Pleasures Pawn Ch. 01

*This is a new long-term project I have been thinking about for a while now. It was actually one of the first ones I had planned. The story revolves around 2 main characters:

Aria: Aria's background is one of modest beginnings in the world of prostitution. She started as a lower-tier prostitute. Even though she was a futa, she often took on the role of a sub, especially to her pimp. Despite her lack of power and influence, Aria possessed a keen understanding of human desires and the art of persuasion. Through her charm and manipulation, she managed to elevate herself slightly above her peers but not by much. Her life changed the day she met Gabe.

Gabe: Gabe's journey into the world of high-end prostitution was not one he embraced willingly. Struggling with his own identity and societal expectations, he initially viewed his involvement in the profession as a necessary evil, a means to survive in a world that offered him few alternatives. However, as he became more entrenched in the lifestyle, he found himself experiencing conflicting emotions. On one hand, there was a sense of empowerment and liberation in embracing his desires and exploring his sexuality without judgment. On the other hand, there was a constant internal struggle, a nagging feeling of inadequacy and loss as his sense of masculinity slowly diminished with each encounter.

This chapter is a bit of an origin story for both of them. Hope you enjoy. As always, please let me know if I did something wrong or have another take, I am open to constructive criticism

The city at night was a maze of towering buildings and buzzing neon lights, a chaotic symphony of noise and motion that seemed to swallow Gabe whole as he trudged through its crowded streets. With each step, he felt the weight of his empty pockets and hollow stomach grow heavier, a constant reminder of his desperate circumstances. He had run away from his foster home years ago after living in less-than-ideal circumstances and abusive parents. But as he dredged through the streets he was reminded of the hot food and warm bed he had in that home. It had been years since he had even seen them, not that he wanted to, but that was the last time he had a nice meal. He had spent most of his time on the streets stealing left over food and unfortunately going through garbage.

He crossed multiple restaurants and cafes with shining bright displays showing off their expensive food, cakes, pies and other mouth-watering delicacies. Gabe knew he couldn't afford any of it outright, and there didn't seem to be anyway for him to steal anything. His only option at the moment was to wait and go through the trash, hoping that the people in the richer side of town were more likely to leave more leftovers. He walked into one of the alleys that led to the back entrance of one of the cafes. It was still a busy night and it seemed fairly lively so he just sits by the dumpster, hoping someone would come out from the back with some leftovers and he could hopefully get them comparatively cleaner and avoid the dumpster diving. He sits as the hustle bustle of the city at night slowly turns into a monotonous white noise that he soon falls asleep to.

He is suddenly awoken as the back door swings open and a large man steps out. He's wearing a hairnet and a tight shirt with an apron. Despite being sweaty and sort of dirty looking he is still a very muscular and attractive looking man. He carries over a large bag of half eaten food over to the dumpster, not even noticing Gabe until he finally speaks up.

"E-excuse me sir." Gabe piped up, slowly standing up as his back rubbed against the buildings wall, getting as much support as his body could get.

"Huh!" The man panicked, not expecting to see someone so late at night in the dark alley. He raised his fist and angrily screamed, "Whose there! I don't have any money but I do have a knife!"

"No! No! I don't want any trouble!" Gabe raised up his dirty little hands as if he was ready to defend himself from a beating.

Seeing the hands and the weak little cries gave the man a bit of an ego boost, additionally the soft voice and dark alley meant he couldn't really see Gabe that well and for a second thinks it's a girl. "What do you want!?"

"Well sir, I was just hoping I could get some food, you're throwing it away anyway."

"No, you can't we're not allowed to in case something gets you sick, we can get sued"

"Please sir! I promise I won't do anything like that! Even if I do get sick!" Gabe begged, getting on his knees with his hands together, almost crying.

As he fell to his knees, the man finally got a better view of his face and realized he was dealing with a man. He examined Gabes face, hands and body and almost instantly came up with an idea tht would serve him well.

"Well I suppose I could maybe consider giving you some of the food, if you give me something" He smiled cheekily.

"I would love to, but I don't have any money to give."

"Oh, don't worry, I'm not asking for money, I was thinking of something more like a blowjob?" He grinned as he looked down at Gabe's now surprised face.

"Wh-what! But I'm a man! I can't do that to another man!" Gabe nearly screamed as he was taken aback.

"Exactly! So even if you do get sick and try to sue, you'll have to tell people that as well." He grinned as he slowly undid his pants, ready to pull out his cock once he needed to.

"I don't know, I've never done something like this before" Gabes face was perplexed as he thought about it.

"Well, try it? Maybe you like it?" The man responded as he dropped his pants and pulled off the apron.

In the dim light of the alley, Gabe could just barely see what was right in front of him. He recoiled as he saw it pulled out for the first time, but not wanting to insult the man, he swallowed his pride and tried his best not to make too much of a fool of himself. Gabe's eyes carefully examined it. It was thick and veiny, unlike his small little excuse of a penis. The pungent smell was strong, and easily filled up Gabe's nose that he choked up a bit. But despite all this, there was a part deep within him that seemed to actually like this, a part of him that was curious about all this, the smell, the look, the feeling, the taste, it was like something inside him had awoken. He gently reached out his hand and grabbed the mans cock with his hands and looked up at his face while blushing bright red.

"L-like this?"

"Y-yes, yes, now gently move your hand up and down, like you're giving me a massage." Barely able to speak, the man had never felt such soft hands, despite regularly going to the red-light district. This boys hand job was already better than any he had ever had before.

Gabe gently continued to rub the mans big cock, slowly moving the foreskin back and forth as the man let out soft little moans. He could feel his own tiny little cock get hard. He kept thinking about how weird an uncomfortable this was, yet also so enticing. He considered how much of a man he was if he actually liked doing things like this. Was he really just a homosexual? His own tiny penis was nothing compared to this mans, was he really so small? His thoughts were quickly diminished as the man gently grabbed his head and softly guided it towards his cock that Gabe tightly gripped.

"N-now put it in your mouth..." He whispered as he held his breathe, leaking precum just from a hand job.

Blushing bright red and still unsure about this whole situation he gently moved his head forward. He breathed shakily as he got closer and closer. He closed his eyes tight as he finally felt his soft lips brush against the man's skin as he finally took the man into his mouth. He finally tasted what he was both eager and unwilling to taste. It tasted like it smelled, bitter and salty, yet with an heir of fascination and entrancing. The man helped by slowly sliding deeper into his mouth, stopping as he felt his tip touch the back of Gabes throat and pulled back. He couldn't help but let out soft moans as his cock was enveloped in a wet little cave as it was held in by soft plump lips.

"Good girl" He whispered as he slowly pulled back, leaving just his tip in Gabe's mouth. "Now move your head back and forth, like you're giving me a massage again, but with your mouth"

Gabe gently moved his head forward, letting the mans cock glide across his tongue as he tried to cradle it. As he felt it touch the back of his throat, he would lean back quickly, letting the mans big cock swirl inside his mouth. As he bobbed his head back and forth, his mind raced, thinking what this was, why he hated it, why he was secretly liking it. He convinced himself the only reason he was doing this was the food, no other reason, and he only liked it because it meant he would get food, right?

As his head bobbed up and down, back and forth and his mind raced, he was suddenly interrupted as the mans soft moans turned into a longer, louder groan, his body tensed, and Gabe suddenly felt the rush of a salty, thick torrent going directly down his throat. His tongue instantly coated in the man's semen. He tried to push back but the man held him down tightly onto his cock as he panted and whispered. "No, no, you have to swallow it first, okay?"

Gabe's eyes widened as he did not want to swallow it, but he knew there was no way out. With all his might, he swallowed all that he could as the mans now flaccid cock was limp in his mouth. As he did the man finally let go and leaned down, "show me."

"Okay." Gabe grimaced a bit, and opened his mouth wide, sticking out his tongue.

"Good girl!" He pet Gabe's head while smiling, knowing he was a boy.

"Bu- "

"You've definitely earned a reward, wait here!"

Gabe sat outside, waiting patiently, yet still thinking about what had happened. He was still trying to convince himself that he only did it for the food, but why did he like part of it? Why did his dick get hard just from looking at a bigger penis? He also felt less hungry, had the semen satiated his hunger?

His thoughts were again disrupted by the man suddenly bursting through the door. Now instead of carrying a large bag of leftovers, he held a giant plate with hot food. Gabe could see the trails of steam coming off the buns, bread and meat. He almost couldn't believe what he was seeing. The man smiled as he put it down in front of him and stood beside him, letting him eat. Gabe quickly scarfed down the food, quickly forgetting the taste of semen and replacing it with bread, meat and buns. The man watched, laughing at how hungry the boy was. He also felt pity for the boy, and waited for him to finish.

"I see you liked the food, huh?"

"Yes! It was delicious! Thank you so much!"

"So where are you going to go now?"

"I- I don't really know, I guess maybe another part of the city."

"Ya know, I do know someone who might be able to help you out."

"Does it mean I'll have to give more blow jobs?" He asked a little scared.

"Hahaha! Don't worry. I'm sure my friend will make it worth your while and you'll get more than just food. If you're interested you can come with me."

The man picked up his own bag and slowly walked towards the other end of the alley. Gabe took a few minutes weighing his options, and quickly rushed behind him, willing to take his chances.

In another corner of the city, known as the red-light district, Aria, a young beautiful futa sat in a bar, half passed out, drunk and just barely caring about the world around her. She had once been part of an affluent family, but after her parents passed away her brother took over the family fortune and decided that it would be better for Aria to grow up away from the family home, and the city would be a better option so she could see the world. She was meant to stay with an aunt, who never really took care of her, or paid attention to her. At the same time, she craved adventure, and soon made friends who were prostitutes, not realizing what that meant. Soon she left her home with her aunt and went completely unnoticed.

At first it was just her and her friends hanging out, using her looks to seduce men and trick them and rob them. Until a futa, known only as Maeve happened to cross paths with her. Maeve took her in and saw her skill and beauty, she taught her how to use her looks and silver tongue better, unfortunately she also tricked her into a debt. Having no other skills, and stealing just not doing the job, she turned into a prostitute. At first hating it, having to deal with old, ugly men who often were too drunk to even aim right, she used her silver tongue, convincing her more drunk customers they had already had sex. If they wanted more, she would charge them double or even triple. Soon she got close to paying her debt, but every time she got close, she would somehow increase her debt, whether it was her drinking, clumsily losing her money, or getting caught stealing. She hated being a prostitute and wanted to change her position, she wanted to be a pimp, just like her idol Maeve.

The bartender pushed her head, waking her up from her nap. "Wake up! Either order something or get out!"

"Yeah! Yeah! Don't get your panties in a knot!" Aria responded with a chuckle.

She sat up and downed her drink in one move, slammed the money on the table, smiled a very cheeky smile at the bartender and got up. Still a little drunk she looked out at the people in the bar, scanning and searching for a target. She saw a handsome well dressed young man, sitting alone. She slowly walked over to him, holding another drink, she sits next to him.

"Hey there handsome, how about a drink?" She gently places it in front of him.

"N-no thanks" He responded, a bit shyly

"What's the matter hun? You seem a bit worried, is there anyway I can help?" Aria smiled as she gently placed her hand on his lap, feeling for his cock, but he moved her hand away.

"It's nothing, please, I'm waiting for someone else." Just as he said that, a young beautiful woman walked into the bar, and the young mans face lit up. And just as soon as it lit up, A tall, fat, and very wealthy man came up behind her and held her arm, pulling her to her table as she laughed and giggled with him.

Aria watched all of this and decided to use this to her advantage. "Hey! Forget her! You can have me!"

"No! The only reason I come here is to see her. I just want to be with her."

Aria crossed her arms and slouched in her seat, thinking what she could do. Suddenly she had an amazing idea. She stood up and grabbed his arm as he continued to stare at the love of his life enjoying her time with other men. She pulled him while smiling.

"Come with me!"

"No! Let go of me!"

"Trust me! You'll have her!"

He suddenly stopped fighting back, letting Aria do what she wanted. They crossed the girl and the fat rich man and entered a room behind them with a bed.

"I know that girl, she loves big dicks more than anything, but she sucks at knowing what big is, hahaha"

"Okay, but how does that help?"

"We're going to convince her you have a big dick, and she will love you for that."

"That's great and all, but how are we going to do that?"

"Simple, we'll pretend you and I had sex, I'll scream and moan so loud, and they are right behind this wall so they'll hear all of it."

"Yeah, okay, but that doesn't explain how I have a big dick."

"Well, if I'm the one screaming, she'll know you must have a big one. Especially since I'm bigger than you."

"Excuse me!?"

"Yeah, I'm a futa, and I already know I'm bigger than you."

"No, you're not, and I'm willing to bet on it!"

"Sure, If I'm bigger you have to pay tw- three times my usual rate. Done?"

"Done! And if I'm bigger you have to give me the same amount"

"Done!"

The young man smiled, gently pulling down his pants with a slight grin. With great confidence he pulled forward the waistband of his underwear and slid out his rather impressive cock. He smiled as it hung down a bit limp at just a little under 8". Aria blushed, she had seen big cocks, but never really this big. Maybe she had bit off more than she could chew, she though as she stared at it.

"Well, what are you waiting for?" The man smiled as he flopped his cock by swaying side to side, showing off his size. "Let's see yours then!"

"Y-yeah" Aria gulped, as she pulled up her dress.

Both looked down at her crotch as she pulled her cock out and slid her panties to the floor. She held her cock up, as the man pulled his cock up. They both looked roughly the same size. Seeing the massive cock and scent of her musk caused the man to get hard, and ended up with their cocks touching and rubbing as they both got hard. Aria let out a low moan as the man couldn't help but lightly touch her cock. Suddenly Aria stopped him.

"Wait!" She pointed down as both of them we're now rock hard, but there was now suddenly one clear winner. While Arias cock was touching the man's balls, rubbing and nuzzled between them, while the man's cock was just barely able to caress her balls. "Guess we have a winner!"

"Hmmm." The man was silent, a little embarrassed.

"Well now," Aria stuck her hand out in front of him as she pulled her cock back, "that'll be $600!"

"Fine!" The man seemed angry, now that he had lost, and was also a little humiliated. He pulled his pants back on and pulled out his wallet, taking out $600 and slapping them into Aria's hand. "Now how are you going to help me?"

"I'm sorry help you?" Aria smiled back.

"Yes! You said you would help me!" The man responded a bit angrily. "That's why we're in this room!"

"Oh, right. Well, I was going to help you, but you insulted me, were rude and didn't really seem interested. If you still want my help, it'll cost you... hmmmmm, an extra $300!"

"What! You're crazy!"

"$400."

"That's too much!"

"$500." Aria smiled, knowing she had him by the balls, figuratively.

"Fine! Fine! Here!" He pulled out another $500 and put it in her hand, which she eagerly counted.

"Good, now sit down, and follow my lead."

Slowly, Aria started making low moans, soon getting louder and louder. The man just stared at her as she grabbed the headboard and started slamming it against the wall every few seconds. Her moans slowly getting louder and louder, she picked up speed slamming the bed harder and faster. She slowly picked up speed over time, by the end her moans turned to screams and groans. When she finally stopped, she ripped her dress up a bit, and sprinkled herself with water to make it look like sweat. She smiled as she grabbed the man's shirt and pulled half of it out, also unbuttoning and rebuttoning it but wrong. She then grabbed his arm and walked out with him, nearly hanging off of him. As soon as they exited the room, people we're already staring at them. The man awkwardly smiled until his eyes fell on the beautiful girl who had yearned for. She was looking at Aria, with a clear look of jealousy. Aria, smiled, looking drunk on lust and kissed the man on the cheek before announcing loudly enough for the girl to hear, "free of charge for Mr. Big Dick!"

With that Aria pretended to stumble to the bar, looking back only to see the girl trying to get the mans attention. She smiled as she looked down at her money, sliding out a few bills, she placed them on the table and signaled over the barkeeper who came over with a drink. As she sipped the drink, she noticed an old client she once had sitting a stool over with a cute little boy.

"Hey, don't I know you?" Aria asked, looking over the guy.

The man looks over from his drink, "Yes! Yes you do, I've been looking for you!"

"Huh, oh right. I remember now." She grimaced as she was reminded of the time he had penetrated her once; it was not a fun experience for her. "Sorry, but I'm not available tonight."