Cuckold Jack

As it worked out, none of that was necessary. Caroline was a different person after her father's death. It broke her spirit completely. She simply ignored all the gossip about her affair. She didn't file for divorce and I hadn't planned to, but the Caroline I knew was gone. We legally separated while we waited for the divorce to become final. She is back in therapy and I really wish her well.

* * * *

* * * *

I left the company. I certainly didn't need to work anymore and I slowly got over my lost marriage. Despite its strangeness, it was a good one and I was sad to lose the vibrant woman I had loved.

It was nearly a year later when I knew I was whole again. I had started thinking about Amanda. The web site was long gone, but I did have a number for her and wondered if it still worked. I texted her and asked if she was available for dates. She responded that she had retired.

I laughed to myself and texted back, "Good for you. Looks like both of our predictions were right."

She called me and got right to the point, "What do you mean we were both right?"

"Well, I'm doing fine. Thanks for asking."

"Jack, I knew you would be doing fine. I never doubted you. But what do you mean we were both right?"

"Well, I said you would be retired before I could afford your company again and you said that day would come long before I was 70. We were both right."

We got together for lunch and she looked better than ever. She was just entering her peak years and she was even more stunning. I told her my story and how I was now a multi-millionaire. She told me that she had saved a large enough nest-egg that she felt she could retire. She had even tried real dating but none of men she dated came close to matching the men she "dated." She made it very clear that she still wasn't at all interested in a traditional, bourgeois lifestyle.

I thought that was perfect and I made her a proposition. I wanted to travel just as she did and I would pay her to be my companion for two years. In addition to a generous stipend of $500 per day, I offered to pay all travel expenses including all lodging and dining. She would be my personal escort and provide me an ongoing 'girlfriend experience.'

She sat, looking at me for the longest time, and then said yes. Years later she admitted she would have traveled with me even if she had to pay her own way and really wouldn't have minded being my real girlfriend even then. Of course, she also said she wasn't giving the money back either. That's my girl!

We had a great time. I always envied the jet setters of the 60's and we tried emulating them. I despise the TSA security theater and we flew charter jets everywhere we went. Skiing in the Rockies and the Alps, sunbathing on the French Riviera and Rio, sailing the Caribbean and the Mediterranean, sightseeing in Europe and the American West, and fine dining in Paris and Las Vegas. Good food, good wine, good company, good times.

Amanda was still the accomplished courtesan and the sex was fabulous, but I finally realized an interesting thing. Caroline as a girlfriend made the escorts' vaunted 'girlfriend experience' seem like an amateur high school play. The problem was that Caroline was, in clinical terms, batshit crazy.

Amanda, on the contrary, despite her unconventional profession, was as normal as anyone I have ever met. Sex with her wasn't a circus but simply a joyful experience. She enjoyed sex completely but wasn't into kink at all. It was a totally fulfilling experience for both of us. So, when she came to me at the end of our two year journey with her own proposition, I was a happy man.

Amanda asked me if I was seeing anyone else and, since I certainly wasn't, I said so. She nodded her head and said she wasn't either. She said she wanted to make our arrangement explicit with both of us committing to be exclusive with each other.

I thought of us as already exclusive so I had no problem making it explicit. But it was the next thing she said that caused me a little concern. First, she handed me her blood test results indicating that she was disease free, the said, "Now that we're exclusive that means you no longer have to use condoms."

I paused before replying and then said, "Amanda, I have never had sexual intercourse without a condom. A girl once tried to claim me as the father of her child, which I wasn't, and I have never been willing to risk anything like that again. I always wear condoms to ensure that no one gets pregnant from me."

Amanda nodded, smiling, and said, "I fully understand, Jack. Given my chosen profession, I've been on birth control medication since I was 18 and I always insisted on condoms as well. In addition, I keep a supply of morning-after pills always available. I don't believe in unplanned pregnancies either.

"So, here's my offer: you can have condomless sex with me any time you want because I will put you in charge of my birth control. You can ensure that I take the proper pill every day and I will take a morning-after pill any time you think it's necessary. While I would be proud to carry your child, I want you to decide when, or even if, you want that to happen."

I sat silent for a minute trying to understand what this meant. "Amanda, are you saying that you want to settle down and have a family? I thought you despised middle-class convention."

"Well, not exactly ... I mean, I'm not saying you have to marry me or anything."

"Why not? What if I did want to marry you? Maybe that's something I might like to do. In fact, ..."

"Yes?"

"Will you marry me?"

* * *

Obviously, our life experiences put us well outside the mainstream and we never pretended to be a conventional couple. But, I seriously doubt the existence of this so-called conventional couple. Every relationship requires compromise and change, or, as I often say, you're lucky if you get what you pay for.

So, of course, we had an iron-clad prenuptial agreement. I was pretty pleased with what I came up with and after thinking about it carefully, even Amanda had to admit it was more than fair.

Basically, it said that if we divorced for any reason in the first ten years of marriage, Amanda would receive $500 per day for each day we were married. Essentially, our marriage would be converted into a 'girlfriend experience.' After ten years, she would be entitled to 40% of my assets unless adultery could be proven against either of us. Then it would either increase to 50% of my assets or reduce to 25% of our combined assets.

I was disappointed that I couldn't set up child custody and support in the prenup, but it seems the courts think they know how my children should be raised better than I do and even require me to support anybody's children if my wife has them while married to me. I planned to set up 529 plans and trust funds but only for my biological children.

All of this may seem cold-blooded, but that's what I needed so that I could have a happy future.

And, so far, so good.

I discovered that sex without a condom is the most intimate thing I have ever experienced and Amanda and I now have two boys and one girl. All three are loved and simply wonderful. Amanda insisted on paternity tests for each of them at birth even though I said I fully trusted her. But she said that the reason I trust her is because she gives me no reason to ever doubt her. That woman is smart, beautiful, sexy, and wise.

We did have one major disagreement, though. Well, perhaps it was actually more like a difference of opinion. Amanda could not understand why I insisted on buying a bat, a ball, and a glove for a two year old, but I insisted that if he's old enough to walk, he's old enough to being learning the fundamentals of baseball.

We do bring the three children to home games and we all sit in my first base box. So far, the kids are more interested in the food than what's going on in the field, however, I do think Amanda is beginning to enjoy baseball almost as much as she enjoys the opera. ... Well, OK, maybe that's too much to expect.