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Your usual clientele are definitely in a higher tax bracket than most people, but you’ve never been with someone as rich as Robert Fischer. The second he had you literally sign an NDA you looked him up, seeing that he was next in line to take over his father’s business. That’s when it all started to make sense. Usually men pay to take you out, show you off, and then more often than not, fuck you. But Robert made it clear from the start that he wasn’t interested in those services you offer. He just wanted to fuck you, and he wanted to do it discreetly.
He bought a hotel room for the night and paid for your ride here, as well as the clothes he requested you wear. What would’ve normally pissed you off if he were paying the usual price would’ve been how nit picky he was. He told you exactly how to do your hair and make up, where to shave and where not to shave, even down to you fucking perfume— it just had to be something sweet like vanilla. You were glad that all of the details were discussed over the phone because you would’ve rolled your eyes and laughed in his face at all of his demands.
He also told you exactly how to act— submissive, obedient, subservient. You’re not normally that kind of submissive, but, again, you agreed simply because of the money.
Staring at the clock on the nightstand, your foot bounced incessantly as you waited for him. You’ve never been this nervous for a client. He’s paying you so much money… what if you fuck something up? It was almost ironic that your overthinking was putting you into the headspace he requested.
At 8:59, you moved down to the floor and waited on your knees with your head down, like he requested. Your heart pounded in your chest from the anticipation and it took everything you had to keep your head down when you heard the door open.
Even though you’re used to fucking ugly, old men, you prayed Robert would be an exception, but you knew that being hot on top of how much he was paying you would be too good to be true. He sounded decently young on the phone, but you still had no indication on whether or not he’s actually attractive. You heard him walking somewhere in the room, then glass clinking, then a drink being poured.
“Less than a minute in and you’ve already disobeyed me.” He said calmly, making your heart drop. How?? You haven’t even done anything yet! He answered your silent question for you. “Hands behind your back.” You immediately complied, feeling a little dumb for forgetting something so simple. “You’re lucky I’m in a forgiving mood tonight since I’m assuming you’d prefer to leave here with the agreed upon amount?” You weren’t sure if his question was rhetorical or not. He let out a soft sigh and you heard his footsteps before he landed in front of you.
“Answer me.”
“Yes, sir. I do prefer that..” When you saw his hand moving forward you almost moaned at the sight of just his fingers. But your chance to admire them went far too quickly when he placed a single digit under your chin and tilted your head up. Your eyes widened and your breath caught in your throat when you saw his face. You figured there was a small chance he might be attractive, but you didn’t actually think he’d be down right gorgeous. You bit your lip as your gaze trailed all over his face, taking in every inch.
“Did you do everything I instructed?” He released your chin and took a sip of his drink, still staring down at you.
“Yes, sir.” It felt like you were still in shock, just from seeing his face.
“Good. The dress looks nice.” You couldn’t help but blush at the compliment.
“Thank you.”
“Stand up.” You did as he said, then waited for the next instruction. “Give me a spin. I want to see if it was money well spent.” You blushed, but turned around for him. “Slower.” He suddenly said, making you freeze, then continue at a slower pace. He hummed in appreciation and you could practically feel his eyes running over every inch of you. When you were facing him again, you waited, watching as he downed the rest of his drink then walked over to the table to set it down. You didn’t move, not sure if you were allowed to or not, and he sat down in the arm chair, then cleared his throat.
“Show me the underwear.” You slowly lifted the dress until it was resting around your waist, exposing the lacy panties. “Come here.” You walked over and stood in front of him, trying to keep your breathing steady when he gently placed his hands on your thighs and snaked them up to your hips. He used his grip to turn you around, then moved one hand to grope your ass. You let out a surprised moan at the sudden spank and he hummed in approval again.
“Very good.” You had to swallow down a whine when his hands abruptly left your body. “Face me and get on your knees.” His eyes moved up and down your body, taking you in again as you did what he said. “Remove my shoes.” You reached toward his feet, but he stopped you. “Carefully. Just one of those is worth double what I’m paying you.” You nodded and gently untied the laces of his dress shoes before slipping them off his feet and placing them neatly on the ground beside the chair.
“Should I fuck your mouth? Or should I just get right to fucking your cunt.” You were mostly sure he was talking to himself and not actually asking you. He has you for two hours, so he has time for both. He seemed to finally come to a decision and he leaned back in the chair, staring down at you. “Be a good girl and show me how that lipstick looks on my cock.” He suddenly said, making arousal pool in your stomach.
“Yes, sir.” You squeezed your thighs together to relieve a little bit of the ache as you worked on opening his pants. Once his belt was unbuckled and his pants were unzipped, you pulled them and his underwear down just enough to free his length since he didn’t lift up to let you take them fully off. You stroked him slowly, marveling at how big he felt in your hand, even just half hard.
“Did I tell you to give me a hand job?” He asked impatiently.
“N-no, sorry…” You swallowed thickly and leaned closer to start mouthing at the tip. Your hand remained unmoving on the base just to keep it steady. He let out a pleased sigh as you suckled on the head of his cock, being sure to lick up any precum.
“Go on, whore. Let’s see if you’re worth what I’m paying.” You blushed as the crude name and squeezed your thighs together even tighter. Not wanting to make him get even more impatient, you started bobbing up and down his cock, keeping your tongue flat against the underside as you hallowed your cheeks. You moved your hand down to cup his balls as you took him a little deeper. When he let out a heavy breath and gently grabbed your hair, you looked up at him. You continued the same pace, sometimes flicking your tongue over the tip when you went up. After a while though, he huffed and tightened his grip on your hair.
“Are you one of those whores who can’t deepthroat? Because I don’t think I should be paying full price for a shitty blowjob.” You immediately took the hint and went down until he reached the back of your mouth. After taking a deep breath, you pushed the rest of the way, breaching your throat barrier. You focused mostly on stimulating his balls as you stayed buried on his cock for as long as you could take it. Only a few seconds later, you were pulling off, gasping in breaths and trying to calm down to do it all again. You took him in your mouth again, not stopping until he was buried in your throat.
“You can do better than that, whore.” He started moving you up and down his cock, forcing it down your throat with each bob of your head. It wasn’t long before you were choking and sputtering as tears filled your eyes. When he pulled you off, you coughed, but didn’t have a chance to collect yourself before he was pushing your face against his balls. You whimpered at the degrading act, trying to ignore the feeling of his spit soaked cock resting on your face.
When he tightened his grip on your hair and pushed you into him harder, you started mouthing at his balls. You licked and sucked, pushing down the embarrassment to focus on making him feel good. This isn’t the first time you’ve had to do this, but it is the first time you weren’t completely disgusted by it. Robert kept himself well groomed and you found yourself getting even needier despite how dirty and used you felt.
Once he’d had enough, he pulled you back and forced you down on his cock again, all but impaling your throat with how fast and hard he did it. You gagged instantly, but he ignored it and started using your mouth the same way he would a fleshlight. On a particularly harsh thrust, you let out a strangled whimper and the tears in your eyes began to fall.
“Stop fucking whining.” He spat. It almost seemed like he started going faster simply because of how much you were struggling to take it. Your hands grabbed his thighs, digging your fingers into the covered skin, and he used his free hand to slap your cheek. “Hands behind your back.” He scolded and you hesitated, but eventually obeyed. The next time he forced you all the way down, he held you there, keeping a firm grip on your hair to prevent you from moving.
“Stick your tongue out.” You did your best to do what he said. “Good girl. Lick my balls.” You let out a strangled sob at the utterly vulgar and degrading order. Regardless, you stuck your tongue out farther and did your best to lick them. “Look at me.” Your teary eyes fluttered up to meet his gaze and he let out a breathy groan at the sight. “No waterproof mascara, just like I said.” He said almost proudly as he used his free hand to cup your cheek and brush his thumb over what you assumed were mascara tracks.
When you started gagging and sputtering and trying to pull off, he let go of your hair, letting you move back. You coughed lightly and cleared your throat, doing your best to collect yourself somewhat quickly.
“On the bed. Face down, ass up.”
“Yes, sir.” Your voice was already hoarse. You stood up on shaky legs, feeling unstable in your too high heels, and walked over to the bed to kneel on it. He remained sitting on the chair, watching you closely. When you leaned down to rest your head and chest on the bed, a light blush tinted your cheeks.
“Arch your back.” You could faintly hear wet noises and the knowledge that he was jerking off just to the sight of you almost had you moaning and squirming. You arched your back, but he still wasn’t satisfied. “More. Spread your legs apart.” You shuffled your knees out and bent your back even more, starting to feel the strain and discomfort. When he didn’t respond, you assumed he was happy with the position.
“Do you always get this wet when you're working?” His tone was far too innocent for the vulgar question he asked. Your blush darkened even more once you realized that your arousal was already soaking the fabric of your underwear.
“No, sir..”
“Speak up.” He snapped.
“No, sir.” You said again, a little louder this time.
“Is it the money that turns you on?” His voice was closer now, like he was standing at the foot of the bed.
“No.” Even though the money definitely helped, it was primarily because of him.
“Really? Are you sure?”
“Yes.”
“Why don’t you tell me what it is that’s getting you all worked up then.” With the way that he spoke, you could tell he already knew and just wanted to tease you about it.
“You, sir.”
“Me? What about me?” You hated the way that he was playing dumb like this, but you mostly hated the fact that it turned you on.
“Y-your cock… And the things you do and say to me.” This was almost more humiliating than sucking on his balls with his cock laying heavy on your face. You felt the bed dip as he presumably kneeled behind you.
“You want my cock?”
“Please, sir.” You tried not to whine when you spoke.
“I’m not entirely convinced you really want it.” You couldn't swallow down the whine this time.
“Please, sir. I want your cock.” You begged, unconsciously pushing your hips back. “Please fuck me,” You jumped when you felt his hands on your ass, then moaned loudly when he ripped a hole in the crotch of your underwear. “Please— I need you to fuck me, sir.” You whined.
“That’s better.” You gasped when the head of his cock dragged through your folds, spreading your arousal. He finally pushed in and you fisted the sheets as your lips parted in a silent moan. He’s just so fucking big. It’s not that you can’t take it, it’s just that he’s filling every part of you perfectly, satisfying every craving you have.
“Fuck— Oh fuck,” You moaned, burying your face in the bed to muffle your sounds. Once his hips were flush with your ass, he didn’t bother giving you a chance to adjust before starting a slow pace.
“You’re pretty tight for a whore.” He commented casually, making you sob out a moan. You’ve never particularly liked being called a whore, but for some reason when he says it, you just just get infinitely more turned on. “I half expected I’d need to fuck your ass instead.” He said amusedly.
“Sir,” You gasped out, arching your back more and pushing your hips toward him. “Please.”
“Please?”
“Please go faster, or harder— anything.” You begged pathetically. You’ve never genuinely begged a client for something like this.
“I didn’t know I was paying you to make demands.” You whined, a little too bratty for his liking based on the way he slapped your ass hard enough to leave it stinging for a few seconds. “You’re not some girl I picked up and took home. You’re my whore for the night. Fucking act like it.” You couldn’t help but mewl at his words.
“I-I’m sorry. You just feel so good, sir.” All of a sudden, his hand was grabbing your hair and pulling your head back until you were looking at the ceiling. You held yourself up with your hands on the bed, but the position was still uncomfortable.
“Every time you talk back, you lose a hundred.” He warned, making you whine. “That includes whining.” He spanked you again with his free hand and you cried out at the sting. “Do you understand?”
“Yes! Yes, sir, I understand.” As soon as you got the words out, he shoved your head forward and released your hair. Your face landed against the bed with a startled grunt that cut off into a moan when he sped up. He was still going far too slow, but you bit your lip to keep yourself from whining or begging.
“Even as a whore you’re fucking useless.” He scoffed. You let out a choked sob and grabbed the sheets harder. He sped up even more, forcing out little grunts and whimpers from you with each thrust. You ached to reach a hand down to your clit, but you knew you couldn’t. Not after his warning about “making demands.”
“Fuck— I’m already close.” You couldn’t help but notice how pretty his voice sounded as he continued becoming more and more breathless from the pleasure.
“Remember to pull out.” You said, breaking character for a moment. On the phone, when he asked if you had any rules or limits, the only thing you said was that he can’t come inside. You don’t care if he fucks you raw, just so long as he pulls out. With a frustrated growl, he flipped you onto your back, immediately pushing back in to keep fucking you.
“How much?” He leaned over you, his face level with yours. The feeling of his breath fanning your lips was making it hard to think.
“What?” You asked dumbly.
“To come inside. How much?” His pace was becoming even more frantic and he was beginning to pant heavily from the exertion.
“Robert…”
“Name your price. What do you want? Ten grand?” Your eyes widened at his offer. “Fifteen?” There’s no way he’s being serious right now. When he noticed your disbelief, he paused, then reached in his pants pocket to pull out his wallet and toss it on the bed next to you. When your disbelief turned into confusion, he explained. “A down payment.” His thrusts picked back up again, forcing a moan out of you as he resumed the unrelenting pace. “Well?” You glanced at the wallet, seeing how much cash was inside, then let out a heavy breath.
“Fuck— fine. Fine.” You could immediately see the shift in his expression, showing how pleased he was with your answer.
“Good girl. I might just have to hire you again.” He grinned at the thought and you felt your stomach fill with butterflies. “Now why don’t you be a good little whore and beg me to fill you up.” His grin turned into a smirk and he started fucking you even more desperately somehow.
“Please fill me up. I want your come, sir.” You whined, back arching up into him. Despite your rule, part of you was being truthful. The thought of him fucking his come into your needy, abused hole was enough to make you clamp down on his cock, forcing a choked moan out of him. “Please!”
Without another word, he buried his face in the crook of your neck and rutted into you until he finally fell over the edge. He grunted with each snap of his hips, his panting breaths feeling hot against your neck. You squeezed around his cock again, wanting to make it as pleasurable for him as possible. Based on his low moan, it was working.
He finally stilled and his sounds quieted into heavy breathing as he put some of his weight on you, letting himself rest without actually crushing you. Even though you were submissive enough right now to mostly only care about his pleasure, part of you was still disappointed that you wouldn’t get a chance to come on his cock.
When his breathing calmed down, he lifted himself up to sit on his knees and slowly dragged out. He pushed your legs up, so you took the initiative and held them close to your chest for him. At the first sight of his come trickling out of you, he released a contented groan.
“Fuck… Fifteen it is.” He said through a breath. Your holes fluttered as you pushed out more of his come, making him curse under his breath. “Take off the fucking dress before I rip it off and make you go home nude.” He threatened, making you instantly release your legs and scramble to take it off. He ripped your underwear clean off your body, then flipped you onto your stomach.
“What are you doing?” You gasped, when he straddled your thighs and lined his cock up with your hole again.
“I paid for two hours. I’m not stopping until I either run out of time, or run out of come.” You choked on your spit at his words, feeling too flustered to figure out how to respond. Before you could even attempt to just think of something to say, he was pushing back in, ridding your head of all thoughts except for him and his cock.
When you woke up the next day, you saw that he had transferred the original price, plus fifteen thousand. You blinked rapidly and rubbed your eyes, thinking that you read it wrong in your sleepy state, but the number was clear as day. As was the memo reading: You’ll hear from me again soon.