dildos of varying thickness daily for over a month. And wearing a butt plug for several hours a day makes a big difference. Heck, I’m even practicing right now,” the leggy pop star answered.
“Now? Right now? You have something in your ass right this second?”
“Of course. I’m leaving today for a weekend chock full of anal sex. I need to make sure my once tight caboose is as loose as possible,” Taylor answered before reaching under her dress. After a moment, she pulled her arm back out and in her hand was a gold-colored butt plug that was an amazing 2 inches in diameter at the thickest part. “See.”
“Oh my God, Tay,” her friend gasped. “You really are a savage.”
Taylor only replied with a wink before she went back to put the metal butt plug back into its home. She didn’t even wince as the tapered tip pressed against her asshole until the sphincter gave way with ease. There was a time only a short while ago where the feeling of her ass taking something inside it would cause the pop star to wince and whimper in pain. However, after 6 weeks of training, Talyor only felt the smooth metal expand her anal ring as it nestled into it’s place a good 4 inches deep in her rectum. Not only was it not causing any discomfort, but whenever she sat or reached back to twirl the base of the toy, the leggy blonde derived a great deal of pleasure.
“I think you’re coming home from your trip with an exclusive relationship,” her friend said, still amazed at Taylor.
*   *   *
“This is amazing,” Jase commented.
The amazing thing the man in his 30s was referring to was the fact that one of his random hook ups was flying him to a private island somewhere in the Caribbean on her private jet...that she owned. Currently, they were just entering airspace off the coast of Florida, giving them roughly another 45 minutes of flying before they touched down. In the meantime, they had to put up with ridiculously comfortable leather chairs, watching movies on an 80 inch flatscreen and drinking whatever and how much of it that they cared. This currently meant the pair were onto their 3rd scotch in just over an hour of flying time.
“It’s not so bad,” Taylor replied with a smirk.
“Not so bad! Not so bad! I can’t think of how this could get any better,” the excited man gushed.
“Oh? I can think of one way,” Taylor replied, unclicking her seatbelt.
If the leggy blonde didn’t have his attention before that comment then he certainly had it now. The private jet only had 4 actual seats with two on each side of the aisle facing each other with a table in the middle. With a signal she must have flashed to the only stewardess, the uniformed woman came and cleared the table for them, at which point Taylor pressed a button at the table’s edge that made it retract down. Now, with nothing between the gorgeous couple, Taylor had nothing preventing her from dropping to her knees.
Jase fought the urge to undo his belt and open up his jeans because he found it so Goddamn sexy watching a girl as smoking hot as Taylor Swift do it for him. Sure enough, by the time she had things undone and required him to lift his ass from the fine leather shair to pull them down the rest of the way, the lucky man was rock hard.
“Is this for me?” Taylor asked innocently.
The blonde was clearly in the mood to have fun so Jase was all the happier for it. While her crazy schedule and wild mood swings were the negatives in dating Taylor, sex in general with the leggy singer more than compensated, but her blowjobs in particular were more than stellar. Still playing along, Taylor extended her tongue fully so that the very tip just touched his piss slit. Wagging it several times accomplished her goal in getting a nod from her guest.
“All yours, babe,” he gave in, wanting so much more from the blonde.
Taylor gave an awed look up at her common sex partner, as if it was an honor for him to allow Taylor Swift to suck his cock. Always a showman, Jase felt the pop singer grip the base of his cock before using her tongue on his rod once again. However, rather than just a little flick at his head, this time Taylor used the broad part of the wet muscle to lick the underbelly of his 8-inch dick from root to head. She performed this three other times, one time each to either side and the top side before Jase felt the warm moist environment of her mouth enveloped the head.
“Ahhh,” Jase sighed, spreading his legs wider and letting himself sink a little deeper into the chair as Taylor pushed more of his cock into her mouth.
Taylor had her flaws and Jase believed that no one was perfect, but when it came to performing oral sex, Taylor Swift was without arguement flawless and therefore perfect. He thought back to the first time they slept together and how much of a stud he felt like to pull the largest pop star on the face of the Earth into his bed. However, that soon gave way to embarrassment as the leggy blonde made him bust his nut within five minutes of a blowjob! Luckily Jase rallied in a big way, getting hard almost instantly as Taylor never stopped sucking his cock despite cumming right down her throat to her stomach. They ended the night with an hour long fuck session with Jase cumming a second time and the gorgeous woman collecting three of her own. Every since then they had been at the top of each other’s rotation of sexual partners.
Feeling lips grip around his cock snapped the lucky man back to the present. Taylor had ceased simply licking his cock and was now getting down to brass taxes. Opening her mouth wide, Taylor gave a small bob of only his head, her lips lightly thumping over the ridge of where the shaft met its tip. After that brief introduction, Taylor’s next descent down his pole was taking a good 5 inches into her mouth. It was just enough of his manhood that his sensitive head didn’t repeatedly smash against the hard palate in the back of her mouth, but only just barely. Having her range, the leggy singer built momentum and gave the seated man a dozen bobs of her golden head in quick succession.
“Fuck me!” Jase groaned, resting a hand on the top of her head.
The fucking would come soon enough, either on the plane if there was time before touching down or immediately after getting to the mansion they were staying at. However, that was putting the cart before the horse. In the present, Taylor was going back down, performing another handful of lightning fast bobs of her head, taking over half his cock in each stroke before pulling off him. A quick intake of air and the blonde was back to work, but her speed vanished and Jase could feel her lips as they slid down his pole, inch by inch. She passed the 5-inch mark and the lucky man felt his tip poke the back of her mouth. Knowing what came next, it took Taylor only an instant to relax her throat, opening her gullet fully for him. Pushing her head downward at the same speed, his cock slipped into Taylor’s throat without any sputter or gag.
“Jesus Christ,” Jase groaned.
Though capable of holding in her gullet for much longer, Taylor was just starting her oral performance and wanted to keep it moving. Therefore, as soon as her nose was pressed against his flat abdomen, she was pulling back, her lips massaging every inch of his slobbery manhood as she retreated. They had been fucking together long enough for Jase to know that her deep throating his big dick wasn’t a fluke, but Taylor was always keen to remind the lucky man at every oppurtunity. Thus, the pop singer bobbed once to the 3-inch mark, twice to the halfway point of his cock then relaxed her throat and took him completely into her mouth, down to his balls. In fact, Taylor even found the time to extend her tongue and actually give his nuts a little lick as she held all 8 inches of hard dick in her gullet.
“God this dick is so nice,” Taylor cooed, her fist stroking him a mile a minute due to how slippery his flesh was from her spit.
“What about the stewardess,” Jase worried and instantly kicked himself. Why would he try to stop Taylor Goddamn Swift from deep throating his cock?!
“She’s cool,” was all Taylor replied.
Taylor resumed her blowjob, not caring in the slightest that the private jet’s workers could and were watching her masterclass in oral sex. Jase shrugged his shoulders and ignored the onlookers, focused on deriving every ounce of pleasure from Taylor’s lips, tongue and throat. Going right back to work, the blonde performed another salvo of head bobs with the first 5 inches of dick pistoning into her mouth before she relaxed her throat and swallowed all 8 inches at one time. Her throat bulged out as it was filled with hard cock, her nose pressing into the neatly trimmed patch of pubes Jase kept and his balls met her chin. Holding herself there for a lengthy time, long enough that she had to actually not gag on his cock, Taylor eventually pulled away. This time as she did so, her pretty face was red, his cock had more saliva covering it and there were even several strings of spit connecting her mouth to his pole.
As she leaned back to his lap, this time Taylor showed the lucky man she wanted to be her permanent boyfriend the other end of the spectrum. While her last several bobs on his cock were slow and she kept her face in his crotch for a good 10 seconds, this time Taylor went for speed while taking all of him. Essentially using her mouth to fuck him balls deep, Taylor kept her throat relaxed as she rocketed her gorgeous face down into his lap. Once Taylor had impaled her mouth fully with his cock, making her throat bulge, she retreated back up with length. With only his tip remaining between her lips, Taylor reversed course until her nose was smashing against his stomach. Despite the fact that the constant barrage of deep throats would make her voice a little hoarse and and all the blows her nose was taking was causing her eyes to mist, it was well worth it given how much Jase was grunting.
“Fucking fuck, Tay,” Jase hissed through clenched teeth as his hand subconsciously tightened to make a fist with her golden locks.
“Oh sorry,” Taylor played, as if she had anything to apologize for. “Should I slow down?”
This time instead of taking him back into her mouth, Taylor tilted her head sideways and ran her lips up and down the side of his shaft. Not forgetting about the other side, Taylor turned her head all the way to that side next, tossing her luscious golden locks over her shoulder in order to massage his cock with her lips as her tongue glided along the underbelly.
“Nope. You do you baby,” Jase commented.
“Thought so,” she grinned in response.
Instead of rubbing her lips back along his cock, Taylor went back to deep throating. This time she gave the lucky man no warm up and simply parted her lips, relaxed her throat and pushed all 8 inches into her mouth at one time. She held him in her throat, her lips wrapped around his base and flashed her electric blue eyes up to meet Jase, who she knew would be watching her suck him off. She held his gaze as she bobbed up and down, spending no time to make the transition from retreating along his spit covered shaft to plummeting back down it. Once every 3 to 4 times she deep throated him, Taylor would take an extra second to hold him in her gullet so she could make a side-to-side motion with her head, which only accelerated how much sooner he’d need to cum into her mouth. In fact, the latest time she did this, Taylor stayed down on his dick for almost 10 full seconds until she pulled all the way off for a gulp of air.
“You are something special,” Jase commented as her face returned to a normal shade of pink instead of the deep red it was periodically becoming during her deep throating exhibition.
Taylor didn’t reply as she had more important things to do, such as suck the big dick in front of her face until it exploded its gravy into her mouth. Keeping her throat relaxed and mouth in a perfect O shape, the pop singer thrust her head down with speed. If this move was done with poor aim or not having your throat opened enough could cause damage for both him and her, luckily Taylor was a professional when it came to sucking cock. In fact, she was certain she’d make the Olympics if they had a version for sex acts. Regardless, Taylor slammed her face down until her throat bulged with cock and her lips touched the base, at which point she reared back until she was 6 inches away from his manhood.
“Oh my God! Jesus, Tay,” Jase practically screamed as she threw her face down into his lap once more with the same reckless abandonment.
With each successive bob of his entire cock going down her throat, the amount of distance Taylor pulled away from him shrank until she was leaving the tip on her mouth before bobbing back forward. Resuming her normal deep-throat variety of blowjob, Taylor was in constant motion as her lips and throat tried desperately to milk the cum right from Jase’s balls.
“Ms Swift, we’ll be touching down in a few minutes,” the stewardess said to the cock sucker.
“Thank you, Marie,” Taylor replied before getting his dick wrapped around her lips once more.
“Oh thank God,” Jase hissed, knowing he could let his resistance down and finally get his sweet release.
“Someone need to cum?” Taylor asked while stroking him with her hand only.
“So badly,” Jase agreed immediately.
“Then give me your cum, baby,” Taylor practically begged from her knees.
Knowing that her man wouldn’t last much longer plus the plane was going to land soon, Taylor stopped playing with her food and went for the kill. Shortening her strokes with her mouth so that she was only sucking on the first 5 inches, the less distance meant a much faster blowjob. With all the spit covering his shaft, his pecker was practically frictionless which meant Taylor’s lips could go that much swifter as a result. Using her peripheral vision to spy his hands tightening on the arm rests, Taylor used one last trick and took him all the way, deep throating him once again before pulling off and resuming her half-cock length bobs.
“Jesus! Cumming!” Jase screamed loud enough for even the pilot to hear.
The moment Taylor felt the first squirt of man gravy against the roof of her mouth she treated Jase to shooting the rest of his load directly into her stomach. Shoving her face forward, Taylor deep throated him for the last time so that his next blast of semen was in her throat immediately. The sudden balls deep sucking made the climaxing Jase squirm in his chair from pleasure overload, yet the kneeling blonde kept his dick firmly in her gullet. Knowing she wanted to be taking his semen right down her throat, Jase reached down with both hands and held the back of her head in place, making a retreat for Taylor impossible. Of course, the leggy blonde had no intention of going anywhere, content taking stream after stream of warm cum into her throat and into her tummy.
Taylor had several ways of knowing her man was spent. For one, it had been a few seconds since any more of his sperm shot down her throat. Secondly, the iron grip that he had on the back of her head with both hands had fallen away. Third, his grunts had turned to shudders as Taylor continued stimulating his hyper sensitive cock. And even if she missed all those signs, the fact he wasn’t lifting his ass off the leather chair anymore to essentially fuck her face as he came was another sign. Therefore the pop star slowly pulled her mouth from his cock, eye contact the whole time, until her lips pulled away from his manhood for the final time.
“Wow,” was all Jase could find the words to say.
“Thanks for the big reward,” Taylor replied, scooting back into her own chair and applying her seatbelt. “That was seriously a lot of cum. Hopefully I didn’t drain the well. I have big plans for you this weekend.”
“No worries about that babe.”
*   *   *
Within 10 minutes the tires were rolling on the tarmac and several minutes after that Taylor and her latest beau were disembarking from the airplane. They stewardess and pilot made sure to show class towards the leggy singer and not embarrass her for the very public and noise blowjob, but both employees couldn’t help but give Jase a knowing smile. Caught between returning the grin and his face flushing, the lucky man thanked the crew for the travels and followed Taylor down the runway.
“Is that where we’re staying,” Jase asked as they came into view of the mansion.
“All to ourselves,” Taylor grinned in reply.
The taxi ride from airstrip to mansion was short or else Jase was sure he and Taylor would have continued their weekend fuckfest during the ride. However, it was too brief so after he beat Taylor to tipping the driver generously, he grabbed their modest luggage and they made their way up the lavish walkway to the extravagant house.
“I can’t wait to repay you for the epic blowjob on the flight,” Jase commented as his leggy girl punched in the code to unlock the door.
“I can’t turn down that offer but I have a fun weekend planned for us. Including everything that you love,” Taylor replied, giving her hips a quick swing side to side to help get across what she meant.
“Oh? Is that right,” Jase asked.
With a shit-eating grin, hoping he knew what Taylor meant, he enveloped the singer in an embrace by wrapping his hands around the slender woman and hoisting her up. Taylor knew the routine and allowed herself to be picked up before wrapping her mile-long legs around the powerfully built man and locking her ankles together. As the pair kissed deeply, Jase used one hand to grope Taylor’s small but bubbly ass while his free hand pushed open the door to their weekend villa.
“Adios mia! Ms Swift! I’m so sorry but the house is not ready yet,” the maid shrieked in surprise. “I thought your flight wasn’t until later.”
“Oh that’s okay,” Taylor replied after Jase set her back on her feet.
“Maybe you should enjoy the beach?” another of the staff commented. “Another hour and we should be out of your hair.”
“I suppose a little sun and surf couldn’t hurt,” Jase spoke.
“Let’s change and head on down.”
*   *   *
Jase had no idea Taylor had to pay to rent this place but between the massive manor, private runway and now the beach, it was worth it. While usually at a tropical vacation the beaches were packed with tourists, that wasn’t the case with their slice of heaven. White sandy beaches, aqua blue water and not a soul to be seen other than some boaters. So in essence, Taylor and Jase had the beach to themselves.
Jase originally was planning on just fucking the leggy blonde, hopefully in the butt, down on the sand. However, after the long flight, beautiful scenery and warm weather, both he and Taylor were excited to get in the ocean. The pair had fun in the waves, swimming, kissing, and him tossing her in the air before crashing back down in the surf. After over an hour, Jase felt like he was good and retreated back to the white sandy beach to towel off. After a few more dips under the warm picturesque water, Taylor made her way back to the sandy shore where her boy toy was waiting for her. She gave him a kiss, before dropping to her knees and writing a message into the sand, a simple one with the capital I overtop a heart overtop the letter U.
"Awh, you heart me," Jase teased.
"And you love watching me shake my ass in a tiny bikini," Taylor replied as she started to rock her body up and down, making her bubbly ass jiggle rhythmically.
Though she was a slender girl, ever since she sorted out her eating disorder she had started to gain weight in all the right places. She still possessed a flat stomach, but now had an ass that was more shapely than ever before, not to mention she had to replace her bras as she was now a busty B cup.
"Well you're playful today," Jase commented with a wide grin on his face, watching the normally reserved woman twerking on the beach. Apparently being out of the public eye did wonders for her flirty side.
With a quick look around to make sure they were still alone, Jase bent down overtop her and undid the string on the side of her bikini bottoms. They didn't fall off her until he pulled the loosened bottoms downward, and to his delight she didn't protest or even stop what she was doing, which was now swaying her hips side to side. Now normally the sight of Taylor Swift’s naked ass was enough to make him excited, but Jase was in for an astonishing surprise. Right in the middle of her crack was a circular gold object that the man instantly knew was a butt plug. Knowing she had his attention, taylor reached back, pulled the 2-inch wide, 4 inch long anal toy from her rectum and showed off what was truly an awe-inspiring gape in her asshole. How a slender woman could have her butthole yawning so far open was a mystery for Jase, and he found he had to snap his jaw shut for fear of drooling all over the sandy white beach.
"Come on, let's go back to the house," Jase insisted. "I feel like we should have a proper setting for what you have in mind."
It was less than a 5 minute walk back to Taylor’s rented villa, which the happy couple passed by sharing kisses and grabbing each other's fit bodies. They both couldn't wait to get inside and tear the few pieces of clothing from the other's body before getting into bed and having their real fun. However, they had barely locked the door behind them when the phone rang in what was the ringtone denoting it was coming from Jase’s business phone.
"Go answer. I’m not one of those girls making you pick her over business. I need to shower and rinse the sand off anyway," Taylor insisted, already bounding up the stairs to the master bath.
Jase answered it but the image of Taylor fucking Swift with a massive butt plug in her ass, stretching her backside for him kept dancing in his mind. Answering the phone, Jase pretended that there was too much static given his remote location. Hanging up, he texted his assistant back in the US to follow up with the client before shutting the cell phone off. He had seen an amber liquid in a crystal vase so poured himself a glass of what was sure to be Taylor’s favored scotch before getting the idea to go join his girlfriend in the shower. Though the mansion was large, Jase traced Taylor’s initial path before using the water noise to find the correct room, sneaking soundlessly inside. It was only until he stealthily joined her in the massive shower behind her and reached out to lightly tug Taylor’s golden ponytail did she realize he was there.
"Hey," she said in mock outrage, hands still rubbing over her taut body. "Such a pervert coming in and spying on me."
Since he was there and she was still in a playful mood, Taylor continued showering but really played it up for his benefit. She focused on rinsing off her tits at first, using her hands to work the mounds of flesh to get them soapy. The pop singer grinned as she saw how enticed the playboy was before she went to his favorite area to wash.
Turning her back to him, Taylor pushed back her ass, arched her back and bent her knees, all to make her slim yet bubbly ass look even more appetizing. With soapy hands she 'rinsed' herself off, letting her fingers slid along her crack, down to her pussy and even pulling apart her firm cheeks to give Jase a good view of her sex. Of course, the big difference he noticed right away was the lack of butt plug wedging her anal sphincter apart, and in only the few minutes since it had been withdrawn her asshole looked tight as ever.
"Scrub that ass," he encouraged, getting an extra wiggle from the blonde. "Show me where my cock's going."
Though Taylor wasn’t always into being talked to like that, Jase had guessed correctly that she was in the mood for some dirty talk currently. In fact, she kept her cheeks pulled apart with one hand and with the other she stuck her middle finger out and ran it from her pussy up to her asshole. Instead of moving away quickly, she lingered over the puckered entrance, first with little circles and then finally by actually dipping the suds-covered digit into her rectum. Knuckle by knuckle her middle finger disappeared as her rectum was now filled entirely by her lengthy digit. Showing she wasn’t resting on her laurels, the leggy singer retreated her digit before plunging it back into her cavernous poop chute.
"Mhmm...awhhh," Taylor moaned as she fingered her own ass with a portion of her digit. “I think this is the place you want cock this weekend.”
"Jesus. Who are you?” Jase wandered in amazement.
She’d been so against anal in the past. Sure, she’d let him rim her asshole while he ate her out and on rare occasions lap his finger around the rim, but she didn’t even like a thumb up her caboose while taking it doggy. Yet here she was, having had a butt plug in her ass the whole time at the beach for hours and now in the shower finger blasting her asshole without issue. In fact, her moans told him that Taylor was thoroughly enjoying it. “
Can I take over?" Jase inquired, his hand already resting on her arched lower back.
"Would love nothing more," she said, pulling her finger out.
"Don’t worry. I’ll go slow and gentle." Jase reassured her, knowing she was quite anal adverse in the past though her attitude today was making him rethink that.
“No. I don’t have to be,” Taylor said with self-confidence.
The second her finger was out of her asshole, Jase’s thumb reached down and filled the void. She cooed, and to her credit didn’t wince, as her bowels were forced open by the bigger appendage but he stayed true to his earlier promise and gently pushed only the first inch into her backdoor. However, not only were her moans becoming louder as he moved in and out of her asshole, but he found her hole was well accommodating. Listening to her body language and the comment she made before he started thumbing her backsde, Jase started to push more in, doing a sawing motion which allowed his entire digit to make its way into her brown eye.
"God that's so sexy," he said, pulling his thumb from her ass for the first time in over a minute.
"Did I do that," Taylor asked as she flipped around to face him and noticed the large tent in his swimsuit he was sporting.
“You did…”
Jase didn’t have a chance to follow up with anything clever or quippy as the leggy blonde quite literally left him speechless. Much like when he found Taylor wearing a butt plug as they played on the beach, Jase was astonished as Taylor locked her electric blue eyes onto his and clutched his wrist. Initially thinking she would use the arm to drag him somewhere, the surprise came as she lifted his hand, isolated his thumb then proceeded to place the thick digit, which had just been fucking her asshole, into her mouth. If she was grossed out by the filthy thumb now on her tongue as she sucked her anal juices from it then Jase had no indication as nothing flashed on her face or in her eyes throughout the next 30 seconds.
"You gonna let me put this cock in your ass," Jase asked as she maintained eye contact as she sucked his thumb clean of her anal juices.
"Whatever you want , babe," she found herself saying without thought.
“Oh, I definitely want,” the eager replied as he reached around Taylor’s slender form with his free hand to clutch her ass once more.
Jase was so excited that he needed to act now before the old, anal hating Taylor came back out. He was expecting a fun weekend away with the blonde with lots of lingerie and sex like normal. He never guessed that Taylor would have a switch flip and agree to anal sex, figuring it was a lost cause with pop star. However, as Jase helped her to her feet and spun her back away the other direction, he may have grossly underestimated how dirty and sexually expansive Taylor Swift could be.
With Taylor facing away from him, Jase reached over and grabbed some body wash to lather his dick up with and by the time he looked at the blonde singer she was bent over, and ass back towards him. Her hands were also reaching back and pulling her firm butt cheeks apart, giving him sightlines on his crinkled target. However he still sensed some tension in the leggy woman so instead he aimed his bulbous head lower and sank half his length into her pussy.
"Oh God, yes," Taylor cooed as Jase also praised the Lord.
With Taylor being at the top of his rotation, they had fucked frequently enough that he was able to stroke his entire length into her pink snatch by the second pump. Three thrusts in and she was already loose enough for his ripped abs to be tapping against her firm ass at a brisk pace, making a dull slapping noise heard even over the rushing water. Though they both wanted his cock in her ass, Jase opted for an audible by slamming into her pussy instead, at least for a moment or two. He figured it would help to take away any lingering anxiety the slender girl possessed before he moved to his real target. Therefore Jase started to thrust faster into the blonde, his balls swinging up to tap the wet folds of her pussy as he drove deep into her. Just like he had done a few minutes ago, he used the same thumb and placed it overtop and then actually inside her asshole, stretching it out and getting it prepped for when something bigger tried going in.
“That’s not what I had in mind when I said you could fuck my ass,” Taylor cooed, looking back over her shoulder at her would-be boyfriend.
“My mistake. You know I struggle with big words,” Jase replied with a grin.
Jase was originally planning on delivering an orgasm to Taylor first. Not only would that clear his ledger that he felt he owed Taylor after the masterclass blowjob she gave on the plane ride, but an orgasm would relax her asshole. However, the leggy singer clearly had her own thoughts on the matter and who was he to disappoint her by withholding his cock from her asshole any longer? Pulling out of her pussy, Jase completed a few motions all in the space of seconds. His hands worked as a blur, reaching for the body wash before working the suds onto his shaft again to work as a makeshift lube. He also took Taylor’s arm and brought it up between her thighs until she got the hint and started rubbing her snatch, which would aid relaxing her. With lube and a distraction in place, all Jase had left to do was use his hand to grab his cock and aim it.
“Better?” he asked with his cockhead pressed firmly against her crinkled starfish.
“Definitely found my ass this time,” Taylor groaned as she felt his increasing pressure mounting against her anal sphincter. Remembering to use her fingers on her clit, Taylor did so. The combination of her pussy stimulation and Jase’s steady force on her backdoor worked. When his cock suddenly popped past the tight ring of her sphincter, Taylor groaned and paused to enjoy the penetration.
“Such a tight ass,” Dan grunted as she started pushing back on his cock, the universal sign that she was ready to take more of his cock into her asshole.
Knowing the proper protocol for inexperienced anal newbies, Jase took things slow but steady. With both hands gripping on Taylor’s wet firm cheeks, he pulled them apart to give her sphincter more loosening while always moving his hips in a smooth thrust. Though he was only currently using the first 3 inches of his manhood, he felt Taylor relaxing by the passing second, finding it easier to go a little deeper.
“So big,” Taylor corrected, wiggling her ass in a successful attempt to get another 2 inches of his massive dick into her booty in one pass. “Ugh. That’s better.”
Putting her hands on the tiled wall, Taylor lexed her arm muscles perfectly in time with Jase’s next thrust into her ass. She felt confident of taking his entire 8 inches into her rectum for the first time and she thought it surprised both of them when his cock pushed forward until his stomach thudded against Taylor’s wet ass. They both let out a groan as Taylor’s ass was taken balls deep but after enjoying the new sensation for a heartbeat, they were both back in motion. With Taylor clearly able to handle an anal fucking and Jase more than happy to provide it, he took hold of her hips and used them to push and pull her, all while Taylor used the wall at her disposal to heave her petite frame back and forwards as well.
She had been preparing for this occasion for weeks now and all her hard work was paying off. Not only was she taking a cock in the ass without pain, but she was thriving. The fingers rubbing through her snatch was adding an extra thrill to the proceeding but even the pleasure from having her ass fucked was deriving a good deal. All this while Jase and his considerable dick was going faster and faster, always slamming fully into her bowels.
“You liked a dick in your ass, don’t you?” Jase asked, a hand wrapping around to grope her soap-covered breast.
“Uh huh,” Taylor said, turning her head to find Jase’s lips for a tongue-filled kiss. “But how about we move this party to the bedroom for more fun?” Taylor asked, and by fun she meant comfort as she was quite enjoying herself in the shower.
“Towel?” Jase asked as he pulled out, noting the gape he left in her once tight asshole.
“Screw it. Come on.”
The horny couple left a trail of water from the bathroom to the first bedroom they found, one of 8 in the mansion. Jase threw open the door before pulling Taylor towards the bed. The leggy singer let herself be thrown onto the mattress where she assumed a position on her hands and knees. With her in such an inviting position, Jase was powerless to kneel behind her, one hand guiding his cock back into her still gaping asshole and the other holding her hips.
“Fuck, uhh, me,” Taylor hissed as Jase wasted no time in pulling out of her ass and driving back into it.
Gripping her hips, the lucky man plunged in and out of Taylor’s ass with breathtaking power. Each thrust echoed through the bedroom, followed by a similarly loud grunt from Taylor as her ass was skewered. Jase was driven by only passion, his desire to sodomize Taylor Swift since the night they first fucked. And now here she was bent over like an animal on the bed, all control ceded to Jase as Taylor gave herself fully to him to fuck her ass however and for as long as he wanted.
Jase was in full control, and with that control he decided to take the briefest of breaks from pumping her ass. Pulling out, his dick was only exposed for a moment before he lowered his aim and sheathed his entire 8 inches into Taylor’s slick pussy instead. Having gone from the tight but focused muscular ring of her asshole to the wet inferno of Taylor’s snatch was sensory overload for Jase, and apparently Taylor as well. The switch had caused her already loud moans to turn into full fledged screams of pleasure as he hammered relentlessly into her pussy. After another minute, Jase signalled his pending change in hole but taking aim and spitting a glob of saliva down into her open asshole, at which point he pulled out and parked his dick back into her rectum.
“Fuck me! Ass, pussy, whatever,” Taylor screamed her desires.
“Play with your pussy,” Jase reminded her as his hips became a blur of motion.
With Jase’s cock plowing her ass, playing with her pussy made sense to the desire-ridden girl. Slipping a hand underneath her, Taylor found her pussy and drew her finger in circles over her clit in an ever faster fashion. Despite the speed and force her asshole was being hammered into, Taylor was finding that an orgasm was hurtling towards her at a neck breaking speed.
“Ohh ohhh ohhhhh,” Taylor moaned, the twin sensations of her ass stretched and clit massaged drove her pleasure to new heights.
“Almost there,” Jase said, recognizing the signs in Taylor.
Wanting to push her along, Jase pulled out his ace in the hole. Moving one hand from her hips, he reached lower until he was beneath his pistoning cock. Between his thrusting dick and Taylor’s circling fingers, Jase squeezed two fingers togethers and pushed them into her wet snatch. Instantly Taylor bucked before releasing an ear piercing scream.
“AAAHHHHH! YYEESSS,” Taylor suddenly squealed as the combination of cock in her ass, fingers in her pussy, and rubbed clit pushed her over the edge.
“Fuck! Me too. Where…” Jase began to ask.
“Face,” Taylor answered without hesitation.
That word alone was enough to take Jase over his peak and into his own climax. The fact that an elegant, classy 30 year old woman wanted to take his wad of jizz onto her face after he obliterated her asshole for the past hour was simply too much for him. Giving her bowels a few last thrusts, Jase pulled out of it’s vice-like grip. Taylor felt the sudden emptying of her bowels and immediately rolled onto her back. Having seen this, Jase reacted by crawling up the slender singer’s torso until he was perched over her perky tits and his cock was being beaten right in front of her face.
“Jesus!” Jase screamed as he climaxed.
Even though he fucked a lot of different women, most girls weren’t big fans of taking a cumshot to the face. Therefore since it was a rare occurrence, not to mention it was Taylor Swift’s face, Jase kept his eyes open the whole time. He watched as the first rope of cum propelled itself and streaked across Taylor’s nose all the way up to the forehead. The second streak hit the same target then he decided to paint another area of her pretty face. This time Jase splattered into her closed left eye while the fourth jet hit the side of her head and nestled into her golden yellow hair. The last remaining wads didn’t have the same quantity as the earlier ones, but there was still enough left to coat the rest of her face, making the pop star’s mug look like a Jackson Pollock painting.
“Oh my God,” Jase cursed, thoroughly exhausted.
“Glad you enjoyed yourself big boy,” she told him before sucking on his sensitive tip, tasting her ass juices again, this time from his filthy cock. “Not a bad start to the weekend, huh?”
“Not bad at all,” Jase grinned wickedly, knowing they still had another 2.5 days in anal paradise.
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Taylor Swift - End Game