It's Brutal Out Here

Disclaimer: This is a work of fiction. I do not know or own Olivia Rodrigo or Jenna Ortega or any other celebrities. I do not make any money from the writing of this story.

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Olivia Rodrigo and Jenna Ortega were about the same age, both had shows on the Disney Channel at the same time, and Jenna had even guest starred on Olivia's show, as an old friend, no less. In real life, Olivia would happily describe them as friends. Not best friends or anything. But whenever their paths crossed, they had been very friendly.

Jenna was just such an easy person to talk to, and whenever the other girl contacted her about hanging out, Olivia knew she would be in for a good time. And she was sure it would be this time, as she approached Jenna's hotel room, and got ready to knock on the door. However, it would likely be different to other interactions between them.

Because this was the first time they had met since Olivia had been introduced to the kind of things female celebrities liked to do with each other, and very recently, she had upset Beyonce, who had probably let all of her bitches know that Olivia Rodrigo was available for topping. Was Jenna one of those bitches? Maybe. Maybe the timing was just coincidence, and Olivia was going to leave here disappointed?

Or something far worse, as the last thing she wanted to do was hit on another girl, and be rejected. Also, while Jenna would probably be cool with it, there was a chance that Olivia would lose a friend if she misread the signs, so she couldn't help be nervous as the door opened. Although luckily, Jenna put her at ease.

"Hi?" Olivia greeted nervously.

"Hi." Jenna smiled warmly, holding out her arms for a hug, "Come here."

"Awww, thanks." Olivia beamed, happily closing the distance, and hugging her friend, "You're the best."

"I know." Jenna quipped with a grin, enjoying the hug for a few long seconds, then pulling away and insisting, "Come in, come in."

"Thanks." Olivia said, quickly closing the door behind her, and walking into a surprisingly small hotel room.

"Sorry if it's not what you're used to." Jenna teased, she saw Olivia looking around.

"No, no, no, it's nice. Great. Really. It's just-" Olivia stammered.

"Small?" Jenna offered, before shrugging, "I know, I could afford better, but unless I blow up in the next few years, I figure I should save my money, just in case, you know?"

"Isn't the new Scream about debut?" Olivia questioned, "That's sure to be hit, right?"

"Yeah, but the last one didn't get sequels, so who knows." Jenna shrugged, before admitting, "But, I didn't ask you here to talk about my career."

"Why did you?" Olivia asked softly.

"You'll find out." Jenna said cryptically, "But first, would you like a drink?"

"Is that a drink, or like, a drink?" Olivia questioned, before quickly insisting, "Because, I'm cool. So cool. Like, I'm totally cool with just coffee, or water, or even juice. But..."

"Sweetie, relax." Jenna reassured, pulling out a bottle of wine, "I got you. We're not Disney girls anymore. But no pressure, if you don't want to."

"Gimme, gimme, gimme!" Olivia encouraged happily, before cringing and adding, "Erm, please?"

In response, Jenna just laughed, and poured them each a glass. She even used proper wine glasses, so clearly, she had thought this through. Then again, it wouldn't be the first time Olivia had done something like this. Although in the past, it had been a pretty friendly thing. Just a group of girls, sometimes one friend, watching a movie together, or talking about boys.

But Jenna didn't seem interested in watching a movie, and boys were briefly mentioned, and dismissed. Which was definitely a good thing, as Olivia couldn't take interest in them right now. Not when she's constantly thinking about Sofia Wylie, and more importantly for that particular moment, Jenna Ortega, AKA, the beautiful girl in front of her. Her friend, Jenna Ortega, who just might be flirting with her.

Admittedly, Olivia had been known to be slow on the uptake with these things, and for all she knew, Jenna had been flirting with her in the past. Maybe not when they first met, but certainly in the past year or so. Whatever the case, she had a good feeling about right now, and did her best to flirt back.

Unfortunately, she was still new to flirting with another girl, and while it had been easy with Sofia, she was convinced that Sofia was a bottom, and she knew she liked women, so it was very different situation. Luckily, she had the opportunity to swallow down a glass or two of liquid courage before trying to make a move, something else which Jenna made easy.

"So, did you just want to catch up, or is there some reason you wanted to meet?" Olivia finally blurted out.

"Do I need a reason to see you?" Jenna teased, really enjoying watching Olivia squirm.

"No, no, no, it's not that! Really. Like, no way." Olivia babbled, struggling to find the right words, "It's just that..."

"You were wondering if I had heard you were in the game?" Jenna quipped.

"Right." Olivia gulped, then nervously checked, "Meaning?"

"Meaning, you fucked Sabrina Carpenter in the ass." Jenna said dryly, before shrugging, "Not that it's a big accomplishment. Everyone's had that ass. Everyone! But, it's a start. Especially since she told me you were really good, And yes, it doesn't take that much to please a butt whore of that calibre. But it's definitely something."

"I..." Olivia began with a huge blush on her face, as she again struggled to think what to say.

"I also know you got broken in by Beyonce's little protégé, Sofia Wylie, before having a turn with you herself." Jenna continued, then when she saw the look on Olivia's face, she explained, "Sabrina told me everything. And yeah, I knew she promised not to, but don't be mad at her, okay? Sabrina is the kind of butt slut who would literally do anything for a cock up her ass. And trust me, when these things happen, news travels fast.

Something which can be a very good thing, if you want it to be. Although, it's also a lot to take in, so I thought I would offer to help. Answer any questions you might have? Like, for one thing, you shouldn't feel bad about getting butt fucked by Beyonce. I'm pretty sure it happens to all of us, eventually."

"So..." Olivia gulped, this time being allowed to ask a question, "So, you're a bottom?"

"God no." Jenna said, before grinning, "I'm a switch."

"What?" Olivia frowned with confusion.

"A switch." Jenna repeated, before explaining, "It means I like topping and bottoming, depending on my mood. Sometimes, on the same night."

"Yea, yeah, I know. Well, I like, read it online. And yeah, you're not supposed to believe everything you see on the Internet. But..." Olivia rambled, before saying, "It just feels right."

"Oh, it is." Jenna reassured, quickly adding, "Beyonce and her little friends like to insist there is no middle ground. That you're either one, or the other. And just because you're getting fucked by a great top, and agree to be her bitch, that's a legally binding contract, and you couldn't possibly change your mind later. That's one of the things I wanted to talk to you about, actually. Because, what I hear, you might be like me.

Or, maybe you prefer one over the other. Or maybe you'll decide on one label now, and change to another later. My point is, you have options. Fun options, which I know from experience, are fun to explore. We can even explore them now, if you want."

"You mean, like, have sex?" Olivia asked nervously, but excitedly.

"Only if you want to." Jenna quickly added.

"Oh, I want too." Olivia quickly insisted, grinning widely, "I like, soooooooo fucking want to. Because seriously, have you seen you? Because like, wow! Wow! So yeah, I wanna fuck you."

"Thanks." Jenna beamed, "You're very fuck-able too."

"Yeah, I am." Olivia grinned, before asking, "So, are you in a topping mood, or a bottoming mood?"

"How about, both?" Jenna suggested, "If that's good with you?"

"Erm, sure." Olivia agreed, then bit her lip, and asked, "Soooooo... how does that work, exactly?"

"Simple, you top, then I top. Or vice versa." Jenna explained simply, "Like... I really want to taste you, and I'd love to eat your pussy all night. But, it would also be cool, if whenever you're ready, you returned the favour. Or just fingered me, or something? Just, as long as you get me off, I don't really care. Whatever you're comfortable with."

"Oh?" Olivia frowned in confusion, "I thought eating pussy was a submissive thing? Or, were you thinking I would top first? Because, I don't know, maybe you should do it first?"

"That's Beyonce's logic, not mine." Jenna shrugged, before further explaining, "But, as much as I want to taste your pussy, I also want to fuck your ass. And, after flip-flopping between topping and bottoming, maybe it would help to do them both in one night? Or at least try? It can be hard, but trust me, when you get it right? Mmmmmmm, there's nothing like it."

"I don't know..." Olivia bit her lip, before asking shyly, "Can't I just, you know, fuck you in the ass first?"

"That's the easy part." Jenna shrugged, before further explaining, "Trust me, it's easy to do all the work, then just lay back and let someone else take over. But going straight from bottoming to topping? Now that's a real achievement. Of course, you don't have to, if you don't want to. Or you don't think you're ready. It's just, I want to help you, and it feels like the best way to do it."

There was a pause, then Olivia nodded her head, "Okay."

"Okay?" Jenna pushed.

"Let's do this." Olivia confirmed, then quickly adding, "But can we skip to the ass fucking? I really want to eat pussy with you, but that's tiring enough. You know?"

"Oh, believe me, I do." Jenna beamed, "And you being the one to suggest that? Mmmmmmmm, that's a really good sign that I was right about you. Seriously."

"Right about what?" Olivia frowned in confusion.

"That you really are a switch, like me." Jenna said, stating the obvious.

"Oh, right." Olivia blushed, and then questioned, "So, is this the part where you tell me to bend over?"

"No, this is the part where we kiss." Jenna grinned, leaning towards Olivia's face in the process.

"I'm good with that." Olivia grinned back, and happily accepted the pair of lips which pressed against her own.

Olivia of course welcomed those lips with her own, the two girls becoming lost in that soft kiss, which eventually turned more passionate and enthusiastic, once their tongues were added. Part of Olivia had been worried that it would be weird, given just how long they had known each other.

However, ever since she had first hooked up with Sofia Wylie, Olivia had been thinking about all the other women 'in the business', with the ones she knew personally at least towards the top of her list. So, instead of being awkward, like she had been afraid it would be, it felt like it was a longtime coming. And so very good, right and natural. Jenna was a great kisser, and effortlessly put Olivia at ease, so she could just enjoy it.

Then all of a sudden, it was over, as Jenna was pulling away from her and stood up. Luckily, before Olivia could truly freak out and/or embarrass herself, Jenna began taking off her clothes, causing Olivia to grin with relief, and excitement. Of course, if they were going to do this, they needed to be naked. So, she was happy to follow suit.

Admittedly, the actress seemed a lot more confident about it, although the singer knew all about forcing herself to be brave when she wasn't feeling it. Something that she definitely needed, when they were both completely naked, and just staring at each other. Luckily, seeing the beauty in front of her calmed her nerves. Especially as the other girl seemed to like what she saw.

Another thing which filled her with confidence was the fact that Jenna smiled wickedly down at her, then pushed Olivia down onto her back, and got on top of her. Then, more kissing, which could definitely be described as making out. Like, the best kind of making out. When clothes were gone, and their bare bodies pressed against each other in all the right ways.

Maybe especially for girls. Like, Olivia could feel hard nipples pressing against her boobs, and vice versa. And also, thighs were against wet pussies. And oh, they were even grinding against each other. They probably weren't even trying it was just happening. And it was glorious. And yet, it was still only preparation.

Preparation which lasted longer than Olivia thought that it would. Not that she was complaining, given that again, Jenna was an excellent kisser. At the same time, she was relieved when the other girl moved on. Hell, she would have welcomed just a hand moving down. In fact, that would've been better, at least in the short term, as it would mean that the other female form wouldn't be removed from hers, leaving Olivia feeling horribly neglected.

Which was of course, short-lived, as Jenna retrieved a strap-on dildo, attached it to herself, and covered with lube. Something that she wasn't sure she would ever get used to seeing. Especially considering what the other brunette was planning to do with it. At the same time, she was feeling very excited.

"I've been waiting a long time to say this to you..." Jenna revealed with a wicked smile on her face, "Bend over."

"Ooooooooh yes... Mistress Jenna." Olivia teased, quickly doing as she was told, even shaking her ass once she was in position.

"Huh?" Jenna hummed, as she got closer to her target and inspected it, "No butt-plug.

"Is, is that okay?" Olivia asked nervously.

"Well, I'm surprised Mistress Beyonce doesn't have you wearing one." Jenna said thoughtfully, "Unless, she has, and you're being naughty?"

"Maybe." Olivia blushed nervously.

"But honestly, I'm glad." Jenna revealed with a grin, "Mmmmmmmmmm yeahhhhhhhh, it's the perfect excuse to prepare you thoroughly."

"Oh, I like that kinda preparation." Olivia grinned, before beginning to moan happily, as she got it.

Jenna got that moan from the other girl by pressing her face in between Olivia's ass cheeks, sticking out her tongue and sliding it over her target. That target of course being, the tight little butt hole of Olivia Rodrigo, to get the now Grammy-winner ready for an ass fucking. Honestly, it would be exciting to do this anyway, given just how hot the other girl was. But add in the fact that she had blown up recently?

Then wow, this just might be Jenna's biggest conquest so far. At least in terms of bedroom conquests. Yes, it was a shame not to taste the other girl's pussy, especially with it right there, looking and smelling so good. But again, for what she had in mind, it felt good to skip straight to the butt sex.

Which admittedly, was a really, really good problem to have. And at least she got a taste of Olivia's butt, which was just as yummy as it looked. Also, just big enough to cover her face with. If she pressed her face really tightly in there. Of course, she eventually spread the cheeks apart with both hands, so she could get more access to that yummy little back door. Start swirling her tongue around it, as well as simple licks.

She even tried to push her way inside. Given what she had heard about this girl, it wasn't surprising that she didn't get very far. But she got just enough to suggest she wasn't dealing with an anal virgin. Sadly. But it was still really tight, which would be really fun to fuck.

Honestly, just tongue fucking it as much as she could was really fun, especially as it would be worth a comparison once she had truly loosened this hole up. Because as eager as she was to give Olivia her ass, at the same time, Jenna was hoping they could go back and forth throughout the night, give or take a few breaks. Maybe that was beyond the capability of a girl who was still new to this?

Then again, Jenna just had a good feeling about Olivia Rodrigo. And she certainly hadn't been disappointed so far. In fact, it was very much the opposite. Oh yes, this girl had a yummy little ass hole, and she'd been so quick to give it up. Give it up for a rim job, and so much more.

She should probably move on to the other things, but it was just so easy to get carried away eating another girl's butt, that this probably lasted for several minutes more than necessary. And even then, Jenna didn't go straight to using her strap-on. Not with a booty this tight. No, when she removed her tongue from that ass hole, Jenna replaced it with her right index finger, which was still covered in lube, thanks to retrieving the dildo.

As a result, she was able to push her finger into Olivia's back door pretty easily, and eventually even a second one. With predictably good results. Which thankfully, was the now world-famous Grammy winner moaning with seemingly blissful happiness, she was prepared for a 'real' anal violation.

"So, are you ready?" Jenna asked softly.

"Yesssssssss!" Olivia moaned happily, and even added for good measure, "Fuck me. Fuck my butt, Mistress Jenna! Please?"

"If you want it, you know what you have to do." Jenna grinned, but clarified anyway, "Spread your cheeks for me! Give me your hole, like a good girl. Like a good little anal slut."

"Oooooooooh, yes, Mistress Jenna." Olivia happily replied and obeyed.

Olivia didn't know, like 100%, if she should be calling her old friend by that particular title, or if it was too formal. But honestly, it was fun to call her that, and so far, 'Mistress Jenna' didn't have anything bad to say about it. In fact, it had the other brunette smirking with delight, and moving further with her wicked plans. Which in this case, meant pulling her fingers out of Olivia's butt, and replacing them with her strap-on.

Admittedly, the anal penetration didn't happen that way. No, that dildo was pressed firmly against her back hole, but it was then just rested there, as Mistress Jenna took her time sucking her fingers, and more importantly, teasing her target. Although, initially, she did push forwards, causing the forbidden hole to stretch.

Given that she wasn't quite the natural anal loving bottom that say, Sabrina Carpenter was, or Sofia Wylie should and would be, the initial stretching of her butt hole felt really weird to Olivia. Exciting, but definitely weird. Same for the official anal penetration. Although sadly with that, came almost unbearable pain.

Thankfully, it was only agonizing for a moment, and this time Olivia was greatly comforted by the knowledge it would feel much better later. Which wasn't just a promise, it was a memory. And was really helped by her friend. Not just with a pause to adjust to the sensation, but words of encouragement. Just not the kind which she had received before.

"Wow, you look really cute with a cock in your ass?" Jenna quipped, almost causing that cock to pop out, as she and Olivia laughed.

"You should see me taking the whole thing?" Olivia shot back, when she was pretty much over that laughing.

"Mmmmmmm, I very much accept that offer." Jenna moaned, and happily obliged.

"Ohhhhhhhh yessssssssss, fill my butt!" Olivia then encouraged.

It was very possible that she said more after that, but Olivia was understandably distracted with the feeling of a strap-on slowly sliding through her back door and increasingly deep into her back passage. Which again, was an incredibly weird sensation, and definitely uncomfortable, but it also came with an incredible thrill. Maybe even more so than with Sofia or Beyonce.

Sure, she'd known Sofia for quite a while, and worked with her closely. A lot more closely than with Jenna. But she had known Jenna since before puberty, which made doing anything sexual with her particularly twisted. And obviously, there could be nothing more twisted than taking it up the butt for another girl. Well, nothing that Olivia wanted any part of.