Speakeasy Girl Ch. 04

When I'd first gone to the table, I'd had a small jar of Vaseline hidden inside the tissue paper. I reached out for it now.

"Tom - Tom, please - please stop. I want to - to try you in - in my butt," I panted.

"Sure," he said, and pulled slowly out of me, leaving me feeling a little empty. He kept his hand cupped over my mound, and by now he was stroking my button again, making me fizz all over again.

I reached behind me and passed him the Vaseline. "Put lots of this - on your dick - please. Gotta be - well greased up - or it'll - it'll hurt." I'd already worked a lot of jelly into my ass when I was in the ladies' room, but with a dick the size of Tom's, I wasn't taking any chances.

He took the jar, removed his other hand from my pussy, and there was a pause. Then I felt the head of his dick, cold and slick with the Vaseline, press between my buttocks. I pulled my butt cheeks apart with my hands and tried to relax.

"Slow, Tom," I breathed. "Real slow." I braced myself as I felt the familiar pressure on my ring. I had grown to really like this part; the dirty, sexy, thrilling moment when I was bent over, spread and helpless, knowing that something big, hot and meaty was going to force its way into my dirtiest of holes. Now that I knew how to relax, I craved the pleasure/pain stretch and some strong and thrilling sensations as a guy's hot dick eased its way inside me. So far, that guy had been Mr. Walsh. I hadn't dared introduce butt-fucking to Benny yet.

But now the yearning to be filled and to feel all of those oh-so-naughty sensations, fuelled by the knowledge that I was behaving as a slut and loving every minute, were a little off-set by the fear that Tom might be just too big. Despite the booze-induced fog in my brain, I couldn't escape the fact that this was the biggest dick I'd ever seen in my life, and it was going up my butt. I tried to shut out memories of Susan's experience with Jimmy. "Tom isn't Jimmy," I told myself. "He's gentle and he's already made you come. He wants to enjoy you and he wants you to enjoy him, I'm sure." I had to keep telling myself that, over and over, because I knew that was the only way to relax enough to receive that hefty dick.

I guess it must've worked, at least a bit, because I felt him begin to move inside. The stretch started OK, but got more and more intense. In the ladies' room I'd done the fastest douche, lube and stretch that I could. I'd shoved the ball in and out a half dozen times, but I could hardly walk around with it in, could I? Tom's dick didn't have such a rounded head as Mr. Walsh's. It was a little more tapered and that meant the stretch was more gradual, but as he pushed deeper and deeper, the pain was beginning to outrank the pleasure and was starting to tell me that I shouldn't be doing this. I moved my hands to the table to brace myself.

"Tom, stop! Please! Just - hold it there - for a moment. Need you to - to pull back - just a little - before you - before you go in - any further."

Now I felt sure that if that had been Jimmy, he'd have taken no notice. (Susan had told me that when she'd asked him to go gentle, he'd just shoved harder and told her to 'take what you're given, bitch!') But Tom did exactly as I asked, easing back a little and then slowly pushing in some more. He did that maybe three times. Then, to my surprise, he pulled out completely. I felt him fumbling for something, and then he was back, with another cold shock of some extra Vaseline. This time he rocked his way deeper and deeper with each stroke, spreading the jelly deep into my insides.

There was more discomfort as he reached a point where no man had been before, deeper than my fingers, the carrot or Mr. Walsh's dick could reach. I winced and cried out. There were tears running down my cheeks. I was making a hundred bucks here, and it felt like I was earning every cent. And then Tom slowly pulled back and out again, applied even more Vaseline, and this time it actually felt good as he retraced his previous path. Gradually, a fraction of an inch at a time, he worked that big dick up my ass until I felt his body press against my butt cheeks. I gasped.

"OK Alice - now you have all of me. How does it feel?"

"Jesus Christ, Tom, you're so damn big! I don't know how my little ass could take it all."

"Well it has, Alice. It feels great to me. Are you ready for me to start moving again?"

"Slow. Gentle. Please Tom, just - just slow and gentle. Oh my God!"

The sensations on the backstroke were so strange. The friction that I had so enjoyed on previous occasions with Mr. Walsh, that got me excited enough almost to come - that was there, but even more intense, almost bordering on pain. And my poor little ass was protesting against the stretch, telling me that it never oughta be bent out of shape in the way it was getting right then. And the over-stretched tube deep inside me, closing up again in relief after being forced to stretch to its limits, was a sort of relief sensation. Like I say, the mix of feelings was pretty intense.

Tom pulled back to maybe halfway, then slowly pushed in again to maybe three-quarters. Then he did it again, a little more quickly, a little deeper again. Then he moved one hand onto my hip, and the other back to my pussy, and slowly increased the range of his strokes, so that, after what seemed like hours but was probably only a minute or so, his dick was moving from just inside my ring to balls-deep in my ass, slowly at first and then a little quicker.

The strange thing was that the sensations got better. I was afraid I'd get sore really quickly, as I knew the friction from Mr. Walsh's normal-sized cock could be pretty intense. With something the size of Tom's, the friction was stronger, as well as the stretch. But soon Tom was taking maybe a second to fill me and another second to withdraw almost all the way, and he was rubbing my slit, and my boozed-up brain was thinking 'there's this handsome movie star sticking his big dick up your ass and rubbing your pussy, and you're gonna come real soon.' And then I thought 'and what if he doesn't? How much more can your ass take?'

Just as I was starting to peak, Tom pulled right out - and then stuck it all the way in. And then he did it again. "Oh God, Tom, you're fucking my ass so hard!" I squealed, not because it hurt - that had died down quite a while earlier - but because he was really hitting all the pleasure spots.

"Bet - bet you like it!" he gasped back.

"Oh God yes! YES! Oh my God! Fuck me - fuck me - Tom. Fuck my ass! Oh yes!"

When he thrust right in again, I started coming so strongly, gripping his dick so hard that he could barely move it. "Oh Tom, can you - can you feel me! I'm coming - coming all around - your hard dick - fu-fucking my asssss!!" My climax was so strong I was thrashing my head up and down, and he was holding my hips steady as he kept thrusting, thrusting - and pulsing.

I felt the throb as he came and a wave of relief swept through me, joining my climax and making me feel like my body was tingling all over. One last mighty thrust had driven his dick right up into me and nearly lifted my feet off the floor. Both of us were moaning and gasping, and it seemed that the more my ass squeezed Tom's dick, the more it pulsed and pressed my pleasure points, and the stronger I came.

At last we both collapsed onto the table, the weight of his body pressing my titties onto the baize surface. Slowly, very slowly, Tom pulled back and out of me. As his dick popped out and he moved back a little from me, I felt a dribble of spunk on my leg. I grabbed some sheets of tissue paper and quickly covered and plugged the empty hole, gripping the paper between my butt-cheeks and wiping up the spillage as well as I could. Tom saw what I was doing, took some sheets of paper from the table and wrapped them around his dick. Then he reached out, put his arms around me and kissed me. It was another of those lovely, melting, sexy kisses, and it felt beautiful.

"Alice, that was fantastic. You were quite extraordinary. That was only the second time I've ever fucked a girl up the ass. The only other one was - well, she's a movie actress you may have heard of. She's somewhat larger than life, and she's been called a nymphomaniac. Anyway, she did it but said she probably wouldn't do it again because I was too big. Most girls take one look and say a definite no - even those who've taken it up the ass from other guys and liked it. But you, Alice - I've never felt a girl come so strongly like that, and certainly never from being ass-fucked. Didn't it hurt?"

"Tom, it was wonderful. Sure it hurt at first, but you were so gentle that it soon felt good, and then it felt amazing. Thank you, Tom. Thank you for everything."

"No, Alice, thank you. I'd like to see you again. May I?"

"That might be difficult. I don't think I can do anything like this at work again, and I'm afraid I can't meet with you outside, for reasons I can't go into. Maybe - maybe drop by and see me when you're next in town." I kissed him again. He was very good-looking. "Now I've gotta go."

I went to the door, picked up the banknotes and stuffed them into my garter. I was grateful that all I needed to put on was the brassiere and the dress. He helped lace me in, then kissed me again. I didn't want to leave him, but I guessed I'd been gone for maybe a half hour, and I was sure I'd been missed.

"Before you go, Alice, here's another twenty as a gift from me. It was a truly amazing experience. I'll send you tickets for my show. I hope you can come."

I took the twenty and slipped it into my brassiere. I kissed him again. "Of course I can come, Tom. You made me come twice, remember?" I giggled a little. "But I'll see whether I can make it to the show. Now I've gotta go. Wait a couple of minutes and then slip out and head down through the bar. I hope to have the pleasure again sometime."

I gave him another quick kiss, unlocked the door and opened it a little. There was nobody in the corridor, so I slipped out and headed toward the ladies' room. Just as I got there, Pauline emerged.

"Oh, so there you are! Where have you been, young lady? People have been asking for you." She looked annoyed.

"I was - with a customer," I said, a little lamely.

"Oh really? And what exactly were you doing with this customer, may I ask?"

"I was, er - entertaining him," I replied, blushing.

"And was this entertainment mostly above or below the waist? You know that Mr. Walsh doesn't like the girls here having sexual relations with the guests except with his explicit permission. And you know that the house takes a cut of any money paid?"

"I'm sorry, Pauline, I didn't." I thought hard. "The guy..." I looked around. "The guy offered me twenty bucks to suck his dick. He wanted it then and there. I couldn't exactly go ask Mr. Walsh if it was alright, could I?" I gave her a weak little smile.

"Well I hope you gave him his money's worth. Your makeup is a mess. Go and clean it up. Oh, and where's the twenty?"

I produced Tom's 'tip' from my brassiere. Pauline took it.

"I'll take this, miss. See me before home time and I'll give you your cut."

"But Pauline, I earned that!"

"Sure you did - on our premises, with one of our customers. The house takes fifty percent, that's the rule."

"Oh, that's not fair! I had to..." I looked around again and lowered my voice. "I had to swallow the guy's spunk, and I get a lousy ten bucks! The house should be grateful that I kept a customer happy."

"It is, which is why we employ you. Tidy your makeup, get a guy to buy you a glass of champagne to task the taste away, and get - back - to - work!"

I went into the ladies, shut myself in one of the cubicles and had a little laugh. I'd been so lucky with the tip. If I'd had to retrieve the money from my garter I'd have lost fifty bucks. As it was, the house got a lousy ten, and I got to keep a hundred and ten dollars. I hid the cash with my toolkit in my secret hiding place, then cleaned up my butt. The hole was still stretched, and I had to push some more toilet tissue inside to stop the leak. Then I cleaned up my face - I looked a mess, as sucking dick and getting butt-fucked had brought a few tears to my eyes.

I don't know what it was, but for the rest of the evening guys were falling all over me. I got bought another six drinks, though I only actually drank two. I persuaded two guys who were losing big-time to stay in their games and lose some more. Another guy wanted to feel me up, but I just smiled and said "maybe another time."

At the end of the evening, I'd made another twenty in tips. Mr. Walsh called me to his office, and at first I was terrified he'd decided to butt-fuck me. He'd know straight away that I'd fucked someone else. But all he said was "Alice, while you're working here, you only fuck me and people I ask you to fuck. Do you understand?"

"Yes, Mr. Walsh. But - but you made me shave my - my pussy, and you make me leave off my panties so guys can see, and so - and so guys keep making passes at me. What am I supposed to do, Mr. Walsh?"

"Alice, you told me you were a happily married woman, and you didn't want me to turn you into a whore. It seems like you're doing that to yourself now. Just because the guys like to look and touch, doesn't mean you have to sell 'em the goods." He stepped closer and to my horror, lifted the hem of my skirt and placed his hand over my mound. His finger went into my slit. "So it seems this new role of yours keeps you wet. Well, Alice, I'd love to relieve you of your sexual tension, but tonight I have to revisit Gladys's delicious ass. Susan wants to assist again, so I think there could be some three-way fun, but three's company and four is too much for one dick. Perhaps in a few days I could fit you in - or rather, fit into you. But surely, what's his name - Benny? Surely he's doing the business for you?"

I was getting angry. (Also, Mr. Walsh's fingers in my slit had started to make me horny again, but I didn't want to say so and I absolutely didn't want him to see my ass with the toilet paper still in place.)

"Mr. Walsh, this is not about me getting horny. Honestly, it's about how to deal with the customers. I want them to feel happy and come back and spend more money. It's obvious that a lot of them want me, especially after they've seen up my skirt, and sometimes it would be nice just to give one of the guys something extra, like I did tonight. It keeps them coming back, hoping that next time they'll be the one to get their dick sucked, or even feel me up a little."

Mr. Walsh looked hard into my face. "Very well, Alice. If that's how you feel, then perhaps we can give you a little license. If you decide you want to treat a customer to something special, we'll make some facilities available to you. You have to develop a signal to Pauline to let her know where you'll be, and of course the house gets 50%. I need to stress that this is your choice, Alice. I'm not trying to pimp you - I hope you understand that. How you square that with your husband and your conscience is your concern. Now if you'll excuse me, Gladys will be here soon, and she has developed this delightful technique of straddling me and riding my dick with her sweet ass while I gaze at her pink, wet virgin cunt and play with her clitoris. I'm really looking forward to it. So if you're still wet, go home and fuck your husband. Goodnight, Alice."

In the cab on the way back to my place, I was in turmoil. I'd started to sober up a little and the full impact of what I'd done began to come home to me. I'd mentally defined 'being faithful' as not letting anyone but Benny into my honeypot. I'd also kinda got the idea that my butt was for Mr. Walsh and Mr. Walsh alone. Tonight I'd given both holes, plus my mouth, to a handsome stranger, and I'd liked it so much that I'd wanted to do it again, and even begged Mr. Walsh to let me. So I'd been unfaithful to two men - and enjoyed it. And I was going home with $130 in my purse as a result. This wasn't the wages of sin that the nuns talked about back at my Catholic high school. I felt so conflicted; fidelity to my husband, loyalty to my boss, curiosity about sex and sexual pleasure - and the ability to earn as much money in half an hour as Benny earned in a month.

I'd been careful with my money and gifts. I gave Benny my basic wages, which had started at around fifteen dollars a week, had gone up to twenty bucks when I was the cigarette girl, and was now thirty as the hostess. That was more than most guys earned unless they were managers. But I also had an old tin hidden away at home where I put my tips - at first mostly dimes and quarters, but more recently a lot of bills - and the little presents Mr. Walsh and some of the customers gave me. There were a few good pieces of jewelry with real gold and real stones that I knew were worth something. When I counted up what I had, including the hundred and ten dollars from Tom and the rest I'd picked up as tips during the evening - it had been a very good night - I guessed I had close to four hundred bucks stashed away. That was enough to keep me and Benny for around six months if we didn't get too extravagant!

I thought long and hard about it. If I turned more tricks like I'd done tonight, even if I only got ten or twenty a time after the house cut, it wouldn't be long before we had, say, a years' money. And Benny had managed to get himself some bits of casual work, which brought in a few bucks here and there, so maybe we could use my little stash to give us some real security in these difficult times. I told myself that the end justified the means. If I had to - to fuck some guys for it, then so long as Benny never found out, it was OK. It wasn't like I was a common streetwalker. I mean, I'd only fuck guys that I'd chosen, rich enough to give me the cash I needed and handsome enough to provide me with the pleasure that I'd discovered I craved.

I looked in at Benny. He'd been doing some work on a construction site, and was fast asleep. I could smell perspiration. After getting so beautifully fucked by Tom earlier in the evening, I decided against waking Benny for something more. Besides, my butt-hole was still stretched and, when I replaced the tissue paper, it seemed I was still leaking spunk. So I cleaned up, then I got out my toolkit and worked the ball in and out of my ass while I rubbed my special spot and thought about Tom's dick inside me. I put a clean wash-cloth in my mouth so that when I climaxed I could bite down and muffle my noises.

When I cleaned up again afterwards, it all seemed clear. I would work at the club as hostess and (highly selective) part-time whore. I would keep that part of my life separate from my marriage to Benny. I would do what was necessary to make seven, eight, nine hundred bucks, maybe a grand. And then me and Benny, who by then I would have educated and turned into the lover of my dreams, would go away somewhere exotic and cheap like Mexico and live a comfortable life for a few years until the world got back on its feet and we could do something respectable for a living.