New Prostitue on the Block Pt. 02

[Author's note: Feedback is greatly appreciated. Creative suggestions are also welcomed. Thanks for reading.]

James' mind immediately ran with the news and filled itself with all sorts of possibilities for how Chloe was going to get fucked. She would truly learn what it meant to be a good prostitute. He briefly pondered on the text from Eli, "She's too sophisticated for her own good..." Sophisticated in what regard? It wasn't like she thought she was too good for the acts she's had to endure. He put the car into gear and began to drive as he questioned, eventually arriving at the conclusion that she wasn't cock-hungry enough. She wasn't drooling at the thought of being taken advantage of, and for Eli if they weren't throwing themselves at any man who passed by then they weren't a good whore. Along that same train of thought he warned Chloe, "Things could get rough out there, if shit turns south just do as you're told until it's done. That's basically what you're paid for anyway."

The words flew straight in one ear and out the other for Chloe, as she was trying to calm her nerves about what was next. Thus far having to suck two dicks didn't seem so bad compared to actually being fucked. No matter who it was, just the fact that it was a stranger was severely daunting for Chloe. Her mind screamed as James drove along, getting deeper and deeper into the city. She glanced at a sign and noticed he had just passed 66th street, giving her mere minutes to prepare before she was set loose. For some form of distraction she glanced down and fixed her appearance, adjusting the black dress which hugged her thighs and blindly touching up her hair to resolve the mess Eli had left. She also noticed a slight dampness on the dress near her neck which she realized was her own spit as she attempted to wipe it down.

Before Chloe could finish cleaning up the remnants of her time at LaBello's James had parked on the side of the street. "This is it," he said. Chloe looked around, the buildings were small and many of them looked rather decrepit. The street itself was dotted with trash bags and even from the inside of the car the air had a certain stink to it. Oddly enough regarding the state of it all many people roamed about. Even as they sat there she could count maybe 10 on her side of the street alone.

"Certainly reeks of 'pretty good,'" Chloe remarked sarcastically.

"It's the people that make is special." A wink from James went unnoticed. "I'm sure you have some premonition that prostitution is all about getting in cars and doing your business there, but that's only half the case. See all these people?" he asked, gesturing with his eyes as they followed the streets up and down. "A good majority live a minute or less away on foot, and if not, you better bet they know a spot to take you."

"Oh..."

"It's really a good thing, you'd get tired of getting in cars all the time, I promise."

Chloe slowly came to realize the reality of her situation, no longer just going into the cars of strangers but rather their homes. Harder to leave, she thought.

James cut her off before she could do anymore thinking, saying, "Well you look slutty enough I suppose, no point in waiting." He clambered out of the car and waited for Chloe to join him on the sidewalk. She took a deep breath and stepped out. "Now, for your first and only your first, I will help you find a client. After this, you will be mostly responsible for getting work on this street. There are some edge cases where Eli receives a specific request that he deems you best suited for, but I wouldn't expect one of those anytime soon. For now, this is your new place of work," gesturing with his hand up the street. "Make connections here and you can leave this dump with some urgency," no longer even joking about the quality of the street.

"Great. So... how do we get started?"

"Like this," responded James, walking up to a random man walking by. "Excuse me Sir, I think there's something wrong with my girl. "My Girl" Chloe thought. "I'm not sure if it's her ass or her tits but something feels... wrong. Would you mind taking a feel?" James asked, gesturing straight at her.

The man laughed a moment, "Well shit, you don't gotta ask me twice," taking one hand and gently pressing it on one of Chloe's boobs, being sure to give it a slow and sensual squeeze. Chloe visibly cringed and looked at James, he looked back with an evil glare suggesting he was proud of the sick joke he pulled.

"Here don't be shy," James exclaimed as he brought his hand roaring around to Chloe's ass where he caught a firm grip. The man took after James and slapped her across the ass, chuckling in delight. Chloe again looked at James, he was primed to hand her over to him for a test drive or the likes. But, before he could open his mouth, his eyes darted to the side where his expression changed from sadistic joy to true joy. "Lenny!" he shouted, leaving Chloe and the man alone as he hugged a man of similar size and stature. Chloe watched them through slitted eyes as the stranger continued to entertain himself with her body, being sure to feel every nook and cranny. His hands glazed across her pussy through the dress before landing on her neck where he continued to inspect her.

"My my, I like you," uttered the stranger into Chloe's ear.

Chloe responded, "Thank you," in the most unintentionally awkward manner possible. Her mind was preoccupied on James and the man he called Lenny. As if attempting to distract herself from the man's advances, she examined Lenny. He was on the stockier side of men with a tan complexion, and truthfully aside from his skin tone he looked as if he could have been James' brother. They were only a few steps away yet still out of earshot as they conversed. Jokes were seemingly exchanged as the men laughed and patted each other's shoulders. Chloe could hardly pay attention however as the stranger got more and more familiar with her assets. Thankfully, before he could get too familiar James reapproached and pulled Chloe away for a moment where he introduced Lenny.

"This is one of Eli's oldest buyers, he's been picking up prostitutes for so long we named a discount after him," James said with a laugh from both him and Lenny. "But uh, I figured since it's your first real client there's not really a much better place to start than with Lenny. Especially on these streets," again laughing. "Tell 'em Lenny."

"Yeah well I like to treat you women with respect," Lenny remarked, as if that statement meant anything outside the world of prostitution. "Nothin' you don't want and just a good time for the both of us." If what he said was true it really didn't sound so bad, certainly better than the alternative Chloe thought. Speaking of, the first man had all but disappeared as he dipped around a distant corner, surely enjoying what he had gotten to feel.

James paid attention to this and noted, "Hey, seems like your friend left, all the more reason."

Chloe remembered the advice she was told, accept every offer that comes your way. She put on a fake smile and said, "Sure, I'd love to!"

"Oh that's wonderful," Lenny said, "You won't regret it I promise."

"I'm sure you won't Chloe, now I best be on my way," muttered James as he rummaged through his pockets, looking for his keys.

"Oh no way man, come swing by my place, I'll give you a beer," offered Lenny.

James stumbled over his words for a moment, "Ah- Oh well I really would love to but I don't wanna get in the way of you and Chloe here now."

Lenny shrugged him off and said, "Don't worry about it I'll pay for the extra time. And plus, who would ever turn down a good beer?"

"You know what, yes, I'll stop by."

"Alright sounds good, well I'm only about a block away so you'll be in and out," Lenny said, beginning to lead the way up the street. James turned to Chloe and offered a somewhat reassuring smile before catching up and walking alongside Lenny. Chloe too began to walk at their side before remembering what she was told and lagging a few steps behind. On the way there the men didn't talk much, leaving Chloe alone in her head as she paid attention to every eager pair of eyeballs ogling at her somewhat exposed features. Hungry looks, she thought. The endless gazes ended however as Lenny showed them both into his apartment. Immediately Chloe noticed just how small it was, it practically made hers seem like a mansion. Right as you enter the front door a bed takes up most of the space, facing a TV and lying just in front of the kitchen. James and Lenny walked around the bed, taking seats in the kitchen. Chloe further took in her surroundings as Lenny shouted, "You can go ahead and get ready on that bed there." The same bed that was clearly visible from the kitchen where both men sat.

She sat down awkwardly and noticed the men were both holding beers and facing her from the kitchen. Feeling the pressure, Chloe slowly removed her dress and heels, setting them aside on the floor. Now she sat in her plain underwear, awkwardly facing the wall in front of her. "Don't stop there," Lenny said calmly. Chloe listened and removed her bra, followed by her panties. "Beautiful." Then, Lenny set down his half empty beer and approached the bed, stripping as he walked. Chloe turned red as he clambered next to her on the bed, dick free as the wind. She had only caught a glimpse but it looked about average, and the smallest of what she's had to withstand so far. Without a word he maneuvered himself on top of her in a position akin to missionary and began to massage her breasts with his hands. He let out a soft moan and moved his mouth close to Chloe's chest where he subtly licked all sorts of sensitive areas. In an instant he had become quite immersed in her body, exploring its many avenues with his tongue, which actually felt good to Chloe. That was the first time she felt that way in the past 2 days. One of the few things detracting from that feeling was whenever Chloe looked up and away from Lenny, she saw James standing in the corner, sipping away at his beer. In fact he seemed to be watching as if this were TV for him, not exactly sexually invested like a cuck might be but invested nonetheless.

She turned her focus back to Lenny as she found herself growing quite involved, letting out involuntary moans and squirming in delight. Lenny certainly knew how to pleasure Chloe as he licked and softly bit at her neck and chest, occasionally brushing his now hard dick against the outside of her pussy. Lenny began to explore Chloe's body further, feeling her thighs and ass in his hands as he took in all of his senses, giving more and more care to her clit. At first, he only used a finger to massage it, but before long he was massaging it with his tongue, causing Chloe to become quite wet. She looked up for a moment to see if James had left while she was distracted, only to meet his eyes in an intense gaze while Lenny ate her out. Her attention very quickly shifted as Lenny brought himself up and lay atop her, looking into her eyes. He smiled a moment and whispered, "Here we go baby," slowly gliding his unprotected dick into Chloe. She let out a soft whimper as her eyes rolled back, legs now pulling Lenny in close. He continued to fuck her slowly and gently, pushing as deep as he could go to drive moans out of Chloe. He even brought his mouth close to hers as if he were teasing a kiss, just to pull back with a grin seeing the disappointment in her eyes when he didn't follow through.

He continued to thrust slowly, getting both himself and Chloe warmed up and acclimated to each other's body before picking up pace. The headboard of Lenny's bed beat softly against the apartment wall with each movement of his hips. James, deciding to leave the couple alone, made his way to the front door where he exited mostly unnoticed. That was aside from Chloe who opened closed eyes as her mind reentered reality, now remembering some crucial details: she was alone with Lenny now, and he didn't put on a condom. She shifted uncomfortably following these realizations, unwrapping her legs from Lenny and ever so softly pushing against his chest. These slight protests didn't quite register to Lenny however, who continued to fuck the beautiful doll in front of him. Chloe's heartrate grew steadily as she thought about a stranger cumming inside of her, she certainly couldn't afford a baby or even an abortion.

"L-Lenny..." she stammered in between thrusts. Lenny looked down into her eyes, visibly frustrated.

"What is it?"

"C-Condom, please?"

Lenny's brow furrowed in a bout of anger, visibly thinking as he continued to fuck Chloe. His train of thought was interrupted however as Chloe now spoke in a more panicked tone, "Lenny?" expected some form of answer from him.

However she didn't quite get the answer she wanted as Lenny responded in a rushed, sharp manner, "Shut up." Immediately, sparks set fire to Chloe's mind as the panic really set in. Lenny now channeled his emotions into his fucking, ramping up speed and intensity by a sharp factor. The soft thuds of the headboard now grew into loud pounds, with the only other sounds in the room being the repeated slap of Lenny's balls against Chloe's ass. Her pussy no longer felt sensual and warm, instead turning numb and sore. She heeded Lenny's words for a moment while her mind raced, wondering if she should fight back or let it happen. Words and advice from the past flew through her mind, remembering that it was best not to resist. Her own thoughts screamed at each other, fighting to take control. Ultimately, some form of survival instinct decided she would resist. Chloe immediately pushed hard against Lenny's chest, responded by only being fucked harder. She tried writhing her legs and body relentlessly but the weight of the man atop her stopped this effort before it even started. Her eyes met Lenny's for a moment; his conveying hunger and rage, hers conveying pain and fear.

He grunted loudly as he drove his dick as deep as he could muster over and over, leaving no breathing room for Chloe. She began to conjure up some form of a plea for help, quickly met by Lenny placing his hand firmly over her mouth. Chloe's shouts and screams came out as a pathetic muffled sound that only drove Lenny to fuck her harder. She batted at his chest and even began to try and claw her way out which led to being met with a swift and strong slap across the cheek. Lenny now removed his clamp on her mouth and pinned down each of her arms, almost daring her to start screaming. But now, her mouth was zipped shut on her own accord, fearful of any further physical violence. Moans of pain were the only sounds to escape her lips, synchronized with each full force thrust into her. Tears began to stream down Chloe's face, dripping onto the bed sheets. This is it, she thought. I'm being raped. Never had a thought come so clear to her in such an intense moment but now the words bulged through her mind, echoing endlessly. The physical pain alone was enough to derive tears, let alone the humiliation of being slapped and fucked into submission.

After minutes of agonizing torture Lenny began to slow his pace before suddenly pulling out without cumming. "See you stupid bitch? I won't cum in you." His words stung like ice. "Doggystyle. Now," he commanded, removing his body from on top of Chloe. She took a moment to gain the calmness to move, a moment too long for Lenny as he grabbed a fistful of her hair and dragged her face next to his. "I said now." Chloe's survival instincts flew into high gear, moving herself into position without a word, screaming inside at the degradation she was enduring. Lenny licked his lips at the sight of Chloe's ass in full glory, leaning in close and spitting a glob of makeshift lube right on her pussy as some form of mercy. She almost yelped at the sudden sensation before silencing herself in fear of another act of aggression.

Lenny groped Chloe's cheeks with some tenacity, being sure to prepare them for what he had in store. He then spread them and once again inserted, slowly and softly. Chloe let out a loud gasp of surprise and sensation, seeing that Lenny's even just average dick was hitting newfound spots. He quickly picked up pace, reaching a speed just outside of comfortable for Chloe. Her pussy ached as it was violated again and again, Lenny was fucking with so much force that she had to brace herself on the bed to not topple over. His dick went balls deep and he brought his chest forcefully against her ass with every thrust, creating another rhythmic clapping sound. He began to moan more and more with each passing second. He even extended a hand to pull Chloe's hair, causing a yelp to escape her lips. Her mind was blank at this point, simply accepting the position she was in and not trying to cause any more problems. The endless sensation of being pounded grew numb but never quite vanished, and the many sounds associated with her rape simply became background noise.

Much to her relief Lenny neared the finish line. In a blaze of ecstatic glory he pulled Chloe's hair even harder as he let out a few final furious pumps, digging as deep as his dick could go before pulling out only at the last second to cum on her ass, getting some on his sheets. He moaned loudly as he pushed the last drops of cum out and wiped his dick clean on Chloe's bare cheeks. Lenny then stood up, and returned to the kitchen, still naked. He spoke clearly across his apartment to Chloe, "I can see why you got put here. You're a shit whore." He rummaged through a drawer momentarily. "Keep putting up little fights like that and one day something much worse is going to happen to you," he now walked over to where Chloe sat on the bed, carrying a wad of cash in his hand. "Now, say thank you. Say thank you for going easy on me."

Chloe sat astounded for a fraction of a second before remembering what might meet her if she delay any further, "Thank you for going easy on me."

*SMACK* Lenny's hand flew across Chloe's face. "That's 'Sir' to you."

Chloe let out a sob and caught her breath, "Yes, Sir."

*SMACK* Lenny now sent Chloe toppling backwards with the force of his slap. "What was that?" he barked.

Chloe fought through tears to reply, "Thank you for going easy on me, Sir."

Lenny threw the wad of cash at her naked body and stepped away towards the kitchen, "You're welcome slut, now run back to your owner and tell him what a good time you had." Chloe sat up and held the cash in her hand, the wad was rather thick. The skin on her right cheek roared and stung in agonizing pain as she slowly put her underwear on, followed by her dress and heels. Finally, she put the money in her purse and left Lenny's apartment, neither person saying a word as she exited to the street, cum still coating her ass beneath the panties.

The outside air felt cold across Chloe's body as she briskly walked back to where James had parked. She looked down as she went, attempting to dodge any lustful gazes along the way. Regardless of this, she was still met with numerous cat calls that served to diminish her even further. She walked faster and faster before she finally reached James' car where he sat in the driver's seat on his phone. Chloe hurriedly swung open the passenger door and sat down, immediately breaking into a meek cry. James paid no notice to this or her disheveled appearance, instead asking, "How much did he pay you?" She sat stunned for a moment, trying to calm her frantic mind so she could even just breathe. Eventually, she reached into her purse and handed the wad of cash to James. He counted through it, "$200, quite generous." He then split the amount in half, handing $100 to Chloe who stuffed it into her purse. Raped for $100, she thought. Could she even handle doing that once a night, let alone multiple times? Her query was met with the acknowledgement of necessity, she had to do this. James did give some form of care to Chloe, opting to give her a few minutes before pressing her to get back to work. He watched as her breath steadied over time and her overall presence oozed less panic.