Speakeasy Girl Ch. 05

Chapter Five - The Demands of the Job

It was nearly two weeks before Mr. Walsh called me to his office again. After my evening with Tom, sex hadn't been nearly as exciting. Sure, Benny was beginning to learn to do the business. When he was working on the construction site, he would take a bath when he got home, so he smelled a lot sweeter. He'd learned to lick my pussy and to finger me in a way that got me excited, and he could even make me come if I let him go on long enough. He'd developed better control, so that when he fucked me, it was a lot more pleasant than it had been before.

But I felt it was too soon to introduce my husband to the delicious and dirty world of butt sex. Benny was getting more broad-minded, but this was quite a lot for him to take in. I'd been telling him about this (fictional) 'adventurous' lady at the club who'd suggested all the things we were now trying, but persuading him that it was a good idea to stick his cock up my ass still seemed a little premature. It was probably illegal in most states at the time anyway. Though at the club, everything was illegal, so it hardly seemed to matter there.

So when Mr. Walsh asked Ginni and me to come to his office after work one night, I was excited. He'd spent a lot of time with Gladys over the past few weeks. Sure, she was sweet and pretty, but from someone who'd sobbed at the thought of having to take it up the butt, the new cigarette girl had turned into an anal slut in a very short time.

"Do you like it when he pushes in really deep? I love it! Oh my, I like to shove my butt down hard so I have all of him, and I've learned to squeeze my butthole so it really milks his cock. It's so good when I can feel him pulsing right inside my ass. And when he teases my pussy at the same time, we both kinda climax together. That feels so - so wicked!"

The skinny little kid was starting to irritate me, in part because Miss Goody Two Shoes had turned, almost overnight, into Miss Butt Slut 1933, but mostly because Mr. Walsh seemed to want to fuck her - and Susan, his regular mistress - so much that the rest of us never got a chance to enjoy the experience that we all knew we craved.

And yes, perversely, we did all crave it. I remembered how shocked and terrified I'd been at the thought of having to do that scary and disgusting thing, the first time. But now - now I found I enjoyed it even more than regular sex. Maybe it was because of the extra naughtiness, or the fact I could do it without fear of getting pregnant. Or maybe because I enjoyed having my boss pleasure me while I was pleasing him. But then I'd loved it when Tom had done it to me with his much-bigger cock, so maybe it was just that I'd become a slut who liked perverted sex with handsome men.

So I was delighted about the summons. Since Tom, with the permission of the Boss, I'd sucked off two clients, let three finger my pussy, and jerked off two more. And from all this, I'd taken home a lousy fifty bucks. Sure, fifty bucks was good money for doing very little that I didn't want to do, but it would've been a hundred if the house hadn't taken its cut. And of all these, only one had made me come. He was really kinda cute, and for another twenty or thirty I might have let him fuck my butt if there had been time. His finger work in my pussy was good enough to give me a climax, although I did have to eat his spunk, which wasn't too tasty, and I'd rather have had it deposited six inches inside my ass.

And now I finally had 'the call', though why he'd invited Ginni to the same session I had no idea. But I found our real soon. When we arrived, Mr. Walsh was sitting in the chair at his desk. As soon as the door closed, he swiveled around, and we could see that his dick was out, and hard.

"Ladies, suck time, if you please." We both knew what we had to do, so we dropped to our knees, and took it in turns to suck Mr. Walsh's cock and lick his balls. We'd both done this individually before, and I'd sucked him during my initial session with Susan, but I'd never really done it alongside another woman in quite the same way.

I watched as Ginni went deeper and deeper on Mr. Walsh's cock, until her nose pressed against his belly. Mr. Walsh let out a long moan. "OHHHH! Fuck, Ginni, that's amazing."

Ginni slid her mouth up and down Mr. Walsh's dick a few times, each time pressing him into her throat and shaking her head, I guess to improve the sensations for him. I watched, sometimes licking his balls - and, I have to admit, sometimes with my hand between my legs, teasing my pussy.

When Ginni next came up for air, Mr. Walsh said "Wow, Ginni. I'd forgotten just how good it feels when you take me right down like that. Why don't you have a try, Alice?"

"Mr. Walsh, I don't think I can. I'd probably puke all over your pants."

"Try it, Alice. I'll give you a bonus if you can do it."

Ginni smiled at me. There was some gooey stuff around her mouth which looked a little like jizz. "Get your mouth really wet. Take a few breaths and try to focus on relaxing your throat. Then work his cock slowly back. If you feel like you're gonna puke, pull back a little and let the feeling subside, then try again. Little by little. I'll help. Meanwhile, watch carefully as I do it again."

I really didn't want to do this. I mean, after I'd taken Mr. Walsh's cock up my ass for the first time, it started to feel good, and after a little while it was feeling so good that it got close to making me climax. But I couldn't see how having a cock down my throat could ever feel good. Still, he was my boss, I had to do as he asked - and he'd promised some more money if I did it. And I guessed that if I hated it and it made me puke over his nice suit, he wouldn't ask me again.

So I tried. I took some deep breaths and then let my mouth fill with saliva, as I watched Ginni slide her mouth slowly over Mr. Walsh's cock and move her face closer and closer to his body until her forehead was pressed over his belly-button. Her eyes swiveled sideways to check I was watching. Then she winked, and slowly pulled off his cock.

"Now you try," she said in a voice that sounded a little hoarse. "Wet your lips, open wide and slide on down."

I did as she said. The first three or four inches were OK; basically it was what I'd already done. I paused, took another breath through my nose, and then pushed down further. Another inch and I got a strong gag reaction. I jerked back - but found Ginni's hand behind my head, preventing me from lifting right off.

"Steady, girl. Breathe. Let the sensations subside. Then ease down again, slowly."

I swallowed hard, and the urge to puke receded. Without waiting for me, Ginni gently pushed my head down. I guess if I'd fought back, I could've gotten Mr. Walsh's dick outta my mouth, but I realized I had to at least try to do it. Back down to the same point, and again the gag. With Ginni's hand there, I couldn't easily go back, so I breathed again, tried to relax - I mean, it wasn't easy - and then pushed a little deeper.

It took a minute or so of rocking my head slowly up and down, pausing, breathing and pressing on before I felt the head of Mr. Walsh's cock finally start to probe through my throat. At that point, I had to push back against Ginni's hand, and use my own hands to press down on Mr. Walsh's hips or I really would have sicked-up all over him. It was good that I hadn't eaten or drunk anything for a couple of hours, apart from an odd sip of champagne, so my stomach was empty and there wasn't much to bring up.

"Good girl, Alice. Nearly there. Just a little more."

Mr. Walsh seemed pleased with my efforts, so I swallowed and breathed. Then I made myself think of his cock going up my ass, of his mouth and fingers in my pussy, and despite what was happening in my mouth, I began to feel horny again. 'OK', I thought, 'if Mr. Walsh wants me to be sluttier than ever, to let his cock go deep inside all my holes, I'll try to do it. He's generous and he looks after his girls, so I'm sure it'll be worth it.' Another deep breath and I started down again.

The tip of his cock entered the opening in my throat. I fought down the gag reaction, paused again to breathe, and pushed further. The hole didn't seem big enough to let him through.

"Move your head around. Make those hawking noises in your throat and you'll get more juices to help him through." Ginni was close to my ear, urging me on.

I did as she said. I found that some goo was forming in my throat, like very thick saliva, and it helped lubricate the hole. But Mr. Walsh's cock-head was big and it was forcing my throat to stretch in a weird way. I gagged again, gulped as best I could, and pushed harder to see if he could go through. And then...

And then Ginni shoved my head down. Mr. Walsh's cock-head was forced through my throat. I started to puke, but nothing could get past this huge plug in my gullet. I tried to swallow as hard as I could - not at all easy with a big lump of meat in the hole - and this seemed to ease the need to throw up as little. But after a couple of seconds, I realized I couldn't breathe and my throat tensed up again. I pushed on Mr. Walsh's hips and slid backwards as quickly as I could, gasping for air when his cock finally fell out of my mouth.

"Hey, Alice, that was great for a first attempt. Now you know what to do." Mr. Walsh was smiling down at me, as Ginni took his wet cock in her hand and stroked it up and down.

"That - that wasn't nice, Ginni. It hurt," I croaked. "And I couldn't breathe!"

"Hey, sweetie, I'm sorry, but you need to learn to do that for Mr. Walsh, and yeah, I kinda threw you in at the deep end. But you managed it."

"But - I don't think I could do that again," I gasped. "At least, not tonight." My throat felt strange, kinda bruised and sore.

"You need to practice, but you've shown you can do it. Let me make sure Mr. Walsh is good and hard, and then he can decide what he wants to do with this nice cock of his."

What Mr. Walsh decided he wanted to do next was fuck Ginni in her pussy. I remembered that the time he'd done that to me, he'd deliberately held back, so I hoped he had enough control to satisfy both of us. He got Ginni to undress down to her garter belt and stockings, lie on the couch and spread her legs. She was smiling - obviously pleased that she was going to get something she enjoyed, and she looked so slutty, spreading her long legs like that and gently rubbing her pussy as she watched Mr. Walsh undress. I also thought she looked very attractive for a woman in her thirties.

When he was naked, with his cock pointing straight at Ginni's pussy, he paused, looking down at her. "Now, Ginni, what do you say?"

"Please Mr. Walsh," she said, with an exaggerated expression of excitement, her eyes wide. "Please, sir, would you please fuck me?" She pronounced the word with relish, as if she was a naughty schoolgirl saying a dirty word for the first time, like it was in defiance of her parents.

"Really, Ginni, you sound so slutty. I might do it, if you ask nicely. Or nastily." He grinned. "And exactly where would you like to be fucked, Ginni?"

"Oh, in my tight, wet, juicy, silky, slutty, dirty little cunt, sir." She gave him a naughty smile. I still found the word hard to say, but clearly Ginni relished it.

"Not in your even tighter little asshole?"

"If that's what you want, sir. My drooling little cunt and my freshly-greased, tiny asshole are both just longing for you to fuck them with that beautiful hard cock. Just fuck me, sir, however you like. But please make me come."

I was shocked at how Ginni was goading Mr. Walsh with all those filthy words. This was Ginni - the older lady who looked after all of us younger girls. But he seemed to love it. He smiled.

"Oh, Ginni, you know I'd love to make you and Alice here my best and most expensive whores. I knew the first time I fucked you that you were a deliciously dirty little minx. And between you and Susan, you're helping me to make sweet Alice here into a first-class slut. I could pimp you both out to some seriously rich men and, when you arrived, I know that your cunts would be drooling juices down your legs and you'd show the client that you were the best damn fucks in this entire city. But instead you prefer to work in my club, so I get to fuck every tight, wet hole in your delicious bodies - and you, Ginni - you beg me to do it! I am a seriously lucky fucker." He leaned in and kissed her, sliding one arm around her and cupping one of her nicely-shaped breasts with the other hand.

And then Ginni let out a little shriek, and I guessed that Mr. Walsh had stuck his dick in her. Her legs hooked around his back, and Mr. Walsh started fucking her quite hard. Ginni definitely seemed to be enjoying it; her moans got pretty loud.

"Fuck, Ginni, you're so hot. You're gonna make me come, right up your juicy cunt."

"Please - please don't do that, sir."

"What do you want instead, Ginni?"

"Come - come inside my - my tight little ass. Please, sir?"

"No, please, sir, come in my ass," I blurted out. "I need it so much, sir!"

"Oh, fuck, ladies. This is - this is more than - than one guy can take!"

He swung his hips back - and then forward. Ginni gave a loud howl. "OH FUCK!" she squealed. "OH SHIT THAT'S - OH FUCK!"

I guessed that Ginni was getting what I wanted, but just a lot more brutally. I started rubbing my pussy. I expected that, if this continued, I wasn't going to get fucked that night.

"Oh sir, please - please rub my pussy! Please, I want to come, but - but you're - you're pounding my poor ass - so - so hard!" I wasn't sure whether Ginni was moaning because she really wasn't getting what she wanted - and what I wanted. Maybe Mr. Walsh was just getting off on causing her pain.

But he turned to me. "Alice, rub Ginni's pussy. Do it, girl."

So I reached in and did as I was asked. Around a minute later, Mr. Walsh let out a loud roar. I could see that he was coming, but Ginni still wasn't there, so I kept rubbing and reached out to tweak Ginni's nipple, which she'd told me she liked. Maybe thirty seconds later, as Mr. Walsh seemed to have finished pumping his jizz into Ginni's ass, I finally got her to come too.

I was feeling very frustrated. My pussy was soaking wet, my ass was greased but unstretched - at least, unstretched by a cock - and my throat was sore from where they'd forced Mr. Walsh's cock through. They'd both had their fun, and I'd just had to watch and help out, with no release for me. I was getting pretty desperate. As Mr. Walsh had come up Ginni's ass, I guessed there wouldn't be a nice hard cock left for me.

But I was wrong. I watched them separate, and saw the thick stream of semen dribble out of Ginni's ass. "Clean that up, Alice, will you?"

"Sure, sir," I replied. I looked around for a cloth. "Do you have a handkerchief, sir?"

"Handkerchief? Fuck, no. Lick it up girl."

I was shocked, almost revolted, He was asking me - telling me - to swallow his cum that was leaking out of Ginni's asshole. I hesitated.

"Get in there, girl. Don't let it dribble all over the couch." Mr. Walsh seemed to be in quite an aggressive mood, and I wondered if anything was wrong. But it was clear that he wasn't going to take no for an answer, so reluctantly I knelt down and started lapping up the dribbling cum. To be fair, it didn't taste as bad as I'd thought it would. There was a hint of Vaseline, but I was afraid it would taste of shit, and it didn't. I guess Ginni must've cleaned up real good to start with.

"You still want to get fucked, Alice?"

"Oh, yes please, sir!" was all I could say. I must've sounded like an eager kid, but I did, desperately. Watching Ginni take it up the ass from Mr. Walsh had got me so horny, and if nobody else was going to do anything, then I'd have had to go to the bathroom and play with my pussy until I came. And really, that wasn't how I'd hoped the evening would end.

But then Mr. Walsh did something strange. He picked up the phone on his desk. "Send Louis up here."

"What? What's happening, er, sir?"

"You'll see," he replied enigmatically.

A minute later, the door opened and in walked a tall, handsome guy with slicked-back hair and a kinda half-Latino look about him. Mr. Walsh didn't seem in the least worried to be seen naked - with one of his girls effectively also naked on the couch - by one of his male employees. I could tell that, under his sharp suit, the guy had an impressive physique. His shoulders were broad, his hips were narrow like George Raft's - and there was the tell-tale bulge of a gun under the jacket. I tried to see if there was the tell-tale bulge of a hardening cock under his pants.

"Louis, meet Ginni and Alice, two of my best girls; well, two of my naughtiest girls who aren't working your floor. Ladies, I don't think you've met Louis before. He's been running the third floor very successfully for a while, and I've just promoted him. Dutch Shultz's boys hit my downtown club three nights ago. They murdered the manager and also killed a customer and two of the girls working there in a shoot-out. So I'm fucking furious and I need to get even. For now, I'm going over to run the place myself for a few weeks until I'm happy that it's secure, and I can get the clientele back and appoint a new manager. Susan and Pauline will be coming with me; maybe Ginni too, if she's nice to me. In the meantime, Louis here will be taking over, running this joint. You might find it a good idea to be nice to him - kinda how you're nice to me. Understood?"

I looked Louis up and down. He was maybe thirty, built a little like a boxer but much prettier, and seemed very confident-looking. It looked like Mr. Walsh wanted to make sure that our sexual needs, and those of his protégé, were being taken care of. "Yes, Mr. Walsh," Ginni and I chorused.

"Now, Louis, one of the perks of the job is you get to fuck the horny little sluts who work here; not just the girls on your own floor. Now, Ginni, here, whose delightful assets are on full display, has encouraged me to fuck her to within an inch of her life tonight, so I don't think she's ready for another cock just yet. The delightful Alice, on the other hand, is wearing nothing but stockings under that skirt. The only thing she's had penetrated this evening is her throat, so she's absolutely dying to get her ass fucked - aren't you my dear?"

"Y - yes, Mr Walsh." Well, I had been hoping to get Mr. Walsh's cock inside me. I wasn't sure about this stranger, even though he was good-looking.

"Oh, and Louis; a word of advice. If you make Alice, or any of my girls, pregnant, I'll cut your balls and your cock off and feed then to my guard dogs. Understood?"

"Sure, Mr. Walsh. So are you saying..."

"What I'm saying, Louis, is that Alice here, and several of the other little minxes around this club, have discovered that they need regular sexual exercise. It seems that their boyfriends - or, in the case of ladies like Alice here, their husbands - are not doing the business. Now Alice is one of my favorite little bitches. She makes the most delightful noises when I fuck her ass, and I love to feel that sweet little butthole throbbing around my dick when she comes. She's not quite as dirty as Ginni here, or as enthusiastic as little Gladys to get a dick in her ass, but she's classy and has a great body, and she performs for me just fine. So assuming that Alice is willing, I'd like you to fuck this little cutie until she makes those lovely little noises. Alice, would you like that?"

I looked at Louis. He was a big guy. He could easily overpower me, make me do whatever he wanted. But he didn't seem to be like that brute Jimmy who'd abused Susan. For a moment, I pictured what it might be like to have him, naked, between my legs, or sliding his cock in my asshole.