Cuckold Jack

I took a look and thought to myself, 'Damn, John's seeing a high-end escort and he doesn't care who knows.' Then someone said, "That's Caroline Miller, the boss's daughter."

I thought, 'OK, the boss's daughter is an escort' and I sat down and tried to ignore the fuss. But, even after she left with her father in tow, her presence was still felt. People couldn't stop talking.

It seems she wasn't an escort at all, but simply, at age 24, a three-time divorcee, now back living with her father. They were saying she was having problems, which seems like a bit of an understatement for a woman who blew through three marriages in six years.

I tuned out the gossip. I certainly wasn't interested in getting wealthy by marrying 'the boss's daughter' and begging for scraps from the table, especially when the daughter was as fucked up as Ms Caroline Miller seemed to be. This wasn't any of my business and I intended to keep it that way.

* * *

Man Plans, and God Laughs. The Millers' company firmly believed in morale building. We had regular award ceremonies and frequent picnics and parties. We were a big happy family and now that she was living at home with her widowed father, Caroline became a regular fixture at all of it.

I was aware of her presence and noticed that she was outgoing, pleasant, and popular, but I really had no interest in dealing with her and was simply polite and formal in an attempt to minimize our encounters. It had exactly the opposite effect.

I realized too late that she was one of those pretty girls who needed continual validation and who thought that she should have any boy she wanted. My failure to act like a puppy dog, craving her attention was simply a challenge. She began to search me out and I continued acting the same as I had been.

At one party, she was with a small group of men and as I was walking by, she called out to me and waved me over. I walked over and, looking at her admirers, I smirked and said, "Like moths to a flame, young men to a pretty girl."

Caroline smiled, "So you do think I'm pretty?"

I thought that this was really too easy as I responded, "Well, I know you think you are."

The look in her eyes was so brief that I would have missed it if I hadn't been looking for it. I was actually looking to see if she was angry, but, surprisingly, she was hurt. She dismissed me with a slight wave of the hand and a little, fake laugh and I continued on my way.

She still continued to seek me out at our company get-togethers and I still continued to "neg" her. In hindsight, it was really a stupid thing for me to do but I just kept doing it.

After an awards banquet, she came up to me and asked me how I was doing and instead of answering her question, I said she had some food stuck in her teeth. She left immediately for the ladies room.

At a picnic, she accidentally(?) bumped into me and when she said "Excuse me," I pinched my nose and said, "You really should watch the onions. Whew, pretty strong." She turned red and walked away again.

I was sure she would take the hint. No one would subject themselves to that time and time again. But, I was wrong as I discovered when John asked me if I'd talk with him in his office about a personal matter.

"Jack, you know my daughter Caroline has been living with me since her divorce, right? Well, she's angry with me because she thinks that I've asked you not to date her."

I didn't see that coming at all and I wasn't sure how to respond. I could laugh; I could get up and walk out in a huff; I could indignantly proclaim that I had no intention of ever dating his daughter, but I just sat there with my mouth open.

He continued, "Look Jack, I don't get involved in any of the staff's private lives, I know it's none of my business, and I also know I'm way out of line here, but I need a favor."

"A favor ...?" I was bewildered.

"Could you ... I mean, would you ... take Caroline on a date?"

I should have said no and been done with it, but there was something so bizarre about the whole situation that I convinced myself that this was the easiest way to end it. I'd take her on a date, we'd hate each other's company, and that would be that.

* * *

Obviously, baseball's opening day should be a national holiday, but around here, opera season's opening night is pretty important. It's always a lively and memorable time, seeing and being seen, but tickets are hard to come by and invitations to the best pre- and post-parties are impossible to get unless you know someone.

I had no doubt Caroline would enjoy it. And, of course I was right, but things didn't go quite as I expected.

As a long-time season subscriber, I am always part of the opera festivities and I always play host to two of my buddies and their girlfriends. The two couples had been together for a number of years and both pairs were probably headed to the altar. The two women considered me a bad influence on their boyfriends but that didn't stop them from being eager guests.

What I didn't count on was that Caroline so out-classed these two harpies that they were quite intimidated. Things started out catty and got worse.

Janet started it, "So Caroline, you know about Jack I take it. He is a bit of a cad and a womanizer. You better watch yourself."

I was annoyed, "What would you know about my womanizing, Janet. Didn't I treat you well when we dated? Oh, wait a minute, I never did ask you out, did I? Jealous much?"

If they couldn't get by me, they decided to do a bypass. Marilyn asked, "So, what is it you do Caroline? Charity work maybe or do you actually have to work for a living?"

I expected Caroline to speak for herself, but she just sat there with her hands clasped and an impassive expression on her face. She surely had to have dealt with this sort of snideness before and I had no idea why she wasn't dealing with it now, but I decided to put a stop to it.

"Ladies, please. Caroline is just coming off a bad divorce and she's home trying to get her bearings. Give her a break, OK?"

Everything changed in an instant. Caroline looked up at me with a strange look and the two women immediately became her best friends as they began commiserating with her about how horrible men were and how she needed to get over the cad and get on with her life. She deserved so much more. It went on and on.

I looked over at the my two buddies and just shook my head.

The group dynamic may have improved but Caroline's behaviour had taken a strange turn. She continually watched me closely for the rest of the evening. As we sat watching the performance, I turned to make a comment to her and found that she was looking at me and paying no attention to the stage.

It was rather disconcerting and I was no longer enjoying myself as I found myself beginning to worry about her. I just wanted the evening to end so I could get her home safely. I drove her to her father's house and walked her to the door.

"Would you like to come in for coffee or a drink? My father's out of town for the weekend."

"Thanks, but I probably should get going. I do want to thank you for joining me this evening. I hope you enjoyed the opera."

"Jack, I'm the one who should be thanking you. It was a wonderful night. The parties, the people, the opera. Thank you so much."

She opened the door and was about to go in when she stopped, turned back to me and said, "Did you know that when you defended me to Marilyn, it was the first time you ever said anything nice about me?"

That made me pause, but she was right. It had been my intention to never say anything nice about her and I had slipped. "OK, then," I said lamely. "Sorry about that."

"Can I ask you why?"

This really had not worked out quite the way I planned.

* * *

Since I didn't have a rational reason for being unkind to her, we began dating on a regular basis. I discovered that Caroline really was as nice as she seemed, but I was surprised to find that despite all of her physical charms, she really was terribly insecure.

Our time together was almost magical. She really was the unicorn: a lady in the living room, a partner in our daily activities, and a super freak in the bedroom.

She was smart and funny and had something intelligent to say to just about anything. OK, she was terribly wrong when she defended the designated hitter rule, but I tried hard to forgive her.

She was always available when I wanted to do something. She dressed well and looked good when we were in public together. Heads always turned when she walked by but I never saw her even look at another man.

She was completely sexually responsive and I never did find her limits. She bought me a book of sex positions and asked me to mark the pages I wanted to try. She told me she would never wear panties in my presence unless she was in her period and then she would wear bright red lipstick to remind me that her mouth was always available. The sex was almost too intense, like the time she brought out the ropes and asked me tie her up and rape her. There was a lot more like that.

We spent a lot of time together and she did spend many nights in my apartment, but, I didn't want her to move in with me and I never asked. That didn't seem to be a problem and she never tried to push the issue. We certainly never discussed marriage, but, she once again had her father do the dirty work. One day he simply asked me if I had given it any thought.

I responded honestly that her three previous marriages hadn't been very successful and that was a concern. He then gave me a copy of private investigator's report on Caroline and her three husbands and it made for interesting reading.

Caroline first married at 18, three months after her mother died of breast cancer. It ended six months later. She had gone to a party without her husband and hadn't come home. He came looking for her and found her in bed with the host. The divorce was quick and her father brought her home. That was when Caroline began seeing a therapist.

At age 22 she married her college boyfriend. She managed to have three affairs in 18 months but she only got caught during the last one, obviously. After the divorce, her father brought her home again.

At age 24 she married her third husband. It was an expensive wedding with an extended honeymoon in the Caribbean. She had her first affair while on the honeymoon.

The divorce was cheaper than the wedding and her father brought her home again. What was different this time was that Caroline initiated the divorce proceedings. That was interesting, but there was no further explanation in the report.

I skipped reading a lot of the details of the affairs. They all started to sound alike: cheap and sleazy. Her affairs amounted to nothing more than one night stands with young, pretty boys. It didn't paint a very good picture of Caroline and it didn't look like her therapy sessions had accomplished anything at all.

I assumed the point of giving me the report was to warn me off from marriage, but that wasn't John's thinking at all.

"Jack, Caroline's therapist feels that she has abandonment issues because of her mother's death. I've worked hard to be there for her, but it doesn't seem enough.

"But, we've seen a major change in her since you two got together. She doesn't seem to have those dark episodes I've seen so many times before. I think you're good for her and I think she may have a chance with your help."

I thought he was crazy and I was trying to come up with a way of saying that without being completely rude. If by "we" he meant Caroline and himself, I was ready to end everything immediately. If he meant the therapist and himself, I would slowly wind things down. I had read the report and I certainly saw it as a warning.

Before I could formulate a response, John continued, "I know you don't see any reason why you should be victim number 4, but I have my own proposal for you."

I waited for him to continue.

"As a wedding present, I will give you $5 million in Dow 30 stocks. This will become community property to be split 50-50 should you divorce at any time and for any reason.

"In addition, I will place $25 million in Dow 30 stocks into a trust fund that will be turned over to your personal control if neither you nor Caroline files for divorce before your 5th anniversary. Otherwise, the trust will be dissolved and the stocks returned to me.

"I believe that if you two can stay together that long, then there is real hope for the longer term and I would want you to be in charge of what I like to think of as an early inheritance."

* * *

I had never considered marriage with Caroline at all and I certainly had no illusions about the situation. I had nothing to offer her in marriage. We were dating only because I had been difficult to enchant. Like most women, she simply wanted what she couldn't have. Despite what her father believed, if Caroline and I married, it wouldn't be long before her insecurities resurfaced.

The question was, could I stay married to her despite her behavior. It was definitely a high risk endeavor, but $25 million was real 'fuck you' money and a guaranteed $2.5 million was a lot more than mere "crumbs from the table".

I decided to go for it, but, as usual, there were two things to do first. The first was my due diligence.

The fact that she had initiated the last divorce certainly bothered me. If she was the cheater, why would she file for divorce? Did they both cheat on that honeymoon? It didn't make sense either way, so I had to find husband number three and learn what happened.

The second thing I needed to do was finish the negotiations with my future father-in-law. A promise of money was useless without an enforceable contract and, as with all contracts, the devil is in the details.

Once I was satisfied on those two issues, we married. We first signed a detailed prenuptial agreement that basically separated everything except for the $5 million in stock and an account that we both funded for common expenses. Since it was Caroline's fourth wedding, it was a low-key event. It was still a very nice ceremony and celebration. Everyone wished us luck and some even meant it.

I made a real effort to assure Caroline that I loved her and appreciated all that she was to me. And that actually seemed to work. We were good together and continued to enjoy each other's company. But then, about six months into our marriage, I had to stay late at work to deal with a major crisis.

She was livid that I wasn't home at my regular time and actually accused me of cheating on her. She was totally irrational about it and only calmed down after I had her father confirm that I had been at the office the whole time. It was a side of Caroline that I had never seen before but I was sure it was her insecurities showing through. She calmed down but there was a definite change in her attitude. I believe it was at that point that she began to cheat on me.

She was discreet but it really wouldn't have been difficult to catch her. I simply never made the effort.

I had discovered from her third husband that the reason she was the one who filed for divorce was because he had proof of her infidelity but never confronted her or took any other action. She learned the truth, called him a worthless cuckold, and told him he needed to grow a pair. She then divorced him.

I did what I could to keep our personal life and our love life little changed. I suspected that she thrived on the knowledge that she was fooling me and I played the clueless fool. I knew that she was absolutely cuckoo; I carefully avoided any hint that I suspected infidelity; and I purchased a countdown clock for my desk at work.

* * *

George Carlin, the late comedian, used to do a whole routine about how much he hated golf and he had a line about the good news that 10 golfers a year are killed by lightening. I found that it's not that funny when your father-in-law is one of them.

Caroline and I had just celebrated our fourth anniversary when we were notified about her father's death. She was devastated and I made damn sure that the trust fund would not be affected in any way.

At the firm there was considerable turmoil while the two other brothers tried to deal with their own loss. Since I was John's son-in-law, they asked me if I would take over running the legal department. I was not about to take on the responsibility without an equity stake and since Caroline inherited her father's share, they thought that should take care of it.

Our prenuptial agreement said exactly the opposite, so I only agreed to do it for a limited time until they could get a full-time replacement through an executive search service. I also demanded a hefty bonus.

The next several months were a terrible time. I was working 80 hour weeks just when Caroline was pulling away from me. She retreated into herself and we were practically strangers to each other.

Then I received that damned package.

* * * *

* * * *

I was afraid to open it but I knew I couldn't avoid it. And it was worse than I could ever have imagined. The photograph was right on top. I'm sure she didn't know the camera was there but Caroline was nude and bent over at the waist looking directly into the lens. Standing behind her, obviously fucking her from the rear, was her father. Well, it wasn't really her father, just someone who looked a lot like him.

If she had abandonment issues about her mother, it seems that she had a bunch of other issues about her late father. This was not good.

The cover letter was succinct. The wife was going for the jugular. Not that it would make much difference in a no-fault state, but she intended to make as much of a stink as she possibly could. She was angry, hurt, and out for vengeance and I needed to find some way to slow her down; my countdown clock needed more time. I called the number given in the letter and asked for a meeting. I asked her to not take any action until I had a chance to speak with her. Then, the day before we were scheduled to meet, I called her and asked if we could reschedule for a week later. She was annoyed and agreed only reluctantly.

* * *

Joan Thompson was a prim and proper woman, a real church lady, and she wanted Old Testament vengeance. I tried to convince her that a quiet divorce was better for her since the gossips wouldn't have anything to wag their tongues about, but she said that the tongues were already wagging and she needed her dignity back. I used all of my negotiating skills on her but the best I could get was a two week delay. Fortunately, that was enough.

My father-in-law's original proposal regarding the trust fund had been that we had to reach the five year anniversary date before either of us filed for divorce. I argued, successfully, that filing did not necessarily mean divorce. A forgiving husband, especially one with my skills, might be able to negotiate a reconciliation even as the clock ticked toward a final decree. We agreed that still being married at the five year mark would be sufficient and that was how the trust fund was structured.

The way a no-fault divorce works is that a petition for divorce is sent to the spouse who has 30 days to respond. Once it is accepted or ignored for the 30 days, it's filed and the divorce becomes final six months later. My delays had worked well and when I met with the aggrieved wife, Caroline and I had been married for 4 years, 4 months, and 2 weeks. That meant that with a two week delay there would be no way Caroline and I could be divorced before our fifth anniversary.

I don't think I actually needed the two week delay. It easily would have taken that long for Caroline and her lawyers to find out about Mrs. Thompson's actions, process the paperwork, and get it to me. In addition, I did have an emergency option. It would have been like going to Traffic School to kill a speeding ticket but I could have demanded those mind-numbing, useless counseling sessions. That would have dragged things out for a few more months.