Speakeasy Girl Ch. 02

Chapter Two -- Giving it everything

It was two days later that Susan came up to me around midnight and said "Mr. Walsh would like to see you in his office after work. He's asked if I can go along too. You -- you do know what he wants?"

"I -- I guess so." My heart was suddenly fluttering. I'd practiced with the carrot twice more since the first time, and I was kinda liking it, but this was the real thing and I still felt scared.

"Don't worry, Alice. I'll be there to help you. I promise it won't be so bad. I'll show you what you have to do." Susan smiled disarmingly, but I guessed this was gonna be a bit of an ordeal.

Like I said, I'd used the 'tools' several times, and I'd tried keeping the rubber ball in my butt for up to an hour at a time during the day. I'd also tried Ginni"s suggestion, pushing it in and then taking it out, and after the first few times it didn't hurt and started to feel -- well, interesting. So when Susan warned me it was my turn to visit Mr. Walsh, I took the first opportunity I could to douche, fill my butt-hole with as much Vaseline as I could, work it with the carrot and then slide the rubber ball inside. It was the first time I'd kept the ball in place at work, and it felt strange to be sashaying around the club selling cigarettes to the customers with this soft, springy thing rubbing against the insides of my butt. And the strangest thing was that it didn't feel painful or unpleasant. Now that my butt was used to the sensations, it actually felt rather -- well, perhaps not 'nice', but certainly a little naughty in a good way. My honeypot started getting wet.

But I was still awful nervous when Susan led me into Mr. Walsh's office. I'd only been there twice before. It was a very big room on the third floor, reached by a private staircase guarded by Johnny and Paddy, a couple of heavies who worked for Mr. Walsh. The carpet was beautiful and deep, there was a big desk with a leather swiveling chair, a leather couch, and a couple of big side tables with crystal decanters full of liquor and some expensive lamps. Windows with some beautiful drapes looked out on two sides into the bar and the gambling floor. I found out later that he also had some hidden panels to look into the rooms on the third floor where the 'other activities' took place.

Most of the customers were gone or leaving from the bar and the poker and craps tables by this time, and I noticed that the drapes were closed.

I'd taken the ball out of my butt in the toilets about ten minutes earlier. Actually, I'd taken it out and pushed it back in again a few times, just to make sure my butt was as loosened up as it could be, and because -- oh, God, this is going to sound so dirty -- and because I actually liked the sensations. I was surprised to find just how wet my honeypot was when I pulled my panties back up.

When I walked in with Susan, Mr. Walsh smiled at me. Yes, like Ginni said, he was handsome in a rugged sort of way. I guess he was about forty, tall, with broad shoulders, tanned with gray curly hair and very blue eyes. He looked pretty powerful and sophisticated in his tuxedo. When I walked in, carrying my tray, he came across to me and selected the largest Cuban cigar I had, sealed into a metal tube. He lifted the tube up in front of my face.

"Good evening, Alice. Can I offer you something like this?"

"No thank you, Mr. Walsh. I -- I don't smoke."

"You don't need to smoke," he said with a smile. "You just need to put it in your mouth and suck on it. Isn't that right Susan?"

"Yes, Mr. Walsh," Susan said.

"Good. You see, Susan understands these things. Put down that big tray, Alice and let me get a proper look at you."

I put the tray down on one of the tables at the side of the office and took off the strap that went behind my neck. Then I went and stood in front of Mr. Walsh with my hands behind my back, feeling nervous.

"My, you're pretty, Alice. How old are you?"

"I'm twenty, nearly twenty-one, Mr. Walsh," I answered, trying to sound happy.

"I understand you're married?"

"Yes, Mr. Walsh."

"And does your husband... what's his name?"

"Benny, Mr. Walsh."

"And does Benny like it that you work here?"

"He -- he's glad of the money I make, Mr. Walsh," I told him truthfully.

"Hmmm. And, you, Alice. Do you enjoy working here?"

"Sure, Mr. Walsh. It's a nice place."

He smiled again. "Good, I like my girls to be happy. But Alice, has Susan told you about the extra services I expect from my girls?"

"Y -- yes, Mr. Walsh." I blushed.

"Good. So it won't be a surprise to you when I tell you to suck my dick, then?"

"I -- I..."

He seemed to enjoy the flustered look on my face. "Does Benny enjoy it when you do that for him?"

"I -- Mr. Walsh, I -- don't -- I don't suck Benny's -- d-dick," I stammered. I was a little confused. I remembered that Ginni had mentioned this, but I'd only thought he would mostly just wanted to bend me over and put his dick in my butt.

"But you have sucked dick before, Alice?"

"N-no sir. I -- I sorta -- sometimes -- kinda lick him a little, but -- but I've never..."

"Open your mouth Alice, as wide as it'll go."

People tell me my mouth is a little on the large size. I opened as wide as I could, and then Mr. Walsh took the cigar tube and guided it into my mouth. I felt it touch somewhere near my throat and suddenly had the urge to throw up. He must have noticed, because he pulled the tube back a little.

"Close your mouth around the cigar, Alice. Try not to touch it with your teeth. Press your tongue against it. Good."

He slid the metal tube in and out of my mouth about a half dozen times. The metal didn't taste too good, but otherwise -- apart from the way it felt sorta dirty and depraved -- it wasn't too bad. He seemed to get bored with his little game quite soon, so he put the cigar down on the desk beside him.

"Good, Alice. That's the basic idea. Perhaps Susan would like to show you how it's done. Would you like that, Susan?"

Susan gave a broad smile. "Sure, Mr. Walsh." She got down on her knees and unbuttoned the fly of Mr. Walsh's pants. She lifted his dick out, and it was only sorta half-hard, but she took all of it in her mouth and started sucking on it. I watched as she looked up at Mr. Walsh for approval, and he reached down and stroked her long dark hair.

Mr. Walsh was obviously enjoying Susan's mouth, because he kept muttering "Oh yes," and making little moaning noises. I watched as Susan started rocking her head back and forward, and I could see that Mr. Walsh was now hard, and quite a lot of his dick was going in and out of Susan's mouth.

"OK Alice, I'd like you to take your dress off, please."

The dress fastened up the front with little hooks, so I undid them carefully so as not to damage my nail polish. I slipped the dress off and draped it over the chair. The underwear they'd given me when I got the cigarette-girl job was really nice. There was this silky black corset that pushed my boobies up so that the dress could show them off, and cinched in my waist. They'd also given me three pairs of silk French knickers to wear, though I had to take them home and wash them myself. And there were silk stockings, not the cheap lisle ones that the waitresses wore, with silk garters that fastened high up my thigh. It was all much more expensive than I could afford to buy. Benny liked to see me wearing the corset outfit at home sometimes -- the dress had to stay at the club.

It seemed that Mr. Walsh also liked to see me in it, because he had this big smile on his face -- though I guess that may have been because Susan was sucking his dick. He looked me up and down and said "My, Alice, you look so pretty in that outfit. Now I need you to get a cushion from the couch, put it on the floor here and kneel on it. Oh, and before you do that, I'd like you to take off your panties. Can you do that for me, Alice?"

"Y-yes, Mr. Walsh," I stammered. I turned around and slid the French knickers off. I put them on the chair with my dress, picked up a cushion from the couch and, holding it in front of my bush, walked back to where Susan was still kneeling, sucking Mr. Walsh's dick.

Mr. Walsh was looking more flushed. "Now Alice, don't be shy. I -- oh yes, that's good, Susan! OH! Oh yes! -- I -- I really want us to be friends -- intimate friends. Put that cushion down and -- and let me look at you."

I dropped the cushion onto the floor beside Susan and immediately moved my hands to cover my bush.

"Alice, stop being so demure. Take your hands away and show me what you've got."

Reluctantly I moved my hands to my sides.

"Alice, that looks very alluring. I love blonde -- no disrespect to young Susan here -- and you keep your curls nicely trimmed, I see. Now, I think it's time we gave Susan a rest and you showed me what you can do, don't you?"

"I -- I guess so, Mr. Walsh," I said, a little shakily. I knelt down on the cushion, taking care not to snag my lovely silk stockings.

"Good. Now Susan, baby, stop for a moment, please. Please, Susan?"

Susan pulled her head back. A line of saliva trailed from Mr. Walsh's cock to her mouth. "Didn't you like what I was doing, Mr. Walsh?"

"Susan, that was excellent, but you know that if I let you carry on you'd get a mouthful of spunk and poor Alice would get nothing, and we can't have that, now can we?"

"I guess not, Mr. Walsh, sir," she said with a little pout.

"It's OK Susan, you'll get all the things you like a little later. For now, I want you to help Alice to learn to do the things you do for me so well. Now Alice, will you please open your mouth wide like you did before, and suck my dick like you did that cigar?"

I looked up at him. He was smiling down at me, his dick, wet with Susan's saliva, bobbing a few inches from my face. "C'mon, Alice. I promise it won't bite you. Just make sure you don't bite it. Just give it a nice, deep suck, the way you saw Susan doing."

I took a deep breath, closed my eyes and opened my mouth wide, moving forward so I could feel the head of his dick slide into my mouth.

"Careful with your teeth Alice," Mr. Walsh warned, and I felt him push his dick deeper into my mouth.

'Damn, this is hard,' I thought, trying to work out how to keep my teeth out of the way while letting him use my mouth like it was my honeypot. I'd worked out that if I curled my lips down over my teeth, I could avoid scraping his dick. I started getting used to it, and to be honest, it wasn't too bad. I found I could take quite a lot of it, but he didn't make it any easier for me, as he kept pushing his dick deeper and deeper into my mouth, until I felt I was gonna puke.

Then I heard Susan say "Hey Mr. Walsh -- can I have another suck, please?"

He pulled his dick out, making me gasp, and I saw him stick it straight back into Susan's mouth. If I thought he was a little tough on my mouth, then he was even less gentle with Susan. He was shoving it in, hard and deep, and she was making little noises in her throat like she really was gonna throw up. The expression on Mr. Walsh's face showed he was really enjoying what Susan's mouth was doing to his dick. His eyes were closed and he was breathing heavily. I guessed that any time he was gonna be squirting his stuff into Susan's mouth. I wondered what it would taste like.

But then, to my surprise -- and, I think, Susan's -- he pulled out again. He was breathing hard and I could see his dick, throbbing and glistening.

"Thank you -- thank you, Susan. An excellent -- first course. But now -- now I need to -- move to the main event -- with young Alice, here. Stand up -- please -- both of you."

I climbed to my feet, still shaking a little from what Mr. Walsh had already done to me, and what I knew he was gonna do next. I guess I'd been hoping that he really would squirt into Susan's mouth, and then I wouldn't have to -- have to...

Mr. Walsh suddenly cupped his hand around my bush and slipped his finger into my slit. I gasped.

"Well, Alice, I'm very pleased with you so far. Not only are you learning to suck my dick, but it seems that something's got you nice and juicy." He rubbed his finger back and forward, and I let out a little moan. "You like that, don't you?" His face was inches from mine. He looked flushed, but he had this wicked smile on his face.

"Y-yes, Mr. -- AH! AH! -- oh yes! Oh!" was about all I could say.

"Oooh, you really do like that, don't you. And your sweet pussy is nice and silky and wet. I bet Benny's hardly stretched you at all. Maybe I should try out that wet little cunt for myself."

I gasped. I don't know whether it was because of what his fingers were doing in my slit, or the way he used such a crude word so casually to shock me, or because I was terrified that he'd do what he'd just said and put his dick in my honeypot and make me pregnant. Certainly his fingers felt good.

"P-please, Mr. Walsh. Don't -- don't -- don't make me pregnant," I stammered.

His fingers pressed deeper, probing inside me. It felt exciting. The sensations were some of the best I'd felt.

"Alice my dear, I have no intention of doing that. But your sweet cunt is so tempting. You're deliciously wet, so I guess you must be quite excited by what we're doing. Or is it the thought of what we're going to do?"

"I -- I -- don't know, Mr. -- OOOH! Mr. Walsh, that -- that feels so nice, I ..."

"Oh I'm sure it does, young lady. Who would have guessed, with your sweet face and your big blue eyes and your demure little looks, but it seems you're quite a little slut, Alice."

"Mr. Walsh, I'm not. Really -- really I'm -- OH! OH! OH!" His fingers were doing amazing things inside my slit.

"Now, Alice, being a slut isn't a bad thing. No, not at all. You say you don't want me to make you pregnant?"

"Pl -- Oh! OH! Mr. -- Mr. Walsh. I -- no, please don't -- AH! AAH!" I couldn't make any sense right then, the sensations were getting to be so good.

"So that means you don't want me to fuck your tight little cunt?"

I was shocked again at the way he used such crude words so casually. "N-no -- no sir. Please -- please don't."

"Hmmm. Well, I've already sampled your mouth, Alice, so that leaves just one hole to try. You don't want me to fuck your cunt, so I guess you want me to fuck your ass instead. Is that right, Alice?"

By now I didn't know where I was or what was happening. The sensations between my legs were so raw, so strong that I didn't want them to stop. My heart jumped every time Mr. Walsh used those crude, ugly words to shock me. And now he was asking whether I wanted -- actually wanted -- to have him put his dick in my butt. How could I say that no, I didn't want his dick in my butt or my honeypot. All I really wanted was for him to keep rubbing my slit like he was doing until I had another of those weird, delicious explosions I'd felt the other night.

"I -- I..."

"Don't play games with me, girl," he said softly but with an edge to his voice. "Do you want me to fuck your cunt or your ass?"

How could I respond to that? I gasped "my ass," in a weak voice.

"Sorry, Alice, what was that?"

"My -- my ass, Mr. Walsh. Sir..." I murmured, trembling now with a combination of fear and excitement.

"Speak up, girl. If you don't want me to fuck your wet little cunt -- which seems a shame, as it feels so nice in there..." He swirled his fingers inside me and I let out a squeal from the strength of the sensations. "...then you need to ask me -- nicely -- to fuck your ass. Can you do that, Alice?"

I was now a total mess. The sensations from my slit were just incredible, and I was desperate for him to continue. I really, really didn't want him to put his dick inside my butthole. But he was goading me, making me ask him -- beg him -- to do the thing I was dreading, so that he wouldn't do the thing I was dreading even more.

"Oh Mr. Walsh! I -- I don't use words like that. AH! AH!! I'm -- not that -- kind of girl...!"

"Sure you are, Alice. I know a slut when I see one -- and feel one -- and I've got my fingers up a slut's cunt right now, and she seems to be loving every minute." He did something with his fingers and I nearly swooned. "So please, Alice, do as you're told. Ask me nicely to -- to do exactly what it is that you know you want. Do it now, Alice, or I could lose my patience with you. I don't like little sluts who jerk me around. Of course, if you really don't want it, then Susan here will be glad to oblige me -- and to become the next cigarette girl..."

This was it. I had to do what I'd been dreading or lose my job. "P-please Mr. Walsh. Please -- please... please f-fuck me in the -- the ass. Please."

"Now, that wasn't so hard, was it Alice. I'm so pleased you want it, because I want to fuck your peachy ass just as much as you want me to fuck it. Susan, my dear? Could you please make sure there's plenty of Vaseline in Alice's asshole?"

I watched Susan go around Mr. Walsh's desk, open a drawer and take out a jar of Vaseline. I guessed she knew from experience where to find it. I couldn't believe what was happening here. Susan and me, we'd been good, Catholic-school-educated girls. OK, so I let Benny feel me up, and I even stroked his dick, before we were married. But I'd been a virgin on my wedding day, and I'd always thought that Susan was the same as me. I was shocked at her behavior; she wasn't even married, and she seemed to be willing to do so many totally depraved things.

But now it was me who had to do the depraved things. Mr. Walsh turned me around and told me to lean forward, place my hands on his desk and stand with my legs wide apart. I almost growled in frustration when he took his hands away. I so needed those sensations to keep me excited.

Then I felt a cold stab, as Susan pressed a large blob of Vaseline onto and around my butthole, and worked a finger inside me. Like I said, I'd used the ball less than half an hour earlier, so I wasn't as tight as I might have been, but the shock of the cold jelly in my butt made me tense up. Susan slipped a finger right in, then, after a few strokes, stuck in a second one.

"I think she's ready, Mr. Walsh," she said after only a few moments.

I wanted to scream "No I'm not! My butthole is really tight and it's not ready to be forced open by a dick!" But I could say nothing except to whimper "please, please put your fingers back -- back in my slit. Please?"

"Susan, play with Alice's pussy while I fuck her ass, will you? Alice, are you ready?"

"I -- I don't know, Mr. Walsh. I mean..."

"Alice? Are you ready? I can't wait forever, you know. You tease me by asking me to fuck your ass, and now all you can do is bleat about having your pussy played with. Now ask me again, and ask nicely, and then get ready to receive what you told me you wanted. Understood?"

"Yes, Mr. Walsh." By now, there were tears running down my cheeks. I knew I didn't want this at all. So OK, the game with the carrot and the rubber ball had been kinda fun in a strange, dirty way, but this was for real. I'd seen, touched and even tasted Mr. Walsh's dick, and to me the idea of that going into my butthole was still scary. In those days I didn't know that guys can be different sizes. Mr. Walsh was fortunately about the same size as Benny, and I'd had his one inside my honeypot lots of times. But this time it was going in my butt, and I had no choice in the matter. And he'd asked Susan -- another girl -- to play with my pussy. That seemed so perverted to me. But then having a dick forced up my butt was pretty perverted too.

I braced myself on the edge of the desk, sniffed, took a deep breath and said in a weak voice, "OK, Mr. Walsh. Please..." I took a deep breath. "Please fuck my ass." It came out in a rush; I just wanted to get it out, get it over with. "But Mr. Walsh -- I've -- I've never done this before. Please be gentle. Please?"