Giandro's Gentlemen Club: Prologue

A quiet hum of jazz music played through the speakers while cigarette smoke filled the room. Beneath the scent of tobacco was a light hint of ****. There were multiple pole-dancing platforms with tables and chairs around them, and a large stage at the back of the room reserved the main event. While that was currently void of activity, all five pole dancing platforms had a woman teasing the groups of men enjoying their show.

One of the women watched from the staff room, however, a look of yearning in her eyes. She wanted more. She wanted to stand above the other women subtly flashing their panties or subjecting themselves to 'accidental' nipple slips for more money and cheers of the horny men watching them.

She took a deep breath and resolved herself, turning around to move deeper into the employee lounge. She intended to have a conversation with the boss of the strip club.

For many men in the club, it seemed to be another slow night. Multiple eyes darted between dancers and other patrons. Each of them had different ideas about the place, but all had heard from somewhere that Giandro’s was a good spot to find some tail. So far it seemed that every girl in the club was working on a strict ‘look but don’t touch’ rule, if the massive bouncers were any clue.

One man, a tall older gentleman, sipped a glass of whiskey on the rocks while sitting at the bar.

Between all the dancers, the strippers, the patrons and even the bartenders, he wasn't sure if his luck would get any better that night. If push came to shove, there was always a brothel or a whorehouse, but he was hoping to find some fresh tail tonight, instead some tired or doped out girl... he would have to see.

One of the men sitting on an adjacent seat nudged the man on the arm. "Hey... Hey buddy," he said, speaking just loud enough to be heard, but not loud enough to get anyone else's attention. "First time here?"

The dancer in front of the two men was a blonde bombshell wearing a matching bra and panties, coloured in striped red and white. Whenever she showed her ass to them, they could see the outline of her ass crack and pussy lips through the clothing. And whenever she saw any of the men touching themselves, she simply smiled and winked, but showed no other sign of noticing.

---

Lisa ascended the stairs to the owner's room. There were two large bald men standing outside his door who glared at her. She rolled her eyes, thinking that after knowing her for so long, you'd think they'd let their guard down by now. "I need to see Giandro."

—

He nods at the man briefly before returning his attention to the blonde dancer waving her goods at him. He could imagine the heat of her pussy and buns pressed against his face, the thought of it only making his cock swell beneath his trousers.

"Yeah, it is." he finally says. "What of it?" he asks, wondering what the guy was gonna try selling him. He had to admit that if at that point he had offered up one of the girls, he would take it.

The patron grinned like a shark smelling blood. "You want one of these girls, don't you? Looks like you're packing too, buddy." He chuckled, staring at the meaty bulge in the old man's pants. "Yeah, you can't hide something like that... You know, if you're willing to sweeten the pot a bit more, just pay a little bit more money, I know of a way to get one of these women alone with you... willing to do whateeeever you want."

---

It took a lot of guts to stand before the guards without batting an eye, but Lisa managed to outlast their infamous glare until they started laughing at her.

"Guahaha, damn you really are made of sterner stuff, aren't ya?" One of them asked, a pale-skinned man with a thick orange moustache. She recalled his name being Jamie.

Lisa knew what he meant by that. They apparently treated all the women like this, staring them down until they turned tail and ran or started crying.

"Yeah alright, go on in then," Jamie said.

—

The old man sighs. He was unsure if the guy even worked in the club, or if he could deliver on such a promise. “That so?”

“Yup!”

The old man had an air of elegance to him, and the way he sipped his whiskey was charming. “Tell you what, let me know how you plan on doing that, and I’ll consider it. Or maybe I’ll just bash your head in with this glass for wasting my time.” He delivered the threat with a cold calmness and a level tone in his voice before taking another sip of the drink. Half of his life was spent in the army, and then almost another ten years after that working alone at sea as a fisherman hardened his heart. He had become a bit of a callous, blunt individual. With so little time to waste in his old age, he hated anyone that thought to waste his time. It was a commodity, after all.

The patron raised his arms defensively, placating the old man. "Easy, easy! Look... I work here." Normally he wouldn't reveal that information, but he thought the old man was just... another old man. Not someone who would threaten him with **** and likely succeed in doing so if he actually tried. "This is the uh... the game. I tell fellas like you, the ones wanting to really get their rocks off that they can have any girl they want, and then you're all pudding!" His mirth vanished when he realised his choice of words. "M-most men, not meaning you of course. So uh... Go to the bartender over there and say you want the Giandro Special."

---

"Lisa..." Giandro said, a sparkling toothy grin for her, his eyes hidden by wide sunglasses. He was sitting on a wide cushioned chair with a deep seat and long arm rests. On her knees beside him, like a loyal guard dog was a woman of Asian descent wearing a mask that only covered her eyes.

"Giandro, Sir..." Lisa nodded respectfully at Giandro, then looked at the kneeling woman for a moment. She didn't know what to make of her, so she just said "Elle," greeting her by name.

"What can I do for you?"

Lisa decided to come out and say it, no beating around the bush. "I think I can do more for your company and I want a chance to prove myself. Let me be your top girl."

—

“And then what?” The old man asked, after putting the empty glass down. “What happens after I go to the bartender and say I want the ‘Giandro Special?”

Seasoned and experienced, the old man was tempted but he wanted to know more. This snake-like stranger could be leading him into a shakedown. He knew some places, especially the shady ones like Giandro’s, were known to lure lone men to their ‘private shows’ in order to beat them down and strip them of anything they owned. And while the old man could defend himself against one or two of the beefy bouncers, if they brought in more, he would find himself in trouble.

The sleazy undercover worker formed a 'shhh' motion with his finger to his mouth, "Quiet, quiet, man! Not many people know about this. We gotta keep it on the downlow, you know? Alright, I get it… Listen, my name is Tomasso, alright? If anything does go wrong, you can come back here and kick my ass. You look like someone who has beaten a few asses down in your time." Tomasso understood why the old man was so distrustful. As someone who used to be part of a group who did very bad things to unsuspecting people for money, his pitch was suspicious for sure. But he left that life behind. For the most part at least. "I assure you. It's all good buddy. You can talk to any bartender here. They all know the game. They know the rules.I promise it will be worth it.

---

"Everyone wants to be the top girl. Isn't that right, Elle?" Giandro said, reaching forward to pat the kneeling woman on the head. She just grinned in reply, not taking her eyes off Lisa.

"Well, what can I do? What do you like to see most in your girls?" Lisa asked.

Giandro continued to pat Elle's head. "Take initiative, girl. Show me you got what it takes to go above and beyond. Do something to stand out."

—

The old man leaned forward and with the speed of a cat, gripped Tomasso by the collar of his shirt and sunk a free hand into his pocket. With a quick motion, he retrieved the man’s wallet and released him. “I’ll be keeping this, then,” he said, looking at the man’s ID card. He confirmed the man’s name was indeed Tomasso, so at least he wasn’t lied to. “If you were lying to me, things would have been very bad for you, young man.”

Standing, he looked around and straightened his jacket, before walking towards one of the bartenders. A pierced and tattooed girl, in her late 20's. One of the few there that had no need to be grinding against a pole or bouncing her naked tits to earn her keep.

"Hello, I was... suggested to get the Giandro's Special by one of the... regulars here. Is that a thing?" he asks, his tone a lot softer towards the barkeep and leaning forward so that only she could hear it.

The barkeeper leaned her head a little to the left to see Tomaso staring back at her, straightening his collar and shrugging at her with a smile.

"Yes, it is a thing," she said to him in a soft whisper. "One moment, please."

---

Giandro raised a finger, cutting Lisa off as she began to speak again. He held his phone to his ear and said, "What's up?" He listened for a few seconds while a voice on the other end spoke. A big grin formed on his face as he looked at Lisa. "Is that right? ... Yeah... Perfect. Got one ready for him, too."

He hung up the phone and unzipped his pants, taking his cock out so casually that Lisa almost didn't even question it. But he saw the look of confusion on her face and chuckled. "Don't worry, this isn't for you." He looked down at Elle and said, "It's meal time." The masked Asian got to work immediately, burying her head in his crotch.

Lisa didn't know what to say, she just stood there in awkward silence.

"Got a job for you down stairs if you're ready to prove yourself. Someone has asked for the Giandro Special... I'm sure you've heard the stories. You know what that means, right?"

Lisa couldn't help but watch Elle suck the man's dick.

"Yeah, that's right," Giandro said, grinning. "This is what you'll be doing. So get down there. This is your chance to prove yourself. Make it count."

One of the girls who was working a strip pole left her station temporarily and escorted the old man. The way her tight ass jiggled with every step as he followed behind her had gotten his beef stirring again, having lost his earlier arousal thanks to the conversation with Tomasso. “Am I a lucky man today, sweetheart?” He asked her, “I’d say so if I get to spend any more time with you.”

The woman giggled, “Much to my regret, I won’t be the one servicing you tonight, Sir.” She punctuated with a bite of her lower lip. “Just stay here and someone will join you shortly and, uhm, take care of you…” Her hand gently stroked the sizable bulge on his pants before she left him alone in a private booth.

That contact sent some blood to his crotch and his dick flexed in anticipation. He looked around, seeing the small couch, which looked oddly cleaned under the dark light on the ceiling, and a bucket with a bottle of fizz and two glasses.

That didn't look like a trap. Too many things that could be used as a weapon, too much furniture. The drink could be spiked, but he would cross that bridge once he got there. His mind was racing with the thousands of scenarios, and he didn't even consider that they DID indeed provide those kinds of services for the willing to pay customer.

Eventually he sits down, leaning back and waiting. He had no idea how much time passed. Places like that had the incredible ability to make the passage of time "blurry", at best.

—

As Lisa made her way through the work floor, past patrons and working girls alike, she was met with stares. The men often looked at her when she passed by, especially when she worked the platforms and pole danced. But the looks she got from the women were more like knowing stares. As if they knew what she was about to get up to. She felt a little ashamed but couldn't feel any malice behind their stares, as if they've all been where she's going now.

She entered the booth and saw a large, muscled old man sitting in the chair. Even at such an old age he looked bulky and dangerous, and she wondered what kind of life he led in youth to have such a powerful frame. There was a glass of fizz waiting for her and she grabbed it, drinking down its contents in three large gulps. There was pressure on her that came from her own expectations, as well as the expectations of the other women. She got down on her knees in front of the man.

The old man was surprised by the raven-haired girl. She knelt in front of him without a word. He was so distracted with his own thoughts that he hadn’t even noticed her entering the small, curtain-closed room. Sloppy. Very sloppy.

“Hello, sweetheart,” he said, his lips forming into a charming smile.

“Oh,” Lisa looked up at him, her cheeks burning as she realised she hadn’t even greeted him. “Hello!”

When speaking to women, the old man’s face kept a kind and warm expression. “So, you’re the one that drew the short straw, hmm?”

That made Lisa laugh, easing the tension she felt. “Short straw? No, no, I’m volunteering!” She moved a bit closer to him, running ideas through her mind as she urged herself to be more sexy, more exciting and enticing. Her tits were almost spilling out of her dark top as she rubbed against his knees.

“Mmmh, I love what I see, but you gotta walk me through this a bit, hun. First time I’m asking for this kind of… well, special,” he states. His cock was straining against his trousers at the sight of those creamy-looking, full tits pressing against him.

She licked her lips, looking up at him with what she hoped was a confident grin. "I don't really know about how this all works behind the scenes, but let’s not even think about that. I want to be the reason you cum today. Is that okay?"

The old man grins, his cock now fully erect beneath his pants at that confession. And she smelled so good, too, her deodorant reminding him of sweetened cherries. “Mmh, that so? Well, you’re already looking the part. As for the rest…” He reaches down and pulls his cock out, veins dotting along the shaft as the head drools a large pearl of precum.

"Think you can handle this, my dear?" he asks. "I am quite sure that I'm exclusively using your mouth, maybe your tits too, but be glad I can't have your other holes. You'd be walking funny for a few days." he teases, even tapping at her face a few times with his swollen cock. That precum flung off his cock, leaving trails of wet whiteness on her forehead that dangles down past one of her eyes.

The smell of his cock was getting excited. Its size obscured her vision as it lay over her face. She needed to be more slutty. More ****. Even if she didn't entirely feel that way, she'd fake it until she really felt it. To succeed and rise to the top of Giandro's Gentlemen's Club, she needed to be more eager and willing to do whatever it takes.

"Unnfh, yeah we have rules here. I'm so glad I get to be the one to suck... this, though..." She said, starting to kiss the underside of his cock. "It's too much cock for me to handle... but that's what makes it so exciting," her voice soft and sultry as she slowly pulls her dress down just enough for her tits to slip out.

The old man chuckles. "Oh come now. A cutie like you probably has had a lot bigger. But if not, you're always welcome to call backup." he teases, tapping his cock against her face a few more times, even as she kisses the underside of it. "Mmmm in the future... might look into getting more than just your mouth... that bubbly ass is made to be squeezed and smacked." he praises.

He wasn't there to praise or talk. The old man lets go of his cock and leans back further against his seat. "But enough pleasantries, little raven. Time for you to do what you were sent here to do." he says, smirking impishly.

She smiled at his flirting but wasn't comfortable enough in this role yet to indulge in it. But he was right. She had a job to do. She was still racking her brain thinking of what she could do to stand above the other girls, or just stand out in general. For a moment, she did imagine entertaining his subtle request to bring in other women, but that wouldn’t serve her purposes. She needed to do this herself, not share the glory with the other girls.

Her best trait was her singing voice, and that was perhaps the only time men looked at her as more than something that could make their dicks hard. Her voice was endearing and encapsulating. And while looking at the man's cock, an idea finally came to her and she felt a lot more confident.

She stuck her tongue out, starting with a soft lick on his bloated, wrinkly nut sack. She wondered if his age made his cock taste... better? She wasn't sure if she liked that strong, earthy taste or not but the more she licked, the more she wanted to explore that flavour. <3

The old man was enjoying his new treat, feeling her lips and tongue sucking and lapping at his heavy and full nutsack. His cock twitched against her face as a spurt of precum escapes the tip, adding a bit more white goo to her gorgeous features.

As his warm precum trickled down her forehead and along her cheek next to her nose, the dancer knew she found a soft spot and decided to give it more attention. Those black lips spread and closed around the large sack, sucking his balls deeper into her mouth to give him a proper massage on the underside of his sack with back and forth strokes of her tongue. Faint black lipstick marks were left on the sides of his balls and she raised her hand to start rubbing along the top of his dick, grinding his meat against her face.

She moved her head back and forth a little, pulling gently on his balls as if wanting to see how far they could stretch. The grip of her lips around his sack loosened, allowing his balls to slip free with a wet plop. "Unnfh, do you like it when I suck your balls? There's a lot of precum on my face," she said, giggling as she wrapped her hand around his cock to start jerking him off properly.

"Let me put it this way.... you're lucky I can't fuck you. Otherwise you'd be having that tight pussy of yours railed right now, just from how fucking hard and hot you're making me, little raven." he grunts.

For someone so old, Lisa thought the man leaked a lot of precum. She found herself getting excited with her expectations of how virile and thick his orgasm would be. It was hot, sure. But the excitement came from how effective her glorious finale would be later.

Lisa grinned, using a free hand to grope one of her tits, raising the breast slightly while making sure he got a good look. "You've got so much precum, too. I bet when you cum for real you're going to drench me, aren't you?" She asked, wanting to confirm her thoughts, her voice hoarse with arousal. She brings her black lips to his crown to start sucking on the tip, swallowing all that pre nut. The flavour was strong and salty, a creamy, slimy texture as it travelled down her throat.

She was starting to like how his body would stiffen from pleasure. It excited her knowing that she was the reason he was feeling so good. She felt ashamed at first for volunteering to do something so slutty and **** to rise to the top, but if this is what it takes, she'd happily do it over and over again. It was like she just found her calling. Showing her appreciation, she takes the old man's cock deeper into her mouth, those black lips parting further to accommodate his girthy size.

She didn't consider how much difficulty she'd have when trying to give him a proper blowjob, though. The head of his cock pressed against the entrance of her throat and her eyes shut with her attempt at resisting the urge to gag. Saliva trickled from her wet black lips, running down the aged dick meat to nestle into his pubic region. Her tongue rolled back and forth in her mouth, massaging the underbelly of his cock to earn another trickle of precum that she felt ooze down along the back of her tongue and down her throat.

The old man’s arousal had gotten the better of him, bringing out his more self-serving, harsh nature. He grips at the back of her head with one hand, the other gripping at her jaw. "Do better." he spits out, and suddenly rams her head downwards as he shoves his hips up to her face, punching several inches worth of cock down her throat, to the point where her neck bulged slightly with the sheer size of his cock. He starts to facefuck her, throatfuck her, pounding her face and mouth as if it was any other of her holes, the sheer **** making the other breast bounce out of her dress, as he skullfucks her like she's a common street whore.

"Ggguuurrgggh!" Lisa gagged loudly and violently on his dick. He'd feel the sloppy throat goo forming around his dick as his facefuck churned out pale-white slime that ran from her nose and mouth to bathe his crotch in a filthy mix of snot and spit. "Ggghrrk, gghhrk, uurrgghk!" Suddenly she didn't feel so confident anymore. It hurt. Tears spilled down her cheeks, gradually ruining her makeup. Black streaks ran down her cheeks, passing through the blush powder that once made her look enticing like a femme-fatale. Now she just looked like a common whore.

Another thick dollop of precum blasted the back of her throat that quickly washed up through her nose, making her cough hard around the tip of his cock as it rested momentarily in the entrance of her throat. He seemed happy to let her gag on the tip for a moment, using her convulsing uvula to massage his meat for a few seconds before plunging his cock back down her throat.

"GGGGHHRRRGGHK!"

"Cumming," the old man warned her, and just as she worried she might not be able to carry out her 'masterful plan', he let go of her head and allowed her to pull back. Maybe he wanted her to taste his sperm instead of unloading it straight down her throat.

Lisa withdrew a bit, letting the cock rest in her mouth as her tongue worked him to orgasm. His body stiffened and short, sharp breaths escaped his lips as he blew rope after rope into her mouth. The potent jizz quickly filled her gullet up and she had to pull her lips free, only for his cock to release more sperm onto her face, coating it in old man nut.

—--

It wasn’t exactly Janus’ dream to work at a Gentlemen's club, and certainly not as its janitor. He always saw himself as more of a leading or authority figure, someone who would do well in leading a squad in the military or a chief officer at a police station. Hell, even the idea of upper management was something he liked to think about, handing out job assignments to the worker bees who make the office go around at God-knows-what kind of pencil-pushing type of place.

Giandro, the manager of the Gentlemen's Club, offered him a job as the janitor with cash-in-hand payments. Which probably means the club is a shady business, and he likely isn’t the only one who gets paid off the record. He got the call one late afternoon while he and his brother were helping a friend with his gardening business. Janus never found out how Giandro got his number, or why the man contacted him specifically, but in his two months working at the establishment he has been able to square off all his debts thanks to Giandro’s generous payments.

So, he’d never be able to list Giandro as a reference or include the Gentlemen’s Club as part of his work history, but as long as he kept getting paid he’d do whatever dirty work necessary. Including cleaning up after the sexual activities of the women and their clients.

No one seemed to mind Janus talking and flirting with the female staff. He couldn’t resist when they smiled at him or caught him staring dumbly at their bare chests or asses. When he first began working at the club, he had to shyly try and hide his stiffies from the women, but he learned quickly that they didn’t mind. Well, not all of the staff wanted to see him walking around with a hard-on, such as the bar-workers or the bouncers. But who cares? Fuck ‘em. His erection beneath his jeans seemed to flatter the ladies, which in normal society would probably get him thrown in jail and yet they just kept flirting with him.

So, he didn’t really mind giving the girls a bit of cash out of his pocket when they hinted that they needed extra money to cover their bills. It started off as a fifty here and there for one of the dancers, Sophia. Then, another approached him, Eliza, and told him her issues as well. She smiled at him and mentioned how all the girls think he’s just so nice and kind. He gave her some money as well to help her… whatever it was. He couldn’t remember the reason she asked for money. He kept helping the ladies out, and they kept coming back for more.

When Lisa approached him and asked him for a favour, he told her he’d do anything for her. She smiled sweetly at him and asked him to prepare the stage for her, and to drop hints to the customers that the Gentlemen’s Club would have a special show tonight. He didn’t know what to expect, and apparently Giandro didn’t either. Because like Janus and everyone else in the lower floor of the club, Giandro was looking down at the stage from the upstairs lounge.

—-

The old man’s cum had a powerful and sour taste to it, with a mostly sticky texture but an excess watery fluid that kept her mouth full and close to bursting. It was obvious to the other women she passed in the halls to the main stage that she had something in her mouth, and she could feel a trickle of the gooey stuff leaking from the corner of her lips.

As she ascended the five steps to the stage and reached the centre of the marble platform, the stagelight shone on her and she looked nervously at the surprisingly large crowd watching her.

There weren’t this many people before I left with Tomaso, she thought, momentarily forgetting she had a mouthful of cum. She opened her mouth to speak and let just a little bit more of the spongy fluid run down her chin, but she closed her mouth before too much could escape.

You can do this Lisa… It’s make or break time. Just be confident. He’s watching… She gazed up to the VIP lounge and saw Giandro. She thought, with hope, that he was excited to see what she’d do. Taking a deep breath through her nose, she approached the microphone, and began to sing.

The pianist had difficulty discerning what song she was singing, and began playing a tune trying to match the tone in her voice.

The crowd seemed confused, but Lisa continued to sing, keeping her head tilted back to ensure the sperm remained in her mouth.

—-

“What is she doing?” One of Giandro’s friends asked, a gruff man with scars on his face.

Giandro hadn’t found that answer yet either, despite now being thirty seconds into the performance. It sounds like she’s trying to sing with a mouthful of water, gargling. Then it dawned on him.

“Have the video staff do a close up of her face and display it on the back screen,” he said calmly to a woman standing behind him.

—--

I failed. I didn’t think it through. I thought I could sing and impress these horny assholes. A songstress singing with a mouthful of cum? Why would anyone think that’s special?

The wall behind her lit up, and she turned around to see the back of her head on the projection. Then she turned around with realisation and understood that no one could actually see what was in her mouth. Harshly, she imagined them thinking she was some kind of special needs person who just happened to have a good body. She could hear them talking among themselves now, the people in the crowd.

“She’s singing with cum in her mouth!”

“Oh my god, what a slut!”

“That’s so fucking hot!”

“Who’s the lucky guy?!”

“Sing with my cum in your mouth, baby!”

Spurred on by the chants and encouraged, Lisa really got into it now. She let some more of the cum trickle down her chin and the whole crowd got a good view on the projection behind her as the pearly white sperm ran between her tits. Loving the attention, she wiped up some of the cum with her finger and smeared it on her right cheek.

The more cum that ran from her mouth, the easier it became to understand the lyrics of her song.

What if you go, what if you stay, I love you…

But if you're cruel, you can be kind, I know…

There was never a man like my Johnny…

Like the one they call Johnny Guitar…

Once the pianist realised what Lisa was singing, his keys became much more focused and fine. What started off as a confusing waste of everyone’s time now had the whole crowd listening intently, enjoying the music while feeling tightness in the crotches of their pants.

Once the song ended, Lisa made a dramatic show of swallowing Tomaso’s cum, and then took a bow to a cacophony of cheering and applause.

“Encore! Encore! Encore!”

Lisa’s heart was racing with excitement, and her pussy was soaked with arousal. An encore? Could she? A quick look up stairs at Giandro gave her all the confirmation she needed as he nodded at her, clapping along with the crowd.

“You know,” Lisa said, slightly out of breath into the microphone. “An encore means I need a fresh load in my mouth!”

...

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