Cuckold Jack

When I returned from lunch and saw the large mailing envelope on my desk I knew exactly what it was. For just the briefest moment I hoped that perhaps it has been sent to me by mistake, but I really knew it wasn't. The real question was who sent it to me.

I sat down, picked up the thick envelope and examined it more carefully.

The envelope was addressed to Mr. Jack Burton and since that was me, I knew there was no mistake. It was sealed with additional packing tape at the flap and it was marked in large, bold letters: PERSONAL AND CONFIDENTIAL - TO BE OPENED BY ADDRESSEE ONLY. It didn't have a return address and the postage meter stamp gave only the date sent. I guess it wouldn't be confidential if the sender's name was right on it.

I didn't need to open it to know that it was certainly a private detective report regarding my wife's infidelity. Caroline and I had been married for nearly five years and I'm fairly certain she began cheating on me within the first six months of our marriage.

I never let it bother me; Caroline was nearly perfect otherwise. She was a loving and attentive wife and had always been discreet while making sure that my needs and desires were always well taken care of. If she stayed true to form, her little flings would involve pool guards, parking attendants, waiters, personal trainers-all young studs who had no money and little promise of ever having any.

If these guys had anyone who was hurt by their behavior, I doubted they had the resources necessary for expensive detective work charged by the hour, so that meant it wasn't them. I suppose my late father-in-law might be behind this, perhaps a bad joke from beyond the grave, but that seemed rather unlikely; it just wasn't his style. But whoever was behind it was creating a real problem for me, one I would have to deal with as quickly as possible.

* * * *

* * * *

My attitude toward women, and people in general, was altered forever when I graduated from high school. I was 18 but I might as well have been 9 for all that I understood about the world.

Jody and I dated all throughout high school. Our parents were friends and we all got together for birthdays and holidays. We were just one big happy family and everyone knew that it was just a matter of time before Jody and I would be married.

Then two weeks after graduation Jody came to me crying and told me that she was pregnant. She was in a panic and wanted us to get married before she started to show; she was worried what people might think.

"But, Jody, how can you be pregnant? You said you wanted to wait until we were married. We've never had sex."

"Jack, please pay attention here. My baby needs a father, so we need to get married as soon as possible."

I was certainly innocent and I might have been in love, but I wasn't that stupid, "Uhh, I don't think so."

Then the shit started. She wailed and cried and went running home to her parents who starting making legal threats. Then her brother started making physical threats. They all insisted that I had to do the right thing.

My parents loved Jody like a daughter and they were actually ecstatic at the news that she was pregnant. My mother called Jody's mother and began planning the wedding in detail.

I tried to explain again, "Dad, Mom, I'm not the father. I'm not marrying Jody and raising someone else's kid."

"Son," my father said, "you can't start acting like this. You have to do the right thing here. Man up and don't try shirking your responsibilities."

I was reeling at this point but I had no intention of being railroaded into this marriage, "Let me be perfectly clear: Jody is fucking someone and it isn't me. I'm not marrying a goddamn whore!"

They looked at me for a moment and then angrily berated me as an ungrateful, selfish child. When I still refused to marry the bitch, they told me that if I couldn't be an adult about this, I could just leave because they were disowning me immediately.

I realized then that I really didn't know these people and even though it was still June, I immediately left for college. I had scholarship money and student loans and I quickly picked up a summer job in town there. I found a place to stay until the dorms opened in September and began a life on my own. I was baffled and heartsick but I intended to survive and get on with my life.

When classes started I ran into a few people from back home and I guess my reputation had been dragged through the mud because all I got from them was the stank eye. This continued until just before spring when a guy I knew slightly from home sat down with me at lunch in the student cafeteria and told me that Jody had had her baby. It was a healthy boy but because he was half black, Jody decided to put him up for adoption.

I never did learn how that worked out. I thought there might be a chance for reconciliation with my parents and I sent them a Christmas card with my return address but I never did hear anything from them. Finally, enough time went by that I reached the point where I no longer cared. I was just glad I got out in time.

* * *

There's a lot about college that's a waste of time, but one class, Psychology 101, was worth the price of tuition. Like most people, I thought psychopaths tore wings off flies and set fire to kittens before going on murderous rampages, but I learned that psychopathy is a continuum. All of us have psychopathic tendencies that cover a whole range of behaviors. Then there were the narcissists and then the narcissistic psychopaths.

As I read about all of this, I finally realized that in my entire life I had been surrounded by a bunch of crazy people well along the psychopathic route. While I was being Mr. Nice Guy, everyone around me was living in a different world. Jody was just like my parents and that was probably why I dated her in the first place. I was just a young fool who didn't know any better.

I realized then it was time to grow up. I realized that all relationships are transactional and from that moment on, whenever I met anyone, I'd ask myself "What do they want and What's in it for me?" Everything had a price of some sort and the only question is, "Are you getting what you paid for?"

With this revelation, I decided on Psychology as my major and when I graduated, I went for a law degree to specialize in contract law. I found that I really enjoyed the negotiation process. Honest negotiations were pretty straight-forward, but sometimes you'd meet a psychopath and I really enjoyed nailing them.

After passing the bar exam, I quickly found employment and began living the life of a bachelor with money.

Weekends partying with my buddies in Las Vegas were always great fun, exceeded only by March weeks in Arizona where we would golf each morning, watch a baseball game at one of the spring training facilities in the Valley of the Sun, and then hit the bars in the evening for some late, and later, night fun.

I often dated two or three young ladies at a time but at least I was honest about it and my intentions. I always promised to buy each of them an expensive wedding gift when they found the man of their dreams and settled down.

Life was good, but as I neared my 30th birthday, I paused to take stock.

An interesting thing that we used to do in Las Vegas was to sit at a casino bar, watching couples at the table games and trying to identify the women as wives, girlfriends, or hookers. After a while it became almost too easy.

The wives were usually overweight and either drunk or controlling, dragging their husbands away from a good time at the tables. The girlfriends would either sit looking totally bored or would actually start flirting with other men there. The hookers simply followed the money. If a guy was ahead, there would be a race to get close to fawn all over him. When the sucker smiled at one of them, the others would go looking for other fish. It was all pretty sad actually.

One time, though, we were baffled. The woman was extremely attractive and well-dressed with an elegant look that was eye-catching. But she had no interest in anything except the man she was with. When he was on a winning streak, she was as excited as he was but the surprising thing was when his luck turned.

It was obvious to anyone watching that the guy was a typical gambler, totally intent on giving back all his winnings and more. But before he got very far with that, this woman bent down to whisper in his ear. He turned, smiled at her and picked up his chips. They left together.

We were arguing among ourselves which of the three she was. A wife probably would have scolded him for losing and made him even more determined to stay. A girlfriend would have started whining that she was bored and he might have given her a few chips to leave him alone as he continued to lose. And, of course, since he was well into a losing streak and wasn't paying attention to them anyway, the hookers would have already moved on to someone else.

We just couldn't figure it out. The bartender had been listening to our speculations and finally leaned forward toward us and said, "She's been here before. She's a high-end escort and she's earning her fee right now. She's making sure that his 'girlfriend experience' here is better than with any girlfriend he's ever known. She wants to keep him happy and gambling losers are never happy. They're probably heading back to his room now."

We started talking about "the girlfriend experience." My buddies were adamant that if you paid for sex you were hiring a hooker not a girlfriend, but I had a more nuanced view.

"Does your doctor invite you to his parties?"

"No dude, he's just the guy who gives me my Viagra pills."

"Do you try to date your car mechanic?"

"That's not even funny. My guy does good work but he's just not my type."

"Well, that's my point. Everyone is selling something and everyone has a specialty. Honest work deserves honest pay."

"Honest work, my ass. It's not like these girls are anything real. These bitches just act the part and only suckers pay for it and fall for it."

"Well, I don't know. We're all suckers for good acting. How many people still think that John Wayne was some kind of war hero? He was actually a draft dodger but he played the part well enough that the Marine Corps Association actually honored him as 'Man of the Year.'

"It seems to me that in this life the best you can hope for is to get what you paid for. Just look at how badly these wives and girlfriends treat their men. Granted, your common hooker is worse, but it sure looked to me like that guy was being treated quite well. If that's what an escort is all about, I may have to look into it."

* * *

Setting up the date was an interesting experience. It was all handled over the internet. There was the public website with a few pictures and not too much information. Then, after I paid a fee, I was given access to the complete site and the full profiles of the women.

The website said that The Girlfriend Experience provided by these women offered BBBJ, CFS, DFS, and DATY plus any extras each one included. I guess I was supposed to know what these abbreviations meant but I had to look them up:

BBBJ-Bare Back Blow Jobs (fellatio without condom not including CIM or Cum in Mouth).

CFS-Covered Full Service (condom intercourse only).

DFK-Deep French Kissing (just what it says; supposedly, hookers don't kiss on the lips).

DATY- Dining at the Y (it took me a while to figure out that meant pussy eating).

MSOG-Multiple Shots on Goal (when I learned that meant she wouldn't keep a count, I wondered what the record might be.)

They women themselves were a mixed lot. Some looked like typical call-girls. They weren't particularly attractive and were heavily made up. Some were real sex-pots and dressed the part. Some were more exotic. And then there was Amanda.

She was an extremely good-looking blonde with a very natural look, In her photos, it didn't look like she was even wearing make-up. She even seemed to have some standards since she made it very clear that there would be no spanking or bondage with first dates.

I had thought about going for a full weekend 'girlfriend experience' but I wasn't about to pay that much money and find that things didn't quite work out, so I signed up for an overnight date. We texted and called back and forth to handle as many of the details as we could. We agreed to begin with dinner and would meet at the restaurant.

* * *

The restaurant was quite popular, one of those places that made you wait at the bar even if you had a reservation. So, even though I had a 7:30 reservation, I figured it would cost me a hefty tip to get a table before 9:00.

It was pretty noisy when I approached the reservation desk so I raised my voice a bit to be heard, but just as the first words were out of my mouth, the noise level dropped suddenly and I was nearly yelling, "I have a 7:30 but my guest isn't here yet."

Behind me, a soft voice said, "Hello, Jack, I'm here for you now."

I turned to see an elegant beauty, what used to be called a classy woman until that term was debased to refer to reality TV sluts. Amanda was even better looking in person than she was in her on-line glamour photographs. I might have been mistaken when I thought the waiting area had quieted as everyone looked at her, but I was entirely sure that the maitre d' was impressed when he said, "Your table is ready," and had us immediately taken to a table. I didn't even get a chance to tip him.

Once we were seated, I looked at her more carefully and noted that she actually was wearing makeup, but it was so subtle that it simply enhanced her looks instead of trying to change them. After we ordered we continued the conversation we had started over the phone. We were getting quite comfortable with each other.

Amanda asked me about my job and I reluctantly tried to say something interesting about contract law, but she picked up on that quickly and asked me, "Well, if work isn't your passion, what is?"

It was a very good question and on a normal date I would have lied and said something else, but here was a good chance to see how she handled it.

"Since you ask, my passion is baseball. Do you follow baseball?"

She smiled, "No I'm afraid I don't. But why is it your passion? What is it about baseball that excites you so?"

Well, she was good. We weren't talking about baseball, we were talking about me. I was impressed and actually found myself responding to her feigned interest. It took me a while before I recovered and threw it back to her, "Well, is this your passion? How much do you actually enjoy being an escort?"

Obviously, she got that a lot. She told me she was 25 and had been doing this since graduating from college, "But it's not exactly a passion. I do this because I love money and sex. I intend to retire after a few years to travel the world, but for now, my price and my standards are high enough that it's almost always an enjoyable experience, like tonight for example. You're younger and better looking than most of the men I see."

See, I said she was good. I was the center of attention throughout dinner and I found that I didn't miss hearing the typical stories about her nasty ex, her sloppy roommate, and her daily problems as I tried to pretend some sort of interest in the hope of getting laid.

Instead, I found that she was well-read, curious, and a fascinating conversationalist. Then we went to the room I had reserved, I found that she was even better at sex.

* * *

I knew better than to get a cheap motel room for this but I probably went overboard in getting a suite at the downtown hotel. It did have the advantage of masking any sense of sleaziness this encounter might seem to have.

In the room, Amanda asked me to sit down and I bounced down on the bed. She started to slowly undress for me. Surprisingly, I didn't find it erotic; I think it reminded me of something you might see at a cheap strip club. I must have had a slight look of distaste on my face because she stopped and said "Would you like to help?"

I jumped at the opportunity. I caressed her body as I removed each article of clothing. Her lingerie was extremely sexy without being sleazy and it looked and felt very expensive. I cupped her breasts which were "real and magnificent." I stroked her flanks and she certainly acted like she enjoyed it.

I stepped back and looked at her naked body and that was enough to get me hard. She was nearly perfectly proportioned and was easily the most beautiful woman I had ever known. Her smile was dazzling and she came over to me and said, "Let's get you ready."

She unbuttoned my shirt and as I removed it she unbuckled my belt, open my fly and knelt down in front of me as she pulled my pants and boxer shorts down. She smiled up at me and then leaned forward to kiss the end of my cock.

I intended to get my money's worth out of this, but I'm not some porn star who can cum 5 or 6 times a night. I've never managed more than twice in a night. Fortunately, Amanda was expert at her chosen profession and I achieved a personal best that night plus once more in the morning. Missionary, doggie, cowgirl, and anal, then, as we showered in the morning, I fucked her face and she finished by jerking me off. I was totally depleted but happy.

When we finished our room service breakfast and dressed to leave and end our date, Amanda said that she hoped to see me again soon.

I laughed, "Amanda, I've enjoyed every minute with you and I'd love to see you on a regular basis, but I'll be 70 and you'll be retired before I can afford that."

She smiled her beautiful smile and said, "Jack, from what I've seen, you're going to be very successful, very quickly. In the scheme of things, it won't be very long before you can have whatever you want."

* * *

So now I had a simple goal: wealthy before 70.

I was good at what I did, but I wasn't on any track for great wealth. The manufacturing company I worked for was owned by three brothers and was a multi-billion dollars business. The brothers were extremely wealthy but remained hands-on owners. One headed manufacturing itself, one handled hiring and personnel, and my boss handled legal.

I was part of a team that handled contracts and contract negotiations and, honestly, I was the best of the group. One guy thought that negotiation meant that whatever a vendor bid, he would cut by 10%. When I looked at some of these contracts and analyzed the costs, it became clear that the vendors he dealt with simply began inflating their bids by 11.2%. It was a smart move; one that I would have made.

Another guy actually kept a copy of Sun Tzu's "The Art of War" on his desk and said he used its precepts in his negotiations. If that sounds stupid, it's because it is. I do know that his hardball tactics ended up putting some of our vendors out of business and he spends a lot of time trying to locate new ones.

My method was simpler in theory, but certainly more difficult in practice. I made sure I knew exactly what was needed and just what it would cost to provide it.

I visited our own and our vendors' shop floors to see things for myself. I analyzed all costs and knew exactly what a fair price would be before negotiations even began. I simply took "due diligence" to its ultimate end to be sure that everyone was satisfied with the result.

My work was appreciated and well-compensated, but it wasn't going to make me rich. I had to come up with another route.

* * *

I was actively considering my options the day I first sighted Caroline.

An elegant young woman came walking through our section headed for the boss's office and everyone, and I mean everyone, stopped to watch. She was tall with professionally-styled hair and make-up. Her clothing was expensive and tailored to accentuate her curves. If you weren't completely intimidated by her, you thought she was a walking wet dream.