Pirate Booty

Disclaimer: I do not own Life Is Strange. I do not make any money from the writing of this story.

*****

Chloe Price was admittedly biased, but as far as she was concerned Maxine Caulfield was the cutest thing ever. So she really, really hated it when her Max got insecure about herself. Luckily there was some privileges that came with being Max Caulfield's girlfriend. Namely that Chloe no longer had to rely on her mouth to make Max feel better.

Correction, she did, but now it was in a more pleasurable way. Oh yes, Chloe Price almost always said the wrong thing, but now she didn't have to rely on words, and could simply slide her mouth all over the other girl's body. And she did mean all over. Right now though, she was simply concentrating on the most innocent area, namely her girlfriend's lips. Well, innocent compared to where she was heading for.

Of course what they were doing tonight was a big deal, so it seemed only right to spend a lot of time on those lips, help ease Max into this. Also, she would never, ever get tired of kissing Max Caulfield, and honestly it felt like she could just do this all night long. Which was super sappy, but that's just what Max did to her. What loved did to her.

Because don't get her wrong, the only thing that may be better than this was sex with Max Caulfield, but there was definitely something to be said for this romance shit. Especially considering it was not long ago that her life sucked, and one of the major reasons why was because she thought she would never see this girl again. But now here they were, in her bed and making out, their naked bodies pressing against each other.

Suddenly Max broke the kiss and whined, "Chloe!"

"What?" Chloe protested, genuinely unsure what she had done wrong now.

Max blushed, lowered her gaze, and then pleaded, "Just... do it, before I lose my nerve."

Which broke Chloe's heart, so she gently grabbed hold of Max's chin, pulled it upwards, and softly told her, "For like the billionth time, we don't have to do this, you know?"

"I know..." Max blushed again, before gently pushing, "But... I want too. I, I... I want you to have all of me."

There it was, the words which drove Chloe crazy, as although she knew it was wrong, she couldn't help but be possessive of this girl, so against her better judgment she ordered, "Then turn over."

Which Max somehow interpreted as get on all fours, which caused Chloe to chuckle, and in turn triggered her girlfriend's insecurities, "What?"

"This isn't a porno. Just lay down on your stomach." Chloe commanded, and then when Max gave her a look she pushed, "Just trust me, okay?"

"Okay." Max said softly, doing as she was told.

Admittedly Chloe totally wanted to go all porno, and do this doggy style, as well as every other position she could think of. Hell, she had years worth of fantasies she wanted to try out on her precious Max. However, this was Max's first time doing anything like this, and Chloe had a plan for making it as gentle and loving as possible.

Partly so Max might be up for more pornographic positions, and things in general, but mostly so that she could make it easier on her girl. Which was also why, unlike last time, she did make a show out of retrieving her strap-on and putting it on. No, she just got it done as quickly as she could, almost breaking something the process. She then covered it in lube, while bringing her lips back down to her girlfriend.

This time she concentrated on her shoulders and neck, before slowly making her way down Max's back. Like all the way down, until she reached her final destination, namely that cute little ass of hers. Something Chloe just had to admire for a few long seconds, and then again when she grabbed both of those cheeks and pulled them apart to admire Max's most intimate area.

To her delight, if not surprise, the other girl was wet. She had made another girl wet for her! And not just any girl, but Max Caulfield! Oh God, her gay little hard almost couldn't take it. Although to be fair, exactly how naughty they were about to be probably had a lot to do with it, Chloe thought with a smirk. Still she just couldn't resist leaning towards and sliding her tongue over that wet pussy, before moving up even further to a super forbidden area.

Max cried out loudly at the surprise lick to her pussy, making her grateful there was no one home at the moment. Well, no one except the two of them, obviously, although even then she was a little embarrassed about how loud she was. But then again, that was just the effect Chloe Price had on her. Oh God, she loved her best friend turned girlfriend so much, and would do anything for her. Even this.

Especially as this particular thing Chloe had done before, and made surprisingly enjoyable. Namely, when she slid her tongue all the way up Max's ass crack, and then repeated the process, albeit this time without touching her pussy. In fact, those licks became shorter and shorter, until they were just focusing on her butt hole. Oh God, Chloe Price, her Chloe, was giving her a rim job. Her childhood friend! Another girl! Oh God.

Some combination of those words echoed in Max's mind for an embarrassingly long time, especially considering Chloe had done this before, and that had been without asking first. Which, rude, but Chloe was the queen of pushing people to see what she could get away with, so why should it be different with her girlfriend? Especially when it was one of the things which had made Max fall in love with her.

For better or worse? Besides, more often than not Max enjoyed whatever Chloe pushed her into doing, and she could tell that the other girl wanted to go further. To have her in every way possible. And honestly, that's what Max wanted too. That's why she had suggested Chloe take her anal cherry, beating her friend turned lover to it.

The idea both frightened her, and excited her, but now she was definitely more frightened now the moment was getting closer and closer, despite Chloe giving her a long, drawn-out rim job, in which she didn't just lick up and down that forbidden hole. No, she swirled her tongue around it, and even tried pushing it inside. She didn't get very far, but it was still an incredible experience.

In a way, so was getting a finger pushed into her back hole, but it also felt really weird, and frightened her even more, considering that was nothing compared to the size of the strap-on Chloe was now wearing. Although she had to admit, she did get quite a thrill out of how much her girlfriend was enjoying it.

"Fuckkkkkkkkkkk, Maxie, you're so tight." Chloe moaned lustfully, before trying to break the tension with a bad joke, just like her girl, "I always knew you were a tight ass, but seriously, babe... if we're going to do this, you need to relax, okay?"

"Easy for you to say." Max grumbled.

There was a brief pause, then Chloe grumbled back, "Hurting you isn't easy for me."

Which made Max cringe, and somewhat apologetically push, "I know, I'm sorry. Just keep going, okay? I'm fine, I really am."

At that point fine was a bit of an exaggeration, and Chloe knew it, but mostly because it still felt weird, and Max was worried about what was to come, more than actually feeling pain. In fact, the rest of the fingers slid in fairly easily, and it wasn't even that bad a few minutes later when Chloe added a second finger. It was definitely not as amazing as having Chloe's fingers in her pussy, but it also felt kind of good.

Which again, she had felt before, albeit when the other girl had been eating her pussy. Still, it made Max hopeful that she would enjoy this. Or at least enough so that she would be able to do this again for Chloe. Because honestly, she would do anything for this girl. Absolutely anything, including this.

"Rub your clit." Chloe ordered softly as she pulled out her fingers and grabbed a hold of her cock, "Make this easy as possible on yourself."

"Okay." Max softly gasped as she felt the wet dildo against her now equally wet back door, and then did as she was told, reaching down underneath her body to start rubbing her clit.

Given that Max seemed to like this a little bit, but not enough for her liking, Chloe then broke out her last resort, which run the risk of ruining the mood, namely adopting her old pirate voice as she questioned, "So, First Mate Max, ya seen any buried treasure around here? Cause Captain Chloe wants some Pirate Booty!"

There was a brief pause, then Max burst out laughing, "Chloe! You did not just... oh my God!"

Chloe almost felt bad about being so hella sneaky, but it was for Max's own good. And it worked like a charm, Max obviously relaxing during her fit of laughter, allowing Chloe to start slowly stretching her girlfriend's butt hole without Max even noticing. Of course, that changed fast when the hole stretched wide enough to allow the head of Chloe's cock to slide through it, and thus into the other girl's ass, meaning that she had officially done it.

Oh God, Chloe Price had just taken Max Caulfield's butt cherry! Another girl's anal virginity! Her Max had just made the ultimate sacrifice for her, which overwhelmed poor Chloe with so much love and affection, and a twisted sense of pride and dominance, she thought she was about to explode.

For a few long seconds, or possibly minutes, those words, those thoughts, echoed in Chloe's poor little head. Or at least, she would've liked it to be minutes, so she could savour this for as long as possible. Maybe grab Max's camera, and take a shot of Maxine Caulfield's ass hole wrapped around the first few inches of her dick.

Which was surely more beautiful than anything her girlfriend would ever take, despite what a brilliant photographer she was. But no, Chloe needed to focus on Max, and making this moment as easy as possible on her girl. Who didn't seem to be taking her own advice, instead of frozen in place and whimpering softly. So Chloe pressed herself down against Max's back, which was a little awkward, but she just about did it.

The feeling of their bodies pressed against each other, was something they always enjoyed, but it was especially good now when Chloe could whisper into her lover's ear, "Are you okay? Scratch that, dumb question. I mean your ass was like, you know? But... it's a first time, you know? It always sucks at first. You just need to concentrate on relaxing, and shit."

"I know..." Max said weakly, before surprising Chloe by pushing, "More."

Which stunned Chloe into silence for a few long seconds, then she grinned wickedly, "More cock up your ass? Or more pirate talk?"

Max blushed furiously, but then admitted with a blush, "Both."

"Ooooooooooh, my Max is full of surprises." Chloe chuckled gleefully, before fulfilling one of those wishes, and then the other, "Ya wish is my command, First Mate Max. Mmmmmmmmm yeahhhhhhhhhh, Captain Chloe is going to bury some treasure in your Pirate Booty! Ohhhhhhhhhh yesssssssssss, take it! Take it in your Pirate Booty, Maxie. My First Butt Mate. Oh yeah, mmmmmmmmm, Captain Blue-Beard, and Long Max Silver exploring... previously uncharted waters? Hidden depths? Mmmmmmmmm yeahhhhhhhhhh, argh, shiver me timbers, me hearties, I'm plundering booty! Argh, argh, arrrrrrrrgggggggggghhhhhhhh, ooooooooooohhhhhhhhhhh fuckkkkkkkkkkkk!"

She was probably taking this whole pirate thing a little too far. Okay, she definitely was, but it turned what would probably be a few long minutes inflicting pain on Max, while Max was either forced to suffer in silence, or whimper and cry out, and turn it into a giggle fest. Admittedly it didn't exactly put them in the mood for sex, but so was the fact that she was causing the love of her life pain right now.

Something that was obvious from the way that Max actually continued crying out and whimpering throughout the plundering of her booty. In between her constant giggles of course. Then all of a sudden, things took a turn, when Chloe realized her girl had tried touching herself, meaning that she was feeling more pain than necessary, which was completely unacceptable.

Desperately wanting to change that Chloe reached down and guided Max's hand back to her pussy, causing the giggles to quickly fade away. In fact, for a few long seconds the room was eerily silent, and Chloe began to worry whether she had made a mistake. Whether this whole thing was a mistake. Because seriously, what was she thinking? Someone as uptight as Max Caulfield would never actually like it up the butt.

Then came the soft moan, which sounded deafening in the otherwise quiet room. Oh fuck! She actually did it. Max Fucking Caulfield moaned in pleasure from the feeling of something fucking her in the ass. And not even that, this was still part of the butt stuffing, which no one should like. God, maybe they really had stumbled across hidden treasure, Chloe thought with a wicked grin.

Max blushed furiously because of that moan, but to be fair, she mostly felt pleasure from Chloe indirectly touching her pussy. After all, it may be Max's hand that was sliding up and down her pussy lips, but it was Chloe who was actually the one that was moving it.

Also while it should've been off-putting, given that it reminded her of the childhood they had shared, the blue haired girl did a good job at putting the brunette at ease, taking her mind off of the pain as she was still very much in as more and more of that strap-on cock was slowly introduced into her back door and then deep into her back passage. However, there was another part of it. It was a part, which Max found easy enough to enjoy at first, but that quickly changed as the anal penetration was truly complete.

When Chloe's thighs came to rest against her butt cheeks, announcing every inch of that dildo was buried inside of her. Buried inside of her butt! Chloe! Chloe was buried inside of her most private orifice, all the way inside her, as deep as she could go. Admittedly she had been this deep inside her before with this exact same device, but certainly never in that hole, which was an overwhelming experience.

Especially as Max couldn't believe that she was able to take the entire length back there. Something which gave her a weird sense of achievement, which was quickly forgotten when for better or for worse Chloe went back to her laughable dirty talk. No, definitely for the better, as it distracted her, and made what came next easier.

"Oh fuck, oh fuck, oh fuck, oh fuck, OH FUCK! You did it Max! Holy shit, you really did it!" Chloe babbled at first, before adding with a wicked grin, "You just took every, single inch of my dick up your butt! Ohhhhhhhhhhhhh yeahhhhhhhhhhhhhh, Long Max Silver, the best First Mate a Pirate could ask for, just took every, single inch of my big dick up her Pirate Booty! Yeahhhhhhhhhhhhhh, oooooooooooh fuckkkkkkkkkkk, mmmmmmmmm, First Mate Max is the best! The best Butt Mate! Mmmmmmmmmm yeahhhhhhhhhhh, I love my First Butt Mate Long Max Silver, ooooooooooohhhhhhhhhhhhh, and her cute little Pirate Booty. Now relax Max. Mmmmmmmmmm, fuck yeah, relax and let me plunder that cute little Pirate Booty! Arrrrrrrrgggggggggghhhhhhhh!"

"You try relaxing with the giant cock up your butt." Max grumbled.

"Please, you're way too much of a bottom to strap it on." Chloe scoffed, before softening her tone to add, "It's okay, I'm going to make this as easy as I can. I promise. Just trust me, okay?"

"Always." Max said softly, turning her head back in hopes of getting a kiss.

She of course got one, Chloe, forcing herself to be brief as she had other things to do, and then told her girl, "Love you."

"I love you too." Max replied without hesitation, and with a soft smile, "I always have."

"I know." Chloe grinned, "Now relax and give me that Pirate Booty."

"Oh God." Max blushed, but did her best to relax.

Initially Chloe at least showed some mercy on her by moving her hands away from Max's pussy, and staying perfectly still, so they could just concentrate on their latest banter. Of course Chloe just had to keep talking as she gently pulled her hips back and then push them forwards, officially starting the butt fucking. Oh God, Chloe Price was officially starting to butt fuck Max Caulfield!

Wowsers, that thought, and the reality of what she was feeling, was so overwhelming. Max was robbed of the ability to think for quite a while. Especially as some attention returned to her pussy, except this time Chloe was using her own hand to do it. No, the other girl was touching her directly, and thus making the experience so much more intense.

Even though it was just a gentle brush of her fingertips against her pussy lips, combined with thrusts in and out of her back door which was as slow as possible, it was still maybe one of the most intense experiences of Max's short but eventful life, which was really saying something. Of course, Chloe's running commentary added to it, to the point that Max was delirious with pleasure, even though it continued hurting for quite a while.

Although she barely noticed it was fading, until it was completely gone, and that realization really made Max blushed. Because oh my fucking God, she was feeling pure pleasure. Now from getting fucked in the ass. Something which unfortunately Chloe quickly realized, and then made it clear that she would never live this down.

"Mmmmmmmmm yeahhhhhhhhhhh, my Max is taking it easy now. Mmmmmmmmm, soooooooooo easy in her butt. Oh yes, it's sliding easy in and out of your tight little ass hole. Mmmmmmmmm, Long Max Silver is taking it in her cute little Pirate Booty so good, mmmmmmmmmm, soooooooooooo goooooooooooddddddddddd, oh fuck." Chloe babbled, before hearing something which totally changed things, "Holy shit! Did you just moan? Oh my God, you did! Max Caulfield just moaned in pure fucking pleasure from getting butt fucked! Oh my God, this is so great! My girl is an up the butt girl, ooooooooooh, and I'm totally a butt fucker. Oh Max, we're gonna have so much fun. I mean, Captain Blue-Beard, and her First Butt Mate Long Max Silver are going to have so much fun. Ohhhhhhhhhhhh, fuck yeah!"

This time Max had no witty comeback, because seriously, what could she possibly say? Chloe was right about everything, all of it, and as embarrassing as it was, it wasn't like she could really complain, given how wet she was. So all poor Max could really do was bury her face in to the bed sheets, and hope that the girl who claimed to love her more than life itself, would show her some mercy again.

Unfortunately that wasn't the case this time. Not really. Because sure, Chloe started lingering her fingertips against Max's clit and teasing her entrance, and even increasing the pace slightly, but it was crystal clear she was going to have to ask for it, if she actually wanted to cum.

She was going to have to beg Chloe Price, the best friend she'd ever had, for the privilege of cumming for her. Again! Oh God. It wasn't exactly a surprise, as after the first few times they'd had sex Chloe had developed quite the kink for making her beg for it. And honestly, Max enjoyed it too. But could she really beg for this?

Both figuratively and literally, because while it would be embarrassing to do it, poor Max was so overwhelmed in that moment she wasn't even sure she could form words. However, as it turns out the growing desire to cum was a great motivator, even if she completely embarrassed herself in the process, with her constant moans, whimpers, gasps and cries of pure pleasure in between her words.

"Please..." Max began with a soft whimper.

"Please what Max?" Chloe pushed gently, although a wicked grin crossed her face as she added, "Tell me what you want, in detail."

"Please..." Max gulped, taking a deep and calming breath, before reluctantly giving Chloe what she wanted, "Please, make me cum! Oh God, fuck me harder and make me cum! Oooooooooooh fuckkkkkkkkkkk, make me cum for you. Oh please Chloe, fuck me hard! Make me cum nice and hard, like you always do. Please?"