Welcome to my first maxoline fanfiction. This is purely M rated and contains BDSM content, if anyone is not familiar or not comfortable with it, it's okay and kindly see yourself out :)
Max Black does not back down from a challenge, she's badass and all, and if you think she's going to back down from a little 29 year old boy who is also her boss from the crappy Williamsburg Diner, you are wrong.
Just another slow night at the Williamsburg Diner where Max questions why they would even have customers in the first place, the place looks like its from the 80's and her pay is like from the 60's.
"Pick up, beef and salami sandwich with fries! " Oleg yells while ringing the bell at the same time, Max slowly takes the plate and puts it in front of the customer at table 3. Then, she goes back to doodling on her notepad when Han walks up to her.
"Max! What are you doing? Can't you see there's customers raising their hands? Seriously, if you can't even get the order, you can at least get a new attitude!" Han scolds with a frown.
"Look, Miss Han who has a case of Benjamin Button, they will get their order soon once I'm done drawing a dick wearing a hat here." Max chuckles while her boss huffs in frustration.
"Max, if you can't even wait here, I don't even know why I even thought of assigning you to the party tomorrow! I might as well get some volunteers who actually work and get my money worth."
"Hey hey hey, lemme stop you there. What party and by the way, my customers always get their money worth. " Max points to her rack and gives Han that devilish smirk.
Han shakes his head, " There is a huge party at the Channing Proper at Manhattan tomorrow night, I need you to be there and do some waitressing!"
"Channing as in Martin Channing? That rich man who probably owns everything?" Max snorts. "Why does he need a little ol waitress from Brooklyn? I'm sure he has fancy staff doing all the work. I mean, he is rich rich. "
"Yeah... here's the thing. " Hans slowly says while Max narrows her eyes. " I need you to sneak in as a waitress and sell cupcakes in the name of Williamsburg Diner, well and take some pamphlet with you." Han slowly reveals a handful of pamphlet behind his back.
"What?! " Max snatches the pamphlet and narrows her eyes even more. "'Williamsburg diner's Homemade Cupcakes? A Brooklyn Must have??' What crap is this, and honestly why do we even have to do this? "
"Yeah, about that, the Diner have some financial problem... "
"I always have a financial problem -"
"No, the diner has some loan with the bank and if we don't get the name outside and get some more customers, I can't pay the loan and possibly the bank will close down the diner. Point is, my mother is coming to see me next month from Korea, she needs to see what a success I am, I am the family star boy! You have to help me Max, unless well you can't do it. "
"Of course I can do it, what's in for me? "
"What do you want, you can have it. "
" Deal, I want a 3 dollar pay raise per hour and two days off after this." Max says while pointing her finger at Han. "Because Han, that is a lot of cupcakes to bake at such a short notice, plus I have to sneak in and give out lame pamphlet?"
"Fine, you can have it. Now go do your job! "
XXXXX
Han gave Max the day off to bake the cupcakes and the cab fee because she is not going to deliver 200 cupcakes using the subway.
She sneaks in easily from the doorman because there is a huge crowd and using the excuse of delivering cupcakes order. The Channing Property is huge, expensive champagne and wine are rotated by actual high class waiters around the crowds. Once Max puts the cupcakes on display, she steals a drink or two because god knows she can't deal with rich people sober. She's wearing a decent enough black little dress that shows off her cleavage (because her girls always make the job easier and also she can't wear that horrible yellow waitress dress from the diner.)
"Ugh rich people." Max mumbles, looking around and ignoring the stack of pamphlet on the table. She eyes momentarily freeze when she sees a blonde walking down the stairs as if she just walked out from a fashion magazine or the New York Times. The blonde wears a white customize dress that fits her slight curves perfectly and probably worth more than Max's entire life. She has a shoulder length hair cut, wears actual diamond jewelries and smiles a perfect dazzling smile. She walks with confidence, in control and gives out the vibe that she gets whatever she wants. Max doesn't doubt that. The woman is literally a real like Barbie.
That must be Caroline Channing. Martin Channing's only daughter, everyone knows her.
Caroline turns her head slightly and for one single moment, their eyes met. Her gaze was so intense,it completely rattled Max speechless and has a tingle down her spine. Max stares as the rich woman's lips lift up into a smirk before their gaze was broken by another woman talking to Caroline.
"What the hell just happened to me?" Max shakes her head off the fumes clouding it. "Must be the rich people vibe again."
Max lost sight of the billionaire for a few hours,it was past 11 and her cupcakes are down to 50 or so, the crowd thinned out. The stack of pamphlet however, didn't go far. "Can't blame me, we all know it will end up on the floor. At least I did tell those who came to me where the cupcakes are from."
"Hey did you make this cupcakes yourself? " Out of nowhere, the blonde goddess takes her cupcake and asks. Max panics and she doesn't know why she is stuttering.
"Oh umm hey, yeah I did. They are from the diner, I sell my cupcakes there.. " wow, she's more beautiful close. Wait, what the hell? You are even into girls! Penis, I like dicks! Max winced at herself.
The Blonde smirks again "You sell your cupcakes at the diner? Maybe I should check it out one day." Her tone is definitely filled with sexual innuendo and Max finds herself getting aroused and embarrassed.
"Yeah, hahaha. That's maple bacon spring break cupcake! " She laughs awkwardly and chastised herself again, she never gets flustered! She usually is the one doing the flustering!
" It's delicious." The billionaire takes a bite of the cupcake, elegantly, might she add, and slowl licks her lips with another intense stare at Max. Max's mind went blank and she simply stares at the other woman's lips.
"Thanks.." Max mumbles, the blonde throws her a wink and walks away with a sway to her hips.
Another one or two hours passed, though the crowd thinned, the party does not seemed to be ending anytime soon. Max is exhausted, her cupcakes are now all gone and she just wants to go back to her one bedroom illegal apartment. She looks around the beautiful home and thought what the hell, might as well explore it a little before I go back to that small bedroom back in Williamsburg.
She couldn't see Caroline, and had lost sight of her since she last 'talked' to her. She shrugged and continued her walk around the bungalow, or mansion considering how huge of the property this is. She walks upstairs, fake smiles at some people and walks down the fancy hallway. She is probably not allowed upstairs because the second floor is deserted. But then again, she isn't allowed into this property in the first place so why care now? The voice thinned out as if the entire floor is sound proof, Max double takes and thinks it probably is. She's just gonna take a look around and go home.
As she walks towards the end, she hears something she is all to familiar with. Buzzing, stable buzzing with little moans of pleasure. Max's heart jumped into her throat, is it Caroline's room? She knows she should walk away but she's Max Black, she makes poor questionable decisions. The door is only thin line ajar,
what is she thinking, leaving the door open when she is masturbating?? With her heart thumping loudly, she steals a look through the gap. She can't see anything, cursing under her breath she pushes the door bit more. She's slightly drunk, she's allowed to do questionable and unjustified thing, though to be honest she can still do these things sober.
Fuck. That is so hot. Max's eyes widen at the sight, there she is, the billionaire with her legs slightly spread open, one hand grabbing her breast and the other pushing a dildo into herself, back slightly arching and mouth open. Max swallows as she salivates. She has never been attracted to woman, sure a few experiment in high school but that's it, so why now? And why a billionaire? She hates rich people.
Suddenly her worst nightmare happens, her phone rings. A shriek can be heard from inside the room as Max jumps and panics, taking her phone to quickly answer it.
"Hi Max, it's past midnight I was wondering how the cupcakes-" Han's voice ring out immediately.
"Han I got to go, don't call me!" Max whisper yells.
"Who's that? " The Blonde calls from inside, strictly. Max's palms starts to sweat, the number of the word 'Shit' comes into her mind like a jackhammer. Run or stay, funny or serious?
"Don't try to hide, because there is camera and security all around. " The billionaire says sternly.
Max gulps nervously and pushes the door open, revealing herself to the woman in bed, clutching the sheets to her chest.
"I was just looking around, I swear I didn't see anything. I Uhh, should go home now, bye! " Max rambles and quickly turns around, cheeks blushing like a tomato.
"Stop! " Caroline says again, and something about the way she says it completely stops Max in her spot. "Come in and lock the door." Max slowly turns around and enter the room, locking the door behind her back. A guilty look on her face.
"Look, lady, I'm sorry I shouldn't have peeked. It's not like there's anything to see anyway hahaha... " Max says jokingly and immediately knew she shouldn't have said that.
Fuck Fuck Fuck, I screw this up AGAIN! SHUT UP JUST SHUT UP.Caroline raises her eyebrow. "What's your name?"
Max considers to give a fake name and quickly thought of the pamphlet she left downstairs and thinks its better not to lie.
"Max Black."
"Well, Max. You do know it's rude to peek?" Caroline crosses her arms. "I can't have you walked away after you seen me just like that."
Max gulps again. If there's anything she knows about rich people is to never say no, who knows her body will be floating on the river the next morning or buried 20 feet underneath this house.
"Take off your clothes." Max nodes slightly and starts to take off her dress. Her dress pools at the bottom of her feet. She wished she has at least wore a nicer underwear, those thongs and bra have seen better days. Her breasts spilled out after she took off her bra, she grins at the look of amazement across the billionaire's face before it went back to neutral. When she takes off her underwear, the blonde speaks again.
"Sit at the dressing table and touch yourself." Max is surprised at the request and blushes deep. She's not a prude, she's done this before just not in front of a practical stranger, she doesn't even enjoy it when her past lovers asked her to do it. However somehow, she is secretly aroused at the thought of touching herself in front of this gorgeous woman. She sits down on the marble table, her back touching the cold mirror that sends a shiver down her spine. She looks into the blonde's intense gaze and starts to pinch her nipples which is erect by the cold air. She pinches harder and arches her back involuntaryly, sucking in her breath. She gropes her breasts just the way she likes it before snaking her right hand between her legs.
"Spread your legs."
Max closed eyes opens immediately and connects with ocean blue eyes. She slowly spreads her legs, never once leaving her gaze. She has never been more turned on,she slides her hand between her legs and gasps.
Fuck, I'm so wet.The Blonde's eyes darken with lust as her gaze lowers to the hand between Max's legs.
"Spread your lips for me." The billionaire says again, her voice just above whisper, cutting through the sexual tension in the room.
Max bits her lips, a bit nervous now, and slowly spreads her pussy lips. She has never felt more exposed before. Her pussy is so wet it is starting to drip onto the marble table. The blondes mouth is slightly open, she closes it before licking her lips with a predatory look in her eyes.
"Touch yourself."
Max looks into the other woman's eye and slowly circle her clit. At first with teasing touch before touching it steadily, a few rounds and then rubbing it roughly.
A whimpers escapes her lips because a moan is let out. She teases her opening before sliding two fingers into herself.
"Oh God.. " She gasps and arches her back, she's warm and wet and tight around her fingers. In and out, she gets into a rhythm before fucking her self harder, her hips leaving the surface to follow her fingers hungrily.
"Fuck ohhhh gosh!" Just as she feels her orgasm building..
"Stop!" The Blonde stops her again. She groans in frustration but somehow manages to stop her fingers in herself.
The Blonde chuckles at her frustration, "Come here, I want a better look at you."
Max takes her fingers out, letting some more juices out of her pussy and slowly climbs onto the bed on all four.
"Come on closer. " Caroline pats her lap.
Max bits her lips and slowly straddles the blondes lap, her hands on Caroline's shoulders. Being eye level with Max's breasts, Caroline is quick to get into action. Grabbing her breasts and licking her nipples, she moans and let's out her name.
"Caroline! " Caroline responds with biting down on her nipple, hard. Max grabs a handful of blonde hair and almost screams.
" You are not allowed for first name, you need your punishment." Caroline says and bites her neck, leaving a mark.
"Miss Channing. I-" Max says breathlessly, fuck that is so hot, but her sentence is cut short when Caroline presses her lips against hers. She immediately responds to her soft lips. She has always enjoyed man's rough lips with stubbles,but God, this is so much better. Soft lips kissing her roughly, dominating her with her tongue.
"mmmmn!" Max moans in surprise against Caroline's lips as she feels not two, but three fingers push into herself. She can feel Caroline's smile against her cheeks, the blonde's left hand squeezing her ass while the other works inside. It all feels so good. Caroline meets her eyes again as she slowly, very slowly takes away her fingers. She wants to protest but stops at the look Caroline gives her. Caroline takes the three fingers coated with her juice and puts them into her lips, tasting them.
"Hmm you taste as delicious as your cupcakes, Max." Caroline says with a deep voice. Max whimpers at the side, turning completely putty in the billionaire's hands. Sex with woman is completely differently, and she had a lot of sex with man. Everything is way more sensual, everything feels charged, everything you touch is softer, the foreplay actually turns her on and for once, she doesn't want it to end, and most importantly the other person is not thinking about getting himself off. All of these is driving her crazy, she never feels like this before: vulnerable, exposed, willingly giving, submissive."God, what are you doing to me? " She asks breathlessly, she can't seem to breathe normally anymore.
"Just teasing you." Caroline licks her lips and smiles evilly. "I like teasing you." With that, she pushes two fingers inside her again. Max gasps as the fingers play with her, spreading into a 'V' and twisting, and scratching her inside. Max hunched over and tries to catch her breath,grinding desperately,nobody has ever done that to her. When the fingers rub against her g-spot, she arched her back and moans aloud.
"Oh fuck! Ahhhhhhh, right there! Caro- Miss Channing! Mmmmn" She can't think straight, then the fingers stopped teasing and starts to drive into her.
"Ahhhhhhh, Miss Channing." Her hips move on their own accord and she is no longer just grinding, but bouncing up and down on the merciless fingers.
"Oh God, I'm gonna cum, fuck!"
"No, you're not." Caroline takes her fingers out, leaving her pussy throbbing at the emptiness. She groans in frustration, she's going crazy, she just knows it.
"Please... " She begs, grinding desperately.
"No, this is your punishment. I'm not done with you yet." The billionaire whispers into her ear and nips at her earlobe. "You're my slut, remember?"
She whimpers at that, and involuntarily spasm. The blonde reaches over to her side drawer and retrieves something else.
"Now, should I cover your eyes?" Caroline says huskily.
Fuckkk.Max swallows nervously, sure she is pretty kinky, but none of her past lovers were into them, the most one had done was light smacks to her ass. And if she was honest, most of them are just one night stands so it didn't go further than a normal aninalistic fuck, both parties were not trusting enough for kink. And if she was honest to herself, she always secretly wants someone to dominate her this way, but it's hard to convey her wants to her ex boyfriends.
"Max?" Caroline's voice turns surprisingly soft. Max looks into the blonde's eyes and sees a pair of caring eyes looking into her. Somehow, she trusts her.
"Okay." She swallows nervously. Again, Caroline surprised her by gently soothing her back and putting a strand of hand behind her ear. She kisses Max softly and deeply.
"I will never hurt you." Caroline says sincerely.
"I trust you." Max whispers. Caroline smiles.
"Say mercy when you can't take it, can you do that? That's our safe word." Max nods and feels safer, at least she's not completely trapped, she has a choice. A piece of soft scarf covers her eyes snugly, she feels the knot tightens behind her head. Caroline turns them so that she is on her fours. She takes both of her wrist and put them above her head, then raises them slightly to the bar on the headboard.
"Hold onto them." Caroline waits patiently for her to grab onto the bar tightly before continuing, "Now tell me what the safe word is. "
"Mercy. " Her throat feels dry and she wonders if Caroline can hear her heartbeat.
"Good." Caroline kisses her again before sliding her fingers between her legs. She spreads her legs. " Now I have a challenge for you." The billionaire says while teasing the throbbing pussy.
"First, keeps your legs spread at all times or I'll have to tie them apart." Max takes in another deep breath, she can do this. She is Max Black, she is not back down from a challenge, especially not a sexual one.
" Now if you can take your spanking on your ass without coming, I will reward you. But if you cum before you take all of your spanking, I will spank your cunt and you will not be allowed to come for the entire night."
Fuck me.
Her pussy throbs just at the thought of being spanked, she is so damn wet she can only imagine the state of thethe sheets beneath her, both of her inner thighs are soaked.
" I need a verbal answer, Max." Caroline tugs her hair. She moans.
"Yes."
"Yes what? "
Max swallows, fuck her throat feels dry. "Yes, Miss Channing."
"Good girl." Max does not understand why that two single words can make her warm all over, one single praise make her entire body feels charged with energy, almost as if it is eager to please.
"I want you to count to 15." the dominant rubs her cheeks to relax it before the hits.
"Yes, Miss Channing." Max whispers, grabbing the bar tighter in her hands. She gasps suddenly and moans loudly when she feels a vibrator egg in her.
"Ahhhhhhhhhnn!" She screams when the egg starts to vibrate at the maximum before going to a minimum speed. She did not expect that!
"Shhh.." The blonde rubs her clitoris for a few second before laying her first spanking.
"FUCKK!" Max recoils and tenses up, the pain settles into her skin, and turns into a pleasure she never knew she needed after the shock comes off. Suddenly, she is filled with a feeling she is all too familiar with.
High.
That's the only thing she can describe the feeling, she fell instantly addicted to the thrill, and the pain, and heat, the tiny needles, and gosh, it feels so fucking good.
"Breathe." Caroline says gently and rubs her red ass cheeks to smooth it. Max breathes deeply.
"One."
The billionaire hits again, she herself filled with a high only being a dominant can give, she loves the hand print on the beautiful woman underneath her.
"Two! mmmm!"
This goes on until the eleventh. Max can't even think properly at this point, what comes after eleven? All she can focus is the pleasure and pain coursing through her veins, and everything in her seems to just flow to her throbbing pussy. Her red pussy, squeezing desperately against the small vibrating egg, trying to keep the orgasm in. At this point, her pussy is so sensitive she is sure she can cum just with one touch to her clit.
"Twelve! Please, please. Miss Channing, please. I can't!" tears rimmed in her eyes, everything is too much and she wants to let go so bad. The billionaire pauses for awhile.
"Do you want me to stop? "
"NO! " Max all but yells. Caroline spanks her again.
"AHHHHHH!! Thirteen...Please God please, Miss Channing! I can't-" She whimpers aloud. "Please, I want to cum so bad.I can't stand it, please PLEASE. I want to cum! "
"Two more, babe, you have done so well." Caroline says with a soft kiss to her ass. She jerks, a soft kiss is such a contrast to her hot cheeks, and calling her a pet name? She is driving her crazy. Caroline spanks her again.
"Fourteen!" The pain doesn't even turn to pleasure at this points, the pain is pleasurable. Her entire body is trembling, struggling to not cum. She can do it, god help her, she can do it.
Caroline spanks her one last time, actually feeling proud Max did it.
"FIFTHTEENNNN" Max screams, feeling like she's melting into a puddle of pool.
"Well done! "Caroline says softly and takes off her blindfold, she blinks a few times to get used to the light, breathing heavily. Caroline kisses her deeply and softly, but just as passionately.
"Miss Channing, please, I need to cum so bad. Please please please!" Max whimpers, her body close to convulsing but not being to do it yet.
Caroline very gently takes the vibrator out, careful not to trigger anything just yet. Max is very sensitive, and she didn't want her cum just by the vibrator itself. She deserves her reward. She turns Max so that she is laying on her back, her chest heaving heavily.
Caroline kisses Max's forehead and goes straight down to between her legs. She waits until Max looks into her eyes before licking her pussy from the bottom to the below of the clot. Max thrashes wildly, desperate to the point of tears. She quickly latches on the throbbing clot and sucks it really hard, at the same time pushes three fingers into Max.
That was the finishing touch. Max arches off the bed and let's out an impressive scream, her entire body convulses and her thighs trembling on each side of the blondes head. Caroline laps up her cums and continues fucking her roughly until Max screams again no long after, her over sensitive pussy pushing her over the edge again and again. Three orgasms later, Caroline finally takes away her fingers when Max relaxes, her body still trembling slightly, her chest heaving heavily.
Caroline goes up to kiss Max just to find out the brunnette has just passed out from the intensity of the entire night and three powerful orgasm. Caroline gazes at the beautiful brunnette, her own thumping heart jumping hard. She traces her fingers on the creamy skin of the brunettes face, and the wine red of her skin. She definitely did not expect how the night will end, she has never find someone so trusting and so willing. The moment she made contact with Max, the woman with the cupcakes and whom look so out of place. But right here in her sheets, she does not look out of place at all.
She looks like she belongs right here with her.