New Prostitue on the Block Pt. 01

February 26th

The sun peeped through a pair of dreary curtains, partially illuminating a messy bed atop which Chloe had just awoken. Her eyes pulled themselves open to look blindly across her room as if trying to see if what had happened last night really happened. The memories and details came flooding back and tears almost immediately rose to the surface. She sat in bed for a moment, still reflecting on what she should do in this situation. No good answers came to mind so she decided to at least carry out her day like normal. She crawled out of her bed and ruffled through some clothes on the floor to find a pair of pajamas, hoping to at least be comfortable for a while until night came.

She left her bedroom in search of breakfast, not managing to find much of any food except for some expired snacks and a few Hot Pockets which she popped in the microwave. Chloe stood for a moment, staring blankly at the rotating Hot Pockets and letting her mind wander. She thought about what lay before her as of this moment, all the sex and abuse she would likely have to endure just to survive. Maybe then at least she could afford some real food she thought, almost laughing at herself. The microwave ceased its humming and then beeped for only an instant before Chloe had opened it and removed the food, tearing into it with her teeth without even giving it a chance to cool down. The pain barely even registered on her tongue; she was simply too hungry to even care about it. After she had finished scarfing it down, she could feel the Hot Pocket sitting in her stomach, lighting her insides momentarily on fire. Chloe took a deep breath in a feeble attempt to alleviate the pain but ultimately decided to distract herself with work. She booted up her archaic laptop and checked her email which held no responses to recent job applications she had submitted. Even if she decided to throw everything to the wind in order to get out of her situation, she would still end up right where she started. She hoped that sticking through for a while might hopefully reward her with enough money to be financially stable.

Seeing her hopelessly empty email inbox Chloe got up and sat on the couch in her living room, flicking on the TV and tuning into some mindless program. Anything to get her mind off of James and the whole ordeal she thought. Nearly instantaneously her phone buzzed in her right pocket. She checked what it was without thinking and saw a text from an unknown number reading, "I'll be there at 2:00, let's iron out some details," with an attached picture of Chloe's face drenched in cum. Chloe immediately cringed and looked away from the picture before realizing, 2 o' clock was only a couple hours away. "Why is James coming so early?" she asked herself. With fear in her heart Chloe went to her room to get ready, she picked out a simple tight one piece dress that didn't leave much to be imagined. Entering the bathroom she fixed up her hair and freshened up, eyeballing her lipstick but deciding tonight wasn't worth the effort. She hardly even looked at her reflection before returning to the couch to wait idly. Her mind raced while trying to figure out what "Let's iron out some details" meant. Maybe he really did just want to figure some details out, maybe he wanted her for something before the night really started. Whether he was coming to fuck her or not she was scared.

Fear ate away at her for hours before 2 o' clock came and she heard a sharp knock on the front door. Chloe drew a deep breath and slipped into some high heels while also grabbing her purse. Peering through the peephole she saw James waiting and looking at his phone. Partially afraid that he would barge in the moment she opened the door Chloe acted without impulse and swung the door wide open. James looked up and nodded once before turning and walking to his car, not waiting for Chloe to follow behind. She hurriedly stepped outside and locked her front door before rushing to get in James' car, where he was already seated impatiently. Without a word James began to drive the instant she closed her door.

"So, what details are we ironing out?" Chloe asked, giving significant attention to her delivery in an effort to not sound scared.

James took a beat before responding, "There's someone you should meet, we're on our way to a late lunch with them right now. Following that I'm going to show you where you'll be working from and run through some other general things."

Ann calmed for a moment, "Who am I meeting?"

"For short, my boss." James seemingly gritted his teeth. "When we get to the restaurant you will sit next to him, his name is Eli. Go along with what he does and what he says, don't cause trouble. He does not tolerate disobedience."

Ann took a moment to mentally prepare herself for what sort of lunch this was going to be, saying, "Ok."

"Oh, and refer to him as Sir, nothing else."

"So what's this meeting for exactly?" Chloe asked inquisitively.

"Well not that you need to know but he likes to meet all of the new prostitutes, see where they belong on the streets so to speak."

"What do you mean?"

"For example, if he meets a prostitute and she's trashy, loud and disrespectful he'll most likely throw her into the worst block he can think of. If a girl is respectful, obedient and a whore, she'll get placed a little higher. A key thing for him is loyalty and obedience, so do good here and things can get more comfortable for you."

Chloe was initially most caught off guard by James' caring tone towards her but then thought on what he had said. She felt like a dog who was on James' leash, and if she didn't behave she would get sent to the kennel. The remainder of the ride was in silence, ending when James pulled into what appeared to be a quite nice restaurant. "This is LaBello's," he said. "Now, do as I do and follow me." James got out of his car, followed by Chloe. They walked side by side towards the restaurant for a moment, "Walk behind me," James demanded. Chloe obeyed and lagged behind him a step. They entered the front door and James spoke to the hostess in a hushed whisper before he signaled Chloe to follow them. The hostess led them to a secluded corner of the restaurant where a sea of empty tables was broken up by a booth housing one man. James approached the man and shook hands, turning to introduce Chloe. "This, Eli, is Chloe." Chloe gave a shy wave and Eli nodded and patted the seat next to him. Chloe looked down and scooted next to him, leaving ample room. James set next, across from both of them. He silently tilted his head to signal Chloe to scoot closer. She did. Her ass and Eli's were now touching as Eli turned his attention to Chloe.

"So I hear you're new around here?" he asked in a joking tone.

"Yes Sir," replied Chloe awkwardly, now taking the time to understand what Eli looked like. He was a larger built man in a white button up and tie. His hair was dark and slicked back. Chloe picked up the smell of strong cologne masking himself.

Eli smirked proudly as he looked Chloe in the eyes, asking, "Are you a good fuck?" Chloe was dumbfounded at the question and stammered for a moment before replying,

"Um, I d-don't know Sir."

"Not very confident," Eli said, seemingly to himself. "Well, I'm sure before too long I'll be able to answer that question for myself," chuckled Eli to James while softly reaching in between Chloe's legs under the table. "So darling, what will you be getting?" he asked in reference to the menu, looking still into Chloe's eyes as he rubbed her groin slowly.

Chloe still stuttering indicated that she would be having the Alaskan Baked Fish, trying to pretend as if she were comfortable, sitting perfectly still.

"Mmm, mmm. Sounds good," replied Eli seductively. "I like that you don't squirm." Chloe now looked at James, almost asking for help, he mouthed "You're doing great."

Eli now removed his hand from in between Chloe's legs, signaling for the server to come take their order. A server approached from across the room and took their orders, one by one until he walked away, leaving Eli to continue gazing at Chloe. She tried to flash a flirtatious smile but Eli immediately knew it to be fake. Eli frowned a moment before saying, "I look forward to a business relationship with you. Keep in mind what we hold over you, and don't think for even a moment either me or James won't get violent if you decide to go rogue." He paused to gauge her reaction. "We had a girl a few months ago who tried to get out of it all. It's a real shame her body was found in a ditch only a few days after she went off our radars." The threat was poignant and obvious to Chloe, and it was a step above anything James had threatened. Now her actual life was on the line. "Now that that's out of the way I'm bored. Chloe, be a doll and get under the table."

Chloe hesitated a moment, showing clear confusion and panic across her face. Eli flashed a moment of a fake smile before his face turned to a frown again. He glanced at his watch, "I don't have all day girl." James too looked at Chloe to see what she would do, crossing his fingers under the table that she would do what was asked. Thankfully, she very slowly and reluctantly clambered under the table. It was a tight space, trapped between 2 pairs of legs and nothing to hide her from anyone outside the table. As she tried to make herself comfy in the space Eli unzipped his pants and pulled out his dick. Chloe began to analyze it but only go so far before Eli firmly placed his hand on the back of her head, bringing her mouth right onto his ball sack. He wasn't quite hard yet so Eli rubbed Chloe's mouth and tongue all over his junk, spreading his strong smell wherever he could. Within a moment he was hard and now took Chloe's head and placed it onto his dick. Then, he removed his hand and said, "Get to work girl." And so, she did. Slowly and rhythmically Chloe took as much of his dick as she could bare into his mouth, gagging a few times and slobbering intermittently.

As she worked she heard Eli and James begin conversating as if she weren't even there. She heard James joke and say, "Yeah her head is alright, gotta give her a bit of a push to really feel much but with sometime and experience she'll do better."

Eli laughed and responded, "Tell me about it, feels like a dead fish is sucking me off."

"Hey, it's better than nothing."

Chloe continued to pleasure, up and down, partially offended that they thought she was bad at sucking dick. Hearing this she subconsciously started paying more attention to her tongue and lips, trying to give extra attention to sensitive areas.

The table sat quietly for another moment, the only sound being the gurling and slurping of Chloe. James then asked Eli, "So, where do you think you want to place her?"

"Hmm. Well, she does seem to be an obedient bitch, an unskilled one at that though. I do think there is some charm in that but charm doesn't get you far if you don't have the skills. For that alone I can't place her anywhere remotely high class. They expect the finest lays, you know?" Eli responded, taking a moment to gulp a sip of water, which resulted on his dick flexing in Chloe's mouth. She listened intently, trying to split her attention between her work and what they were saying. "As of now she seems to listen to instructions well enough. So I won't put her in any really shitty spots. Keep me posted if she's disobedient though, to you or your clients. I'll have her sent to the slums in an instant, I know they can teach her some manners. I digress, we'll see how the rest of this lunch goes before I make any decisions." He began to say more before a man approached the table carrying food.

Chloe heard the plates being sat down and she began to withdraw the dick from her mouth before Eli very promptly slapped her across the face and planted her mouth deep onto his dick, saying no words. "Looks great son, thank you," he said, speaking as if he hadn't just pushed his dick into someone's mouth right below the table. Chloe knew the server could see her, but he said nothing. Her face stung as she continued to suck Eli's dick, she could smell the food and could tell that James and Eli had started eating. Eli shifted and moved as he scarfed down whatever meal he had ordered, occasionally thrusting his dick forward a little bit, catching Chloe off guard and gagging her. The men ate in silence with the smell of the delicious food over being overcome by the overwhelming stench of dick in Chloe's face. She wondered when she would be allowed to eat, not that she would be able to ask so she kept going. Eli left out a hefty sigh as he scooted his now empty plate, replacing it with Chloe's plate. She had no idea this was happening, she was simply surprised with how much food he was scarfing down, obviously contributing to his size.

James finished his meal as Eli was about halfway done with Chloe's fish. James then surprised Chloe, saying, "Thank you for the meal, I'll be waiting in my car, send the girl whenever you are through with her." Chloe panicked for a moment, coughing up on Eli's dick which was met with his hand being placed on the back of her head, steadying her. She watched as James stood up and left, leaving her alone with Eli. He massaged the back of her head a moment before gripping her hair and pulling his dick out.

"Now, let's see how obedient you are shall we? Remember, the more obedient you are the better work you'll find yourself doing." Chloe hesitated a moment in fear. Her fear was quickly met with disgust as Eli balanced a piece of her fish on the tip of his dick. "Time to eat my darling." He removed his hand from the back of Chloe's head, letting her do this humiliating act completely of her own accord. The piece of fish was only bite sized, resting on the pink head of Eli's dick. She choked down an expression of disgust and wrapped her mouth around his tip, dragging her head slowly back, taking the fish with it. She chewed and swallowed, almost surprised at how delicious the fish still was. Her brain lit up as this was the best single piece of food she had eaten in months. The fragrance of the dick in her face barely even registered in her brain as she waited for another piece to be placed.

Eli smiled to himself, knowing exactly what kind of effect this was having on Chloe. Delicious food only being a reward for sucking dick. He took another similarly sized piece of fish and placed it further back on his dick, now along the primarily length it balanced waiting to be taken. Chloe noticed that it was further back but didn't care, she almost happily took part of his dick down her throat to reach the fish. It was maybe only halfway down his rod but it hardly felt like much when her lips wrapped around the fish. And again, she slowly withdrew and chewed the fish. "Good girl," Eli said, softly rubbing through her hair. Then, he once again removed a piece of the fish and this time placed it all the way at the base of his dick, meaning Chloe would have to strain her throat to be met with the reward. She licked her lips in anticipation of once again tasting the fish. Seeing that the fish was all the way back Chloe took a deep breath and slowly wrapped her lips around the man's tip before pushing her head forward, deeper and deeper. She gagged and choked but pushed past until she could slurp up the fish, then pulling her head back and enjoying the reward. Eli repeated this routine numerous times until what he had left of the fish was eventually eaten by Chloe, whose face was now covered in slobber and drool.

"Time for dessert," said Eli sternly as he placed both hands on the back of Chloe's head, plunging his dick into her mouth, as deep as he could go. In and out she brought her head up and down, gagging the whole time. Chloe tried to just focus on what she could remember of the taste of fish in an effort to make the experience less horrible. It worked to an extent as she could almost still taste the delicious food in her mouth as a dick was plunged relentlessly into her throat. Shortly after the fury of throat fucking had begun Chloe noticed her head was being held down at Eli's base, having his dick fill up her entire throat. She struggled to breathe as Eli moaned and shut cum straight down her throat, making her gag even more. Alas, her head was still held there as ropes of cum stained her mouth. This time however, as she was thinking of the fish, she noticed the cum didn't taste so bad, and swallowed it without much hesitation. Eli then pulled her head off with some force and told her, "Clean up your mess," pointing his dick at her mouth. Chloe examined it and noticed the sheer amounts of saliva and cum that coated his dick. Eli noticed this pause and grabbed her hair vigorously, shaking her head in the process, "Now."

Chloe slowly run up and down his shaft, using her tongue to pick up any excess liquids left on his dick. Then, once his dick looked as clean as it could be, she pulled her head back and swallowed the concoction in her mouth. Eli laughed, "Very obedient darling, I don't know many whores who would do that. I'll be seeing you again for sure." And without another word he zipped up his pants and exited the booth, leaving Chloe still under the table. She clawed her way back into the seat where she looked at the empty plates before her. Her dignity had been stripped away for even basic necessities she thought. She sat for a moment, still tasting a bit of cum in her mouth. One of the plates had a pool of red sauce on it, causing Chloe to look around for a moment, making sure no one was watching before licking up some of the sauce to replace the taste in her mouth. She let out a heavy sigh before leaving the restaurant, feeling as if everyone in the building was side eyeing her.

James sat bored, browsing his phone as Chloe opened the passenger door and sat down. "How did it go?" he asked.

All Chloe responded with was, "I did as I was told," not wanting even James to know what she did.

"Good, I'll be hearing from him shortly to see what street you'll be working." He returned his phone to his pocket. "Some things to keep in mind while working are that obedience is key. Men or even women want you to be under their control. Do anything to make them feel otherwise? Well they might take matters into their own hands or report it to me or Eli, which you don't want. Secondly, accept every offer that comes your way, at least as you're just starting. You're going to be a new face on these streets, make a good impression, word gets around. If anything goes drastically awry call me, no promises I can help you out of a bad situation but keep it in mind." Chloe took a moment to think of what kind of bad situations she might find herself in. "Last thing is I take a 50% cut of all of your profits."

The two sat in silence now, Chloe visibly thinking about everything she had just heard. James found himself deep in thought as well, trying to work out where Eli would place her. He figured she'd probably end up somewhere relatively mid table, a proving ground for her so to speak. Though he had seen girls similar to Chloe placed on some shitty streets, likely to break them he thought. A part of him wanted to see Chloe broken from it all, desperate for anything other than what her life had come to. But at the same time he knew better streets yielded higher profits, for both of them. Nonetheless, it wasn't up to him. And so James and Chloe sat, waiting for the text from Eli telling him where to place her.

The two waited for what seemed like an eternity to Chloe, James had even started to play some music before they both felt his phone vibrate. He unlocked it and read the text from Eli to himself, "She's too sophisticated for her own good, put her on 54th street. She needs to learn to love dick." A remarkably shitty part of town Eli thought, just a step above any sort of slum. He knew the kind of people in store for Chloe and he smiled. "Alright, you've been slated to work along 54th street, are you familiar with it?"