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cursingtoji · 3 years

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Baby One More Time . ִָˑ ⊹ ٬ ✦

my piece for the Oops! ...I Did it Again Collab <3

⊱ pimp!Toji x escort!reader

⊱ Summary: you find yourself in a situation where you would do anything for money, including become an escort, and even though your boss makes it clear that he doesn't fuck his girls you can't help yourself when you notice how lonely he is.

⊱ Warnings: dom!Toji, f!reader, oral (f -> m), hand-job, facial, one spank, dacryphilia, slutty school girl outfit, boss x employee relationship, semi-public setting, pet names: baby, sweetheart, reader calls him sir a couple of times, Nobara plays a small part here, every character is 20+, 3k words.

༺♡︎ JJK M.List ♡︎ Main M.List ♡︎༻

Being convinced by your boyfriend to move into this expensive city didn't seem like a bad decision at first knowing he had a good income to keep both of you living there and attending college.

Although being dumped by him was not in your plans.

After a few months struggling, the only thing you knew for sure was that you couldn't keep going the way you were, bills were accumulating to the point you started to second guess if those gigs you were doing would be enough to keep you in college.

They wouldn’t.

You had to drop out in order to find a day job, which was heartbreaking since your college program was the best in the country.

About three months in as a gym receptionist, you found a former classmate that started to go to the gym you worked at and she asked about you, noticing you were not attending any classes, so you told all about the failed relationship and financial struggle story. You talked for about an hour until she told you as a joke you should get a nightly job, which you joked back saying if it paid well you would take it just so you could keep studying during the day.

The conversation seemed to get more serious when she said she knew a girl that got paid very well.

At first you thought she meant stripper.

But once you actually got to meet the said girl you realized it was way more than dancing on a pole.

"Our boss arranges private parties and takes us there, those rich bastards pay good money just to have hot babes walking around or just sitting on their laps. Luxury clubs also hire us to attract men to the paid vip area" Nobara explained, she was super pretty and when you met her in a coffee shop as arranged by your former classmate she was wearing high-end brand clothes. So you believed her.

"But what about...?"

"Sex?" she laughed, "Our boss is the best, really. During the private parties we have an arrangement, if a guy wants you, you tell him pussy it's not included in the package, but he can pay you directly for it, you can come up with any number. Toji takes his cut from the party and let us take all the money we can make in private, even if you don't have sex with anyone during these parties you still get a share in the end".

You listened and asked her all the questions that came up in your head, almost two hours later you were convinced.

"Great! I'll tell Toji about you then you two can set up a meeting" the idea of meeting a pimp was terrifying and your to-be coworker saw that in your face, "Oh don't worry, he may looks intimidating, but is actually super chill, the only thing you have to worry about is not falling for those piercing green eyes".

Not falling in love with a pimp? Pff yeah, I can do that.

Or that was what you thought before actually seeing possibly the most handsome man you ever had the pleasure of meeting.

Nobara arranged the encounter, texting you the address of an expensive bar in the center of the city and giving some suggestions about what you should wear. Nothing too appealing, but enough to let him see your “assets”.

Arriving there earlier than the agreed time, you ordered only a cup of water, getting a weird look from the waiter.

The first impression you had of Toji when he called your name in a question was something between fear and lust. Your eyes met his green ones looking down at you sitting at a corner table, like a hawk looking at his prey.

Well... he could be slightly uglier to help you keep your word.

But Nobara was right, besides his whole aura intimidating you in the beginning, a few minutes into the conversation he already made you feel comfortable. Toji already knew the reason why you wanted to work for him since Nobara gave him a summary.

As the conversation progressed you tried to emphasize you have never done that kind of thing before.

“So, are you a virgin?” he asked shamelessly.

“No!” you blurted out louder than intended, face heating immediately after, an amusing smile crossing Toji features, but before he could say anything the waiter came to your table, a completely different expression on his face now.

“Sir, can I get you anything tonight?” he addressed Toji very respectfully. Toji ordered two glasses of scotch that cost around what you earned in a week, although scotch was not your thing you tried to keep up with him during the conversation. He told you the general rules and about the people who hired his services.

By the end of the night he paid the bill, leaving a generous tip for someone that only had a couple glasses of scotch, and insisted on dropping you home.

“There’s one more thing, sweetheart” he called when you opened the door to leave the car after a silent but comfortable ride. You turned your head to him, getting shivers from the way he looked at you, “I don’t sleep with my girls, understood?”

“Yes, sir.”

The job ended up being more lucrative than you thought, one month in you had enough to drop your day job, two months in you decided to move out of your shitty apartment, in the third month you were already set in a better place in the core of the city. All of that and all you had to do was walk around in tight dresses, sometimes bikinis, and give some handjobs or orals when they were willing to pay for your rates.

You grew close to Nobara, so whenever you two were alone before or after a job you asked about Toji. Once she told you what she knew about his love life.

“I used to date his niece so that's confidential information okay?” she winked at you, “Maki said he was also a escort in his twenties” your jaw dropped.

“No way,” you smiled.

“Yes way! And hear me out: he only left cause he got married” your smile died down, “But she left him some years later and he used the money and contacts he still had to start this ‘business’.”

“Wait, so he isn't married anymore?” you asked and Nobara shook her head, “No girlfriends?”

“Well there's only so much I know, but I’m still friends with Maki and she never said anything about it, so I guess he never dated anyone after his ex-wife.”

After that conversation you began to pay more attention to Toji and how he behaved.

At this one specific club, you and the other girls were hired to stay on the VIP floor or hang out on the dancefloor to attract customers into paying for the “VIP” experience on the floor above. With the differential that you all had to wear skimpy school girls outfits which was that night's theme.

Toji seemed to be familiar with that club, he soon found an even more exclusive place to sit and observe, a separate and huge couch inside a VIP booth. Some men had rented the other booths, getting the company of your colleagues, but you noticed Toji was alone in his, with only a drink in hand.

So, when the VIP area already seemed full you marched to Toji’s booth, Ijichi, a man you grew familiar with was guarding his booth.

“What’s wrong, sweetheart?” he asked once he spotted you standing by the red rope that separated the inside of the booth from the outside.

“Nothing” you assured, Toji was always attentive, making sure all his girls were okay. “You just look lonely, so I thought about keeping you company for a while” you placed your hands behind your back, posing innocently.

“Ijichi” Toji called the men guarding his booth so he could let you pass, Ijichi was always around, sometimes driving, sometimes just acting like some kind of assistant to Toji during meetings, you once referred to him as his bodyguard making Nobara laugh till she teared up.

“Please Toji doesn’t need any kind of bodyguard'' you remembered her saying. Indeed if anyone was to be a bodyguard was Toji himself, always ready to beat someone if they were abusive to his girls.

You walked to his side, your high heels tapping loudly on the floor, his muscled arm fell on your shoulders when you sat down.

The song coming from the dancefloor was loud enough so that the people in the VIP area had to talk directly into each other's ear to be heard.

“Lookin’ good” Toji complimented, lips brushing on your ear, he was a great boss and you had to remind yourself of that fact every time he called you by a pet name or lingered his hand on your lower back for a second too long.

The only one that seemed to have noticed it too was Nobara, calling you the boss’s favorite here and there as a joke.

“You think so?” you asked fidgeting with your tiny skirt, if you could even call it that.

“Hell yeah” he affirmed in a husky voice, flexing the arm across your shoulders to play with one of your high pigtails, which you had done to match the whole school girl aesthetic.

“It's not good for the boss to be alone, it sends a bad impression” you murmured in a playful tone, turning your body to face him, his arm dropping to your lower back, the exposed skin right above the hem of the skirt.

“I don’t mind,” he replied, with how close your faces were. You didn’t have to talk in each other's ears to be heard.

“I do” you shyly placed your hand on his abdomen, playing with a button of his black dress shirt. The tight piece accentuated his body so well... any women that spotted this delicious single man on a private booth tried their shot, you have seen some of them approaching, but Ijichi had orders to not let anyone beside his girls in, so Toji wouldn’t get distracted, “We know how to stand for ourselves. Besides, the club has security guards everywhere, you should enjoy a bit too” you looked at his perfect jawline letting your gaze drop to the open buttons of his shirt.

“Mmm should I?” his hand caressed your lower back, fingers slightly dipping into the hem of your skirt.

You hummed, leaning to kiss his jaw sweetly feeling his hand squeeze your hip and murmuring your name in a warning tone.

“I won’t tell anyone” you mewled in his ear, dropping your head to leave open mouth kisses on his neck.

Fuck he smelled so good. Everything about your boss intoxicated you.

He groaned and you could actually feel the vibration of the sound with your lips on his throat.

His hand was still on your hip, his chest was rising and falling quickly, Toji was holding himself back, you could feel it.

“You can touch me, you know?” you mewled, kissing his jaw. Reaching back you moved his hand down to your ass.

“Sweetheart…” he bit his lip, fighting himself, yet his hand squeezed the flesh of your ass without any hesitation.

“I want to make you feel good” you cried in his ear, biting his lobe. Toji sighed.

“This is going to be a one time thing, understood?” he grips your jaw making you look directly into his eyes.

Pouting, you remained in silence, not wanting to agree to it.

“Don’t look at me like that” he hissed slightly shaking his head, not needing you to verbally protest his demands to understand you did not want this to be a one time thing.

With his hand still holding your jaw, you let out a whine, reaching for his belt, palm brushing against his growing crotch.

“Ijichi” Toji calls again, releasing your face, free from his grip you returned to his neck, this time you were more audacious, sucking and biting the skin as Toji ordered his assistent to close the curtains that thankfully existed or you would be giving the VIP area a show.

From the corner of your eye you saw Ijichi quickly close the curtains, with a very embarrassed face.

Now you had the place all for yourselves, only the blue and purple lights inside the booth to illuminate the small space.

“Go on” he leaned back on the couch spreading his delicious thighs, “Make me feel good” his palm hit your ass in a light spank.

“Yes, sir” you moaned, immediately getting on your knees and between his thighs.

You thought you would never emotionally recover from being dumped, you kept yourself busy with work as much as you could to avoid thinking about your ex. Yet now you realize that being dumped by him was for the best, your finances were never this good.

And if he hadn't dumped you, you wouldn't be choking on the biggest cock you have ever seen.

Toji was holding himself back from bucking his hips up, your pace was slow but even then you were blinking some tears down your face, mixed with saliva and pre-cum dripping from your chin, Toji thought it was the most beautiful thing he had ever seen. It was beyond wrong for him to be fucking one of his girls.

The number one rule of drug dealing was: never get high on your own supply.

The same thing applied to him, he knew it would be only a matter of time until things went south if he slept with one of them.

So far it has been easy, his girls do what he tells them to do, and never attempt anything else with him.

But you were such a tease, in these three months working for Toji you always insisted that he pick you up instead of Ijichi, always asking his opinions on your outfits and maybe even some help zipping up your dress. It was easy, natural even, for him to develop a soft spot for you.

It was supposed to be just a soft spot, not letting it go further, but how can he hold himself back when your lipstick was all over his dick? His impressive length disappearing inside your mouth. The sight of his bulge in your throat was such a turn on for him, he knew he would be jerking off to this memory in the future.

“Come on, don't tell me you can't take anymore” he smiled from above you when you released him to catch a breath, lips parted as you breath heavily, face glowing from tears, sweat and saliva.

You were still holding Toji by his base, pumping him rhythmically. He reached for your face, index finger under your chin as his thumb rubs your bottom lip, ruining whatever lipstick was still there.

“I was looking forward to paint that pretty face.”

Oh and you were desperate to have his cum all over your pretty face too.

With his admission you went back down, sucking his red tip and circling it with your tongue, while still pumping his base, his cock throbbed when you took more of him, hollowing your cheeks as he groaned.

“Fuck, look what you do to me” you had to hold back a smile, instead squeezing his muscular thigh to let him know that you heard his drunk confession.

His hand moved to your head, grabbing both of your pigtails at once as he guided your movements up and down his shaft.

Toji made a metal note to thank the club owner for the whole school girl theme that he initially thought it was dumb.

'Cause now, seeing your thighs rubbing together in that ridiculously short skirt and cleavage well displayed in the white button shirt tied under your breasts made him reconsider his fantasies.

“Sucking me so good…” you looked up only to see his adam's apple bob when finding your equally lusted eyes, throwing his head back when your hand found his balls, lightly massaging them while working on his dick as he cursed and tightened the grip on your hair. Toji was so big, so heavy on your tongue you couldn't help but gag on it.

“That’s right, keep going like this, baby” he had never called you baby before, some other pet names that made your heart skips a beat, but in that moment baby sounded so intimate you moaned around him, the thing he needed to pull you away roughly by your pigtails and fulfill his desire to paint your face white with his cum, some of it landing on your mouth and having him hissing when you held his balls a little tighter.

“Fuck” he let go of your hair a few seconds later to pat his thigh, extending one hand to help you get off the floor.

You sat on his leg, waiting for the next order. Feeling his cum sliding off your face, you swiped some of it with your thumb, bringing it to your mouth.

“So good for me” he praised.

He knew he should have ended things there, push his now soft cock back to his pants and tell you to go clean yourself, that's what he should've done, and he was about to when…

“Kiss me, Toji?”

Fuck.

Why did you have to ask him that?

Why did you have to ask him that with big teary eyes and lips glistening with his cum?

How could he refuse that?

“Come here, love” he took your face, guiding it towards his, where he wasted no time in swallowing you whole, not giving a shit about the cum all over you, in fact, it only turned him on more.

You placed your small hands on his arms for support, since you felt like you could fall anytime, too drunk on his kisses, the way he moved his tongue, interlacing it with yours made you unconsciously rub yourself on his muscular thigh, thinking about his tongue deep inside your cunt, and the way he held you by your ass, helping your pace on his thigh was too much.

If you weren't head over heels for your pimp until then, you were now.

Thankfully the party was almost over, after you two cleaned up with a tissue that was in his pocket you found your way out of the booth as Toji told Ijichi to go get the car.

“Hey, want a martini?” Nobara offered when you approached.

“Sure, why not?” you accepted, undoing your pigtails now that they were ruined and letting your hair fall.

“Working hard as I can see, sweetheart” she mocked using a deep voice to mimic the way Toji called you.

“What?” you asked a little alarmed, did she see you coming out of his booth?

While sipping on her drink, Nobara looked down at your knees, making you realize they were a deep shade of red and purple.

“Ah, yeah” you laughed awkwardly, “This one guy worth the bruises.”

“Really? How much did he pay?” she asked curious.

“Let’s go girls” Toji approached cutting the conversation as you gave Nobara an apologetic look, taking the arm Toji gave you as Nobara took the other on your way out of the club.

#oops! i did it again collab #toji fushiguro x reader #toji x reader #toji smut #toji x y/n #jjk smut #jujutsu kaisen x reader #toji x you #toji thirst #fushiguro toji x reader #jjk x reader #jjk x y/n

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