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Speakeasy Seduction

Prompt originally from AetherRoom.club
Created: 2022-07-13
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Description
Somewhere in this town, there's a speakeasy operating for the most elite of the crime families, where bosses make underhanded deals to carve this city up even further. And while I expected to be in danger of getting whacked, I did not expect to be in danger of getting fucked.
Tags
first person, detective, femdom, hardboiled, prohibition
Prompt
The fog was draped over the city of Chicago like a veil attempting to cover the dirty dealings going on all over town, but nothing could cover that vile stench. With everybody from the mayor to the cops in the pockets of organized crime, the only ones trying to get a little justice. After a long time of trailing mooks and roughing up one or two of them, I had finally gotten the lead I needed to find what I was after—a speakeasy in the basement of the Williamson, the ritziest, most high-class spot in town. This place was where the bosses drank themselves into a stupor to celebrate their domination of the Windy City, and where I would find my answers. Telling the clerk at the front desk a password so he lets you down to the basement and a simple knock code at the door later, and I found myself in this inner sanctum of villainy. One might have believed that a secret speakeasy for the elites of crime to do whatever it is they do would be more luxurious, like the hotel they were using as a base, but that was not how these bosses operated. This place was rife with thick smoke, the furniture was rustic at best, and the only thing that made it clear this place was top shelf was, indeed, the shelves, which were stocked with the widest variety of alcohol and spirits I had ever seen... and I had seen the inside of plenty establishments that prided themselves on having booze galore, be they legal or illegal. It seemed that I had arrived at a rather dead hour of the day, as there were hardly any people there, though that was fine, since all I intended to do was reconnoiter. As such, I simply made my way to the bar, ordered a sidecar and took in the ambiance. But just as my drink arrived, the knock signal I earlier used to get in again rung through the room, this time with an intensity that caused whatever murmuring conversation was going on to quiet down. I found my eyes involuntarily drawn to the door, which soon opened, and in stepped a dame the likes of which I had never seen before. She wore the kind of clothes I would've seen on the guys around the police station—slacks, shirt and tie, jacket casually slung over her shoulder, and a fedora to complete the look. If it weren't for her long, auburn hair and voluptuous chest straining against the shirt, one could've mistaken her for just your average low rank mob mug. She marched straight to the bar, slamming her open palm on the top and yelling "Old fashioned, and snappy," before grabbing a nearby box, pulling a cigar out of it and lighting it up. It was pretty clear to me that this dame was something special. She obviously looked at ladylike behavior and decided she didn't give a rat's about any of that, and that baffled me. I thought these mobsters didn't associate with the other gender in any real way beyond squeezes and whatnot, but evidently this one commanded some sort of respect. Of course, the fact that she was about one head taller than I was surely helped with that. This woman does not care what you think, that's obvious, and she almost certainly seems capable of backing up her arrogance with force. Slowly, the ambiance of this bar began to return to the level of a vague background mumble as I returned to drinking, wondering how I should handle this situation. However, it seemed that this decision would be quickly made for me. The woman slammed down her drink with the intensity of a career drinker, then turned to face me. "Hey, you some gumshoe or somethin'? You stink of it," she says, an expression on her face that made it clear I needed to tread carefully. Of course, I would not tread carefully. "Who wants to know?" I replied, cocksure. That led to her quickly sizing me up, staring daggers at me. "They call me Red. Remember the name, Stephens, because I remember yours," came her answer. Ah, rats. I was in trouble. Evidently, my opinion of my cover was a lot higher than its actual quality, because she knows me somehow. In a less tense situation, this might have led to a reevaluation of my methods, such as roughing up thugs for info that could easily end up ratting me out to the rest of the crew. And so now I had this mountain of a redhead staring me down with intent. "This... doesn't need to get ugly," I said, trying to stall so I could think of something. A confident grin grew on her face, and she knew she had me cornered. I did not like my chances in a fistfight against her, given her size, and that wasn't even accounting for the six other gangsters hanging around as well. "I agree. Let's take this to the side room," she then answered, motioning to an unassuming door that I very soon found myself going through. This side room was rather spartan in its furnishings. A table, a few chairs, some bottles of hard liquor on the table, and for some reason a bed in the corner. No windows, befitting a basement bar side room that was surely used for all sorts of illicit purposes. And while I was still taking in the situation, the door locked behind me. "So, Stephens. Though you'd sneak on in and get the dirt on the boss, you rat? Well, let me tell you, we know. And we're gonna give you a choice. Either you're gonna find yourself food for the fishes, or you're gonna be a good little gumshoe and dance to our tune," Red continued. For a moment, the thought of my body drifting ashore from the Chicago river raced through my mind, and it was at that moment that I became keenly aware of my own mortality. But before I could even respond, Red suddenly began slowly closing the distance between us, loosening her tie and undoing a few of the top buttons of her dress shirt, drawing even more attention to her... size. "Here's the low-down, mug. I ain't gotten laid in ages because these no-good thugs can't handle a real woman. So if you don't wanna die tonight, you're gonna help me out, and if you know what's good for you, you'll get out of those clothes right quick. You look like a darn fool in them, anyway."... [Click to expand]
The fog was draped over the city of Chicago like a veil attempting to cover the dirty dealings going on all over town, but nothing could cover that vile stench. With everybody from the mayor to the cops in the pockets of organized crime, the only ones trying to get a little justice. After a long time of trailing mooks and roughing up one or two of them, I had finally gotten the lead I needed to find what I was after—a speakeasy in the basement of the Williamson, the ritziest, most high-class spot in town. This place was where the bosses drank themselves into a stupor to celebrate their domination of the Windy City, and where I would find my answers. Telling the clerk at the front desk a password so he lets you down to the basement and a simple knock code at the door later, and I found myself in this inner sanctum of villainy.
One might have believed that a secret speakeasy for the elites of crime to do whatever it is they do would be more luxurious, like the hotel they were using as a base, but that was not how these bosses operated. This place was rife with thick smoke, the furniture was rustic at best, and the only thing that made it clear this place was top shelf was, indeed, the shelves, which were stocked with the widest variety of alcohol and spirits I had ever seen... and I had seen the inside of plenty establishments that prided themselves on having booze galore, be they legal or illegal. It seemed that I had arrived at a rather dead hour of the day, as there were hardly any people there, though that was fine, since all I intended to do was reconnoiter. As such, I simply made my way to the bar, ordered a sidecar and took in the ambiance.
But just as my drink arrived, the knock signal I earlier used to get in again rung through the room, this time with an intensity that caused whatever murmuring conversation was going on to quiet down. I found my eyes involuntarily drawn to the door, which soon opened, and in stepped a dame the likes of which I had never seen before. She wore the kind of clothes I would've seen on the guys around the police station—slacks, shirt and tie, jacket casually slung over her shoulder, and a fedora to complete the look. If it weren't for her long, auburn hair and voluptuous chest straining against the shirt, one could've mistaken her for just your average low rank mob mug. She marched straight to the bar, slamming her open palm on the top and yelling "Old fashioned, and snappy," before grabbing a nearby box, pulling a cigar out of it and lighting it up.
It was pretty clear to me that this dame was something special. She obviously looked at ladylike behavior and decided she didn't give a rat's about any of that, and that baffled me. I thought these mobsters didn't associate with the other gender in any real way beyond squeezes and whatnot, but evidently this one commanded some sort of respect. Of course, the fact that she was about one head taller than I was surely helped with that. This woman does not care what you think, that's obvious, and she almost certainly seems capable of backing up her arrogance with force.
Slowly, the ambiance of this bar began to return to the level of a vague background mumble as I returned to drinking, wondering how I should handle this situation. However, it seemed that this decision would be quickly made for me. The woman slammed down her drink with the intensity of a career drinker, then turned to face me. "Hey, you some gumshoe or somethin'? You stink of it," she says, an expression on her face that made it clear I needed to tread carefully.
Of course, I would not tread carefully. "Who wants to know?" I replied, cocksure.
That led to her quickly sizing me up, staring daggers at me. "They call me Red. Remember the name, Stephens, because I remember yours," came her answer.
Ah, rats. I was in trouble. Evidently, my opinion of my cover was a lot higher than its actual quality, because she knows me somehow. In a less tense situation, this might have led to a reevaluation of my methods, such as roughing up thugs for info that could easily end up ratting me out to the rest of the crew. And so now I had this mountain of a redhead staring me down with intent. "This... doesn't need to get ugly," I said, trying to stall so I could think of something.
A confident grin grew on her face, and she knew she had me cornered. I did not like my chances in a fistfight against her, given her size, and that wasn't even accounting for the six other gangsters hanging around as well. "I agree. Let's take this to the side room," she then answered, motioning to an unassuming door that I very soon found myself going through. This side room was rather spartan in its furnishings. A table, a few chairs, some bottles of hard liquor on the table, and for some reason a bed in the corner. No windows, befitting a basement bar side room that was surely used for all sorts of illicit purposes. And while I was still taking in the situation, the door locked behind me. "So, Stephens. Though you'd sneak on in and get the dirt on the boss, you rat? Well, let me tell you, we know. And we're gonna give you a choice. Either you're gonna find yourself food for the fishes, or you're gonna be a good little gumshoe and dance to our tune," Red continued.
For a moment, the thought of my body drifting ashore from the Chicago river raced through my mind, and it was at that moment that I became keenly aware of my own mortality. But before I could even respond, Red suddenly began slowly closing the distance between us, loosening her tie and undoing a few of the top buttons of her dress shirt, drawing even more attention to her... size. "Here's the low-down, mug. I ain't gotten laid in ages because these no-good thugs can't handle a real woman. So if you don't wanna die tonight, you're gonna help me out, and if you know what's good for you, you'll get out of those clothes right quick. You look like a darn fool in them, anyway."
Author Notes
The life of a private eye was always fraught with dangers, but this I did not expect. A mob enforcer girl I only know by the name Red has made it clear that they know I'm on their trail, and if I didn't want to end up sleeping with the fishes, I'd better back off. I don't seem to have much to say in this situation.
Memory
It was the time of prohibition, and in the city of Chicago, organized crime was flourishing. And into this den of sin came I, Jack Stephens, a private eye with a knack for finding the truth no matter what it takes. With crime families in strong control of every facet of government from top to bottom, it fell to gumshoes like myself to take them down a peg. It was a dangerous job, but I loved the danger. In what was my toughest case yet, I was hot on the trail of a speakeasy operating in the basement of the Williamson Hotel, the most luxurious spot in the entire city.
World Info
View World Info
  • Red

    As a private eye, dames were something I had a lot of experience with, be it getting information out of them by talking with them or by bedding them. But this one was something else. Known to me only as "Red", this woman knew exactly what she wanted and how to get it, primarily by beating the crap out of you. From the moment she stepped into a room, she had a presence second to none, helped by her size that had her standing taller than even most men. Dressed in man's clothes that did little to hide her massive cans and rarely ever seen without a cigar, Red could handle her vices and reveled in them, be it smoking, drinking or fucking. And no matter what, she would not take no for an answer.
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