Pool Party

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Ariel Winter is invited to a secret celebrity pool party.
13.9k words
4.57
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97

Part 1 of the 2 part series

Updated 06/08/2023
Created 09/06/2016
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Happy to share this story with you. This one is a bit odder than the usual fare and I warn you going in that this story involves well hung celebrity shemales. I kind of wanted to save it as a surprise twist, but that seemed a bit unfair to have the story seem like a typical lesbian celebrity story and then have it be about girls with hot cocks instead of cunts.

If that's your thing then have fun. If it's not your thing, well can't say I didn't warn you but if you try it you might like it.

This story is COMPLETELY fictional and not meant for people under the age of 18. This is all fantasy and not any kind of reality.

The story codes for this are FF, FF+, orgy, shemale, oral, anal, mast, voy.

If you like it and want more I am happy to do some sequels so please email me any feedback at my profile.

*****

Ariel Winter couldn't believe how nervous she was. She had never felt butterflies in her stomach like this before. She had never done anything like this before in her life and even though she knew she wanted it, she was still so hesitant to actually take such a bold step.

With each step forward that she took, Ariel wanted to turn around and run in the other direction and get home and turn off the lights and hide under her covers until she forgot how she had ever wanted to do something like this. It was all so crazy and wild and all of it seemed too much for her. Yet here she was.

And it was becoming clear how insecure she was.

"Just relax," a sexy voice said as a hand caressed her back in a supportive way. "Don't be nervous."

"Is it that obvious?" Ariel asked, blushing a little bit as she realized she was coming off like some inexperienced kid, which was what she very much felt like considering she was going to be the youngest one there and she had never done anything like this.

"Just a little," Britney Spears told her. "Don't be scared. This was new to all of us too once and you're going to get over those butterflies so quickly and really get into it, just like all of us did. I know this is a lot for you to handle but don't worry. This is going to be so much fun."

"I hope so..." Ariel said with audible hesitation in her voice. She really appreciated Britney's support and guidance through all of this. She didn't know what she would have done without her and it was still so crazy to Ariel that she could ever be friends with someone like Britney Spears much less have everything in common that she did with the pop superstar.

They had already shared so much with each other, things that would shock so many others who weren't privy to the secret they both had. Ariel never dreamed she would share something so sexy and special with someone like Britney and that made what they had done with each other so much fun. But it had also been so private and Ariel wasn't comfortable putting herself on display like she was going to here.

"It will be," Britney assured the teenager before giving Ariel a sensual kiss on the lips that even in her nervous state Ariel couldn't help but respond to.

The feel of Britney's kisses always made Ariel feel like she was floating on an erotic cloud and her toes curled in her sandals as she kissed the singer back. The kiss was so sexy and Ariel could feel tingles coming through her whole body from it. But it was also brief as Britney only lingered a few moments at Ariel's lips before she pulled away from them.

"Awwww," Ariel pouted, wanting the kiss to last.

"Don't worry, they'll be plenty more of that," Britney promised. "From me and from all the others."

But the promise of "the others" was really what most had Ariel nervous. Ariel tried to keep so much about herself private, especially with the leering eyes of the gossip sites and paparazzi on her. So while she didn't mind walking around in tight cleavage baring tops and shorts that showed off the luscious curves of her ass, her sexuality was private and Ariel definitely didn't feel comfortable showing it off.

One on one with Britney was fine. But something in a group setting was an entirely different story and Ariel had no idea how she was going to react to this when it started, especially if it was anything like Britney had described it would be.

"Do you think they'll like me?" Ariel couldn't help but ask, worried that she wouldn't fit in or that her inexperience would really show and that these other women wouldn't think she was hot.

And Britney couldn't help but shake her head in amazement that Ariel would even ask such a question. She tried to put herself in the teenager's shoes by trying to remember what it was like when she was Ariel's age but it was hard for her. Britney had been so eager to join this close circle of famous friends. She had been so eager to cast off all inhibitions and fears and just enjoy herself in a group of similar women who were all hot and horny for each other.

Her first time to a party like this had been one of the best times of her life and Britney couldn't wait for Ariel to see what it was really like when the clothes came off and everyone was free to be who they were and do whatever they wanted to do. Britney wanted Ariel to be comfortable and let herself go so she again assured her that she was going to be most welcome here.

"Of course they'll like you," Britney assured her younger lover. "In fact they'll LOVE you. This is going to be so much fun. I love going to these parties and you're going to love it too as soon as you see how hot it can be and experience all the fun for yourself. You're going to wish I had brought you here so much earlier because every girl is going to be so hot and so beautiful and so sexy and you're going to fit right in with them."

"Are you sure?" Ariel asked, feeling good by what Britney was telling her, but being around women like this was at the same time terrifying and arousing and it was all coming together to make those butterflies flutter in her tummy.

"I'm positive," Britney assured her. "After all they like a certain kind of girl here and you're just what they're looking for."

"Because of..." Ariel began to say but Britney interrupted her.

"Well yes of course because of that but there's other important reasons too," Britney said. "Mmmm our hostess loves big boobs and you've definitely got those..."

As she said that, Britney's hand softly caressed Ariel's famously large chest, making the girl stiffen a bit but also moan at the most welcome touch of her sexy lover. And Britney's other hand went lower and gave a similar caress to Ariel's juicy, thick ass, running over the curve of her backside and even giving it a sexy squeeze.

"And she's not just into big tits," Britney said. "She's also into big asses and baby mmmmm once she saw how big and fuckable your ass is, she wanted it as much as she wants mine."

"Ooooooooh!" Ariel moaned, unable to let her nerves keep from revealing just how much deep down she enjoyed the idea of being taken by other women, especially if Britney was there too and getting fucked just like she was. It was such a hot and nasty idea and while it also scared the hell out of her to even contemplate letting go that much, Ariel had to admit she liked it too and was so curious to see what it was really like to be fully uninhibited and fully comfortable with her body and in enjoying the hot bodies of other women like her.

"Mmmmm gawd my boobs and butt are so big though. You sure they're all going to like that?" Ariel asked and this time she got a snort from Britney, who couldn't believe the beautiful teenager was still insecure.

"Mmmm baby there's no question they will," Britney promised. "I love your body! Mmmm your big tits drive me crazy and I can never get enough of that hot, fat ass of yours Ariel! Just like I know you love my body, don't you?"

And Ariel definitely did. Britney's body made her horny 24/7 and she relished every single one of her older lover's curves.

"Mmmmhmmm I so do," Ariel swore. "I love your big butt Britney and those big, yummy tits of yours!"

"See! You love my big butt and I love yours and everyone is going to be so into both of us, especially yours because you're the newbie," Britney assured her. "Now let's get out there."

The two were at a very exclusive home nestled away in the Hollywood hills where no one would ever see anything they weren't meant to. That made it perfect for the kind of party that Ariel and Britney were attending, one that had a star studded guest list and promised pleasures they wouldn't be able to find anywhere else. Britney had been attending parties like these for years and since this was Ariel's first time, she wanted to make it special for her.

It was a pool party so neither of them were wearing much. Britney had on a red bikini that pushed up her already impressive chest and had a thong bottom on that showed off her toned, full ass in all its thick glory. She had been working so hard on getting her body in its sexiest shape and Britney loved to show it off. But Ariel had picked out an even sexier suit.

Despite her wearing a one piece suit and not a bikini, Ariel was looking even hotter than Britney. Ariel's one piece didn't shy away from exposing her body. The front of the suit was cut very low to put on an extreme cleavage show of Ariel's double D teenage tits and the back was cut high to let the meaty cheeks of her young ass stick out. It was such an enticing show of flesh that Britney had been forced to use every bit of her restraint to keep from fucking Ariel before they had even left for the party.

The teenager had looked so sexy and Britney had wanted her so bad but she had held on, wanting to instead save all her sexual energy for the party. The both of them had swimsuit covers over themselves but they were both see-through so their lack of clothing was pretty obvious. But since it was a pool party it wasn't like they were going to be out of place.

And that became even more obvious when they walked out of the house and toward the luxury swimming pool. With the sun shining brightly and the temperature in the 90's, it was the kind of day where a swimming pool looked mighty good and this one had all the frills with trees and shrubs lining the back of it amongst the rocks and several waterfalls that streamed water into the large pool and gave it such a relaxing, cool look.

But they were quickly distracted from the pool by something that looked even better.

"Hey there!" a beautiful blonde woman said brightly as she saw Ariel and Britney walk outside. She was sitting in one of the pool chairs and when she saw the arriving duo she got up and walked toward them wearing nothing but sunglasses and a bikini that barely held back her famous body.

"Kate!" Britney said happily as she embraced her friend and eagerly gave her a peck on the lips that was immediately returned. "I'm so glad you're here too! Do you know Ariel?"

"No, but I've heard so much about you," Kate Upton said, turning toward the teenager with a smile and a look in her eyes that showed she was very eager to get to know the younger woman. "You should know that Britney raves about you every chance she gets. She won't shut up about how wonderful you are."

Ariel responded to that with a shy smile and a blush. She could barely believe she was looking at this gorgeous bikini-clad goddess. Kate Upton always looked hot when fully dressed and since she was definitely not like that now, her beauty took Ariel's breath away.

Kate was in a pink sling bikini that couldn't do much of anything to hold back her incredible big tits. They were practically begging to escape with the pink material barely restraining that all-natural rack and as Kate and Britney hugged, Ariel couldn't resist sneaking a peek and seeing that the string bottom of the sling bikini was like dental floss between the cheeks of Kate's thick ass.

Her ass looked amazing like that, barely covered by anything. Kate might as well have been completely bare-assed and Ariel tried not to drool as she checked out the supermodel in a lusty way she never thought she would ever have the chance to do in person.

"Ummm...ummm...yeah...you're looking pretty wonderful too," Ariel managed to stammer out before closing her eyes in embarrassment over saying something so cheesy. She couldn't believe that had been all she could think to say when seeing such a beautiful woman.

It was a line that was so lame it would have gotten her blown off by any woman in the world if she'd been a guy. But fortunately, Kate didn't seem to mind it and laughed it off.

"You're sweet," Kate told the awestruck teenager. "And you're beautiful too so I think you're going to see how wonderful I look without this bikini on pretty soon. And I can't wait to see you out of yours too. I've been wanting Britney to bring you to one of these parties for so long Ariel. She's been telling all of us how hot you are and how good you look naked and I have to say I've been thinking about it a lot."

"Oh sure, forget all about me and go after my girlfriend instead," Britney teased. "That's so typical for a slut like you, Kate."

"Mmmmm damn right I'm a slut and I'll show you how much," Kate laughed before kissing Britney, this time with much more than a peck on the lips. The two blondes fell right into their passion for one another, pressing their bodies together as they lustfully kissed.

Ariel didn't feel jealous though even though Britney was her lover. She wanted Kate too. She wanted to peel that itty-bitty sling bikini off the busty supermodel and get her completely naked. She wanted to watch Britney and Kate make out and she wanted them both naked and Ariel wanted to join in their fun too. She wanted to be naked with them both so there was no jealousy at all, just a growing desire in the teenager.

"Mmmm get this off," Kate urged, pulling Britney's coverup over her head and leaving her in just her bikini. "Ooooooh mmmm that suit looks so yummy on you Britney. It's going to be a shame to tear it off you."

"Mmmmm not if I tear yours off first," Britney responded with a little giggle as she gave Kate's big ass a sexy smack that made the model moan. "Not like there's much for me to rip off anyway."

"Hey I don't like to be subtle at a party like this," Kate said. "I want everyone to see what they're going to get. Mmmmm I don't care if that means I'm a slut. I just love these fucking parties so much!"

Britney and Kate began kissing, the iconic pop singer and gorgeous supermodel kissing and rubbing their big tits together in their bikinis. It was a show that so many men would have done anything to be able to see and Ariel had a front row view of it. And she certainly appreciated the show too. Ariel could feel her nipples getting stiff against her swimsuit and she knew that soon she would be showing her arousal in another way too.

But the two blondes didn't just want Ariel to be a bystander, especially Kate.

"Don't be shy sweetie," Kate urged the girl. "I definitely want to play with you too. How about you get that coverup off you and come a little bit closer?"

That offer definitely sounded good to Ariel. She might have still been feeling shy, but that feeling was dissipating by the second and she was definitely starting to relax. This wasn't an atmosphere she had ever been in but she was feeling less scared by it and more eager to experience it all. So Ariel did just as Kate requested and pulled the coverup for her swimsuit over her head, showing off just how much of her curvy teenage body was exposed by her one-piece and earning a wolf whistle from the model in the process.

"Oh fuck, you look delicious," Kate moaned, this time feeling her breath be taken away by what she was seeing. "You're gorgeous Ariel!"

"So are you," Ariel replied, moving closer to where Britney and Kate were standing, their bodies pressed together and waiting for her.

Ariel could feel the electricity and sexual chemistry really starting to crackle and she was eager to get to know Kate. She had only lusted after her from afar, so turned on by her luscious tits and ass and Ariel wanted her bad. She wanted to kiss Kate like Britney was and Ariel was about to do just that before another voice interrupted them, this time from inside the pool.

"Jesus, would you all get a fucking room or something?" Rose McGowan teased with a wicked laugh as she interrupted the fun. "What do you think this is, an orgy?"

Of course that's exactly what it was and Rose knew full well that it was because it was her party and her home. They were all her guests for the day and she couldn't wait to get the fun started. But she also couldn't help teasing either and seeing the flustered look on Ariel's face when the kiss was interrupted was worth denying herself the surely sexy site of her and Kate kissing.

Rose loved seeing the little pout on the beautiful teenager and she licked her lips at the sight of her in that one-piece swimsuit clinging to her body. It was such a tantalizing layer of wrapping paper over the gifts underneath and Rose couldn't wait to get it off the girl.

Rose had loved seeing the back and forth between Kate and Britney, both of them so sexy in their small bikinis, and feeling the sexual chemistry between the blondes. She had seem them be so naughty with each other many times before and Rose had thoroughly enjoyed them both. That was why they were such frequent guests at her parties. But Ariel was fresh meat and Rose wanted her so much.

She couldn't just watch them. Rose had gone undetected before because she had already been in the pool and had been underwater cooling herself off when Britney and Ariel had walked in. She had to announce herself and since she had popped her head out of the water just when Ariel was about to kiss Kate, she hadn't been able to resist.

"Be nice, Rose," Britney chided.

"Oh I am nice," Rose reminded her. "And your little girlfriend is going to find out just how nice. Mmmmm it looks like you three are eager to start the party early today too. You're not exactly waiting for the other guests, are you?"

"You should talk," Kate pointed out. "You were in the pool before I even got here."

"My house, my rules," Rose noted with a smile. "Besides there's nothing stopping you from joining me in here. Mmmm but I think for this I'm going to come on out so I can get a closer look at our newbie here."

Ariel knew she was talking about her and she gulped when she heard it. She didn't know Rose at all outside of Charmed reruns but her reputation for debauchery had preceded her. Ariel had heard so many wild stories about Rose from Britney and the thought of what a gorgeous and erotic woman like this could do to her was a bit scary and a lot arousing to the teenager. So it wasn't just Rose getting a closer look, it was Ariel too.

And what a look she got too. When Rose pulled herself out of the pool she showed off that unlike the others, she hadn't bothered with a swimsuit. Her body was dripping wet and completely naked as Rose reached for a towel and began to dry herself off just enough to stop the water running off her creamy, pale skin. But she left enough moisture on her body to give everything an enticing glisten and as Rose approached them, Ariel found herself fantasizing about licking those little droplets of water off Rose's skin.

"Ummm wow," Britney said, very impressed by what she saw even though she had seen Rose naked so many times she couldn't keep count. "I thought you said we were all supposed to wear swimsuits."

"Again, my house, my rules," Rose said. "And I don't see anyone complaining about the view, especially Ariel."

And Rose was right about that because Kate, Britney and especially Ariel could not take their eyes off what they were seeing. Rose was pure sex as she strode over to them wet from the pool and completely confident in every motion of her body. Ariel was transfixed at the pale skinned dripping wet woman.