Gambling Payoffs

Author's note: the following story is purely a work of fiction and any resemblance to real people or events is purely coincidental. The author wishes to express his gratitude to Copperbutterfly for her editing to make this a better story.

As the majority partner of a syndicate that owned a floating casino moored permanently on the banks of the Mississippi, I was also the primary operations manager. Most of my partners were silent types that only came out of the woodwork when it was time to rake off their pro rata share of the profits. Other than that and an occasional meeting to discuss possible changes in the future, they let me run the show.

Quite a show it was, too. Situated almost equidistant between two major cities and with more than five million people within easy driving distance, we attracted large crowds almost around the clock. We had four full decks of various types of gaming devices and tables, one deck that was consumed by four large restaurants (well, one was technically a coffee shop) and their respective kitchens, one deck which served as a theatre for live shows, and three decks of hotel-style staterooms for overnight guests. Some parts of the casino were shut down at various slow times in the day but something was always going on and the gaming decks never closed.

As the overall manager, I had the final say on all hiring for the entire casino. That task, although sometimes tedious, had its built-in advantages also. Given the state of the economy in the area surrounding our location, many people were willing to do whatever it took to obtain a regular paying job, especially if they were from one of the small dying towns out in the countryside.

Not that I'd ever ask anyone to do anything they weren't willing to do, nevertheless when the women who applied as waitress or maid or dealer or dancer or hostess stated that they would do anything for a job, I usually let them prove it. I'll admit that I have always been oversexed and this job let me indulge myself in the pleasures I so enjoyed.

With a master key that fit every lock in the entire ship, it was easy to find an empty storage closet or an unoccupied room as I made my daily rounds to take one of the women and let her show me just how grateful she really was. I never had to coerce anyone into showing me. Whether it was a quick blowjob or bending the woman over and sampling her pussy doggy style, I managed to find time to sample the wares of a number of women almost every day. Granted it had not always been like that but over time that is where I found myself.

When running a casino, one of the things you have to be leery about is that players have enough money or other assets to cover their losses. Few players actually leave a casino as a winner, even though they may have won occasionally. Overall the large percentage of people come for the entertainment, whether it is for the shows, to watch other people, or just the joy of pushing the buttons on a slot machine and hoping for a win. Most of the slot players, I didn't worry about because they brought cash or credit cards to play on and their debts were covered up front. Whether or not they could afford to lose what they gambled was not my concern.

Where I had to be more concerned was with people who played at the tables. Those were the people who gambled for higher stakes and sometimes used less conventional methods of payment, like staking out blocks of stock or signing IOUs. The only people we accommodated thusly were people that we checked out and knew that there was some way they could obtain the money to back their play. The vast majority of those IOUs were redeemed at the end of the night when the player would write a check for the amount of his IOU and he left the casino square with us, his reputation still intact.

Occasionally we ran into problems collecting on IOUs. Business people fell on hard times and couldn't cover their debts. On most of those occasions, one of my middle managers would make a call to the player to remind him of his debt to us and payment - with proper interest - was usually forthcoming. On rare occasions when this method didn't work out, I turned the debt over to our in-house collection agency.

Our "collection agency" consisted of three men, each former professional athletes and formidable people. Usually a single visit from these three men would elicit a satisfactory payment or promise for quick liquidation. If a second visit was required, a little pain (and a promise of some new concrete shoes) insured that the debtor would find a way to solve his issue. We never had to send the collection team for a third visit.

On odd occasions, a debtor asked to barter some kind of solution for his debts. I always listened to what they had to offer, and sometimes found my personal fortune enriched by doing so, although I always found a suitable way to insure that my partners got their fair share of the settlement. I have to admit that, on these bartered solutions, the casino always came out with a solution worth considerably more than the original debt, but that was the debtor's choice. Occasionally I would pay off the debt myself and then take the results of the bartering session for my personal use, if my partners were agreeable.

In the early 90s, we were first visited by an industrialist named James Wade from our favorite city to the north. He had made a small fortune manufacturing certain small interior parts for the automotive industry. When he first came to the casino, less than two years after our initial opening, he was a bit player, not interested in the slots but playing a few bucks here and there at the various games. He finally settled down at either one of the craps tables or a poker table.

Mr. Wade would spend several hours at whichever table he selected, slowly losing a few hundred dollars, occasionally winning enough to keep his interest up. He was better at shooting craps than at keeping a poker face but he seemed to prefer the game of poker. At first he only appeared on Friday nights but gradually he began to show up more and more often until he became a fixture almost every night. Even though the dealers and croupiers changed often, he got to know each of them by name and was friendly with most of the waitresses.

It wasn't until he was nearly a nightly visitor that he first brought his wife. She surprised me; while James was a fiftyish man with graying hair and a paunchy belly, she was as beautiful a woman as I had ever seen. I suspected she was in her early thirties, had long blond hair, an exaggerated Coke bottle figure, and didn't mind showing a lot of cleavage and leg. He always gave her a small amount of money to gamble with, much less than he played himself, and she proved to be quite adept at making it last the whole night, often adding a small amount to what she started with. By then, James had moved to the higher stakes tables and was spending a few thousand every night. I wondered how long he could keep it up.

Several times, in making my rounds, I ran into Mrs. Wade sitting at one of the restaurants, usually the coffee shop, having a cappuccino or similar drink, watching people as if she was having fun. I always stopped for a minute or two to talk with her. She was very pleasant and seemed unusually bright. Well, perhaps my expectations were too low for a blonde. I know I respected most women for their minds as well as their bodies.

As time progressed, James moved to the highest stakes games. Like a lot of losing gamblers, he was trying to recoup his losses quicker but all he did was accelerate the speed with which he lost money. He went from bringing cash to writing checks to signing IOUs. He left each night, explaining that he would have to arrange payment by selling this asset or that and for a time he held true to his word. Then his IOUs began to mount.

I had a feeling about the man so I took control of his account myself, rather than assign it to a middle manager. With IOUs totaling in the six figures in my hands, I called Mr. Wade and talked to him about payment. He explained that he was going through a hard time while the auto makers put the squeeze on him but he had a new contract in the works and expected to have a better cash flow soon. He promised to pay the debt and the vigorish within two weeks. I agreed to wait the two weeks.

During that two weeks, Mr. Wade continued to gamble. And the more he gambled, the more he lost. Ten to twenty thousand a night went into the coffers of the casino, even if it was just in IOUs.

On the fifteenth night after our talk, I instructed our collection team to stand watch at the doors and direct Mr. Wade to my office when he arrived. I was sure he would be there and he was either going to pay ... or he was going to pay. One way or another. Like it or not.

He arrived a little later than usual but his wife was with him. My man intercepted them and directed them to the elevators leading to my office. I offered Mrs. Wade a leather chair in front of my desk and watched her sit, her short skirt riding high on her shapely thighs as she settled back. Resuming my seat behind my desk, I watched as Wade settled into the other facing chair, squirming as if he was uncomfortable.

"Mr. Wade, as you know, you had agreed to settle your debts with the casino in two weeks. Those two weeks have passed. I assume you are ready to settle up. We are currently holding your IOUs in the aggregate amount of $470,000."

"Uh, I'm very sorry, Mr. Jenkins. Things have not worked out as they should have and I am unable to make the agreed payment."

My eyes narrowed and in a stern voice, I said, "Mr. Wade, I assumed you were a man of your word. You promised to make payment today. I expected you to find a way to pay your debt, sir. If I have to resort to our collection agency, I'm sure you'll find a way. Do I need to do that?"

"No! No, please don't do that, Mr. Jenkins. I ... uh, I may have a solution." He was obviously aware of what our "collection agency" meant and their reputation for results. His voice was high-pitched and anxious.

"Oh? And what did you have in mind."

"Well ... uh, I know that you ... appreciate ... a good looking woman and ... I've seen you look at Mrs. Wade ... Laurie. If you agree, then Laurie will ... uh, become your woman ... for as long ... as it takes to pay the debt."

"What?" I reacted incredulously. "Are you suggesting that ... that you would turn your wife into a whore to pay your debt? I mean, even if she agreed to do it, do you think a little bit of pussy is worth that much money?"

I glanced at her to see a smirky smile on her face. She didn't seem fazed by the proposal.

"Yeah, I know but you have to admit that she is a beautiful woman. She is very good in bed too, and she'll do whatever you want whenever you want it."

"Man, for 470 big ones, she'd have to move in with me. Are you both prepared for her to do that?"

He ducked his head, then looked into my eyes and nodded. I turned to her and she just smiled. I sat back in my chair and studied them for several minutes. Finally I beckoned for her to come over in front of me.

When she was standing there, I said, "Take off your clothes, please."

Her smile continued as her hands began working on the fasteners of her blouse. Not in a hurry, she proceeded as if performing a striptease. First the blouse was discarded, then her white lacy bra, revealing a pair of perky C-cup breasts, nicely shaped with big pink oval areolas and stand up rosy nipples. Her gaze never left my face.

Her hands went to the back of her waistband and she unfastened her skirt, pushing it sensually down her hips and letting it fall. She turned around, spread her feet to each side of the skirt and bent to pick it up, taking way more time than actually needed. She was wearing black panties, thong style, that showed her beautifully rounded buttocks and when she bent over, the camel toe between her legs was obvious.

Moving the skirt out of the way, she turned back to me, standing dressed in black panties, black garter belt, dark thigh high stockings and black three inch heels. She hooked her thumbs in the waist band of the thong and slowly worked it down, revealing a completely shaved pussy. She asked if I wanted the rest removed but I shook my head no so she stepped over between my legs.

As I put my hands on her hips, I looked at James. The only expression on his face was a silly looking grin. Slowly I ran my hands over her hips and down around her buttocks, gradually making an upward trip, letting my fingers wander deep into her crease. She put her hands on my shoulders and leaned closer, putting her tits at my mouth. I sucked one in and continued to stroke her ass.

A few minutes later, I turned her part way and sank two fingers into her wet pussy. I pulled her down onto my lap and looked at her husband. James was licking his lips and smiling but sitting back in his seat.

I turned back to her and said, "Give me a sample, sugar."

She stood up while I unzipped my pants and pulled my erection out. Then, sliding a leg to the outside of each of my thighs, she lowered herself onto my throbbing member. I have to admit that it felt good. She began to bounce up and down on my prong as I watched her husband. He watched for a little while, smiling at the sight, before seeming to lose interest. He picked up a magazine and began to thumb through it, paying us no attention.

I have to admit that I liked Laurie. And when she squeezed my cock with her internal muscles, sucking the cum out of my nuts, I knew I would agree to his barter solution. Turning her sideways to sit on my still partially erect cock, I fingered her pussy and addressed her husband.

"Okay, Mr. Wade. I'll take your deal on these conditions. She moves in with me and lives with me until I feel that the debt is paid, no matter how many months that is. She will do whatever I require as often as I require. If there is ever any reluctance on her part, the deal will be off immediately. From today on, you will be allowed an IOU maximum of $1,000 per day no matter what you gamble. I suggest you move back to the low stakes tables. Those IOUs will be added to your total debt and extend the length of time it takes your wife to pay them off. Both of you must agree to those terms for it to take effect."

I spread her legs a little wider and drove three fingers up into her sloppy pussy before looking at James. He had jumped up and extended his hand to shake on the deal. Since both my hands were busy with his wife, I ignored his hand and listened to him verbally agreeing eagerly to my conditions. I nodded and looked at Laurie. She grasped my head in both hands and planted a tonsil probing kiss on my lips as her agreement.

"Okay," I said. "Mrs. Wade will spend the night with me tonight. Tomorrow she will come home long enough to pack most of her belongings and move in with me. After that, she will remain here. You may see her any time you are in the casino but you will not be allowed to screw her until the debt is paid, understand?"

He nodded and walked out of the office, relief etched on his face. I turned back to the beautiful blond and frigged her until she came sitting on my lap. When she had sufficiently recovered, I told her to get dressed again but no bra and no panties. That would be the way she dressed as long as she stayed with me.

I have to admit that I took advantage of the woman. Except for the day she went back to pack her things, and the five days out of every 28 when she had her period, I averaged screwing her between four and five times a day. Even on days when she had a tampon stuffed up her cunt, she vigorously sucked me off several times and gave me access to fuck her anus whenever I wanted to. She followed me around almost all the time every day, shadowing me when I made my rounds, letting me pull her into a deserted room for a quick piece of pussy whenever I wanted it. I have to admit that she never complained and always seemed ready when I lifted her skirt.

That didn't keep me from stopping in at the revue dressing room and knocking off a piece of this showgirl or that and Laurie simply watched without complaint. There was something really hot about being so close to her while I fucked another woman, especially the married ones. I know some of the husbands knew that his wife was getting porked by the boss and didn't mind; others probably wouldn't have been too happy if they found out. That made it even hotter when the woman would bare her pussy willingly for me to use.

Of course I treated Laurie to three meals a day at one of our nice restaurants, except for the occasional times when she asked if I would let her cook for me. She preferred to do that at breakfast time so we could spend most of our time keeping watch on the activities around the casino.

One day I asked Laurie if she wasn't getting tired of me always wanting to stick my cock in her. She told me that she didn't think she would ever get tired of it. James had lost most of his sex drive and very seldom fucked her so that she had become extremely frustrated. Now she didn't know if she could stand the thought of ever going back to him.

James continued to come to the casino daily but was limited to the low stakes tables. Still he played every night, always losing everything he was allowed to borrow before he left to drive back to the city. He always spoke very pleasantly to both me and Laurie but he really treated his wife as if she was my wife. He occasionally shook her hand chastely, as if he had never been intimate with her.

Laurie had been with me just over a year when she told me that she was pregnant. I was startled, thinking that she was on birth control pills. She told me that she had been but she decided that she wanted to have a baby and would rather have me be the father than her husband. It felt a little kinky to father a baby with another man's wife but I wasn't complaining.

Two months later with Laurie's tummy just beginning to show the roundness of the life growing within, she told James that she was pregnant with my baby. He didn't seem at all surprised and asked, if he divorced her quietly, would I make our arrangement permanent and somehow eliminate his IOUs. I pondered the question for a while and decided to take him up on the offer if Laurie agreed. She didn't even think about it before saying yes. Six months later, just before our son was born, the divorce was finalized.

At 37 months, I handed James Wade a fistful of IOUs worth more than $520,000. It wasn't an equitable trade, if I had tried to put a market value on the sex I'd received but I had to admit that I was no longer interested in putting a price on Laurie's pussy. James had turned his industry around again and had been bringing cash to play with for nearly a year. However he had limited himself to the low stakes games and was taking a little longer to lose his money than he had before.

There was no talk of Laurie going back to James Wade, neither from her nor from him. Both of them seem to agree that their split was permanent. She let me know daily that she was happy with her new life and liked our relationship. Never once has she indicated that she begrudged me my sexual rewards from other women who worked at the casino. She has even displayed a bit of bisexual tendency from time to time, kissing and stroking my partners while I take care of my urges.

Even though we retain a live-in nanny for four year old Theodore – Teddy – and his baby sister, Loni, Laurie is spending more time in our suite with the kids than she used to. I make a lot more trips to the suite now than I had before, stopping by to see how they are doing and to knock off a quick piece of her pussy before returning to work. Laurie laughs at me sometimes, telling me that with all the pussy around me at work, she is surprised at how often I come home to do it with her. She says that she wouldn't mind if I occasionally gave her a little more rest by spending my time fucking more of the showgirls or waitresses, but I just can't seem to get enough of my "gambling payoff" prize!