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Gambling Debt Cuckold

By: edrider73



Many thanks to Linda62953 for all the hard work in editing and improving this story from a previous version. 

*

I'm not a man who takes chances. I'm very careful about everything I do. I'm Mr. Due Diligence. Of course, you can't be a hundred per cent certain about anything, but I check and check before I make any decision to be sure the right choice is almost a certainty. Sometimes this causes friction at work, but I don't care. And if my boss ever gives me grief about it, I remind her of the many times I've saved her beautiful rear by being too cautious.

The people at the company where I work have no idea that I used to be the exact opposite of what I am today. I was a compulsive gambler, and it was destroying my life. Thanks to my wife, Penny, I was able to quit, and one of the reasons I joined this firm is I wanted to break all ties to acquaintances who might seduce me back into my previous life. It was the first time I was ever overcautious, and it felt so good that I've been that way ever since.

I say overcautious, because I already knew at the time that I would never gamble again. When I quit, I quit cold turkey. I never attended a Gamblers Anonymous meeting, and I never saw a therapist. It sounds like I got off easy, but nothing could be further from the truth.

I didn't realize it, but my cure began one Sunday morning when I came into the bedroom after taking a shower to find Penny lying naked on our bed in a very provocative pose.

"Honey, see the camera on the dresser?" she said. "I want you to take some sexy photos of me. Stand right by that chair. I just made all the settings for the morning light, so all you have to do is press the button as I move around. You can zoom in to get close-ups."

"Let me put something on first," I said.

"No," she said. "Just do it now. I've got my reasons. You'll see."

So I picked up the camera and began shooting. At first, she was leaning back on her elbows with her knees open to display the thick bush between her legs. She knew I loved her pubic hair, both looking at it and feeling it with my fingers and face when we had sex. As I took photos, she began opening her legs wider. What we were doing must have excited her, because when her chubby labia opened, she was already red and moist inside.

She pulled her legs back and moved them in many positions, and she touched her breasts and fondled them. She turned on her stomach as I kept snapping away, and then she got on her knees and slowly moved her beautiful ass higher in the air. When it was high above her face, which was on a pillow, she told me to get behind her and she would move her head so that I could take photos of her legs and butt and get her face in the photo, too. She spread her legs apart so that both her red, wet vagina and her little asshole wrinkle were visible, surrounded by the thicket of hair.

I was concentrating on aiming the camera and pushing the button, but gradually, it got harder and harder. I mean not only my ability to concentrate but also my penis. Penny looked at it a few times and smiled. Finally, she stopped moving and got off the bed.

"Now it's your turn," she said. "That's why I didn't want you to put any clothes on. I want to take some sexy pictures of you, and what could be sexier than that huge hard-on."

I protested that I didn't know the first thing about posing, but she said that didn't matter. She had done some research online, and she would pose me. She began directing me and telling me where to put my hands and legs. I just followed her instructions, which were confusing. Once she got me into a position she wanted, she told me to turn my head to the camera and smile.

She had me lying on my back first, then my side, always showing my engorged penis, and then the positions got more bizarre. There were lots of shots of me on my hands and knees with my back swayed so that my rear was pushed out, and then she had me spread my legs as wide as I could. The breeze from the air conditioner across my asshole tickled a little. She had me kneel on the floor next to the bed and put my upper body across it with my arms spread out, and then she shot from below as she had me move my legs apart slowly. She told me that she got some good close-ups of my open ass with my raging hard-on right below it.

Then she had me stand up and put my hands on my knees and bend over as far as I could and spread my legs at the same time. I almost fell over a couple of times. She moved around me as I held the position until she could get the shot she wanted. She had me move my head, too, because she said she wanted my ass, my penis and my face all looking great at the same time.

After that, there were a few more shots of me bending over the desk in the bedroom and one of me lying over the hassock next to the easy chair. She positioned me so that I was on my chest and stomach and my hands and knees were on the ground. Then I had to spread my legs apart again and turn my head as she shot from the rear.

Finally, she stopped and said, "Are you as horny as I am right now?"

I watched her put down the camera, jump into bed and spread her arms and legs like she was inviting me to give her my answer without using words. It took me only a few seconds to show her I shared her feeling, and then things got wild and wonderful for the next hour.

When we finally stopped to catch our breath, I told her that she was the sexiest woman in the world, and watching the way she moved her body turned me on so much that I felt like I was going to explode before even touched me.

"I know you love to watch me when I'm horny," she said. "I'll give you all the photos, but you have to promise not to show them to anyone. I'm putting your photos up on the Internet."

I laughed. Penny is so funny. She always cracks me up.

I remember that morning as a few bright and happy hours in the midst of many dark and unhappy days. My gambling was out of control, and Penny and I were always arguing about it. She told me I needed help, but I wouldn't admit it. Finally, I stopped telling her how much money I was losing to my sports bookie, but she could tell from my worried expression that things were getting worse.

The weekend before our sexy photo session was a total disaster for me, and for the whole week, I couldn't look her in the eye. I was contemplating suicide, because there was no way I could ever pay off what I owed. Even if I gave the bookie half my paycheck for the next five years, I would still owe more than $30,000, plus interest that would probably equal nearly as much by the time I was able to pay off the debt. Of course, the bookie's boss, a mobster named Lenny Sambuco, wouldn't go for an arrangement like that anyway. He'd soon find out that we didn't have much equity in the house and hardly any savings, and I wouldn't have to worry about killing myself, because he'd take care of it.

Penny noticed how worried I looked and asked me about it several times. I figured she probably knew the reason, but she must have been so upset by the way I looked that she didn't fight with me. She just asked me to tell her what was wrong, and no matter how bad it was, she would help me fix it. Since there was no way she could do that, I kept silent. I figured she planned that Sunday morning to cheer me up, which it did. But by Sunday night, I was totally depressed again, wondering how soon Sambuco's men would come for me, what they would do to me before they killed me and hoping that it wouldn't be in front of Penny.

Monday when I came home from work, she was smiling. She gave me a big kiss, and then said, "You don't have to worry anymore, honey. It's going to be all right."

"What are you talking about, Penny?" I said.

"I've taken care of everything," she said. "You're off the hook. I worked everything out with Mr. Sambuco. Your losses will be wiped out. And I hope that that this will also stop your gambling."

"What?" I said. I was scared, a little for me, a lot for her. People didn't work things out with Lenny Sambuco. They did what he said, or he hurt them -- or worse. Just the idea of her talking to him gave me chills.

"You heard me," she said. "Tonight we're celebrating. I bought some expensive steaks for dinner. But after Saturday, we'll really celebrate. We're finally going to be able to save some money, and then we're taking a really nice vacation together. It will be a working vacation, because I'm going to time it so we can get to work on starting our family."

"Penny," I said. "You're not making any sense. What did Sambuco say to you?"

"He told me what the problem was, and he told me what he was planning to do about it," she said. "But I convinced him there was a better solution. He was stubborn at first, but after we negotiated for a while, he finally gave in to my idea. Well, almost. He needed to get a better picture of what I was wanted to do. I gave them to him today, and now the deal is done."

"What kind of a deal are you talking about, Penny?" I said.

"I don't want to go into it right now, because tonight is for celebrating," she said.

"But I can't celebrate until I know what you did," I said. "I know Sambuco. He doesn't care about anything except getting his money. How is he going to get his money?"

"Don't worry, honey," she said. "I worked out a way for him to get it. It's all settled."

"But where is the money coming from?" I asked. "I didn't think you knew anyone with that kind of money to loan you."

"It's not a loan," she said. "It's going to be worked off. And that's the last I'll say about it until later this week. No more questions. Just accept it. Our worries are over, and we're going to have a fun evening."

I pretended to enjoy myself, but it was hard. I kept coming back to what she said about working off the debt. There was no way I could ever work off the debt, and her salary as an assistant manager of a clothing chain store wouldn't help much. What did she mean? That night I had a tough time sleeping.

In the morning, it hit me. She was going to work off my debt! Maybe she would be a hostess at one of his clubs. No, that wouldn't pay enough. As it dawned on me what her deal was, I began shivering. Sambuco ran most of the higher paid outsource escort services in town. My beautiful, sexy Penny was going to become one of his high-paid hookers. That was the only possible way she could make enough money. My wife was going to pay him back on her back.

The idea made me sick. I racked my brain to come up with some other idea, something I could do so she wouldn't have to do that. But I couldn't come up with anything. First I was scared for her, and then I was ashamed. How could any self-respecting man allow his wife to do that for him? Was death really worse than such humiliation.

When I went downstairs for breakfast, I couldn't look at Penny. I ate quickly and left for work. My mind was going wild. I could barely concentrate all day. I drove home as slowly as I could. It was as if I didn't want to ever get there.

We talked small talk, and I didn't ask her any more questions about what kind of deal she had with Sambuco. I spent some time trying to think of any other kind of arrangement she might have with him except the one I knew she had made. I had a splitting headache.

We were sitting in the living room watching TV. She lowered the sound during a commercial and turned to me. "Do you know what a cuckold is?" she said.

"Yes," I said. "Why do you ask?"

"I had never heard the word before a few days ago," she said. "Of course, I know that some wives cheat and their husbands don't know they are cuckolds. But then I heard that some men get off on watching their wives with other men. The idea made me sick at first. But I was told that even though most men would never want to be cuckolds, a lot of them think occasionally about watching their wives having sex with someone else, and it's a real turn-on for them. Have you ever thought about watching me have sex with another man?"

"No," I said, "not until you brought it up just now, and I can tell you the thought of your doing it makes me want to throw up."

"I knew you'd say that," she said.

I waited for her to say something else, but she turned the sound up, and there wasn't any more conversation that night. It wasn't a night for celebration, like the night before. When we went to bed, she turned off the light and rolled away from me.

When I came home the next day, it was almost a repeat. Not much happened, except while we were watching TV, she said, "Is there anything you want to ask me, honey?" I looked at her, and she saw the fear in my eyes. "Don't worry, honey," she said. "Everything will be fine." I never asked her a question.

The rest of the week was pretty much the same. I was out of my mind with worry as I thought of her prostituting herself, and I had suicidal thoughts, followed by feelings of total humiliation as I didn't lift a finger to help her.

On Friday, she finally told me a little about what was happening Saturday. "We're going to be in a video," she said. "But nobody will know it, because we're going to have wigs on, and special makeup, so our faces will be completely different."

For some reason, I was shocked. I had thought of Penny turning tricks in an expensive brothel or visiting businessmen in hotel rooms, but I had never thought of her doing a video, or of me doing one with her.

"What will I be doing in the video?" I said. I knew what she would be doing, and I didn't want to hear her say it.

"That depends," she said. "I know you and I are going to be great video actors, and if we make a good video, it will all be over by tomorrow night. Everything you owe Mr. Sambuco will be paid off."

"And if we aren't good video actors?" I said.

"Oh, I know we'll do well," she said. "I'm very motivated. Aren't you? I hope you're thinking about how wonderful it will be for us to get a new start. That's what I'm thinking of."

I wasn't thinking about that at all. Now I was thinking about the video. I would be involved. How? Then I remembered the cuckold question, and I nearly fainted. The video would be of her having sex while I watched, a cuckold video. And it sounded like I would have to participate, too. I might have to suck on the man's penis, or place it in her vagina. Would she have to do anal, too? I had seen a video online once where the husband was lying under the wife and licking her lover's balls and her clitoris while the man pounded her. And then there was something even more ghastly. After the other man came in her vagina or anus, the husband had to suck out and swallow the come. When I thought of that, my head started getting dizzy. I almost fainted.

I finally forced myself to stop thinking about what I would be doing, but I couldn't stop thinking about her role. Maybe the video would be one of those gang bang videos, and she'd have to take on a bunch of men with large penises. What if they all came inside her, and I had to suck all of the come out? I thought of her beautiful body, lying there and some large penis pushing into that beautiful bush until it reached her vagina and then spreading her open and going in and out. I wondered how she would handle it. Maybe she would even enjoy it. Maybe she would try not to enjoy it, but she would enjoy it anyway. The more I thought, the more aroused I got. I felt it right away in my pants. What was happening to me? I was disgusted with the idea of being a cuckold a few days ago, but now thinking about it, I was getting aroused, just like she had said. What kind of a disgusting pervert was I?

That night I saw her watching me. I wondered what she was thinking? She was probably wondering what I was thinking. We didn't say much, but when we went to bed, she put her arms around me and held me tight and said, "Honey, whatever happens tomorrow, I want you to know that I love only you, and the only reason we're doing that video is to pay off Mr. Sambuco so we can start over with no worries." Then she kissed me and got into bed and turned off the light. She fell asleep, but I didn't for a long time.

The next morning after breakfast, she drove us to an old warehouse in a deserted industrial district. But there were a few cars in the lot she turned into. We reported to an older woman sitting at a desk who had us sit down and wait. Soon two pretty young women came for us.

Penny turned to me. "There's only one thing you have to remember, Honey," she said. "The next time you see me, they will be filming -- probably even a few seconds before that. So everything you and I say will be on the video. We're going to start with a small conversation. We won't say our names, but otherwise we'll talk the way we always do. It's got to sound natural, so don't try to make things up. But the most important thing is to remember that everything we say will be on the video."

They took us down a narrow corridor, and one led me into a small room while the other one led Penny away. The woman told me to take off my clothes behind the screen in the room and put on a robe. Then she had me sit down in a barber's chair that went up and down and turned around, and she went to work on me. A wig with pony tail hanging down in back was secured to my head and all sort of pencils, markers and brushes were used on my face. Finally, she stopped and turned my chair to face a large mirror. The man I was looking at wasn't me. At least Penny was right about not being recognized, I thought, but it didn't give me much satisfaction.

The woman led me to a large open area with lights all around it and lights shining down from the ceiling, too. In the middle of the area was a large platform, and in the middle of the platform was a large bed. There were two chairs on the floor next to the platform, and the woman led me to one of them. I looked around and saw the other woman leading someone in a robe who didn't look anything like Penny to the other chair. She sat down and turned to me.

"They did a great job on makeup, honey," she said, "don't you think?"

I didn't say anything because I realized that the videotaping had begun. I was so frightened, I clammed up.

"Let's tell the people watching why we're here," she said. She looked at me to see if I wanted to say anything, but my mouth was locked tight.

Then my mouth fell open, because she looked into a camera and began telling the story of our lives for the last few years as I threw all our money away on gambling. She told in detail some of the worst humiliations she had suffered because of my actions. They sounded even more horrible because she was so matter of fact. It was like she was talking to an old friend.

She got to the terrible mess we were now in and said that my creditor had come to see her. She said he had wanted to beat me and torture me and even maim me, but she said that if he wanted his money back, it would be much better if they worked something out together. She mentioned the figure I owed and said Sambuco told her she could work every weekend and one day a week as a call girl and pay off the debt in three years.

"I haven't told my husband about that offer until now," she said, "because I agreed to get his reaction on this video." She turned away from the camera she had been facing and looked at me closely. "Honey, what do you think about your wife working as a prostitute for three years to pay off your gambling debts."

I couldn't open my mouth. After waiting a few seconds, Penny began stroking my arm. "He's really upset by all this, but he knows that if we're going to earn the money to pay back our creditor, he has to participate and help me make a really good video. So he's going to answer my question. In case you forgot, honey, I'll repeat. How do you feel about me selling my body to pay off your debts?"

"I feel horrible," I blurted out.


Gambling Debt Cuckold



"Why?" she said.

"Because I love you, and the thought of you working as a prostitute makes me sick with guilt," I said.

"I knew you'd say that," she said and then added quickly. "Of course, that's just a figure of speech. None of this has been rehearsed? Isn't that right, honey?"

"Yes," I said.

"So you don't know what I'm going to say next, do you?" she said. She smiled, and for a moment, I thought she was actually enjoying being an actress. But how could she, knowing what was ahead?

"Well, I promised our creditor that I would be his whore if we couldn't figure out a better way, and that's when I thought about making this video that we're making. If it's good enough, I don't have to be a prostitute. We can take care of the whole debt today, honey. Isn't that great?"

"Yes," I said. "I guess it would be better just one time."

"What do you mean?" she said.

"I mean if you have to have sex with other men, then just once for the video would be better than three years," I said.

"Would you like me to have sex with other men for the video today?" she said.

"No," I said. "That's not what I meant. I don't want you to do this. But it's better than the other choice."

"Are you sure you aren't excited by the idea of watching me have sex on that bed with another man," she said.

"No," I said. "That doesn't excite me at all. What are you doing?"

She had reached into my robe and stroked my penis and testicles. And in only a few seconds, my penis was hard. She pushed aside the robe and it sprang out into the air. I screamed, "No. This is not what it looks like."

"It looks like you either like the idea of watching me or you had some Viagra for breakfast," she said. I thought I saw her eye wink as she said it.

"Are you looking forward to watching me on that bed?" she said.

"No," I said. "I'm dreading it. I wish there was a way to stop it."

"You're just saying that," she said. "You don't think there's any way to stop it, so you're saying you wish there was. Look how excited you are? My my. Even if you could do something to stop it, I don't think you would."

"Yes," I said. "I swear I would."

"Are you sure?" she said. "You swear that if there was anything you could do to stop me having sex with another man on that bed while you watched, you would do that?"

"Of course I would," I said. "I just wish there was a way." I saw her nod her head, and suddenly I felt two arms holding me tight. I looked behind me, and it was a huge man. Then I saw the woman who had put on my makeup walk up to me with something in her hand.

I said something like "Wha," but before I could say anything else, the woman had stuck a big ball into my mouth and wrapped something around my head to hold it there. Everything had taken maybe 10 seconds.

"I knew you'd say that," said Penny. "Don't worry. The ball gag will come out in a few minutes, but first I want to tell you and the viewers about what they're going to see on this video. Look over there honey, at the tall man standing next to the bed. He's a giant, isn't he? Look at those huge muscles. Now he's going to take off his shorts and his boxers. Do you see that? And it's just hanging there right now. It's one of the thickest and longest penises in the porn industry, and when it's aroused it looks like a fire hose.

"When I was negotiating with your creditor, I told him that you would do anything to keep me from being a prostitute, and I suggested an alternative. He wasn't sure he could raise all the money with my alternative, but I was sure he could. So I found a way to get you to pose for photos in all kinds of sexy positions while you were aroused and sent them to him, and he sent them around to some porn producers. I also told him to tell the porn producers that you have a phobia about your ass, and you can't stand to have anyone, not even me, touch it. I said that there was no telling what you would do if someone tried to put something into it, like that man's fire hose. I guessed that you would probably freak out and struggle and scream and yell and maybe even go temporarily insane. When the porn producers saw those photos and heard about your phobia, they started bidding. I found out today, the winning bid was even more than what we owed, and your creditor generously offered to give me most of the difference. We're going to use it for a big vacation trip after you've recovered from the video.

"We had a friendly bet, your creditor and I. He was betting you wouldn't lift a finger to save me from being a prostitute. But I know you, and I won the bet. I can see you are so panicked right now you might say anything once the ball gag is removed, but your creditor and I agreed that what you said first is the way you really feel.

"So I forgive you in advance for anything you say now. In fact, if you say that you've changed your mind and would rather whore your wife out, it will make the video even better because the people who watch it won't feel sorry for you at all when Mr. Fire Hose starts in on you.

"In a minute, the gag will be removed, and the big man will carry you to the bed and remove your robe. After that, everything will be improvised. You can say anything you want and you can struggle as much as you want, too. All of that will make the video more exciting, according to the producer. For an hour, Mr. Firehouse is going to do lots of things to you and force you to do lots of things for him. Because you'll probably be trying to fight him off and screaming and yelling and crying all the way through, this video will only be sold to certain foreign pay sites. American sites aren't allowed to show this kind of extreme sex. But of course, lots of Americans know how to access those foreign sites and have found a way to pay for memberships.

"You were excited at the idea of being a cuckold, honey. Now it looks like I'm going to be the cuckold, because I'll be watching my spouse making love with another man. I don't know how excited I'll be, but I'll try to keep an open mind. What I'm most excited about is what's going to happen an hour from now, when I take you home and we start a new debt-free life.

"OK, you can take the gag off now. I think they're going to let you talk for a while before you join Mr. Hose in bed."

I can't remember exactly what I said when the gag came off, and Penny never told me, because she said it didn't mean anything. I know I started by trying to be logical. Then I begged and pleaded for a while and gradually got louder until I was screaming. Then I got really abusive. When I was hoarse and breathing hard, they took me to the bed. Penny said she was amazed at how much strength I summoned to try to fight off the man who was twice my size. I used to wake up screaming at least once a week for when I dreamed about it. That happened more than once a week right after, but gradually the nightmares became less frequent, and now I don't get them more than once or twice a year. Except for that, I block that hour totally from my mind.

I took some vacation time for two weeks, but when I went back to work, I was still in terrible pain. A few weeks after that, Penny told me that Sambuco had turned out to be a "gentleman." In addition to giving her the extra money he got, he had called her and said that the people who owned the foreign website wanted permission to call her about a repeat. He said that my video had done so well for them that they would probably offer double or triple the money they had paid. He had told them to stay away from her unless they wanted trouble from him and that if she ever wanted to talk to them to give him a call, and he would put her in touch.

That was the most she had said to me since the event. We weren't talking much for a few months, until the night she asked me if I still had any pain.

"The mental bruises are still hurting," I said.

"I know," she said. "They'll take a lot longer to heal. Since the physical pain is gone, I want to ask you something."

"What?" I said.

"I know you didn't want to do it, and I know you were horribly hurt and humiliated, but now that it's all over, are you happy that you did it rather than have me work three years as a prostitute?"

I knew the answer right away, but I was still so angry that I pretended to think for a long time before I told her. Then I waited for her to stab me in the heart with her response. But she didn't say, "I knew you'd say that." Instead, she pulled me to her. I pulled away, but she wouldn't give up. Finally, I gave in and returned her passionate kiss.

Since then, we've been pretty happy. We have a family now, and lots of money in the bank, and life is good. Penny got the password for the foreign website and has seen the video online. She offered me the password, but that's the last thing I ever want to see. Once she admitted she sometimes watches it, but only when she's really tired and listless. She said it perks her up and gives her energy. After that, I never brought it up again, and neither did she.

There's one small thing she does that I don't like. A couple of years ago, she read an article on gambling addicts. She told me that some research study found that compulsive gamblers were a lot like alcoholics and heroin addicts, who can go back to abusing if they take just one drink or one fix. She said that one or two bets might send me right back on a downward spiral, and then she might have to arrange for another video.

Even though we have a happy marriage, occasionally we have our disagreements. It's rare that we get into a knock-down drag-out fight, but when we do, and Penny is really angry, she starts suggesting bets on some things we are arguing about. She dares me to bet her a dollar on this or a dollar on that.

I asked her about it once when we weren't fighting, and she said she does it just to torment me, and she would never follow through if I took her up on a bet. But it still makes me nervous, even though -- as I said before, I'm not a man who takes chances -- ever again.