Gambling Debt Cuckold

Many thanks to Linda62953 for first editing and improving this story.

Immense gratitude to author/editor ColetteJulie, whose stories are so hot they'll melt your eyeballs, for applying amazing editing talents and enormous energy to make it better in countless ways.

I'm not a man who takes chances. I'm careful about everything I do. Call me Mr. Due Diligence.

Of course, you can't be a hundred per cent certain about anything, but I check and re-check before I make any decision to be sure that I make the right choice. Sometimes this causes friction at work, but I don't care. When my boss gives me grief about it, I remind her of the many times I've saved her beautiful rear by being cautious.

The people I work with have no idea that I used to be the exact opposite of what I am today. I was a compulsive gambler, and it almost destroyed my life. It was because of my wife, Penny, that I was able to quit. One of the reasons I came to work at this company was to break ties with everyone and everything connected to my old lifestyle. It was the first time I was overcautious, and I've been that way since.

I say overcautious, because I already knew that I would never gamble again. When I quit, I quit cold turkey. I never attended a Gamblers Anonymous meeting, and I never got counseling or therapy. 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 wearing my terrycloth bathrobe after taking a shower. Penny was lying naked on our bed.

"I want you to take some sexy photos of me," she said.

"Where is this coming from?"

"I don't want to talk about it. The camera's on my dresser."

"Let me get dressed first," I said, walking to my dresser.

"No," she said. "Please do this first. You'll see why in a moment."

I picked up the camera and began taking photos. She surprised me by leaning back on her elbows and opening her legs to display the thicket between her legs.

She knew I loved her pubic hair, so she let it grow wild. She used shampoo and conditioner to give it volume and make it shine. It felt silky when I ran my fingers through it. It drove me wild as I buried my face in it and felt it caress me while I pleasured her with my tongue.

As I continued taking photos, she began to open her legs. What we were doing must have excited her, because her beautiful puffy pussy lips opened, and I could see that her vagina was red and moist.

She pulled her legs back and moved them in many positions. Then she caressed her breasts until her gorgeous nipples were erect. She turned on her stomach, got on her hands and knees and slowly lifted her beautiful ass higher in the air.

She lowered her head to the pillow and told me to get behind her so I could take photos of her legs and butt and get her face in the photo as well. She turned to look at the camera and spread her legs so wide that her little ass pucker was on display.

I kept shooting, but it got harder and harder -- my ability to concentrate and also my cock. 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. "Take off your robe. I want to take some sexy pictures of you as well, and what could be sexier than you with a big, hard cock?"

I protested that I didn't know the first thing about posing, but she said that didn't matter. She began directing me and telling me where to put my hands and legs. I tried to follow her instructions, which were confusing. Whenever she got me into a position she wanted, she told me to turn my head to the camera and give a "seductive" smile.

She had me lying on my back first, then my side, always showing my hard cock, which I desperately wanted to put into her. From there, the positions got more bizarre.

There were lots of shots of me on my hands and knees with my ass higher than my head and pushed back at her. From that position, she had me spread my legs wide. I could feel a tickle from the ceiling fan blowing across my asshole.

She had me kneel on the floor and put my upper body across the bed with my arms stretched out. I had to turn my head to face her as she took photos from behind and below.

She made me move my legs wide again, bow my back and stick my ass out. My neck hurt from turn to look at her behind me while she snapped away.

"Perfect!"

"What?" I asked.

"Your smiling face, hairy asshole and hard-on all in perfect focus. That one is going to be irresistible."

She had me stand up, spread my legs wide, put my hands on my knees and bend over as far as I could. She moved around me as I held the position until she got the shots she wanted.

"Are you as horny as I am right now?" she asked after she put down the camera and jumped into bed.

Was I! Things got wild and wonderful for the next hour.

"I love you," I panted when we finally stopped to rest. "You're the sexiest woman in the world"

"I know you love to look at me when I'm horny," she said. "I'll give you all the photos you took, but you have to promise not to show them to anyone. I'm sending your photos to a porn site on the web."

I roared with laughter. Penny had an outrageous sense of humor.

***************

The time together that morning was among the few happy hours during dark and gloomy days. My gambling was out of control, and Penny and I were always arguing about it. She kept telling me I needed help, but I wouldn't admit she was right. I stopped telling her how much money I was losing, but she could read me like a book and knew that things were getting worse.

The week before our sexy photo session had been a disaster, and I hadn't been able to look her in the eye. I even contemplated suicide because I couldn't see any way I could ever pay off what I owed. Even if I gave half my paycheck to my bookie for the next five years, I would still owe more than sixty large plus interest, as he put it.

His boss was Lenny Sambuco, who was the real deal. Lenny was both impatient and vicious. If he found out that I couldn't cover the debt with savings or other assets, I wouldn't have to worry about killing myself, because he'd do it for me.

Penny saw how worried I was and asked me several times to tell her what was wrong. She said no matter how bad it was, she would help me fix it, but since there was no way she could do that, I kept quiet. I thought she planned that Sunday morning to cheer me up, and it worked, but not for long. I lived in constant fear of Lenny's thugs taking me on my final car ride.

When I arrived home from work Monday afternoon, she was all smiles. She gave me a big kiss and announced, "You don't have to worry anymore, honey. It's going to be all right."

"What do you mean?" I asked.

"I've taken care of everything. You're off the hook. I worked it out with Mr. Sambuco."

"What?"

I stared at her in absolute shock. How did she know Lenny's name? My shock turned to fear. People didn't work things out with Lenny. They did what he said, or he hurt them - or worse. Just the idea of her talking to him gave me the chills.

"You heard me," she said. "Tonight we're celebrating. I bought some 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 going to take a nice vacation together. It will be a working vacation, because I'm timing it so that we can start working on our family."

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

"He told me what the problem was, and he told me what he was planning to do if it wasn't fixed."

"I'm so sorry I did this to you," I began.

I was trying to be brave so I could talk to her about our insurance and other things we needed to arrange before Lenny's men came for me, but my voice was trembling.

"No need to be sorry," she interrupted. "The problem is fixed. We've been negotiating, and today I gave him a clear picture of what I had in mind. He checked it out, and the deal is done."

"What kind of a deal are you talking about?"

"Not now please. Tonight is for celebrating."

"I can't celebrate until I know what you did. 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. I worked out a way for him to get it. It's all settled."

"Where is the money coming from? Did you borrow it somewhere?"

"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 thinking about Penny's deal with Sambuco. There was no way I could ever work off the debt, and her salary as manager of a clothing chain store wouldn't help much. 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 Lenny's clubs. No, that wouldn't pay enough.

As it dawned on me what her deal was, I began shivering. Sambuco owned most of the higher priced outcall escort services in town. My beautiful, sexy Penny was going to become one of his expensive hookers. That was the only possible way she could make enough money. My wife was going to pay him on her back.

The idea made me sick. I racked my brain for something I could do so she wouldn't have to work for Sambucco. 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?

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 - as if I didn't want to ever get there.

We made small talk, and I didn't ask her any more questions about her deal with Sambuco. I kept trying to think of any other kind of deal she could have with him except the one I knew she had made. I got a splitting headache.

**************

That evening we were sitting in the living room watching TV. I was pretending to watch. She lowered the sound during a commercial and turned to me.

"Do you know what a cuckold is?"

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

"I never heard the word before a few days ago. I looked it up on the Internet. It used to mean a husband whose wife cheated on him without him finding out. Did you know it has another meaning now?"

"No."

"Apparently, some men get off on watching their wives with other men. I couldn't believe it, but psychologists say that even though most men would hate to be cuckolds, a lot of them occasionally think 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. The idea makes me want to throw up."

"I knew you'd say that.

That phrase was part of her vocabulary almost from the time we started dating. Sometimes she said the words at just the right moment to make me -- or anyone else with us -- laugh, because we all knew they were coming.

Most of the time, they were automatic. I think saying them was a loving way for her to remind me how much I meant to her -- that it was important for her to understand me so well that she could predict my reactions. I never imagined those five simple words would one day be devastating.

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

For the rest of the week, I was out of my mind as I thought of her prostituting herself. I had more suicidal thoughts, followed by feelings of guilt because I didn't have the guts to kill myself and save Penny. On Friday, she finally told me a little about what was happening Saturday.

"We're going to be in a video," she said. "Nobody will recognize us because we will be wearing wigs and make-up. Our faces will be completely different."

I was surprised. 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, a porn video.

"What will I be doing in the video?" I said. She didn't answer right away, but I remembered the cuckold conversation from Tuesday evening, and I guessed what my role would be.

She finally answered.

"I'm not sure."

I read that as a lie, along with her reassuring smile. She wanted me to think it wasn't a big deal and that she wouldn't think less of me after this was over.

"What I do know is that you and I are going to be terrific actors. We'll make a great video for Mr. Sambuco and all our problems will be over by tomorrow night. Everything you owe Mr. Sambuco will be paid off."

"And if we aren't good actors?"

"I'm not worried about that. I know we'll do well. I hope you're thinking about how wonderful it will be for us to get a new start. That's what's motivating me."

I wasn't thinking about that at all. I was thinking about the video of her having sex while I watched -- a cuckold video.

Penny made it sound as if I would participate as well as watch. Maybe I'd have to suck on the man's cock, or put it into her vagina. I had seen a video online once where the wife was on her hands and knees in the doggy position and the husband -- at least they pretended he was the husband -- was lying under his wife and licking her lover's balls while the man pounded her.

I remembered something even more ghastly. The wife had been penetrated by two men as the husband watched. One man came inside her vagina and the other inside her ass. The cuckold husband had to suck the come out of both holes. I started feeling dizzy.

I tried to force myself to think about something else, but I couldn't. My thoughts went in horrible directions. Maybe the video would be one of those gang bang videos, and she'd have to take on a bunch of men with large cocks and they'd all come inside her, and I would have to suck all of their come out. I felt like I was going insane.

That night I caught Penny watching me. I wondered what she was thinking. We didn't say much, but when we went to bed, she put her arms around me and held me tight.

"Honey, whatever happens tomorrow, I want you to know that I love you, and the only reason we're doing this video is to pay off Sambuco so we can start over with no worries."

She kissed me and then fell asleep, but I lay awake for a long time.

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

Penny turned to me.

"Honey, the next time you see me, they will already be filming us," she said. "We're going to start with a conversation. What we say will be on the video, so it's got to sound real. Don't try to make anything up. Just follow my lead."

She turned and followed one woman through the door. I followed the other woman. We walked down a corridor and into a small room. She instructed me to take off my clothes behind the screen in the room and put on a robe. She had me sit down in a make-up chair and began to transform me.

She secured a wig with pony tail hanging down in the back to my head. Then she proceeded with my make-up. When she was done, she turned my chair to face the mirror. I was looking at a a ridiculous hippie waiter in a vegetarian restaurant. 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 spacious brightly lit studio. In the middle of it was a 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. A woman in a robe sat down in the other one. She turned to me and smiled.

"How do you like my makeup, honey?"

It was Penny's voice coming from the mouth of the strange woman.

I was astonished, but I didn't say anything because I remembered that the videotaping had begun. I was so nervous that I clammed up.

"Let's tell the people who are watching us why we're here," she said.

My mouth fell open as she looked into one of the cameras and began telling the story of our lives for the past few years. She told how I threw all our money away on gambling. She spoke in detail of some of the humiliations she had suffered because of my actions. What I had done to her sounded even more horrible because her voice was so calm.

She got to how she was so worried about me that she had gone to see my creditor. She explained that he had taken pity on her and told her he would only beat, torture and maim me but would return me to her as a living cripple rather than a corpse.

She had told him that if he wanted his money back, it would be much better if they worked something out.

"Until now, I haven't told my husband what his creditor suggested, so that you could watch his reaction on this video."

She turned away from the camera and faced me.

"Honey, what do you think about me working as an expensive prostitute for six months to pay off your gambling debts?"

I couldn't open my mouth. Penny began stroking my arm.

"You can see he's really upset by all this, but he knows that he has to participate because otherwise we won't get paid for making this video. So I'll ask him again. Honey, how do you feel about me selling my body to pay your gambling debts?"

"I feel horrible," I blurted out. "I love you, and the thought of that makes me sick with guilt."

"I knew you'd say that."

She smiled, and for a moment, I thought she was actually enjoying being an actress. Poor Penny, I thought, she's blocking out what's going to be done to her.

"I promised your creditor that I would be his whore if we couldn't figure out a better way, and that's when I had the idea of making this video. If it's good enough, I don't have to be a prostitute. Isn't that better?"

"Yes, I guess one time is better," I said.

"What do you mean?"

Her voice was melodic and teasing, the voice she used when she was horny and acting seductive.

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

"Are you excited by the idea of watching me have sex with other men?"

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

She had reached down and pulled my robe open. She began stroking my cock. I couldn't believe it. I was hard in a few seconds.

"No!" I shouted. "This is not what it looks like!"

"It looks like you either like the idea of watching me or you had some Viagra in your oatmeal this morning."

She winked at me as she spoke.

"Are you sure you're not looking forward to watching me on that bed?"

"I'm positive. I'm dreading it. I wish there was a way to prevent it."

"Are you just saying that because you don't think there's any way to prevent it? Look how excited you are. Even if you could do something to prevent it, I don't think you would."

"Of course I would."

I knew we were acting, but I couldn't let her doubt my sincerity.

"You really want me to believe you would stop me from doing it if there was a way? Are you sure?"

"Yes I'm sure!" I shouted. "I'd give anything if there was a way..."

"I knew you'd say that," she interrupted in a strong, clear, triumphant voice, no longer seductive and sexy. It sounded as if she had just won a bet.

As she spoke, I saw her nod her head, and suddenly I felt two arms holding me tightly from behind. I managed to twist my head around to see a gigantic man there. The woman who had put on my makeup walked up to me with something in her hand.