Working Off His Debt

The following story is fictitious, of an explicit and adult nature. This story is not meant to be viewed by anyone under the age of 18. If you are under the age of 18, offended by adult material or such material is barred by the standards of your community, please leave this page now.

*

Saturday.

Tommy didn't even look at Gerry. He didn't even turn around. He just sat there at the bar, nursing his Dewar's shot.

"How are we going to fix this, Gerry?"

Zephyr was a small, dingey, run-down oak plank social club in the basement of a Hell's Kitchen tenement. Creaky floors, creaky bar, wobbly stools and splashed with art deco train fare. The place was empty, except for Tommy Desalvo. And now, it also included the tentative presence of Gerry Flaherty. Gerry hadn't said a thing. Tommy knew that he'd entered the club by the rush of air that fanned his back when Gerry opened the door.

Gerry's heart raced. The only time that he ever came to Zephyr was to discuss business with Tommy. Discussing business meant that he owed Tommy money. He never saw Tommy when things were going well.

Tommy was the son of a feared neighborhood wise guy. He was connected, but not a true gangster. That didn't make Tommy any less volatile. His hair trigger temper was genetic and legend.

Gerry stood, frozen. His heart pounding in his ears made the deafening silence press in on every square inch of his body.

"Are you deaf?" Tommy snarled.

"I'm sorry Tommy. I don't have your money", Gerry demurred.

"This is not a good thing, Gerry. It's been two months since the Packers game and the juice gets tacked on every three days. Do you have ANY idea how much you're into me for?"

"I've been working over time. I can ..."

"Bullshit!" Tommy roared, his fist denting the wood of the bar. "You can work over time for a hundred years, and you're still not going to be able to get me my money, Gerry. I've got expenses too. I can't pay my rent with your bullshit excuses for why you're not giving me what you owe."

"I can get you your money, Tommy."

"Yeah, you and every other sad sack fuck. It ends here."

Without turning around, Tommy reached into the left inside pocket of his brown leather bomber jacket.

"Tommy, please don't ..."

"I'm not gonna shoot you, you dumb asshole. I'm getting my cigarettes." Tommy held up the red and white Marlborough hard pack in between his right thumb and forefinger, and waved it for Gerry to see. He then raised himself from his stool, planted his feet firmly on the floor and slowly walked behind the bar.

"What would it get me if I killed you, Gerry? Nothing. I'd still be out hundreds of thousands with nothing to show for it. And besides, Jenny would never forgive me for killing her father, now would she?"

"Are you going to have me beaten up, is that it?"

"Now, what do I gain if you get put in the hospital and can't work?"

"What do you want from me?"

"It's not about the money anymore, Gerry. I'm sparing your life, and from here on in everything in your life belongs to me."

"I don't understand, you want me to sign over my house to ..."

"No, Gerry. Real estate transactions are too ... well, too cumbersome for a man like me. I was thinking about things on a more personal level."

"What do you mean?"

Tommy smirked and burped out a chuckle. "Well, Gerry, I see it like this. If you were to make your payments, I'd probably only spend your money on getting pussy. Know what I mean?"

A hot wave of anger crashed over Gerry. "Are you telling me that you cheat on my daughter, you fucking son of a bitch? Is that what you're ..."

"Temper, temper", Tommy hissed as he patted the left side of his jacket, reminding Gerry of the .38 automatic that everyone knows Tommy has on him at all times. "I'm not cheating on anyone. Your daughter and I are swingers, Gerry. We swing together at intimate little gatherings where Jenny lets guy after guy fuck her ass and her snatch while she watches me get my knob polished by strippers."

"What does this have to do with me?" Gerry rumbled.

"Funny you should ask. You see, your daughter is such a fantastic cocksucker, and I really do mean that, Gerry. When the tip of her tongue starts working your balls, there's only so much you can do not to cum right then and there. And her pussy, Gerry. Jenny's pussy is so tight, but it's soft like velvet inside. Your daughter gets so wet, I can hear all of those sloppy little noises when I'm fucking her. My balls get soaked with her ... "

"So what do you want from me?" Gerry said with uneasy restraint.

"What's your life worth? What is it worth to you to carry on with your life, to keep your house and your car? Tell me, Gerry, what's it worth to you?"

"I don't understand. Do you want me to work for you? Is that it?

"In a way. You WILL continue in the job that you have now, but it's going to be for my benefit. You see, Gerry, I want to see if it's true what they say."

"What do they say?"

"'Like mother, like daughter.' Your house, Gerry, that beautiful little Chelsea brownstone that you have, is going to be my personal whorehouse. Whores included."

Once again, Gerry felt the anger wash over him. "Megan would never stand for such a thing! Jenny would hate you!"

"Oh Gerry, if you'd only had a talent for picking the right score, you wouldn't be in the mess you're in right now. I've already told Jenny about the Packers and the Knicks, and the Red Sox, and the Patriots, and Tampa, and the countless other losers you've wasted your family's money on. When she found out how much you owe, well, let's just say she was a little disappointed in you there, Sport. Jenny thinks you might just have a gambling problem. I'm not a doctor, but I think she may be right. Anyway, Gerry, not only doesn't she hate me, but she's been helping me lay the groundwork for our little arrangement."

"What do you mean?" Gerry inquired, his eyes straining wide.

"What I mean is that she liked the idea. She thought you deserved to be punished for putting every one in harm's way, for risking homelessness, their futures, their possessions and possibly bodily harm on a fourteen point point spread, Gerry. Your little girl liked this idea a lot, so she decided to help make it happen. For the past month, Jenny's been laying down little comments about our sex life to Megan. You know, girl talk. Telling her about my cock, how good it feels, how thick it is, how she loves sucking it. Shit like that. Last week I was over at your place when you weren't home. The three of us had a sit down, and I told Megan about your gambling and how much you owe. Let's just say, she's not that happy with you right now."

"I knew she was acting strange", Gerry whispered.

"Well, about two days ago, we had another sit down, Gerry. That was when Jenny and I clued Megan in on how we propose to fix things."

"Megan would never go for it."

"Wrong again, Gerry boy. Jenny's stories about the sex that we've had really got Megan curious. Jenny told her that it would not only be fun, but that everyone wins. Oh, and by the way, I can tell you that Megan is every bit as good a cocksucker as your daughter. The apple doesn't fall far from the tree, I guess."

"What?" Gerry snarled as he briefly lurched forward.

"Well, to seal the deal, Megan gave me a blowjob right then and there, while I was sitting in your easy chair in the living room. Granted, she was a bit nervous and self conscious at first, but Jenny really put her at ease and encouraged her, and cheered her on. Your wife sucks like a champ. After I came, she looked proud while she was wiping her mouth. Like she really accomplished something."

Gerry's heart sank in his chest, and he brought his right hand over his eyes.

"Buck up, Gerry. As long as we have this arrangement, you get to keep your money and your house, and your family. Oh, and by the way, Megan made me a key to your house so that I can come and go as I please, and cum in whomever I please, whenever I please. What's yours is now mine, Gerry. And don't you ever forget it."

***

Wednesday.

Gerry peeled himself out of the packed E train, and on to the boiling concrete platform of the Twenty-Third Street station. The summer air was napalm in his lungs as he climbed the stairs to Eighth Avenue. And he walked the three blocks to his brownstone.

Gerry turned the key in the lock and entered, placing his briefcase by the door and walking beyond the narrow staircase to the second floor. He entered the first floor living room to see Megan and Jenny lounging about, reading assorted magazines.

"Hi, I'm home."

"Hi ,Dad", Jenny cheerily replied.

"Hi Gerry", Megan chimed in with just as much mirth as Jenny.

"We're chipper this evening", Gerry observed, the glee becoming contagious. "Are we eating dinner out tonight?"

"I guess so, I didn't have any time to plan anything for dinner today", Megan said with a smirk as she turned the page of her magazine.

"Oh, busy day?" Gerry light-heartedly asked.

"Kinda-Sorta. I fucked Tommy Desalvo."

Jenny could no longer contain the laughter that she had dammed up inside. "She spent all afternoon locked in the bedroom fucking him. I wanted to watch, but mom was being a hard ass"

"What?" Gerry bellowed incredulously, white hot with anger.

"Don't pretend like you don't know what's going on here", Megan glowered. "Oh, I admit, that the first time I sucked Tommy's cock ... "

"The first time?"

"The first time I sucked Tommy's cock I did it because I felt like I had to do it to save your life. The next time I did it, it was because Jenny and I were sharing a bond. I sucked him to get him hard so he could fuck her. She sat down on his cock, and I watched her ride him. I watched the pleasure he was giving her, and I felt something. It made my body tingle. It made me wet. And so, I masturbated, and I watched them, and I came so hard I couldn't breathe. The third time I sucked him, I did it for me. I did it because it makes me happy. And today I fucked him. I let him fuck my pussy over and over. You wouldn't believe how sore I am. But you know what? I enjoyed it. And I'm going to continue enjoying it, and that's just something you'll have to live with, isn't it?"

Gerry stumbled his way to the couch and sat beside Jenny's feet. He held his face in his hands. "Did you let him cum in you?"

"Of course, why wouldn't I? Or rather, I should say that you can bet on it. Hmmm, maybe not YOU, because if you bet on it, he'd probably never even get hard again. But more importantly, I came. Did you hear me, Gerry? I came over and over. It was wonderful. Jenny was right, Tommy's cock gets super hard right before he squirts his cum. Just so you know."

"I told you," Jenny chuckled.

***

To be continued ...