Gambler

I watched the pigeons tussle for seeds and other scraps among the cracks in the path. She was with him now but I didn’t have to watch anymore. I reflected on the past eighteen months and the roller coaster ride it had been. From Vegas, Atlantic City and the Bahamas to a park bench watching pigeons.

I had always been a gambler! Even as a kid I loved the thrill of the bet. . .I’d bet on anything. I asked my friends to bet so often that they started calling me, ‘Betcha.’ But I’m not a kid anymore and the eight months of success is still hard to believe from where I sit on this park bench.

I had played poker for years and when Texas Holdem became a worldwide sensation I was caught up on the wave. I was 52, moderately successful in real estate, had a nice home and a lovely, 40 year old wife, Trudy. Some of my friends said she was a trophy and I guess to some extent she was. A green-eyed, auburn-haired beauty, she stood a shapely 5’ 6’’ and looked great in a bikini and was tremendous in the sack. She rode the wave with me and loved to watch me play, and especially, win. As I said, the charmed life lasted eight short months. The cards never let me down and there seemed no end to my luck.

That’s what all gamblers believe so I didn’t worry when I had a few big losses, it was sure turn around. When the losses continued we started to sell off some luxuries; the Mercedes sports car, diamonds and the condo on St. Kitts. Before we knew it there was not much of value left and the real estate market was in decline. My luck had to change soon Trudy and I believed; it was just the next game, the next shuffle and deal of the cards.

I knew Jimmy Cardoza by his powerful reputation only. Some said he was in the rackets and associated with the Mob but no one knew for sure, he was definitely not completely legit but he had never been charged with anything. He’d loan me the money, they said, until my luck turned around and like a fool, I went to him for help. I took Trudy along; I thought that with her standing next to me in that little, short black dress with her big tits half exposed and the tops of her stockings and a bit of garter strap showing, it wouldn’t hurt may case. . .and I was right. Jimmy was a short, pudgy, ugly specimen and reminded me of a gnome.

He was about 65, a few wisps of black hair sprouted above his ears on the sides of his otherwise bald head. Despite his Armani suit he still projected a sleazy image to the world. He rose from behind his desk after we were ushered into his office by one of his assistants, a guy not dissimilar to Luca Brazzi from the Godfather movie. His eyes were all over Trudy as he approached us to shake hands and made no attempt to hide the fact that he was staring at her tits. He offered us chairs and guided Trudy into hers with his hand too far below her waist as he looked down her cleavage as she sat. I thought the little creep might ask if he could feel her ass and tits then fuck her right there on the desk.

He listened to our story while alternating his stare from Trudy’s tits to the hem of her short dress which had ridden up as she crossed her legs exposing her stocking tops, naked thighs and garter straps. ‘So, you want ten grand and you’re sure you will pay me back with interest in a week. Your past indicates that you just might do that, but what if you don’t?

I told him that wasn’t an option; my luck just had to change. He nodded, opened a desk drawer and tossed a wad of bills across the desk.

Of course my luck didn’t change and I was back in Jimmy’s office the next day looking for another ten grand. Jimmy was all smiles and he looked at Trudy’s face for once and asked, ‘Are you 100% with him on this?’ Trudy replied that she was - 110%. Jimmy’s eyes were back on her tits again. He put his elbows on the desk and put his fingers together forming a triangle, ‘That’ll be twenty grand, what if your luck doesn’t change?’

‘It will, it will, it has to, I assured and Trudy agreed.

‘Very well, I’m telling you now that if you and,’ he leered at Trudy, ‘are not back in my office in a week with my money don’t bother coming. I will come to you and we’ll discuss other ways you can repay me,’ again he leered at my wife. I knew it wouldn’t come to that, I looked at my wife and she nodded. Jimmy tossed another wad over the desk and we left to find a game. ‘Oh, by the way,’ Jimmy said just as we reached the door, ‘if I do need to come and see you, your wife will be wearing that black dress, stockings and heels, won’t you Trudy? We just stared at him as he smiled broadly then left his office.

The next few days went well and I had almost thirty grand, enough to pay Jimmy but I needed more. My good luck was back and Jimmy fucking Cardoza could go fuck himself instead of thinking about fucking Trudy. I went all in with a full house, jacks full of sixes and lost to four sevens. There was nothing else to do except wait for Jimmy to come a calling.

‘What’ll I do about that dress Cardoza told me to wear?’ Trudy asked.

‘Better do what he said, we need to keep him in a pleasant mood,’ I responded.

Jimmy called and said he would arrive at seven and we’d better be home. He was prompt and I led him, accompanied by ‘Luca,’ through to the living room. Trudy was seated in a chair with her black dress on; Jimmy smiled, or rather, leered when he saw her. I sat on the arm of Trudy’s chair and Jimmy sat on the sofa with Luca standing at his side. ‘We have a dilemma here, a little matter of twenty grand plus interest and I’m guessing you can’t pay,’ Jimmy surmised correctly. ‘Now, I could get Luca to have a… er…word with you but that would not get my money back, only a little satisfaction. If I’m not going to get my money there must be other ways I can get a lot more satisfaction,’ and his eyes drifted across to Trudy.

‘What exactly do you mean, spell it out,’ I fired back with venom.

‘Now, now, there’s no need for this to be nasty, it’s just a business agreement but I will spell it out for you. I want Trudy. Whenever the fancy takes me, I want her. He looked at me and said, ‘And you and she will do exactly as I say, is that clear?’

‘You bastard, you’re not going to fuck my wife.’

‘Oh, I believe I am, when I want, where I want and how I want.’

‘Never!’ I spat. The thought of this ugly dwarf with my beautiful wife was obscene.

‘Very well, I’ll let my friend here take you downstairs to see if he can change your mind.’ Jimmy motioned to Luca and he started across towards me.

‘No!’ Trudy yelled, ‘don’t hurt him, I’ll do want you want.’

‘No, no, no!’ I shouted but Trudy squeezed my arm and assured me it would be alright.

‘There’s a smart girl, smart as well as beautiful, I like that and I’m sure, in time, you will thank me and be very glad you’ve made this decision,’ Jimmy laughed and pointed to the dining room, ‘Get me a chair,’

Luca picked up a dining room chair and placed it about ten feet in front of his boss. ‘Good, that’s about right,’ then he turned to me and said, ‘Now, please,’ and waved an arm towards the chair. I sat down and Luca took lengths of cord from his pocket and tied my hands and feet securely to it. ‘Just a precaution,’ Jimmy said smoothly, ‘to avoid any unnecessary unpleasantness, some men have a tendency to become violent when they see me fucking their wife. Thank you, that will be all,’ and Luca made his exit, presumably to wait in the car.

‘Now my dear, come here,’ Jimmy said and Trudy walked over and stood in front of him. ‘You are quite beautiful, I’ve wanted you from the first time I saw you and I’m going to have you again and again. Turn around let me see you from all sides,’ he licked his lips, ‘yes, very, very nice, lift your dress slowly for me, please.’

My wife did as she was told until it was up around her waist. From my vantage point I could see her lovely ass and the very narrow strip of thong that ran between her cheeks and knew that Jimmy could see her pussy lips bulging from either side of her tiny thong. His eyes fixed exactly there and he licked his lips again. ‘Now turn around again,’ and Jimmy leered at my wife’s ass, ‘fucking beautiful,’ he breathed through his teeth. ‘Bend over,’ he ordered and Trudy gave me a weak smile and obeyed.

Jimmy rose from his seat and approached my wife. He fondled her ass as though inspecting a rare antique and gave each cheek a few slaps then he rubbed her labia on each side of her thong and finally over the thong. ‘So beautiful, I’ll fuck you in this position but not just yet, stand up. Trudy stood and towered over the little man. Her tits were at his eye level and he gazed at them for a while before exploring them with his stubby fingers, ‘Such lovely tits,’ he said, apparently to himself. ‘Take off your dress.’

‘You’ll need to help me with the zip,’ she said.

‘I’d be delighted to,’ he answered and Trudy turned and he pulled down the zip. She stepped out of the dress and stood before him in bra, thong, garter belt, stocking and stilettos. ‘Push your tits up out of the bra but leave it on, I like the way they stick out over it.’ She did as ordered and even though I couldn’t see, I knew how erotic they would look. Jimmy leaned forward and slobbered all over her tits then pawed them and pulled on her nipples, ‘Very nice,’ he murmured. ‘Now the thong. . .slowly.’

He ogled her as she slowly removed her thong, anticipating his first view of her naked pussy. On seeing the neatly trimmed wedge of blonde pubic hair he sighed, ‘Oh, I love some hair on a pussy, it makes you more of a woman and I’m going to like it down there, you are going to be my slut and in time you will learn to like it. Unless I tell you otherwise you are to always dress in erotic clothing and lingerie for me, it’s a little fetish I have. Now, sit back on the sofa and open your legs; I want to taste that sweet cunt of yours.

He watched Trudy walk to the sofa and sit down. ‘Lie back and spread those lovely legs, let me see your pussy. Oh, you look so horny, you want me to lick your pussy don’t you, you can’t wait for me to fuck you can you?’

My wife lay there with her legs spread wide but said nothing.

‘Don’t you!’ Jimmy shouted.

‘Yes, Jimmy,’ she replied quietly.

‘Louder and say Jimmy darling, yes, Jimmy darling, I like that, so tell me!’

‘Yes, Jimmy darling, I want you to lick my pussy and fuck me.”

‘That’s better,’ he said softly with a smile, ‘you are going to like it, I do know what sluts like and I’m going to give it to you and soon you will thank me, thank me every time I lick and eat your pussy, let you suck my cock and especially when I fuck you.’ He chuckled, got on his knees and buried his face in Trudy’s pussy. He made a lot of noise but after about five minutes he was having an effect on Trudy. She began to moan, quietly and reluctantly at first, but she began to moan louder, wriggle and clutched at the pillows on the sofa. Jimmy’s hands were busy on her tits too, mauling, squeezing and pulling roughly on her erect nipples.

There was a point when she seemed to transcend to a different plane, blocking everything out except the sexual pleasure she was feeling. ‘Oh god, oh god, ooooh,’ she groaned and I knew she had just climaxed. Jimmy might not look like much but he did know how to eat a pussy and he also knew what had just caused to happen.

Jimmy stood and looked at me while Trudy lay panting, her legs still spread wide, ‘I told you I know how to treat a slut, sonny boy, and that’s just my tongue, wait ‘til she feels my dick inside her.’

He walked over to me then called Trudy over. She got up slowly and walked a little shakily to us. Jimmy mauled her tits then played with her pussy making sure I saw everything. It was all part of his plan to show me that Trudy was his to feel and maul and lick and fuck whenever he wished.

‘You’ve been a lucky man having all this to yourself but now this slut’s body is mine whenever I want and I will treat her like a slut, it’s what I do. Now I don’t want you to worry, I will get tired of her when I’ve used her for a while, it might be a few weeks, a few months or more but I will tire of her and you can have her back. Remember, I need to get twenty grand plus interest out of her and that’s an awful lot of fucks and I will get it one way or another but you, sonny boy, will also pay in different ways. Now, my dear, undress me, I want to show your worthless husband what a real cock looks like and how to fuck a slut ‘till she begs for more.’

‘Yes, Jimmy darling,’ she said and began removing his clothes. He was hairy and his pot belly hung over his pants but when he was down to his shorts it was obvious that although short in height that didn’t translate to the size of his cock. Trudy knelt down and on Jimmy’s command, pulled his shorts down. It was semi-hard but big and ugly and sticking out from his little body and curved to the left. It must have been over a foot long and was uncut and very thick.

‘Now that’s a dick, sonny boy and this lovely slut is going to learn to take every inch of it and love it, isn’t she?’ he stared down at my wife.

She looked up and breathed, ‘Yes Jimmy darling, yes.’

‘So, Trudy, my love, go to work and start paying off some of that twenty grand, there’s a long way to go.’

With one hand she reached out and grasped the big cock and pulled his foreskin back to reveal and huge head with an oversize piss hole. She masturbated him slowly and he stiffened to an incredible length and hardness. Her other hand cupped his big ball sack and as she caressed it she moved faster over the long, thick shaft. I was amazed that the little, old gnome of a man who didn’t look fit could muster the blood to fill his huge cock but he could and it looked menacing.

‘Let me feel those lips around by cock, Trudy, my love.’

‘Yes, Jimmy darling,’ she said and her beautiful blood red, lipstick-covered lips enveloped Cardoza’s ugly cock head. I watched as her tongue circled it then flicked the piss hole. With a hole that big he must splash cum like water from a hose, I thought and was ashamed when I imagined it splashing over my wife’s face. Cardoza held Trudy’s head and began to pump more of his dick into her mouth. He looked at me with a sneer as he went faster and deeper causing my wife to choke and shoot spittle over his cock. ‘She likes it,’ he snapped at me, ‘all sluts like a big cock down their throat. I’m ready now, get up, my sweet, it’s time for you to get fucked by a real man with a real cock.’

‘Yes, Jimmy darling,’ she responded and stood.

He bent her over in front of me and roughly fingered her pussy. I could hear that she was very wet and Cardoza’s massive erection pulsed violently as he mauled her pussy and ass, preparing to fuck her. When he came up behind her he realized he was too short and his cock couldn’t reach my wife’s pussy. He made a comment that she was always to wear stilettos when he fucked her so taking them off was not an option. He made her spread her legs wider and bend her knees and place her palms on the floor until she was the right height for him. He rubbed his cock up and down along her pussy lips, forcing them apart.

I felt a flash of shame again as I realized my cock was as hard as Cardoza’s. Finally he pushed into her and she sighed as about two thirds of foot-long, thick cock disappeared. He held it there for a while then began a slow, rhythmic thrusting, deeper and deeper with each stroke. Both he and Trudy were grunting as he slammed into her, his thighs smacking hard against her ass.

After several minutes he and my wife were panting and he slowed to an easy pace, long strokes all the way in then almost all the way out. His hands pawed her ass then held her hips and pulled her back onto his cock. He stopped with his cock completely buried and looked at me, ‘She very wet, she already wants more of my cock and she knows when she has been well fucked.’

Trudy was lost again and quietly whimpering, ‘Oh, yes, yes, it’s so big, oh, yes, more, more, please, give me more, hard deep.’ Cardoza was enjoying the effect his cock was having on my wife.

‘I told you, sonny boy, I told you she would beg me for more cock,’ he said with glee.

After several minutes he pulled out and rested his cock on Trudy’s ass; it looked bigger than before and twitched constantly. How he could do it at his age and apparent physical condition I didn’t know but it’s said that everyone is good at something and his something was fucking, he certainly had more than enough equipment for the job. He moved back and turned Trudy so that her ass was facing me, her legs were still spread and her palms still flat on the floor. I could see that her pussy was wet and it gaped open, he had really stretched her. Fingering her pussy and clit he looked at me and smiled, ‘You see how excited she is, sonny boy, that’s what a real cock can do for a slut, even a beautiful slut like this and she going to get lots more cock in her hot cunt and delicious mouth.’

He was intentionally crude; it gave him a sense of more control over us.

He slapped Trudy’s ass and ordered her over to the sofa. ‘Spread those beautiful legs wide, it’s time for you to feel my cock inside you again.’

She walked to the sofa and opened her legs wide as before. Cardoza watched her go, turned to me and gave a little chuckle and followed her with his huge, hard cock swaying from side to side. He pushed her legs back as far apart as possible as he looked down and watched his cock slide into her pussy. He slobbered over her tits and started to give it to her with long, deep strokes. His stamina was amazing and he thumped into Trudy with great force. As before she was receiving the full length of his dick but much harder this time and soon Trudy was moaning and whimpering continually.

She cried through an orgasm and instinctively her hands grabbed Cardoza’s ass and pulled him onto her shouting, ‘Yes, yes, yes.’ The gnome grunted out loud and Trudy screamed as he ejaculated and pounded into her over and over before slumping on top of her. After a minute or so he withdrew and climbed on top of her chest so she could lick his dick clean of cum and pussy juice. Her legs were still apart and I could his sperm had splashed all around her pussy and a stream ran from her stretched vagina onto the floor. He must have spilled a pint of cum into her from that huge piss hole and there was little doubt that Trudy had enjoyed it.

She had always liked sex and the feel of hot cum spurting inside her but this old lecher’s big cock and the way he had fucked her was something different, he had reached places within her that I never had. It turned her on like I had never seen even though she must detest him. Perhaps she liked being submissive or performing in front of me or perhaps it was just his big, hard, ugly cock and the way he fucked her that excited her so.

Cardoza dressed and went over to Trudy and kissed her on the lips and forced his tongue into her mouth then probed her still gaping, well-drilled pussy with two fingers. They came out covered with cum and he put them in her mouth. ‘There will be lots more of that to come, in your mouth and pussy,’ then he turned to me and said, ‘don’t think about skipping town, I’ll find you and it won’t be pleasant for either of you.

Only a very small instalment has been paid tonight, you’ll be hearing from me. Oh, I almost forgot,’ he produced his wallet from his suit jacket and put several bills between Trudy’s tits, ‘Here’s a grand, go and buy erotic clothes and lingerie. I like my women to look horny and slutty and don’t think of gambling with it, I know what a grand will buy and I’ll ask to see it and make selections for you to wear,’ and he was gone.

Trudy untied me, nothing was said and she hurried to the shower. I thought about what had just happened and couldn’t believe that I had a strong erection watching my lovely wife being fucked by an ugly little gnome of a man with a big cock. I couldn’t deny it and I became hard again as I thought about what he had done to my wife. She came in with a short bathrobe wrapped around her and sat on my lap. We snuggled for a bit then she said in a startled tone, ‘You’re hard, how can you be hard at a time like this?’

‘I don’t know, you seemed to enjoy parts of tonight judging by your orgasms, moaning and the sounds of his cock pounding your pussy.’

‘I hate him but his big cock did feel good inside me. How long do you think this will go on?’

‘I don’t know but I what can we do, we’re kinda trapped.’

‘Perhaps if I encourage him he’ll have a heart attack and die inside me.’

‘If he does you may have trouble lifting him off you, his cock’s so big.’

We laughed and Trudy opened her robe, ‘I’ll have to keep him happy until our luck changes, I guess, but I still like the way you fuck me, fuck me now.’

I needed no further encouragement. I bent her over the chair and fucked her wildly from behind. She was still very wet and highly aroused from the considerable screwing she had received from Cardoza and his cum on my cock was evidence of just how much the old man had ejaculated deep in her pussy. I soon added mine on top of his and we went off to bed sexually satisfied but worried about the future.

The pattern continued; he would call, come over and have his way with my wife. The funny thing was he always gave her a tremendous pounding and released a huge load of cum in her pussy, except one time when he pulled out and she jerked him off. He shot a massive load all over her face; it was in her hair, ears, eyes, nose and mouth. How he could do that at his age was a mystery but he did it every time and I thought Trudy was enjoying it more each time he came over.

I remember one time Cardoza called to say he’d be over at seven and told Trudy what to wear from the selection he had purchased. He was punctual as usual and we went into the living room, he liked to fuck Trudy on the chair or sofa but had fucked her in every room in the house and was very creative when it came to different ways to get his cock into her. He hadn’t tied me up since that first night; Luca was always outside in car so there was no need.

Trudy came down stairs and into the room wearing a cupless red basque, red stilettos, black fishnet stockings and lacy, black, open-crotch panties. ‘Yes, very nice and very horny, we will have some fun tonight,’ the gnome said with pleasure as his eyes were already fucking her. ‘Sit over there in the chair,’ he instructed and I went and sat, ‘and you my sweet, horny slut, will sit with me on the sofa.

No sooner had they sat and he was mauling her tits and pussy and had his tongue down her throat. I could only watch and saw the bulge in his pants get bigger and bigger. He held Trudy’s hand and placed it on the bulge, ‘Get it out and play with it,’ he said and after rubbing over his pants she unzipped him and released his giant erection. She jerked it slowly, caressing the head and his big balls as he continued to maul her.

‘Take your clothes off,’ he said to me and laughed when he saw my erection, ‘you like to watch me playing with your wife, does it get harder when you watch me fuck your sweet, slutty wife and hear her moan with pleasure and ask me for more cock?’

I didn’t answer, he didn’t need an answer; he just liked exerting his power over us.

‘Come here and take my clothes off, I don’t want to stop playing with your wife’s tits and pussy to do it myself.’

I removed his shoes and socks and watched his fingers work in and out of Trudy’s pussy and rub her clit. I was hard and couldn’t hide it. I took off his tie and shirt then his pants and shorts. Her hand looked so small on his massive cock and I could see that her pussy was wet and her labia were puffy with arousal. I thought she must be looking forward to his big cock inside her, that’s why she was so aroused and I loved and hated her at the same time. Cardoza had me kneel between his legs and watch Nikki suck his dick while he allowed me to keep her pussy aroused with my fingers.

‘I don’t see why you should have all the fun my sweet-lipped slut; share my cock with sonny boy.’

Trudy stopped sucking and looked at me then moved his cock toward me. I took it in my mouth as Trudy jerked it back and forth and caressed his balls. The head felt huge and my cheeks bulged as Cardoza, the bastard, bucked his hips. He quickly tired of my untrained technique and Trudy went back to doing the job she did so well. It was just another way for him to show he was in control and that he owned my wife’s body and mine for that matter. He pulled Trudy back beside him and fondled her while she jerked his cock. I stood in front of them, watching, with a strong erection.

My wife’s fingertips roved over the gross, bulbous head of Cardoza’s cock and teased the piss hole then went back to stroking him as he made a point of making sure I saw their tongues entwined as he mauled her tits and fingered her. I began to play with my erection and Cardoza watched for a while as I masturbated. My eyes went back and forth from Trudy’s hand on his giant club of a cock to his fingers working over her pussy and clit. The squelching sounds his fingers made told me she was aroused again and soon she began moaning.

Jimmy Cardoza looked at me with a gleam in his eye. ‘I was going to fuck your lovely slut of a wife on this sofa but I’ve changed my mind, we’ll do something else, together.’ He lay on the floor and instructed Trudy to kneel beside him. I was told to kneel between his legs. ‘Now my charming whore I want you to jerk me and sonny boy here and when he cums direct it all over my cock, is that clear?’

‘Yes Jimmy darling,’ she answered flatly.

‘Good! Then begin.’