I had been in the Organization for six months when I was given the opportunity to move up in the ranks. It was Jimmy who called me into his office one late September night to let me know where I stood and what it would take to start living the "high life" of a Chicago mobster. I thought that I would be asked to make a hit or pull of a heist. Instead, Jimmy unbuckled his pants and put it to me simply. Either I could be his private bitch or he'd put a bullet through my brain for knowing his secret proclivities. Regardless, he'd be pumping something into my mouth before the night was through.
It was an easy choice and Jimmy was easy to get along with. He liked me. He told me this every night after he had emptied his load into my mouth before kicking me out of his office. Stroking his cock under the table while he watched the dancing girls was nothing new for me. I'd been learning to like giving him his secret pleasures while he put on his tough guy straight act. With a few more kicks and a few more strokes I could have him shooting his spunk into my napkin before the next song was over.
I don't know if it was the sparkle of the broach around her neck or some kind of animal instinct but my eyes were drawn across the room to one of the gin joint floozies. But, I gulped, this was no dime-a-dance girl. I had never seen this one before and there was just something about her that made her stand out like the full moon on a starless night.
My excitement over this stellar dish must have translated its way to my arm because Jimmy was cumming before I knew it. Without my napkin there, his spunk sprayed all over my black pants. Fuck! I reached down to take the last few dabs onto my handkerchief before slipping his cock back into his pants. "Thanks, lover," he whispered into my ear as I tried to dab at the cum on my legs.
When I looked back up, she was gone. This wasn't my night. I excused myself and made it to the bathroom as fast as I could, taking the most round-about way to avoid anyone seeing the wetness on my pants and getting the wrong idea.
I made it to the head and closed the door behind me. I grabbed a rag and ran water over it before starting to rub at the spots on my legs. I heard the thunk and creak of the door behind me but didn't give it any thought until I heard the distinct female voice. "You should have used selzer water, that's the best thing for it."
I looked up into the mirror in front of me to see the dancefloor beauty reflect in it. She smiled and locked the door behind her. I tried to play it cool despite the raging hard-on I found myself with and the cummy rag in my hand.
I started down at her low-heeled shoes and I followed up to a low-cut tassled skirt. Liking what I saw, I let my eyes continue to wander over the gentle curves, the alabaster arms, and by the time I reached her pearl necklace I was ensnared. Her mouth was a crimson pout around a cigarette holder. Her hair was done up and I found myself lost in the nautilus curls. She removed the cigarette holder from her mouth and smiled. It scared me. Her smile was captivating and knowing. It was like a beacon that shone through me. She was more Cheshire cat than woman at that moment. Her smile told me that she knew more about me than I might know about myself. The photograph she handed to me (how did she get so close so fast?) proved that she definitely knew more about me than I would have liked.
There in crisp black and white was Jimmy Spitz with his pants down, me on my knees, and Jimmy's cock balls deep in my mouth. I tried hard to not let the panic show on my face but I can't be sure that I did a good enough job. This photograph was my death warrent staring me in the face. Forget about Jimmy being wacked for being a gunsel, it wasn't him on the receiving end. Jimmy wouldn't be seen as the faggot, I would be.
I gulped and tried to say something clever but I couldn't form a word. Her smile changed to a leer. "I represent some people that want you to do them a favor," she said, moving even closer. I could smell her perfume mixed with the bathtub gin she had been drinking. She told me that people downtown wanted Jimmy Spitz out of business, permanently, but they couldn't get close enough to him to do the job. They wanted me to do that job after doing the job that Jimmy enjoyed.
She had me over a barrel and she knew it. She touched my shoulder and moved behind me. There wasn't much room to shake a leg in that john but she managed to glide into the space well enough. I felt her breath on the back of my neck as she spoke. It raised the hairs and sent a cold chill down my spine. "Well, do we have an understanding?" she purred, her hand massaging my shoulder.
"I don't have a choice."
"Oh, but you do. You can do what we ask, or you can continue being Jimmy Spitz's cocksucker until someone puts a bullet into the back of your brain. But, there's one more thing I need to ask for... There's something I want you to do for me to show me that you're serious about all of this."
I liked the tone in her voice. "What's that?"
Before I knew what was happening, she pushed me over the sink and had my belt undone. My pants were falling to the floor as she hissed, "I want you to take my cock to seal the deal." I looked behind me as she yanked my underwear down to see her hiking her skirt up. I couldn't believe what I was seeing when she pulled a quickly hardening cock out of her panties and slapped it against my ass.
"I used to be Jimmy's plaything and I want a taste of what he's been enjoying all these months after he kicked me out of his bed. You take this good and those pictures will disappear when Jimmy does. But your ass is mine from now on." She spit in her hand and started rubbing the wetness over her engorged cock until it shined in the dim bathroom light. She grunted and shoved it inside of me. It felt like my ass was on fire from the pain. I knew she was tearing me up and that I would be bleeding all night. She didn't care. She shoved in farther and started fucking me.
She didn't say anything else for a few minutes while she fucked me over the sinks, my cock pressed uncomfortabley up against the cold porcelain, my head twisted unnaturally to take in the bizarre scene of such a beautiful creature with such an unmerciless cock. Hot tears streamed down my face from the pain and deception. After what seemed like an eternity she grunted and I could feel her filling my bowels with hot cum that mixed with the blood from my internal tears.
She pulled her cock out of me and wiped it off on my shirt tale. She got herself back together before she made her way to the door. "You've got one week," she said before she left. I felt the hot spunk running down my thighs and I tried to pull myself together.
I spent the week trying to recover. The throbbing pain in my ass subsided as the pain in my head, my conscience, got worse. I woke each morning clutching the gun I was going to use on Jimmy before the end of the week.
Every night that week at the speakeasy I saw her on the periphery of my vision, like a guardian angel -- or demon, perhaps, in this case. The last night of my last week with Jimmy he excused himself with a wink to me. I knew that I was to follow thirty seconds later.
I went into the bathroom where I had been raped seven days prior only to find that Jimmy wasn't there. I went outside to see if he had slipped into his car and was expecting a back seat blowjob. Risky, but something he enjoyed. As I made my way to the door I heard a scream from outside. I rushed out, pushing a few palookas out of my way.
I saw the blood first and followed it to the crack in Jimmy's head. He was face down on the pavement, his head split open. There was a car twenty feet away and a woman, ashen faced and crying hysterically behind the wheel. A crowd had already started to gather. I stared down in disbelief. He must have been on his way to the car when he was run down.
I felt a hand on my shoulder, reassuring. "Come on," said a familiar voice. I looked behind me to see her again. My ownership had passed from one person to another. "It's time to go home."
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