A Friendly Wager

This is a work of fiction, intended for adults only.

I had just finished my first week, of a three week stay. I was there to get a new business up to speed, on how our company worked. We had purchased the failing company for a good price. We had plans to put money into upgrading, and replacing some people in key positions to pull the company out of the hole it was in.

My name is Dan Colter. I'm forty-one years old, six foot three inches, about two hundred twenty pounds, and brown hair with green eyes. They send me to most of these companies, because, well because I do what it takes to get the job done. I have a rep as being pretty unfeeling, and ruthless. If some one is not doing their job, I cut the dead weight away, and bring in some one that CAN do the job. I don’t go looking for heads to cut off, but if some one doesn’t take the hint the first time, I don’t give second chances.

The other reason they send me is that I’m divorced and don’t have to worry about pissing anyone off, by staying away for weeks at a time. I didn’t start out as the ruthless bastard, I had become, I had a little help. I was married when I was younger. Right out of collage, I married the girl of my dreams. She was beautiful, smart and funny. We had been going together for over a year, and when it came time to graduate I couldn’t let her go. With my masters in business administration I landed a good job that paid well. After the first year, I had proven myself to the company. They started to assign me to out of town projects. Nothing major, and I was only gone for a couple of days at a time. It was a great opportunity, and it came with a nice raise.

That’s when the trouble started. When I was on the road, I called home at bedtime every night. After I had been going out on the job for a few months, she started to ask if I ever wanted to have a fling, while I was out on my own? I said truthfully, that I never had, and that she was the only woman for me. The next time it came up, she asked again if I had ever cheated? I said I won’t lie to you; I have looked and even done some flirting, but that I had never done more then that. She let it go after that, but it got me to wondering why she was asking me the same question all the time. The next time I went out of town, as was usual, I called home Tuesday night. It was at about ten o’clock at night, and there was no answer. I tried back at ten-thirty, and there was still no answer. When I tried at eleven, she answered. I asked where she had been, and she told me that she had gone out with friends for a couple of drinks. She had never given me cause to think she wasn’t telling me the truth, so I believed what she said.

After that, it happened more and more, that I would call and not get an answer until late. I thought it was kind of nice that she had found some friends to keep her company while I was out of town. Man, I was a naive asshole. So it happened just like the stories you’ve read, I got done early with a job. I called just before leaving to catch my flight, and got no answer so I just jumped on the plane. When I hit town, I hailed a cab and headed for home. When I got there it was after dark, but there were no lights on. Using my key I let myself in. As I was setting my bag on the floor after entering, I heard a muffled female voice coming from upstairs. Thinking she had the TV on up there, and knowing my house well, I just grabbed my bag and made my way up the stairs, without turning on any lights. Once in the hallway, I could make out faint light coming from our partially open bedroom door. As I was walking toward the door, I heard a male voice say that he had never felt anything so good in his life. I stopped dead in my tracks. Setting my bag on the floor, I walked over to the door. As I approached I heard my wife’s voice say, that it had felt fantastic, and how she couldn’t believe how much she enjoyed it so much more with him, then she did with me.

My blood started to boil at those words. I gave the door a shove, and stepped into the room. She let out a shriek, and tried to cover herself. The guy jumped off the bed on the other side, away from me. I looked at her and asked her what the fuck she thought she was doing? All she did was start to cry. I looked at the guy and said, that I hoped he had enjoyed himself, because she was all his now. I looked back at her huddling under a sheet crying, I told her that she had until tomorrow to get her sorry ass out of my house. I told her that as soon as I got to a phone I was calling my lawyer, and that she would have the papers as soon as I could get them drawn up. I turned and started for the door. When I got to the door, I looked over my shoulder at the guy and said, if I ever saw him again he was going to need a body bag, and walked out.

The next and only time I saw her again, was in the courtroom. We each said what was required, and signed the papers. On the way out of the building, she got tears in her eyes and tried to apologize. I just told her thanks for the memories and walked away. I went to a bar and got drunk. It was, I was told to by the bartender, one of my finer moments. He said that I was crying, and trying to get any woman that was there to take me out and fuck my brains out. As I sat there hung over and rubbing my jaw, I asked him why my jaw hurt so bad? He said that I hadn’t let a little thing like, getting my face slapped a few times, stop me from asking these women out, in a very gracious manner. He asked me what I wanted, to help with the hang over. I told him nothing I had had my last drink.

It had been my last drink. Aside from the occasional glass of wine with a meal, I haven’t been drunk since. Another byproduct of that time so long ago was that I now trusted no one. Well that’s not exactly true, I trusted a few people, but I had made them earn it. And it may be a little one sided, but I made it even harder on the female members of our company. It was rumored that if there was a woman that wanted to get me to trust them, they had to promise me their first-born. I didn’t take to that extreme, but I definitely made it harder on them then their male counterparts.

As for women in my personal life, I had pretty much given up on finding the one true love of my life. I found myself turning to hookers. I had enough money to get any woman I wanted, but hookers were easier. They were also more trustworthy. When you pay top dollar for a woman, you know what to expect. There is a sense of trust, because you both know the score. She is there for one reason, and she is very good at it. There is no game playing. When you are done with her she dresses and leaves. She doesn’t want your undying love, she doesn’t want you to hold her and reassure her that she is your one and only. You fuck her, and she leaves. Maybe it was taking the easy way out, but there is a lot to be said for easy.

As I sat in my hotel room finishing up the paper work, from the day, my stomach gave a loud rumble. It had been before eleven o’clock in the morning, when I had last eaten. I looked at my watch and saw that it was after seven in the evening. I pulled the tie from around my neck, grabbed my jacket, and headed down to the restaurant. I stood and waited for the hostess to come and seat me. After a minute a very pretty woman about twenty-four or five, came to the podium and picked up a menu. Smiling one of those fake smiles, of people who are required to do it all day, she asked me how many were in my party.

“No party, just me, and if possible something quiet,” I told her with one of my best fake smiles.

After looking at the seating chart, on the podium, she asked me to follow her. We walked through the restaurant, to the back where there was a selection of booths. She asked, “Will this table be to your liking?”

“This will be fine,” I replied.

She placed the menu on the table, “Can I get you anything to drink?”

“No thank you, I’ll stick with the water for now,” I said.

“Yes sir, I’ll send someone over right away,” she said as she withdrew back to the front of the restaurant.

I looked through the menu, and found a light chicken dish, that I’d had before. Putting down the menu, I picked up a copy of the local newspaper, that I had bought on my way through the lobby. After a moment the server showed up with my water.

“Good evening sir, my name is Pam, and I’ll be serving you this evening. Have you decided on what you would like?”

Looking up from the paper I said, “Good evening to you also. Yes, I have decided.” I turned the open menu towards her, and pointed, “I’ll have the chicken for one.”

“Yes sir, would you like anything else to drink?” she asked.

“No, just keep the water coming,” I replied.

“Yes sir, thank you sir,” she said taking the menu and leaving to place the order.

I turned back to my paper, and was just starting in on the sports section, when I heard a voice in the next booth. The booths were separated by a curtain that hung from the ceiling, they were there to give you the feeling of intimacy, but you didn’t have to try very hard to hear your neighbor if you wanted to. It sounded like a couple, man and woman that were having an argument, as quietly as possible.

“I dressed the way you wanted me to. I made myself up the way you asked. I did everything that you wanted, but I really want to leave with you,” I heard her say.

“I know you did all this for me, but you also know why I asked you to do it. Why I brought you here, and why I want you to stay after I leave. We talked about this, I thought we had agreed,” he said.

“Yes we did talk about this, but we never agreed to anything. I still can’t believe you want me to go through with this. You say you love me, but then you tell me you want me to sleep with another man. Why, what do you get out of this? Do you know, or have you thought about all the things that can happen?” she said.

“Yes I DO know all of the things that can happen. Don’t you think I have been thinking about this? I’ve thought about it a lot. Ever since the second year, after we were married, when I asked you about if you ever had any fantasies. You said you sometimes thought about other guys. When I asked you if you always had an orgasm, you said not all the time. Then I asked you what’s not all the time? And you said that you did sometimes. I started to feel like maybe you deserved more then just sometimes. It doesn’t look like I can get the job done, and I’m hoping that you can get what you need, and still have room for me in your life.”

“What in the hell gave you the idea that I’m not getting what I need? Did I ever say or do anything that would give you the idea that I was going to go looking for something else? HAVE I?” she asked.

“No, you have never given me any reason to think you were going to go looking for something else. I don’t know why you haven’t, but you haven’t. You are a beautiful and sensuous woman. You are a dream come true for me, and I wish could be enough for you, but I can’t stand not seeing you as happy as I know you could be. You and I both know what you do in the bathroom, after you think I’ve gone to sleep. There is no reason you should have to do that. I also know that you have always wanted me to be more forceful in our bedroom. We both also know that isn’t going to happen. I want you to find out what it’s like to have a man take you, and make you feel all the things that I can’t. You have always had to be the one to make the tough decisions, hell you make all the decisions. I know you tried to get me to be more in charge, but you know I am not the type to take charge. I see it in your eyes when we make love, I know you want more, but I can’t help that I don’t last long enough for you. I’ve tried everything, it’s no use, and I guess I just can’t change, but that’s no reason that you can’t be happier.”

“Jon, I’m trying hard to make any sense of this. Do you know what you’re asking for? Do you really know what could happen if I did go out and look for a man that could make me feel the way you’re talking about? What happens if I start to fall for this guy? Are you going to change your mind, when you see me take off to meet with some guy, you don’t even know? You say you want me to find some guy that will take me, and make me a woman, or some bullshit like that. I happen to think I am a woman, a woman that can’t be taken. If it’s there to give then I do, and I do, to you. I only have one other guy besides you to compare with, and I don’t think I could find any better. And I’m afraid of what would happen if I went looking. What happens to us, if I were to go out looking? Do you really think you could handle it?”

“I know I want you to be happy. When we’re making love and I start to think of you with another man, I go off like a rocket. It’s gotten to the point that I think about it all the time. Why do you think I buy you all those sexy cloths? It’s not for me, well I guess it is in a way, but I do it to let other guys see you. I see the way they look at you; I see the way you act when you see that you are getting attention. Most of the time you try to ignore it, but then the right guy looks, and you brighten up. Look, if you go out and try it and find it’s not what you wanted, at least you will know. I just want you to be happy, and I think this is the way to do it. I got you dressed up tonight so that we could try this; you knew it was why we were coming here. I’m going up to pay the check, while I’m gone you decide, but you already know how I feel. I want you to go in the bar and see what happens. I’ll be sitting in the back. If it does happen you let me know if he’ll let me come with you, if not you tell me about it later when you get home.”

“You mean you would really like to watch? I don’t know if I can take this. I’ve never seen you acting like this. I’m going in there. You are going home. If within an hour nothing happens I’ll be home, witch should just about be enough time to get over being mad at you. If, on the outside chance something does… come up, I’ll make my own way home. Even if I wanted to I don’t think I could do anything with you watching.”

There was a pause while one or both of them were trying to think of what to say to the other. After a moment, “Listen Angie, I…”

She didn’t let him get any further, “Jon, we either do it my way, or we both leave right now.”

“Okay, we do it your way. Just remember, you have to give it a chance. You can’t just walk out after I leave. I’m going to take your word on things, but you have to give it a chance. Also remember that I love you, and always will, no matter what happens.”

“No matter what happens, Jesus, I’m thirty-three years old, men are all looking for teenagers these days. I could probably sit in there naked, and they would still just walk over to the young looking hookers. Look I’m doing this for you, one time, so that you have to get off my back about it, when this is over it’s over.”

“Okay, I hear what you’re saying, but you have to promise to give it a chance. Please be careful. You’ve got your cell phone call if you need me.”

“I’ll be careful. I’ll probably be home soon, so don’t worry.”

I heard rustling as they slid out of their booth. I heard them give each other a kiss, and then they started for the front of the restaurant. All I got was a look at the back of them. They appeared to be about the same height. She was maybe a little taller, but it was hard to tell because she was wearing four-inch heels. She walked beautifully. I would guess she was about five-seven, maybe a hundred and twenty pounds. From the back, I could see a lightweight tan sweater that reached the top of a very shapely ass, and a thin, tight black skirt that went down to about mid-thigh. She had dark hair, but it was up so I could tell how long it was. He was in Dockers with a pull over shirt.

As they were leaving, my meal arrived. I spent about fifteen or twenty minutes picking through it, and couldn’t take it any more. I went up to the front, getting Pam’s attention on the way.

She had seen that I had hardly touched my meal. “Was everything alright?”

“It was fine. I just remembered that I have something that I have to take care of,” I said as I was fishing around for my wallet.

I paid for the meal, giving her a nice tip, and started for the bar. I went into the bar near the back, so that I could check things out. There, on a stool, at the far end of the bar sat a nervous looking Angie. I made my way to the bar, drawing as little attention as possible. It was about nine o’clock when I sat down, the place wasn’t packed, but there was a nice crowd. I ordered a club soda, and sat back to see what would happen.

In the twenty minutes that I was there two guys walked up and tried to start something. She turned them both away, without much thought. I could tell that she was biding her time, until she felt she had given her husband his time. I kept wondering what was going through his mind. Why would he ask her to find another man? Was she really as unfulfilled as he had said? She really was as beautiful as he had said she was. Her dark hair was rapped around her head, and piled on top. Under the sweater was a short, tight top. It scooped down showing a lot of skin, but she was ummm… not overly endowed (IBTC). She had huge eyes that had a very slight upward slant to them. Her mouth was wide and generous, with a slight pout. She started looking as though she’d had enough.

I got off the stool I had been on and made my way around behind her. I walked up close. I just stood there for a while. She smelled good, I wondered what that scent was. She looked down at her watch again. I noticed that she had left her ring on. I moved in closer, so that I was right up close.

“Are you getting ready to go, or could I buy you another one of those?” I asked.

As she turned she was already starting to tell me off, “I’m afraid I was just…” She came to a stop as she turned on her stool and was looking into my stomach. I was probably in her space, but she handled it well. “I’m afraid I just getting ready to leave,” said craning her neck up to look at me.

“I have a better idea, why don’t you swivel those pretty legs back around under the bar, and let me buy you one more for the road. What harm could there be in that?” I told her.

She thought about it for a minute, then with a smirk, “Okay, but you’ll have to sit down, otherwise I’m going to pour it all over myself.”

“I think that can be arranged,” I said as I moved to take the stool next to hers.

I got the bar tenders attention, and ordered us another round. Then I turned my body to face her head on. “My name’s Dan, Dan Colter,” I said sticking my hand out.

“Hi Dan my name is ah… Judy, Judy Finch pleased to meet you,” she said reaching for my hand.

I took her soft fingers in my hand, and watched her thinking, we just met and she’s already lying to me. Then I thought, maybe if I were out here with a stranger looking at me the way I probably am at her, I would give me a bogus name too. She turned and smiled at the bartender as he set our drinks in front us. I noticed her eyes were a very light blue, with long lashes.

“So what’s a little lamb like you, doing amongst a pack of wolves like us,” I asked with a smile.

“Oh so you all think you are wolves?” she asked with an arched brow and a smile.

I looked around the room, “Well, maybe some of us more then others,” I said looking into her eyes.

“So, am I to assume you are putting yourself into that group?” she asked without batting an eye.

“I’ve done my share of howling, but the chase is getting less and less appealing. I have found it is far easier to use professionals. There are fewer complications, and no expectations that can’t be met,” I said frankly.

“None, the women you… rent meet all of your expectations?” she asked.