Speakeasy Girl Ch. 04

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Chapter Four – Moving Up

© Bad Hobbit 2022

Gladys looked so pleased when I showed her the cigarette girl outfit and got her to try it on. It needed a little padding around the bust, as young Gladys isn’t as well-endowed as me, but she looked sweet in it and she has nice legs. She thought that the skirt was too short – she’s two inches taller than me, so she showed even more leg than I did – but I explained that it had to be that way. She giggled like a schoolgirl when I had her walk up and down and practice selling me cigars. And then she cried like a baby when I explained to her that she’d have to take it up the butt from Mr. Walsh.

“But Alice, I’m – I’m a virgin! I’m only eighteen. I don’t even have a boyfriend. This is my first job. I live with my mom and dad. What will they say?”

I comforted her as best I could. “If I were you, I wouldn’t tell them about it. Look, Gladys, every girl in this place has been through the same thing. We all still work here, and Mr. Walsh gives us presents when he – when we’re nice to him. Really, Gladys, it’s no big deal. You’ll still be a virgin on your wedding day – just a virgin who knows a lot more about sex than is usual. And I promise you, it doesn’t have to hurt. It can even be pleasant, exciting.”

“How can that be?” she blurted. “It’s gotta hurt like crazy!” She sobbed again.

“Not if you prepare properly.” I showed her the toolkit and explained how to use it, as Ginni had done with me. I’d gone out and bought myself some extra equipment of my own, so I no longer needed the douche or the rubber ball. I’d cleaned them all up carefully before I passed them on. And of course, I’d replaced the carrot! For some reason I didn’t really understand, I also offered to be on hand if Gladys wanted to try out the tools at the club. Gladys went off looking tear-streaked, worried and confused.

Ginni smiled when I told her about Mr. Walsh’s request. “You know, he used to say I had the best ass in the place. I still think I’m the only one who can take all of his dick down my throat.”

“Down your throat? How can you do that?”

“Oh, you know – you just work it back there like you’re going to swallow it, and if you can relax your throat and get past the urge to puke, you can push it on through. Guys love it – especially Mr. Walsh.”

I went away thinking about what Ginni had said. I put on the new hostess outfit and went upstairs to find Pauline. When I got to the top of the stairs, I turned back and Johnny was looking up from the bottom. He suddenly looked sheepish and moved away.

Pauline showed me around the tables, and explained the games. “You don’t need to know the rules like the croupiers do, but you do need to know when a guy has a winning hand. Your job will be to make a guy want to keep playing even when he should quit, and to help the house win back when the guy’s on a winning streak. You have to balance it, mind, because they want you to be their lucky charm, not their bad luck bitch. Lots of smiles, lots of titty and leg on show, and just a hint that there might be more on offer. Which, of course there never is, if you’re a sensible girl.”

She taught me about good and bad hands at poker and blackjack, and showed me how to signal to the croupier what the player was holding without anyone else noticing. It was all very confusing at first, but after working there for a week, I started to get the hang of it. There was a raised platform up a flight of stairs where the blackjack tables were, and some private rooms at the back where the high-stakes games were played. I mostly worked the tables in the main room, going up and down the stairs and along the edge of the platform, idly running my hand along the handrail and knowing that the guys below were trying hard to look up my skirt. Pauline referred to me as her ‘mobile distraction’, and she told me that the takings had risen around 20% that first week I worked there.

I enjoyed the work. In some ways it was better than being the cigarette girl. I didn’t have to try to sell anything. All I had to do was bring a few drinks and cigars, talk to the guys and look pretty – and sexy. Mr. Walsh decided he wanted me three more times in that month. I kept my own toolkit hidden away in the ladies toilets upstairs, so I could prepare as soon as I got the word. I began to look forward to the call to his office, the strange fullness in my ass as he probed deeper, his fingers – or sometimes my own – on my pussy, and the odd stretched feeling afterwards, with his jizz dribbling out of me. He made sure that I climaxed each time, and I got presents. I asked him not to give me a mink coat, because I didn’t want Benny to get suspicious and think I had a sugar daddy. Instead, he gave me cash and some nice pieces of jewelry, which I hid away for a rainy day.

I thought Susan might get a little jealous, but she’d taken on a new role that he’d created, making her the hostess downstairs instead of just the head waitress. He said he didn’t have as Ankara Yabancı Escort much time these days to schmooze with the paying customers, so Susan did a lot of it for him. She charmed the guys and impressed their wives with her elegance, so that some even started dressing a little like her. She also left the club with him most nights, and often arrived with him, so we guessed that she was now his live-in mistress.

I asked Mr. Walsh if he’d like me to become a croupier, but he said “Sure, you have the tits for it, but your legs are much too good to be hidden behind a table”. Still, I learned all I could about the games, to make sure that I could help the house make money. I suppose I should have felt guilty, cheating the poor saps at the tables. A few times I did feel that some sucker or other deserved an even break, but so many of the guys at the tables were brash and loud, showing off their money – money they’d probably cheated out of some other poor sap – that my conscience wasn’t troubled too much.

My hostess job also required me to go into the back rooms from time to time and help out at the tables, bringing free drinks and cigars to the serious gamblers. Occasionally a drunk or a guy with too much self-confidence would make a pass at me. Usually I could just fend it off with a smile and maybe a friendly kiss. Sometimes I had to get Pauline to intervene, and just once Ricky, one of the heavies that worked the second floor, had to step in and tell a guy that his attentions were not welcome. Actually, Ricky was a sweet guy who looked out for me. He wasn’t leering all the time like Johnny and Paddy downstairs, and he always smiled sweetly when our eyes met.

One other thing that happened is that, as a hostess, guys were allowed to buy me drinks. Of course, the prices were a little inflated, and I only drank maybe half of what they bought – mostly champagne – but most nights I’d go home a little tipsy. I found that the booze helped me be sociable, and perhaps allowed me to flirt with guys in ways I wouldn’t have done if I was fully sober.

One night, this good-looking guy was playing the tables. Someone whispered that he was a young actor from Hollywood, and was taking some time out to star in a show on Broadway that was opening in a few weeks. He was smart as well as cute, and he didn’t let me see what he had in his hand. I kept bringing him drinks and standing next to him, and he kept on winning. I gave him my best smiles and my sexiest moves, and he smiled back and bought me four glasses of champagne, but I couldn’t do anything to stop his winning streak. Then, at one point when I was serving him a drink, he reached down and ran his hand up my leg, slowly and deliberately. As he moved it higher, I guessed he was waiting to see what I would do. He was so good-looking, and I still hadn’t been able to do anything about his winning streak, so I let him continue. I stood there while his hand moved up to my stocking top, over my garter and started to stroke the inside of my thigh.

I said nothing. Actually, it felt nice, and going around the place in a short flared skirt and no panties so guys could get a glimpse of my pussy was making me pretty horny. Having someone do something about it – for once a good-looking guy who wasn’t drunk – was fun. When he finally touched my pussy, I think we both got a pleasant surprise. It felt good to me, and he discovered that I had no panties on, that I was fully shaved – and also pretty wet.

He stroked my pussy with his fingers for, I guess, around ten seconds, before people began to look up and notice I was still standing by the table. I was enjoying the attention, but I had to move on before someone became suspicious. “I’m sorry to interrupt your game, gentlemen,” I said, “but would anyone else like a drink or a cigar?” My new-found friend took the hint and slid his hand back down. The other gamblers all shook their heads, so I picked up my little tray and moved away.

Pauline came up to me. “Did I just see what I thought I saw?”

“It wasn’t a problem, really. I was trying to see his cards, but he wasn’t going to let me. I didn’t mind him touching me. It was kind of a game, I guess.”

“Well, if you need any help, let me know.”

A little later I was heading towards the ladies’ room to adjust my make up – and to tell the truth, to play with my pussy, as I was feeling rather fizzed-up after my experience earlier – when the guy emerged from the men’s room. We looked at each other. He smiled.

“Alice, isn’t it. How lovely to bump into you. Is there anywhere we could talk? In private?”

“Sure, Mr…?”

“Call me Tom.”

“Sure, Tom. Just follow me.”

I knew that Mr. Walsh kept a small room at the back for private games with some of his best customers. No-one was using it that night, so I checked that we weren’t being watched, and led Tom inside, closing the door behind us.

“What was it you wanted to say, Tom,” I asked Bahçelievler Escort with my most coquettish smile.

“I’ve been coming here on and off for a while. I know I haven’t been for a month or so, but I haven’t seen you around before. Are you new?”

“No, sir. I worked downstairs selling cigarettes. They asked me to help out up here a few weeks ago.”

“Well it’s nice to see you Alice, and it was really nice to meet you tonight – and to find out some of your more intimate secrets.”

“I was happy to share some of them with you.” Another coquettish smile, my head tilted a little to one side.

“Alice, I’ve had a really good night tonight, and I’d be willing to share some of my good fortune with you if you’d be prepared to share some more of your secrets with me.”

“Mmm – could be interesting, Tom. What do you have in mind?” I don’t know what had gotten into me. I badly needed someone to tease my pussy, but I knew that I shouldn’t be flirting with strangers – or customers – like this. I wasn’t sure how Mr. Walsh would view it, but I knew Benny wouldn’t like it.

“Well, we could start by taking a peek at what I discovered a little earlier.”

“Just a peek? Or were you hoping for a peek and a poke?” What made me say that? I guess it was the champagne talking.

“It depends on what’s on offer, Alice. I understand that the house rule is ‘look but don’t touch’. Does that really apply to you?”

“That depends on how much of your good fortune you’d like to share.” The Devil was in me now, as well as the drink. I stepped up to him and put my hand against his cheek. We looked into one another’s eyes, and then I kissed him. He responded, and it was obvious he knew how to kiss. Benny was always a sweet kisser when we were kids. Now his kisses were warm but a little too cozy. Tom’s kiss was hot; soft, sensual, and left me in no doubt what he had in mind.

I took hold of his hand and placed it over my right booby. He squeezed gently, moving his palm slowly around, stroking the exposed skin in the low-cut neckline of the dress. He bent his head down and lightly traced a line over the upper surface of my breasts with his tongue, which felt really exciting.

After a few moments of that, I turned away, stepped back a couple of paces, reached down and lifted the hem of the stiff skirt to my waist, making a kind of curtsy. I looked at his face to see how he reacted.

“So, do you like what you see?” I gave him my sweet smile again. He stared at my smooth, naked pussy, then looked at my face again and smiled.

“So how much does this cost?” he asked.

“Oh, so far it’s on the house. But to play, you’ve gotta ante-up.”

“Ten bucks if I can touch you.”

Ten was good money. Many girls would be very happy with ten for a fuck. Some would even take ten for a butt-fuck. But I sensed that the guy was loaded and money wasn’t an issue for him. And anyway, I wasn’t a cheap slut. I may have been a slut, but I felt I was an expensive one.

“You already touched me. Special offer; twenty and you can lick me. Another twenty and I’ll suck your dick. Do we have a deal?”

“Well, Miss Alice, you sure don’t come cheap. But you’re pretty, and I want you, so I guess we have a deal. But what about if I want to get my dick inside you? What’s the price for that?”

“With a rubber on, another twenty.” I was asking for outrageous money. I guessed he’d stop at a lick and a suck, and that would suit me just fine. But if he wanted more – well a girl’s gotta make a living.

“And without?”

“No deal.”

“How about another fifty?”

I was stunned. Fifty bucks – on top of the forty I’d already asked – was a hell of a lot of money in those days. I hesitated.

“Wait here,” I said.

I left the room at a run. Three minutes later, I was back, with a wad of toilet paper that I set down on the chair by the door. “Sorry to have to leave you like that, but I have a deal for you. For a hundred you can lick me, I’ll suck your cock, and you can put it in me. But there are two conditions.”

“It’s OK – I won’t come inside you, and I don’t have any diseases if that’s what you’re worried about.”

“That’s good to know, but the deal’s this. Condition one, you make me come. At least once.”

He grinned. “So you get something as well as the money. Sure, I think I can manage that. And condition two?”

“I think you’ll like it. Your dick goes up my ass, not in my – my – my cunt.” It felt strange, saying the forbidden word that Mr. Walsh used with me, but I guessed it would turn Tom on more than something coy.

He looked at me in surprise. “Wow! So that’s what the extra is for! And if I just want your – your cunt, as you so elegantly put it?” He smirked. “How much for that?”

“No deal without the rubber. One hundred dollars. You lick me, I suck your dick, you get to – to fuck me up the ass, mister, no rubber. You make me come. I’m clean – and very tight. I’ll Balgat Escort take all my clothes off, or I can do it in the dress. What’s it to be, big roller?” My heart was pounding. I was selling my body to a handsome guy for enough money to keep me and Benny for a month. But all the while I knew I was becoming the slut that Mr. Walsh said I was, and the whore I told him I wouldn’t be. It was terrifying and terribly exciting at the same time.

He looked at me, then at my pussy. I reached down and began to finger myself. I’d gotten wet just thinking about it.

“Deal,” he said. He reached into his jacket pocket, and I watched as he peeled off ten crisp ten dollar bills and handed them to me. It was a huge amount of money – more than I’d ever seen in one place – but judging by the stash he put back in his pocket, it wasn’t going to leave him broke. I had nowhere to put the cash – assuming that my clothes would soon be coming off – so I put it down on the chair by the door, and picked up the tissue paper. While I was there, I made sure the door was locked.

I moved back to the big poker table in the middle of the room, putting down the paper and leaning against the table. By now, Tom had his shirt and pants off, and was down to his undershorts. He had a great body – all lean and muscular. He came over to me and kissed me again, then reached around and pulled at the bow that fastened the lace-up dress. The dress sorta sagged a little at the top – it was a very tight fit – and he took hold of the neckline and pulled it down, pushing my boobies out of the top of the brassiere. His hot tongue on my neck, then my breasts, then my nipples was thrilling. Just as I was enjoying this, he suddenly spun me around, loosened the dress some more and pulled it down. He unhooked the brassiere, and moments later the dress was on the floor, the brassiere was on the table and I just had on my stockings, shoes and gloves. I had a sudden thought that the gloves covered my wedding ring, so at least Tom didn’t know I was a married woman.

He turned me back around and kissed me, cupping my boobies in his hands, and then going back to licking and sucking them. His hands moved down, his fingers found my slit, and he started to tease me, probing my honeypot. God, I was so wet and it felt so good!

Then he lifted me up onto the table and started to lick me. I was moaning in seconds. God, that guy knew how to use his tongue. He kept me sizzling, getting me close then easing off, for five, maybe ten minutes before I finally came, and he kept licking for a while longer so my climax went on for a long time.

He came up and kissed me again, and I got a good taste of my pussy juices. “OK, that’s two parts of the deal. Now how about part three?”

I smiled, perhaps a little dreamily, and sat down on a chair. He pulled down his shorts, and his dick sprang out. It was then that I realized that he was bigger than Benny. Bigger than Mr. Walsh. Quite a lot bigger.

“Oh my, you have – you have a – a big dick there, Tom! My, that’s – that’s the biggest I’ve seen.”

I took hold of it. I guessed it was maybe an inch and a half, maybe two inches, longer than Benny’s, but what worried me more was that it was also maybe a half inch thicker. That half inch could make a lot of difference. I remembered what Susan had said about Jimmy, and wondered what I’d gotten myself into.

“Does it scare you?” he asked.

“A – a little,” I said, truthfully.

“Sure you don’t want to change your mind about me sticking this in your ass? I can put it in your sweet little cunt if you’d prefer? Of course, I’d need to negotiate a discount…”

“Let me see what it tastes like first,” I said, and immediately took a big gulp. Like I said, I’m fortunate to have a wider than average mouth. Benny and Mr. Walsh, they’re pretty easy to suck. Tom was more of a challenge, but I wasn’t gonna be beaten. I was proud that I knew how to suck a guy off, and I wasn’t going to let Tom’s size get in the way.

And Tom seemed to like what I was doing. He started moaning, and he put his hands in my hair as if to guide me. Fortunately, he didn’t start thrusting into my mouth or I’d have had to stop. After a minute or two, my jaw was starting to ache, but I’d made up my mind.

I pulled my head back and took a deep breath. “Tom, here’s what we do. Special bonus – I turn around, you slip it in my – my cu-cunt” – I blushed at the word, but it was clearly what he wanted to hear – “for a while. If you feel like you’re gonna cum, you pull out. Then, when I’m nicely warmed up again, we try it in my ass. If it doesn’t go in, I finish you with my mouth. Deal?”

“Sounds good to me, Alice. Let’s go!”

I turned around, bent over the table and spread my legs wide. I felt a thrill as he eased slowly into my honeypot, and began some shallow thrusting, rubbing right on my most sensitive parts. As his thrusts went deeper, I felt a stretch that was greater than anything that I’d had until then. It didn’t hurt, it wasn’t even uncomfortable, but I just felt – fuller. Then he moved his hand around and started stroking around my pussy. He kept away from the button at first – I guess he knew I’d be too sensitive – but after a minute or two, I was warmed up again nicely. By then he was thrusting quite hard and very deep, and though it felt really good, I was worried that he might come in me.

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