8 comments/ 230568 views/ 4 favorites Gambling Couple Pays Off Debt By: subFLmale Things had been going very well for me over the past two years. I had been promoted to Vice President of Finance in my company and Cindy and I had finally been financially able to get ourselves into a position where we again owned our own home and were pretty secure. Life looked very good for both Cindy and I at this point, all our problems behind us and nothing but blue sky ahead. Six years ago I lost my job as CFO for a large fortune 100 company, Cindy lost her job as a Financial Advisor and we lost our home and everything we owned within a period of about six months. All because of a little gambling problem that just escalated out of hand. Cindy or I never saw ourselves as high rollers, but the road to recovery has taken us a long hard time. Cindy had begun working for a large company in their department for contract sales. It was a good position with a lot of potential if things went right. Friday night son after I got home Cindy called from work and told me that a very important contractor was in town and she was given his account. She was going to take him out to dinner and out for the evening and wanted to know if I would join them at a local pub where they would wait for me. I really did not have any desire to go out tonight but as a boost to Cindy’s career I was willing to do anything. Forty five minutes later I walked into the corner pub and spotted Cindy sitting at a small table with a well dressed man. Cindy looked fantastic. She always had an instant ability to turn me on and most other men as well. She was not a super model look by any means, but she carried herself well and had a good wholesome look to her. Cindy was 33 years old; she did not belong to a gym but did try to take care of herself. She stands 5’6” and weighs 128 lbs. She has shoulder length sandy colored hair and beautiful big blue eyes. Tonight she was wearing a two piece business suit that I had bought her last weekend. A dark blue mid thigh cut shoulder less dress that looked like it was fit perfect to her body and a professional looking dark blue jacket. Her legs are long and sexy and she wore a pair of dark stockings with a pair of mid high heels. Cindy hugged me and introduced me to her potential customer, Nick. Nick was a New York smooth fast talking guy that was obviously in love with himself. He was about 6’ tall and thin built. He had a dark complexion and jet black wavy hair. He wore lots of gold jewelry and had his shirt opened low on his expensive silk suit. I immediately did not like this guy and thought he was an arrogant self centered ass hole. Nick and I exchanged pleasantries and I ordered a drink. Cindy tried to turn the conversation to a business tone and Nick just cut in talking about himself and all the things he had done in the past. By the time I had several drinks my stomach was churning from Nick’s continued talking about himself. Cindy and I rolled our eyes at each other as Nick built himself up as some type of god to women. Finally just as I thought I would be sick Nick offered that since my wife’s company was footing the bill he wanted to take us to dinner at a local favorite of his. Cindy and I eagerly said yes and we were off in a rented limo with Nick giving directions to the driver. We arrived at a very nice looking private club called the Finish Line. As we walked inside the place was an exquisite design with a lot of polished marble and brass finish. Nick led us to a table and at the table was a set of monitors with simulcast horse racing on each screen. My stomach tightened as I sat down looking at the monitors. Both Cindy and I had been several years in a 12 step program and the temptation was incredible as I could hear the call of the various races around me. Nick ordered drinks all the way around and an appetizer. As the waiter bought the drinks Nick looked at me and asked if I ever bet on the horses. I replied that I had not in a long time and tried to change the subject commenting on the décor of the club. Nick continued to talk about the horses and when the appetizer arrived Nick told the waiter that we would take our dinner in his private box. Nick ordered for all of us and led us to a very elegant and plush private suite on one of the upper levels. The insides were better than any penthouse suite. One wall was covered with monitors featuring races and other gaming venues from around the world. Nick continued through dinner asking if Cindy and I would like to “try our luck” with the horses. We finished a great five star dinner and when Nick went into the bathroom Cindy told me that it couldn’t hurt to play a little on the horses and if Nick was happy and signed a contract with her company it would mean a promotion and raise for her. I finally agreed to go along when Nick returned. Nick asked “Well, have you considered my invitation for a friendly little wager, or should we call it an evening?” I looked at Nick and thought I would love to relieve this arrogant cocky ass hole of a little of his cash and I would love to see Cindy get the recognition she deserved from her company. “Sure Nick, but this is all kinda new to us, will you show us the ropes?” Nick laughed and handed me a small interactive telepad. He handed me a drink and we sat down. Nick asked if $1000.00 was to rich for my blood and laughed again. I knew I had about $2500.00 cash on me and said “Not at all Nick, you pick the race.” Nick picked a race getting ready to begin and put it onto the large screen in the center of the wall. I knew the owners and trainers involved and placed my bet as did Nick. As the race started my horse took a good pace one length behind Nick’s horse and stayed there to the home stretch. Nick was bragging and making rude comments about easy money when my horse pulled out and crossed the line a full head in front of Nick’s horse. Nick tried to downplay his lose as he pulled ten hundred dollar bills from his billfold and handed them to me. Nick chided “Beginners luck, care to let me win my money back?” “I hate to take a man’s money” I replied as Nick switched to another monitor and another race starting. Again I knew the owners and trainers and we both placed our wager for $1000.00. This race was almost an exact repeat of the first only this time my horse pulled ahead to win a full length in front of Nick’s. Nick again reached into his billfold and handed me my money immediately switching to another race and placing his bet. After three more races and having to hand me $1000.00 each time Nick was not so jovial anymore. This time he switched to a Keno channel and placed his bet. Again old lady luck was on my side and soon I was sitting with $10,000.00 of Nick’s cash in my pocket. I enjoyed taking this smug pricks money and was really getting into it. Nick looked at me as he put another horse race back on and said “This time let Cindy pick the horse and double or nothing. I looked at Cindy who knew the horses better than she knew herself. She had a gleam in her eye and before I could speak accepted Nick’s wager. I handed Cindy the telepad and Cindy picked the perfect horse. Both she and Nick entered their wager of $10,000.00 and the race began. Cindy’s horse immediately took the lead and never looked back. Nick had to call downstairs and soon the waiter arrived with a note for him to sign and he gave Cindy the $20,000.00 he owned. We had a few more dinks and some small talk and Nick again offered a double or nothing for the winnings we had tonight. Cindy agreed and soon the race was on with a wager of $30,000.00. Again Cindy picked the winning horse and her horse led all the way around the track with Nick’s horse at least 5 lengths behind only feet from the finish line. Suddenly Cindy’s horse lost its footing and tumbled over loosing it’s Jockey. Nick’s horse crossed the line as our Jockey raised his horse and crossed the line in last place. Nick was doing a little dance and congratulating himself as Cindy and I stared at each other. Dumbfounded I counted out the $30,000.00 we had won from Nick and then reached into my pocket and counted out the $2500.00 I had in my pocket. I looked at Nick and told him I would have to get the balance of the $27,500.00 I owed him in the morning. Nick became furious shouting and cussing at me and Cindy that we played and now we would pay him or suffer the consequences. I tried to reason with him but Nick was in no mood to listen to common sense. Finally Nick calmed down and looked at Cindy and said in a calm business tone, “It would be a shame to end our business deal like this, maybe we could work out a payment agreement.” Realizing her predicament Cindy looked up at Nick and told him that there must be some satisfactory arrangement we could arrive at. Nick looked around and then counted out the money we owed him from his stack of bills. “This represents what you own me, when this stack is gone your debt will be considered paid in full, deal?” Cindy and I both nodded our agreement. “Good, I will give you $1000.00 for your suit.” Nick said as he counted out $1000.00 from the stack and placed it into another pile on the table. Cindy looked pissed as her face turned red and she sneered at Nick, “I am not some cheap slut or whore that you can buy, no way buster!” Nick calmly began to put the money back into one pile and said “that’s fine Cindy, I will just call the police and tell them about your little debt and then call your boss in the morning and tell him why your company will never get my business.” Cindy realized the implications of Nick’s statement and looked down at the floor, “Wait, we can work this out, just don’t call anybody.” Cindy stood and took off her jacket and folded it placing it on the sofa next to Nick and then red faced slipped out of the dress and did the same with it. She stood shaking in front of Nick and I casting her gaze at the floor. “Happy now?” she asked. “Very nice Cindy, I think we can work this out like two professional adults here.” Nick stared Cindy down as she stood in her stockings, heels, lacy black bra and matching boy short style panties that hugged her curves. “I would love to see you dance for me for another $500.00” Nick said as he counted out the bills and moved them to the second pile then turning on some soft music in the background. Cindy swallowed hard and began to dance to the music as Nick sat back in the sofa and gazed at Cindy offering me another drink. The song seemed to last five minutes but was finally over and Nick clapped softly saying “very very nice.” I could feel myself getting excited at seeing Cindy looking so beautiful dancing in front of a stranger who I know had to be getting tuned on from her. “Cindy you look marvelous, I would love to see your legs without those stockings. Tell you what I’m going to do, I will give you another $1000.00 for them.” Nick started counting from the pile removing the money and placing it onto the second pile. Without looking up Cindy said “Fine, Nick, if that would make you happy.” Reaching down to start to roll down her stockings. “Yes, but wait one minute darling.” Nick said as he walked out of the room. A few minutes later Nick returned with two older men who he introduced as Sal, his uncle and Vinny, his brother. Looking at Cindy he said “I have decided to add another $1000.00 and let my family watch you too.” Cindy did not say a word and with a tear swelling up in her eye she bent forward and slowly started rolling her thigh high stockings down her legs. Finally kicking off her heels and handing her stockings to Nick who took them from her and raised them to his nose before placing them into the pile of her clothes on the sofa beside him. Sal and Vinny made several cat calls and poured themselves a drink. Sitting down to watch Cindy’s humiliation. Cindy stood trembling now down to her lacy black panties and bra knowing that she would soon loose them too and that there was nothing she or I could do to stop what was happening. “Cindy honey, I want you to dance for us again and this time I want you to loose the panties and the bra as you dance. I want you to stand up here on the table as you dance so that we can see everything and to bend over so that Sal and Vinny can see your beautiful ass and pussy, I will call your debt an even $20,000.00 when you are done.” Nick said as he began counting bills from one pile to the next. Almost mechanically without saying a word Cindy crawled up onto the table and began to sway as Nick again turned on the soft music. Cindy looked like a stripper as she seductively removed her bra while dancing and tossed it to Nick. As she continued she bent at the hips with her back to us and slowly slid her panties down over her hips and down her legs exposing her trimmed pussy and her crinkled little brown ass hole. As she stood back up she methodically handed her panties to Nick who took them into his mouth and growled like a tiger. As Cindy danced Sal removed a massive fat cock from his pants and began stroking it and Vinny followed removing the smallest cock I had ever seen from his zipper and stroking it with his thumb and forefinger that just about covered it. Nick laughed and teased the two men as he leered at Cindy. Finally the song was over and Cindy stood motionless on the table. Nick clapped and came up behind Cindy climbing up onto the table and grabbing her from behind whispering in her ear just loud enough for us to hear “Cindy you are one incredible women. I will relieve your total debt to me tonight and all you have to do is use your incredible body and make love to me and my uncle Sal and Vinny, I will even let your husband join in the fun however he wants and to make it a deal you can’t refuse I will also sign the contract with your company. The only condition is that you take an active role in our lovemaking and there are no conditions or limits to our night. In the morning – in eight hours you and your husband can leave without owing me a penny and the contract is yours.” Cindy looked around and then looked to me. “Nick you bastard, how could I pass up a deal like that? I just have one question for you to ponder as the night progresses, do you really think you won the wager or do you think it could be possible that I let you think you won just to get what I really wanted?” That’s my wife a true gambler to the core, never let the opponent think he has got you, she had not lost her touch. I could tell by Nick’s body language that Cindy’s comments rubbed him the wrong way, he was a man who had to win, he had to be in control and Cindy’s comments challenged his victory. Nick began mauling Cindy’s breasts with his hands saying “Oh yeah, you think you won here, I will show you who is in control here baby!” Cindy reached behind her and grabbed Nick by the crotch through his pants and began rubbing him, not to be defeated. Nick called for his brother Vinny to get undressed and come over and lay down in front of Cindy. Vinny eagerly complied with Nick’s instructions and in no time was naked and laid out on his back in front of Cindy. Nick said to Cindy “Your going to fuck old Vinny here and every time his tiny little cock falls out of your pussy I am going to deliver a slap to your ass from behind you.” Part TWO in three days!