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Era Erotica Ch. 19

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It's an all out orgy with Taylor Swift's Squad!
9.9k words
4.71
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Part 19 of the 44 part series

Updated 06/09/2023
Created 09/27/2018
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Disclaimer: This a work of fiction. It did not/will not happen in real life and should not be mistaken as such.

Chapter Nineteen: Wonderland

Starring Taylor Swift

Featuring Blake Lively, Camila Cabello, Cara Delevingne, Gigi Hadid, Hailee Steinfeld, Hayley Kiyoko, Karlie Kloss, Martha Hunt, & Selena Gomez

Codes: MF+, M+F,Cons, Anal, Oral, Orgy

*****

2019

Cole was taking some time off while he pondered his next career move. Joining Taylor's marketing team was a big decision and he wanted to be absolutely sure before committing. His unemployment meant days alone playing with Taylor's cats and nights playing with her pussy. Still, only two weeks in and he was already going crazy. All that changed one day while rifling through the mail. A gold leaf envelope caught his eye. Curious and thinking it was a wedding invitation, he carefully opened it, pulling out the letter to read its contents.

Ms. Taylor Swift & Mr. Cole Stephens,

You are cordially invited to the annual Wonderland celebration. Ms. Selena Gomez is hosting and Mrs. Karlie Kloss is our mistress of ceremonies. Ms. Gomez has elected to hold the event at her Los Angeles residence on the 23rd of this month. Please RSVP if you plan to attend.

- Wonderland Planning Committee

P.S. We'd love to see you both there! - Selena

Cole finished reading, no closer to understanding what it actually meant. Wonderland was the setting of a beloved fiction book, and a song off Taylor's 1989 deluxe album. Neither seemed an adequate explanation.

"Hey Swift?" Cole asked, calling out to the other room. "What's Wonderland?"

He heard something crash and a loud curse as Taylor dropped whatever she was holding. Storming into the kitchen, her eyes darted back and forth. They froze at the letter in his hand.

"Where did you get that?!?"

"It was addressed to both of us." Cole said, looking confused and handing her the letter.

Taylor snatched it from his hands, her blue eyes roving over the short script in seconds.

"Every year I give them the same answer!" She threw letter aside and slumped down at the kitchen table.

"What's going on Swift?" Cole asked, sitting down next to her. "Talk to me."

Taylor looked at him, a mixed expression on her face. "I don't want any secrets from you. So here it goes. Wonderland is...an orgy. An annual one. Hosted by members of my so-called squad." She put the last word in air quotes. Cole's jaw hit the floor. "Started in 2013. At first it was just a bunch of friends getting together for a fun and wild night. Things apparently got out of hand after I left, but they had so much fun that they decided to make it yearly thing. They called it Wonderland after the song of mine, because I'd brought them all together. And because they had a wonderful time. Their words. Not mine." She gave a hollow chuckle.

"An orgy, a little out there I guess. Why are you so against it?" Cole asked, trying to focus while battling images of Taylor's many model, singer and actress friends in the raunchiest sexual positions and scenarios.

"I wasn't! All for it really. Until 2015. That was the first year I decided to go...with Adam. Asshole. At the time he seemed really excited. In retrospect, he just wanted a free pass to fuck all of my friends. When we got there and realized I would also be fucking other guys, he freaked out and ruined the whole thing. Haven't been since. Stupid DJ prick."

"Not even with other guys?"

"Nope. Wasn't dating Tom long enough and Joe would have loved to see me get railed by a few dudes, but he wasn't too keen on anyone else knowing that."

"Well, you're with me now. And I say let's go. It sounds like you want to."

"Cole."

"Swift. I don't care if there are other men to fuck. It's only fair. Some women for me. Some dudes for you. Tit for tat. Besides, I know who you'll be coming home with. This guy." He stared intensely, waiting for the argument. "You know you're not going to find a cock as good as this one."

The corners of her mouth twitched. "I do love your cock..."

"Love you too Swift."

She moved in for a kiss. He kissed her back and as they lingered, it turned into much more. Right there on the kitchen table. Afterwards, as Taylor wiped the sticky cum from her torso, she said, "Ok. If you're sure. Let's go."

***

"OH MY GOD! HE'S ACTUALLY HERE!" Was the first thing they heard as they opened the front door of Selena Gomez's Los Angeles estate.

The next thing Cole knew, he was being dragged inside by a gaggle of stunningly beautiful women. They marched him to the living room, forming a close-knit circle. Shameless with their eye-fucking, Cole smiled nervously at the sudden intense female scrutiny. Taylor fought her way through, shooing away her friends like a flock of birds. One-by-one they retreated, resuming whatever activity they had been doing before. Cole still felt many of their eyes upon him. The celebrations were already underway as empty bottles littered the room and music blared from an unseen sound system. The scantily clad women were comfortably dressed, not that it mattered. They'd all be sporting birthday suits soon enough. That wasn't to say they didn't look good. Makeup was on point, hair sleekly styled. And then there was their toned bodies, each one tighter and perkier than the last. Every one of them could have passed for Greek goddess.

"Wow. A lot of your friends are here." He muttered.

"It's a good turnout this year. It looks like we're the last ones." She said nervously. "It's not too late to back out, just so you know."

"Nonsense Swift. I'm good if you are."

She nodded, giving him an anxious smile. Selena came bounding over to them in sleeveless tee. Undeterred by the presence of a bra, her perky milk-makers threatened to bounce right out into plain view. She brushed her shiny black hair behind her ears, rattling the hoops there and hugged Taylor tightly.

"I'm so glad you're here!" She was positively beaming. "And you brought a treat!" Her warm brown eyes roamed up and down Cole's muscular form, noticeably lingering at his crotch.

"Yep! We're here! Cole's been great. Really supportive."

"I'm sure having all these beautiful ladies here doesn't hurt." Selena said with a wink.

Blake Lively joined them, the tightest of tank tops barely able to hold back the ample bosom of the blonde actress and mother of two. She hugged the both of them, pressing her breasts against Cole for far longer than was socially acceptable.

"It's strange to see you here Cole." Selena said. "All of our boyfriends, husbands or significant others are too insecure to come."

"It's fantastic!" Blake cut in. "Ryan wanted to come, but he's on a movie shoot. Usually he's the only other guy that turns up. He'll be sorry he missed it this year!"

"Not sure what all the fuss is, Taylor and I love each other. We know that. A little fun with other people doesn't change that."

His statement was met with aws and ohs, everyone clearly eavesdropping on them. Taylor gripped his hand tightly and gave him the warmest of smiles. Introductions and greetings followed. Cole had met nearly everyone before, but not all. Taylor gave a particularly large greeting to Hayley Kiyoko, who had been a special guest on her reputation tour.

"Hayley! So glad you accepted my invite!" She said, hugging the fellow popstar. "I wasn't sure you would with all the dicks involved."

The half-Asian blonde singer, referred to as Lesbian Jesus by her fans, shrugged and said, "There's also a lot of fine chicks. I'll find plenty of pussy to entertain myself."

Karlie Kloss stood at the head of the room, effortlessly striking a pose as she cleared her throat loudly. The tall lanky model with flowing flaxen hair and blue eyes to match Taylor's, tapped a large crystal goblet with a silver spoon to get everyone's attention. Through the sliding glass doors behind her, the sun was just setting, casting a gorgeous orange glow over the rocky foothills of LA.

"Welcome all to Wonderland 2019! I'm your mistress of ceremonies, so I'll be dictating the events tonight. Before I bring the gentleman out, we need to have a toast and take care of a few orders of business. Drink up everyone!"

Cole looked around as the party-goers gravitated towards the table with an enormous punch bowl in the center of it. He'd been to Selena's home plenty of times before, although the layout looked different this time. An enormous plush ottoman lay in the very center of the room, nearly the size of a mattress. Several couches and chairs were arrayed all around it, almost like seats facing a stage. Her usual furnishings seemed to be gone. The doors to her room and a guest room, both of which lay just off the living room were closed. Cole and Taylor had spent many a night fooling around in that guest bedroom, and even once or twice in Selena's bed when she was otherwise preoccupied. On the wall opposite the punch bowel was another table. Cole stopped mid-walk as he realized what was on it. Spread across the table was every variety of sex toy imaginable. Dildo's, both anatomically correct and otherwise, vibrators, strap-ons, wands, butt plugs, nipple clamps, anal beads and pocket rockets of every size, shape and color imaginable were presented in neat organized rows, clearly waiting to be claimed by a horny owner once the festivities got underway. Taylor tugged his arm and he shook himself. The punch bowl was filled with a bright red concoction. Cole ladled two full red solo cups, taking a whiff. The overwhelming aroma of alcohol filled his nostrils.

"Whoa, what's in this?" Cole asked Gigi Hadid who stood next to him, pouring her own cup.

The model stared with blue-green eyes, her rounded cheeks smirking. "The Jungle Juice? Alcohol."

Cole laughed and gave a cup to Taylor. Once everyone was ready, Selena raised her own cup. "Here's to Wonderland! Cheers everyone! Drink up!"

Everyone in the room downed their red solo cups, chugging down the contents like it was a race. The combination of what tasted like several different types of alcohol made him cough. "Reminds me of college. I think I prefer your old fashions."

Taylor grinned. "Let's get another."

The mingling continued as they all downed a few more rounds of Jungle Juice. After the third cup, Cole began to feel strange. Within the confines of his jeans, his cock stiffened, snaking down his pant leg as it searched for an escape. Taylor immediately spotted it.

"Someone should have mentioned, it's the Jungle Juice. Makes dicks hard as a rock. Clits too." She leaned in closer, whispering. "I'm dripping right now." That did absolutely nothing to help his erection. "It gives everyone the libido to go all night. Because they do. I mean we do."

Cole shifted uncomfortably as Taylor moved to talk with Cara Delevingne. The British model flashed him a wink, sticking her tongue into her cheek and grabbing an imaginary cock with her hand, miming a blowjob.

"Hey Stephens. Long time, no see." Hailee Steinfeld said, the dark-haired singer actress sidling up to next to him.

"Hailee. Nice to see you again. It's been a while."

"It has. Too long. Since you two got together, Taylor's been hiding you!" She leaned in closer, licking full lips. "I'm stoked to see that dick of yours in action again."

Cole nodded stupidly as she flashed a wicked grin and gave his crotch a quick squeeze. Before he could say anything, Karlie called for attention.

"I think we are all sufficiently hard up. Let's get started! Everyone, STRIP!"

Cole glanced around. What little clothes they had on were quickly tore off. Camila Cabello bumped into him, pulling off her blouse.

"Whoops! Sorry Cole." The half-Cuban singer said, now topless and gazing at him. Cole's eyes slid downwards to her perfectly proportioned bronzed globes. Each dark nipple was as puffy and erect as he'd ever seen. "What are you waiting for? Don't be shy. Strip! I've been bragging about your pinga all day."

She gave a high-pitched raspy laugh, pushing him playfully. She reached and gave his trousers a tug. Taylor materialized over his shoulder, her face playful.

"Always so eager to get my man naked, huh Cee?"

"You know it Tee." She said, shimmering out of her short-shorts. "You're a bit overdressed yourself chica."

"Let's change that." Taylor said, peeling off her own shirt.

In a flash, she was naked. Cole followed suit, unbuckling his belt and pulling his trousers down. The blonde Victoria Secret's model, Martha Hunt, gave a hoot as she walked by ogling his ding-dong. She was naked herself, breasts jiggling as she carried a bundle of clothes. Taylor reached for his underwear and pulled, letting loose a girlish giggle as his wang sprang forward, stiff and ready for action. For a moment, the eye of every female in the room was drawn to the thick rod, even Hayley.

Once everyone was done stripping, they clustered around Karlie, who just as naked as everyone else. As far as the eye could see there were toned, fit muscles, breasts that jiggled with the slightest movement, shapely asses that were pinched and squeezed by perfectly manicured hands, pouty lips being licked by tongues in anticipation and eyes wide, filled with excitement in the dying light of the LA sunset. He really was surrounded by a group of goddesses.

"WELCOME TO WONDERLAND 2019!" Karlie screamed, her excitement evident. A roar of noise greeted her words as the call went up all around. Hands clapped, mouths whooped and squealed with glee as the gaggle of women unabashedly rejoiced at the wild fucking that was about to commence. "On the count of three we kick it off! One! Two! Three!"

Every woman reached down between her buttcheeks, to the buttplug tightly nestled there. They pulled. Cole was treated to the sound of ten different and distinct pops as sphincter rings stretched and the glittering trove of anal sex toys were pulled from various rectums. They held them high, triumphantly above their heads, each a different color and shape. Hoots of laughter echoed as they trembled with the sensation. Cara popped hers into her mouth, licking it clean before holding it up. Taylor gave a squeak as hers was removed. Grabbing Cole's hand, she placed it on hers, holding the shiny pink bejeweled buttplug high. It seemed only right, after all, he had helped her put it in that morning.

"LET WONDERLAND BEGIN!" Karlie yelled, her voice an octave higher than it had been moments before.

One set of the double doors banged opened and the gentlemen marched in, butt naked with their fat cocks dangling in front of them. Five prime male specimens lined up next to Karlie, hands behind their back, dick's facing forward. Even Cole couldn't help but marvel at them. A multitude of ethnicities, but all with chiseled jaws, slick haircuts, pretty eyes and muscles that bulged on each of their respective frames. Then there were their cocks. Each one was as long and girthy as the last. Veins spiderwebbed across thick shafts, golf-ball sized mushroom tips were already shiny with precum and large heavy balls swung between their legs. Cole was pleased to see that he measured up reasonably well. Well, expect for the last guy in line. The African-American man was hung like a horse, easily dwarfing every other cock in the room. The ladies squealed with glee as the men made their grand entrance. Selena only had eyes for the black man, her brown eyes following his swinging progress across the room.

"Look at these fella's! Am I right ladies?" Karlie asked, standing behind the nearest one, sinking her nails into his large pecs and biting her lip something fierce.

This was met with further cheering as horny hands began roaming over their owner's and neighbor's bodies. Clits stiffened, lady lips shimmered with arousal and nipples hardened. Martha looked as though she was actually drooling.

"Only five of them?!?" Camila called out, the dismay evident in her voice.

Karlie shushed her before turning to Selena, "Would you care to announce the guest of honor?" She held out a sealed envelope. Selena was still fixated on the big black dick, oblivious to everything else. "Selena!" She was snapped out of her stupor as Karlie clapped her hands together.

"Yea. Right. Guest of honor."

She stepped to the front, perky tits and ass jiggling. "Eh-hem. The guest of honor this year is...a little drumroll please." Hands strummed against tight tummies, muscular thighs or supple asses as the women patted themselves, drumming up a sufficient buildup for Selena to open the card. "TAYLOR SWIFT!"

Everyone turned to Taylor, cheering, giggling or running a hand over her supple body, giving her bits a squeeze. Taylor blushed.

"You know what that means!" Martha shouted. "Get ready for those cocks!"

"What does that mean?" Cole whispered.

"It's mean's she's about to get stuffed airtight!" Blake said excitedly.

As Taylor was pushed forward, she flashed a look back at him. He gave a smile and a thumbs up. Karlie's instructed the men as Taylor knelt on the carpeted floor in the center of the room, next to oversized ottoman. They jockeyed for position around her, hefty wangs swarming her as she gazed around up at them.

"C'mon Tay! Give us a good show!" Selena called out.

Everyone settled down around on the arrangement of couches and chairs, eager to watch the live sex show play out in front of them. Cole wouldn't say he was overjoyed to watch these five dudes rail his girlfriend, but he knew there were no feelings here, only sex. Thankfully as he settled down on a couch, Blake cozied up next, brushing her sizable ta-ta's up against him.

"Don't worry, I'll make sure you don't get too jealous." She whispered and wrapped a hand around his cock.

"Me too." Said Hailee, snuggling up on his other side and likewise gripping his cock.

Taylor gazed upwards at the selection of manmeat around her. With a look of determination and a cheeky grin, she dove right in. Opening her pouty lips wide, she devoured the nearest schlong, taking it straight down the balls and holding it there as she grabbed two more, stroking them fast. Woo's and more cheering greeted her ears as took down another dick, his balls resting on her chin before releasing it with a spit-filled cough and moving to the next one. She spat left and right, making sure the five cocks around were nice and slippery as she jerked them off. Taking inspiration, Hailee leaned over and let loose a long string of spittle onto Cole's cock, spreading it around as her and Blake worked in perfect tandem, stroking every inch of him. Blake reached down to fondle his swelling balls. Everyone else was enjoying the show. Fingers disappeared between thighs, rubbing wet lips or strumming throbbing clits. Breasts were groped and nipples tweaked as they watched Taylor suck down each guy six ways from Sunday. She utilized all her many oral tricks, fast bobs of her head with lips sealed tight, long slow powerful suction strokes with her cheeks caved inwards, gobbling at heavy swinging balls, lapping at gaping oozing pisslits and curling her tongue around every veiny inch.

"Get it Taylor!" Gigi called out.

"Suck those cock's girl! Woooahhh yea!!" Blake added.

Hayley had already given into her baser instincts, busing herself between Cara's legs as she kissed her soaked twat. Cara pinched both nipples, twisting them back and forth as her eyes watched Taylor intently. Selena sprang up from her seat, only to quickly grab something off the sextoy table and hurry back to her chair. She promptly spread her legs wide and fit the large black dildo into her snatch, moaning loudly as she did so. Suddenly, there was flurry as women hurriedly also ran up to grab something. Blake and Hailee remained seated, jerking Cole off. To compensate, he placed a hand on each of their hot wet slits, slipping fingers between velvety folds as moans filled his ears on either side.



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