by Steve Shadow
“Thanks, Serge, same to you.”
We were led to a banquette towards the back of a room that was made to look like a fancy crab shack back East. We were seated. She ordered a bottle of wine from a guy in a red vest. We got menus and when I took a gander at the prices I nearly lost my appetite.
“You sure live high on the hog, don’t you? This is some joint.”
“You get what you pay for. Maybe you were going to take me for a hot dog, is that it? Shut up and enjoy yourself. Or are you a little short in the moolah department?”
“No, no, I’m fine. Just saying, that’s all.”
“Yeah, well, say something else. Let’s eat. We got to get out to the West side by midnight.”
“What’s out there? We going to some fancy roadhouse?”
“You’ll see. Maybe you’ll make some friends.”
She grabbed the menu. “I’ll order. You obviously don’t know good food for shit.”
CHAPTER THIRTEEN
Living this high life was something new to me. Of course having dinner with a lady in a man’s suit was also new to me. It was different but sure beat listening to fat Mobes squeaking all night.
First off, the guy in the red vest came back wearing a silver dish around his neck and carrying a stand with a bottle in ice. He removed the wine bottle from the stand and cradling it in a towel, showed it to Louisa. She seemed to be inspecting the label. I don’t know what she was looking for but she nodded her head and he uncorked the bottle. He placed the cork in front of us and Louisa picked it up and sniffed it. She then squeezed it and put it down. I watched all this with my trap shut because I hadn’t a clue as to what was going on. Once again she nodded her head and he poured a tiny bit of wine into her glass. He certainly knew who was in charge at this little gathering. I was just about to speak up and save my manhood when she picked up the glass, swirled it around, sniffed at it and took a sip. She swished the wine around in her mouth, making her red lips look even sexier. She swallowed and smiled at this pompous little jerk. He then poured some more wine into her glass and some into mine. After replacing the bottle in the stand, he mumbled something I didn’t understand and left.
“What the hell was that all about? Looked like a lot of crap to go through for a little grape juice.”
She now looked at me like I was someone from another planet. “No wonder you’re down to scamming fat, ugly hicks. You wanna get into the big time then you got an awful lot to learn. I just hope you pick things up fast.”
I lifted my wine glass and tilted it in her direction. “Cheers, Miss Louisa. I hope Santa brings you every thing you want.” I took a long pull. I had never had much wine but it wasn’t too bad.
“Sip it, you bozo. Sip it and taste the flavors.” Sure, I thought; what ever you say.
The waiter came to the table and she ordered the food. I figured it was best to let her take over as I was out of my element. She was a real take charge dame and I was feeling stupid enough already.
“We will have the turtle soup with extra sherry. For our entrées we’ll have the Lobster Thermidor and some grilled asparagus with tomato. Thank you, Jacques.” He bowed, gathered our menus and said something that I again did not catch. They must be talking French..
“Well, they sure like you here.”
“Always treat the help well and always leave a big tip. They never forget you and these people see and hear a lot. You never know what information you can pick from them, and information is power. That’s a useful tool in my business and a lesson for you.”
“That’s what I’m trying to figure out. Just what kind of business are you in? What kind of a girl prances around dressed like you are? I know you got some kind of dodge going, but other than conning that chump Max, what the hell else you pulling off to afford swell joints like this?”
“You’ll see. Now let’s enjoy the food. Keep your eyes open; look around. Maybe you can pick up some pointers on how to behave around a higher class of people. I could tell from your banged up face that first time we met the kind of dodges you been running. You’re getting a little long in the tooth for that shit. You got the looks to move up a little. But you need a lot of polishing and a real attitude change for me to be able to use you.”
“Use me! I don’t remember asking to be used. If you got some kind of scam working maybe you ought to spill it and I’ll see what you got. I mean this outfit you’re in has got me a little worried. Just how hinky is your grift? Or is it a grift? What the fuck is going on. Everyone in this joint is staring at us. Ain’t we supposed to fade into the background? No one here tonight is liable to forget us.”
She appraised me like a used car covered in Bondo with bad tires. There was that coldness again behind her eyes, a coldness that sent a chill up my back. I began to feel even stronger that this hot broad I had been jerking off to was, maybe, more than I could handle. I was still hot for her and curious about what she was up to but maybe she was right. Maybe someone like Mobes was more my speed. Whatever confident ideas I had earlier in the day were vanishing in the glare of her cold, hard sky-blue headlights.
The food arrived. It was not the kind of diner food I was used to, but it sure tasted good. We polished off our plates and finished the wine with no more talk. Louisa got us coffee and brandy and when we were done she signaled for the check. She pushed it over to me while she went off to fix her lipstick. I wondered which bathroom she went to; Ladies or Gents? I looked at the bill and nearly lost my meal. It was good I brought a healthy bankroll with me. I was trying to figure out a tip when she came back.
“Leave 25%. I have to come back here.”
I did as she said and on the way out the entire staff did a little scraping and bowing and wished us a Happy Holiday.
CHAPTER FOURTEEN
We retrieved the car from the parking guy and she directed me to head west.
“Where are we going?”
“Outside the city, to unincorporated Cook County land. I use a place out there and that way I only have to pay off the Sheriff. Dealing with the Chicago cops is no big deal but you got too many hands out all the time. The sheriff keeps it all for himself plus I got the goods on him.”
“Oh, yeah,” I said. “What sort of goods?”
“Wouldn’t you like to know? Never mind that. You’ll see what’s going on when we get there. What I need from you is to just do exactly as I say. I can tell you been around a little. For now just drive where I tell you and I’ll fill you in later.”
She turned away from me and pulled out a cigarette holder and inserted a funny looking smoke with a gold tip. After lighting it the smell became so strong that I had to roll down the window for a little air. She said nothing more than to give me directions and after 45 minutes we pulled onto a dark road and into an empty lot. At the back of the lot was a large Quonset style building with no windows. There was a single bulb lighting an entrance.
“Park in back, the door we use is there.”
I wondered what the hell this place was. I spotted a small door that was difficult to see. I parked and we got out of the car. It was bitter cold by now and a few flurries were coming down, being whipped by a sharp wind. We walked to the small door and she pulled out a set of keys and opened it. We entered into a pitch black room. She took a few steps and switched on the lights. We were in a dressing room like you would find in a theatre. It was large and had a sofa, some chairs, closets and a make up table.
“OK, Kevin, if in fact that is your you’re name, let me spell it out for you. Have a seat. What I am is what is known as a dominatrix.” She opened the closets in the room. They were filled with leather outfits and whips and other odd looking stuff.
“Yeah, I know about this stuff. Although this is the first time I met one of you people. So this is where sick guys pay you to hurt them and that shit? Well, who would a’ thunk it. I had you figured out all wrong. So great, now I get what you’re up to but what has this crap got to do with me?”
She sat in the chair
at the make up table and swung around to face me. She crossed her legs and leaned forward. “I have had some problems recently. I got some new clients referred to me by the Sheriff and a couple of them got a little out of hand. I thought you could be my muscle and maybe help out. Some of these gentlemen have asked for a man to be around to watch me work them over. I figured a guy like you, who has been around could handle this stuff. There is good money to be made if we handle it right. Max ain’t wise to my thing. I thought maybe I could use him to help but he’s a wimpy kind of guy and works better as a beard. So what do you say? You up for helping out a poor working girl kick the shit out of some of Chicago areas finest upstanding citizens? You help me and I’ll see what I can do to help you out with Ethel.
She had that look again. I stared back at her. I was calculating the payoff for me. This was decidedly the most hinky deal I had ever been in on. I nodded my head and she threw her hat off and shook out that mop of red hair. Who was I kidding? I was hooked but good. My cock was bursting out of my pants. Sure, I was hot for her but at the same time this scene kind of made me a little queasy. Maybe I was not so eager to be part of this kind of oddball shit.
I got up and walked over to her. I reached out and pulled her to me. She came into my arms. I looked deep into her eyes and felt an equal measure of fear and lust. Whatever doubts I had about getting involved were gone. No wonder she was so good at this game. I almost felt hypnotized. She reached her hand behind my head and pulled my mouth to hers. She kissed me and pushed her tongue into my mouth. I could feel her strength and I knew I had met my match. She stepped out of our embrace and turned to the dressing table.
“Let me fix my makeup and I’ll fill you in on this evening’s activity. For tonight all you have to do is stand in the chamber and look mean. Pull your sap out and play with it. If I need anything else I will tell you. Otherwise, don’t say anything. If this business agrees with you maybe I can work you in a little more.”
CHAPTER FIFTEEN
Louisa redid her makeup and told me that her client tonight was a Catholic priest. She had seen him once before and he liked to be humiliated by a grown woman but she had to be in men’s clothing. Some people sure were screwed up.
She again told me that when he showed up to just go to the corner and stand there, not say a word and occasionally pound my sap into my hand and look mean.
After a few minutes we heard a pounding at the door. I went to a corner of the room and stood there. She opened the door. A middle-aged man in a black suit and a clerical collar walked in and shut the door behind him. She took a step forward and slapped him across the face as hard as she could. He staggered slightly and smiled.
“Thank you, Miss Louisa,” he said.
She had put her fedora back on and was wearing leather gloves. She roughly took his arm and led him to the middle of the room. She reached up above her head and pulled down a contraption that had leather restraints on a pulley. It was at that point that he spotted me in the corner. Fear filled his face as I pounded my hand with the sap and gave him the most hate filled look I could manage. After my years in the orphanage and what I went through, it wasn’t difficult. She stood in front of him and glared in anger. She spit in his face and slapped him again. “You rotten piece of shit, you’ve been bad again, haven’t you?” He nodded sheepishly, as her spittle ran down his face.
“You’re going to pay for your sins. You are going to suffer for your awful, nasty behavior. I am going to have to hurt you. Are you ready to suffer? Answer me, you fucking pile of shit.
He nodded as tears started running down his face. His shoulders slumped and his hands hung limply at his sides.
“Take off your clothes. You can not hide behind your vestments and collar here. Here you must stand naked before your mistress and pay for your deeds in blood.”
She took a step back and kicked him in the balls. He whimpered as he bent over in pain.
“Stop crying, you big baby. Get your clothes off and hurry up about it. Your mistress can’t coddle you any longer.”
If she was acting, it was very convincing. He began to disrobe while she kept hitting him and yelling at him to hurry. When he was totally naked she took his hands and cuffed them in the restraints. She then yanked on the pulley lifting his arms until he could barely touch the floor.
She leered at him with an evil smirk. She then turned and walked to the cabinet and began selecting items of torture. I stood there wide eyed and a little disgusted.
She proceeded to whip him and make him beg for more. She attached a weighted chain to his balls which must have caused excruciating pain. She lashed the whip across his ass and his cock. He screamed in pain but kept asking for more. He began to bleed from the lashings and seemed on the verge of passing out. She stopped for a minute while he gasped with tortured breaths.
She returned to the cabinet and removed a huge black dildo. She stood behind him and screamed, “Now you are going to pay for what you do to little boys, you filthy scum.”
She spread his ass cheeks and rammed the dildo up him. He howled in an ungodly shriek that gave me goose bumps and made me want to run out of the room. I stood their in horrid fascination as she continued to abuse him.
He finally passed out. She called me over and we lowered him to the floor. She undid the restraints and put him on his back. He was a lacerated mess and blood was leaking out of his ass. I went back to the corner of the room as he regained consciousness. He began to moan and keen. She knelt over him and slapped him fully awake. “Thank me,” she said. “Thank your mistress.”
He did as she requested. She then removed her pants and silk underwear and knelt with her knees on either side of his head.
“Open your filthy, dirty mouth and receive the sacrament from your mistress.” His eyes closed and his mouth fell open. She began to let loose a stream of urine into his mouth. She made sure to liberally splash it all over his face. He choked and gagged and tried to twist his head. Her knees held him firmly and he was forced to swallow. I had to look away.
The rest of the night went by in a sickening blur. I may be a grifting lowlife but this shit was a bit much for me. She had a Catholic priest doing things that almost made me want to throw up. What ever feelings I had for this sick bitch began to fade fast as I had to watch what she put this poor fucker through. I had no love for the clergy. I knew most of them were just living off bullshit that they sold to the fools that believed the crap they spoon fed them. I’m sure half of them were fucking the alter boys just like they did in my day. There had to be a reason this guy would pay big money to be beaten and pissed on.
She finally finished her total humiliation of the creep and told him to go in the bathroom and clean up and get dressed.
“Your mistress is through with you. You make her disgusted. Give me the money and get out. You are a vile and evil human being and deserve even more punishment in the future.”
He nodded in agreement and reached into his pants, pulled out a wallet and handed her a thick wad of bills. He gathered his clothes and limped off to the bathroom, trailing blood behind him.
She was shiny with sweat and laughing loudly. Her face glowed with a look of utter satisfaction. She walked towards me but stopped short when she saw the look in my eyes.
“Oh, oh, I guess you didn’t enjoy the performance. Not such a tough guy, are you? Well, this is what I do. Not to your liking, I guess. I can see that. Well, no harm done. You keep your trap shut about me and I won’t say anything to Ethel. Wait here until the creep leaves and I clean up a little and we can get out of here. Looks like you could use a drink.”
It was going to take a lot more than a drink to get the bad taste of this evening out of my mouth. Whatever lust I had for her just went out the window. She was one sick bitch. However, now that I knew how ruthless she really was I was sure she could help me work Mobes.
The priest hobbled out of the bathroom and thanked her once again as he stumbled out the door.
“Do you thi
nk he’s going to be all right? Can he drive himself home? He looked in bad shape.”
“Don’t worry about him. He’s a tough old bastard. As soon as he heals up, he’ll be back for more. These sick bastards love what I do to them. Hell, that’s why I’m gone so much, these fucks pay for me to go all over the country to beat on them.”
I helped her gather up her restraints, cuffs, and other gear. She got back into her suit jacket, brushed it off and we left.
When we got in the car she was quiet for a moment. “I know an after hours joint where a lot of jazz cats go. We can get a drink and hear some music. I need to unwind after a session like tonight. Just head east on Lawrence until we get to Broadway. I see you ain’t got much to say. I figured you for a little harder. Not so tough, are you?”
We drove in silence for awhile. My mind was a jumble. I thought I knew what was going on but sometimes you find out what you’re really made of, and you find it out the hard way. I had to get my hands on Mobes dough and get the hell away from Chicago. This was one nasty town.
She started smoking and then reached in her pocket and pulled out a C-note. “Here, you earned it. You sure we can’t do business? You looked real mean in that corner.”
“Keep it. I don’t want your money. I’ll just have to figure out a different way to work Mobes.”
“What did you have in mind? Just because you ain’t up for my thing don’t mean we can’t still work something out. What were you planning?”
I could hear the calculation in her voice. I was unsure if I could con Mobes on my own and having her on my side wouldn’t hurt. We drove on for about 30 minutes until we got to the Uptown Theatre. I parked the car and we made our way to an unmarked door.
