Chapter One — the tools of the trade

“You do realize what’s gonna happen to you here, don’t you, Alice?” Ginni looked at me with some concern.

“What do you mean?” I’d taken the job at the speakeasy because — well, because there wasn’t any other work around. I started just waitressing, but then after a couple of weeks one of the girls left because her husband got a job in Chicago, and they moved me to selling cigarettes and cigars from a tray. The outfit they — well, mostly Mr. Walsh — wanted me to wear was a little risqué, I guess. It was cut rather low at the top, and showed more of my boobies than I was comfortable with, and the skirt was short — above the knee — and had all these layers of frilly petticoats that made it stick out. But I got to wear real silk stockings, and the customers — well, at least the guys — all seemed to like it. I got some good tips and I sold lots of cigarettes and cigars. Mr. Walsh gave me a bonus for every fifty packs I sold, and every little helps, as they say.

I know Benny wasn’t happy about me working there. I never told him it was a speakeasy, or he’d have stopped me from going, but he was out of work so we really needed the cash. And it paid well. With tips, I could make about as much as Benny had been earning before the Crash, two years ago.

Ginni looked at me with a concerned look on her face. “How long have you been working here, Alice?”

“About a month,” I replied. I was sure she knew when I’d started.

“And do you like it?”

“Sure. I mean, the hours are not fun, but the money’s good.”

“It is. And I guess you need the cash?”

“Ginni, what are you asking? Of course I need the cash — we all do. I mean, none of us would be working in an illegal joint like this if we didn’t need the cash, now would we? So what’s the terrible thing that’s gonna happen to me?” I guess I was getting a little irritated with Ginni. She was nice enough, but she seemed to think like she was the one that knew everything and kinda acted like my mom.

Sure, she did seem to look out for us younger girls — I guess Ginni was around thirty, thirty-five, and most of us were between eighteen and twenty-five. Me, I was twenty. Benny and me had been childhood sweethearts, and we got married when I was just nineteen. Benny was two years older — he was my brother’s best friend. He’d gotten himself a real good job at the freight company, and was headed for being a junior manager after another year, when the Crash came and the company closed down. We were gonna start a family, but we figured that another mouth to feed wasn’t what we needed right away, so we both went to look for work.

Susan, a girl I’d known at school, suggested the speakeasy job. She said they needed more girls to wait tables. Business was booming, and they’d opened a new joint in the Lower East Side. Susan got me the interview and Mr. Walsh had given me the job on the spot. Like I said, the hours were pretty bad — start at five, get home around three in the morning, sometimes later — and Benny had asked me what sort of a place it was. I told him it was a club, and he wanted to know that I wouldn’t be doing anything I shouldn’t. Well, there was plenty of drinking going on downstairs, and cards and craps on the floor above. I’d seen a few other girls come in — real pretty girls — who I knew weren’t waitresses or croupiers, but they just passed through the bar and headed upstairs, so I never really spoke with them. I figured that if anything was going on that Benny wouldn’t approve of, it was happening somewhere that didn’t concern me.

But now Ginni had me worried. “Alice, has Mr. Walsh touched you yet?”

“No — just, just patted my arm once or twice. I think he likes me.”

“Oh, I’m sure he likes you. You’re blonde, pretty, slim with a nice figure. But you’ll be seeing a different side of him real soon, I’m sure.”

“Ginni, now you’ve got me really worried. What — what are you trying to say?”

She pulled me to one side, out of the bar and into the stock room where we kept the booze and smokes. “Alice, Mr. Walsh knows for certain that you need the money now. You’ve settled in well and he’s been watching you. Sometime soon — I guess in the next week — he’s gonna ask you into his office. I suggest you go and do everything he asks. I don’t think you’re gonna like it, but if you don’t do it, he’ll fire you on the spot. So it’s best you know about it and you’re prepared. That way it won’t — I mean, it’ll be better.”

“What — what will he do?” Ginni had got me really scared by now.

“Alice, you’re a married woman, ain’t you?”

“Sure, that’s right. And I Love my Benny…”

“You’d best not think too much about Benny. See, Mr. Walsh has particular tastes. He’d be happy to show you some things that maybe young Benny hasn’t introduced you to.”

My face must’ve been a picture of shock and fear. “Ginni, you don’t mean that he’s gonna make a pass at me?”

Ginni laughed. “Alice, honey, you’re so innocent. Look, Mr. Walsh is going to introduce you to his…” she glanced around, and lowered her voice “his d-i-c-k, and you’d better be ready.”

“But Ginni, I could never let him do anything like that. I’m a — a happily married woman!” Actually, my marriage to Benny wasn’t all moonlight and roses, but generally speaking, we were OK.

“Keep your voice down, girl!” Ginni hissed, glancing back out to the bar. “Sure, that’s right. So what’ll you do when Mr. Walsh asks — or most likely tells — you to undress in his office?”

“I — I’ll quit! I won’t put up with — with that sort of thing.”

“Sure. I pass the soup kitchen on my way to work, so I’ll say hi to you and Benny on my way past.”

“I’ll — I’ll just have to get another job.”

Ginni laughed. It wasn’t a happy laugh. “And who’s gonna employ you, girl. You’re here because there ain’t nowhere else. And Mr. Walsh won’t be handing out no references.”

“Oh God, Ginni. What can I do?”

“You can do whatever Mr. Walsh tells you to do. And you make out that you like it — or leastways, you don’t scream too much. And if he wants some more, then you go back for more.”

“But that’s rape. I’ll go to the cops!”

Ginni laughed again, this time for longer. “Oh if that don’t beat everything! First of all, how will you explain your job? ‘Oh, officer, I work in an illegal speakeasy where they have drinking, gambling and whoring, and my boss tried to rape me.’ I’m sure they’ll be sympathetic. Second, do you think the cops would believe you anyway over a guy like Mr. Walsh — rich, smooth and in a tux? Thirdly, if they did, then Mr. Walsh wouldn’t take too kindly to having cops visiting his establishment, and you and Benny may end up being fished out of the East River. Oh, and finally, see that guy over there, the one in the sharp suit?”

“The one with the big cigar?”

“Yeah, him. Know who he is?”

“No.”

“Commissioner Graham. The chief of the local cops.”

“Oh my!” I was now shaking with fear. What could I tell Benny? “He might — he might make me pregnant. That would be dreadful!”

Ginni smiled. “Well, Alice, my girl, there I have some good news for you. See, you won’t get pregnant where Mr. Walsh likes to stick his dick.”

I looked at her blankly. She had an exasperated expression on her face. “He ain’t too interested in what you have between your legs girl. You can save that for Benny. No, he likes girls to suck him and then take it up the butt.”

I almost fainted, but she caught me. I must’ve looked at her like I’d seen the end of the World coming. “Look, Alice, it ain’t all that bad. And if you do it for him, you get to keep your job, and maybe even get a raise.”

“But I can’t, I can’t! I — I’m sure it would hurt like hell. And what would Benny say?”

“Benny doesn’t have to know. And if you’re stupid enough to tell him, you could end up getting him killed. Some guys would get mad enough to try to pick a fight over something like that, and with Mr. Walsh, they’d only wind up dead. Does Benny have a job right now?”

“He’s looking real hard…”

“Like every other guy I know, so I guess that means ‘no’?” I nodded, feeling pretty miserable.

“Look…” Ginni stroked my hair and smiled. “It’s really not that bad. There are things you can do to make it not hurt too much. I can help you.”

“Has he — has he — done it — to you?”

Ginni smiled again. “Look out there. Into the bar. What do you see?”

“I — I dunno. Customers eating, drinking, smoking. Waitresses serving…”

“Sure. And there’s not one of those gals who hasn’t been through what you’re gonna go through. Sure, one or two girls left afterwards, and one — Connie, remember her — she walked out rather than do it. She had to move back in with her folks. I guess they’re finding it real hard right now. But the rest — they did what Mr. Walsh wanted, and they stayed. So if you don’t wanna try explaining to Benny why you lost your job, I’d suggest you do what Mr. Walsh wants and keep your mouth shut — unless Mr. Walsh wants to stick something in it.” She laughed at the look of shock on my face, then gently rested her hand on my shoulder. “It”s OK Alice, it really ain’t such a big deal.”

But it sure seemed like a big deal to me at the time. When I got home, I couldn’t sleep. Benny knew something was wrong. I told him I’d had a fight with someone at the club and that I was worried that I might lose my job. That sent him into a panic, so I realized that what Ginni had said was true; I had to go through with this or we’d be in real trouble.

The next night at the speakeasy, Ginni called me into the toilets. “Here,” she said, handing me a small bag, “you might like to use these. They’ll make it easier when Mr. Walsh decides he wants you.”

I looked inside the bag at the strange contents; a large carrot, a jar of Vaseline, a rubber tube with a bag at one end, a small rubber ball with a piece of string through it. I gave Ginni a puzzled look.

“See, what you have to do is to make your butthole less tight and able to take a dick when the time’s right. First, you’ve gotta get it clean. You fill the bag with warm soapy water and hang it on the cistern in the toilet. Then you empty yourself out, push the tube up your butt as far as you can, open up this clip and maybe squeeze the bag. When you feel that you’ve got a lot of liquid inside you, you close the clip, pull the tube out and empty it all out in the john. Then you do it again a few more times until the water’s comin’ out clean. Make sure you put plenty of Vaseline on the end of the tube so’s it’ll go in your butt easily.”

This sounded revolting, but I guessed I needed to do it. “Is that really necessary, Ginni?”

“It is. Next, you take some more of the Vaseline on your fingers and you coat the inside of your butthole with it. Work your fingers in deep — try to get two or even three inside if you can. Then you use the carrot.”

“I was wondering what that was for.”

“Yeah, well it ain’t for no coleslaw, I can tell you. It’s tapered, so when you push it up your butt it stretches you a little at a time. Don’t forget the Vaseline or it’ll hurt like Hell!”

“It sounds like it’ll hurt like Hell anyway.”

“Not if you take it slow. The more you do it with the carrot, the less it’ll hurt when Mr. Walsh’s dick goes in there. Just don’t go using the carrot for Benny’s dinner.” She smiled. I didn’t think it was funny, as it was my butthole that would be receiving the carrot.

“What’s the ball and string for?” I asked, dreading the answer.

“OK, so when you’ve got your butt-hole stretched, you pop the ball inside. Make sure the string’s hanging out, or you’ll never get the ball back and that could be embarrassing! And don’t forget to use lots more Vaseline! “

“And then what?”

“Well, you can do two things. Mostly the ball is to keep you open and stretched so’s you don’t close up tight again. You leave it in until Mr. Walsh calls for you, then you take it out and put in some more Vaseline. But you can also pull it out — slowly, mind — and then push it back in again. That’ll get you used to the feeling and help you relax when his dick head goes through the hole.”

“It all sounds pretty awful to me.”

“Well, you may not find it too bad. Your friend Susan seems to like it.”

“Susan? What? I mean, how can you say that?”

“Because she’s volunteered to do it instead of other girls when they get scared. Sometimes she goes in with a new girl and helps them through it.”

“Well, if she likes it so much, maybe she can do it instead of me.”

“I don’t think Mr. Walsh will let that happen. He picked you out to be the cigarette girl, didn’t he? He’s been watching you since he hired you. He wants you, and he won’t take no substitute.”

I looked at the contents of the bag. “Have you — have you tried this? I mean — has he — has he done it with you.”

“Oh yes. On both counts. Although in my case, I only found out about the — shall we say, ‘tools’ — after Mr. Walsh had — had already opened me up with his dick. Believe me, you’re much better off trying it out with the tools first.”

“Did it — did it hurt — a lot?” I was feeling worried again.

“Oh yes — the first time.”

“You mean he — he does it more than once?”

Ginni laughed, but there was no humor in that laugh. “Oh sure. He wants it most nights. Sometimes he wants it more than once a night. Sometimes it’s a waitress, sometimes a croupier from the second floor, sometimes — though not often — it’s one of the girls from the third floor. Usually he just does it to them when they first arrive, to check that they’ll do what he and the customers like. He doesn’t usually bother them after that. See, if he’s giving it to them in his office, then they ain’t earning money for him from the paying customers — upstairs. But you, me, the other waitresses, he can use us however he likes. The only thing is that it doesn’t hurt as much once you’re used to it. In fact, sometimes it can feel good.”

Like I said, I’d sorta guessed that things went on in the place that were more than drinking and gambling, and Ginni had just confirmed it. I sure didn’t want to be one of those girls. But it seemed that I still had to have perverted Sex with at least one man, despite being a married woman.

“I still can’t see how it can feel good,” I said, feeling rather depressed at the thought of having to do this — this thing — with my boss.

“Tell me, Alice. Do you enjoy Sex with Benny?”

“I — that’s a very personal question, Ginni,” I replied, a little embarrassed.

“Sure it is. But it’s no less personal than having Mr. Walsh’s dick up your butt, which is what we were discussing. So tell me — does it feel good now, and did it feel good the first time.”

“Well, yes, I suppose it does feel good now, but that’s because I Love him. It’s quite exciting while it lasts, I suppose. But the first time, well, no that wasn’t so good. It hurt, and it didn’t last very long at all. I bled a lot.”

“Well, imagine that this is the same. The first time it hurts. You’ll be tight and tense, and a guy’s dick ain’t meant to go where he’s gonna stick it. But the next time, well, maybe you’re a little more relaxed. Maybe you’ve had a drink or two first. Maybe you’ve prepared better, cleaned up, used more Vaseline. So maybe the second time is easier. And then the third time you get to thinking ‘Hey, Mr. Walsh ain’t bad looking for an older guy.’ And he’s so nice when it’s over, and he gives the girls little presents. And maybe, maybe if you play with yourself while he’s doing it, then maybe it feels good. Then the next time, you get used to the sensations, and you start to enjoy it.”

I looked at Ginni in amazement at the things she was saying. “Ginni, I — I don’t think I should be — playing with myself like — like that. Good girls don’t — don’t do — things like that.”

She laughed again. “Girl, where did you grow up? Good girls don’t take a guy’s dick in their butt, so if you’re a good girl now, you ain’t gonna be when Mr. Walsh has finished with you. I suggest you try it. It might make things much easier when your time arrives.”

I was just about to say something when Susan came into the room. “There you are. They’re looking for both of you out front. We’re getting low on whiskey and that guy over there needs some cigars.”

I took the bag of ‘tools’ that Ginni had given me through to the changing room next door and hid it at the back of my locker. Then I picked up my tray, checked myself in the mirror and went back to work.

When I got home around 3am, Benny was sound asleep. It had been a strange night. I don’t know why but I got more tips than normal. Maybe there was something in my nervous smile that made guys want to give me the money. Inside, I was in turmoil after what Ginni had said. Any time soon, I could get the call to Mr. Walsh’s office, and I’d have to endure having a dick forced into my butt. Could I take it? Would I bleed, like I had when Benny had taken my virginity? Would I just have to stop working and lose all that lovely money that was so important to us?

I went into the bathroom and locked the door. I undressed and had a long hard look at myself in the mirror. Sure, I was pretty. Guys complimented me on my blonde hair, big blue eyes and wide, friendly smile. If they were a little bit drunk, and didn’t have their wives anywhere near, they sometimes complimented me on my nice figure, though the more sober ones would check my ring finger first.

I knew my Benny loved me, and I loved him. We’d first had Sex on our wedding night when I was just nineteen. That was a year and a half ago. Like I told Ginni, it hurt the first time, and after that it felt OK but not how I had imagined it. Sometimes it was a little sore — I wasn’t always very wet when Benny went in. Sometimes he’d play with me with his fingers, and that felt nice, but he never did it for very long, and when he put his dick into me, it was usually a disappointment. Once or twice it would start to feel nice, and then Benny would moan and squirt his juices into the rubber, and that would be the end of it.

It was a Hot night — Hot like only New York seems to get in August — so I ran some cool water into the tub and soaked for a little while. Then I got out, dried myself off, and sat on the toilet seat, looking at the contents of Ginni’s bag. I didn’t feel like I could sleep, so I thought I may as well try the stuff out.

The douche felt weird. I lubed up the tube and did as Ginni said, four times, until I was squirting mostly clear water out of my butt. By the fourth time, it didn’t seem quite so revolting. Then I got some Vaseline on my fingers and worked it into my butthole. ‘Christ’, I thought as the first finger went in, ‘that feels big enough’. Strangely, though, it started to feel quite nice in a rather perverted way. The second finger was more of a stretch and a little uncomfortable at first, but I found that if I rubbed my fingers around maybe a couple of inches in, it actually felt — well, not pleasant exactly, but a little exciting. To my surprise, my Vagina started to get wet.

So then I thought about the carrot. Looking at it, it seemed like such a totally non-sexy — thing. But I could see why Ginni had recommended it. The skinny end would slide in easily, then it would increase the thickness until it was the size of one, then two fingers. And then it got bigger. I guessed that the big end was about the thickness of Benny’s dick. I hoped I wouldn’t need to go that far. It didn’t occur to me to wonder whether Mr. Walsh’s dick was any bigger than Benny’s. I assumed they were all the same size.

So I covered the carrot in Vaseline, and slowly started to slide it up my butt. The funny thing was that, having used my fingers, it didn’t feel quite so strange. The sensations as I slowly eased it in and out were no worse than feeling Benny’s dick in my honeypot. Actually, in some ways it felt a little better than that.