Pt. 35 - It Shouldn't Have Happened

This is part 35 of my continuing story and I recommend you read the prior stories in order before reading this one.

All characters are well over the age of consent.

This is a work of fiction.

Any typos are mine as I create and edit my own work.

Enjoy!

*******

My recent past comes to the forefront.

Do you recall that I was invited to attend The Reunion on the north shore of Lake Tahoe in the summer? It was where I met Jack Colton for the first time, and he offered me the position of Vice Chairman of the Board of Directors.

That week I met a lot of very smart, beautiful, and rich women, and I ended up having sex with nine of them over a period of about five days. It was fun, playful sex, nothing serious, and I know every one of the ladies had a satisfying experience with me between the sheets.

Almost even before I left the hotel for my next adventure (Tokyo) I was getting emails, text messages and phone calls from these ladies, wanting to know when we could get together again.

They each mentioned, at some point, the name of Doctor Tina Ward. I had no idea who this individual was, or what she did. The ladies also mentioned that Doctor Tina had some connection with Jack Colton.

I admit now that I was both stupid and naïve. If I had taken a couple of minutes to look at the children that these ladies had with them, I'd noticed that these little boys looked a lot like Jack Colton. But I was too busy looking at MILF pussy to see what was right in front of me!

Janet, my third married MILF, gave me some of the background on Jack and Tina but avoided getting into details. But I got the gist of what had taken place. Janet did encourage me to go directly to Jack if I wanted to learn more.

So, I did. I reached out to Jack (my boss) and asked him about Doctor Tina, because these ladies from The Reunion wanted me to meet her.

Jack generously took about half an hour of his time to explain that Tina was a female fertility medical doctor, and that she and his so-called ex-wife, Catherine, had arranged paid sex dates with these women and Jack, with the sole purpose of getting pregnant with Jack's child.

This was all a bit strange to me, but I didn't comment, I just asked some questions to get clarity.

Jack admitted to me he participated, not for the money, for which he was quoted a price of $1 million a pop, and not for the great sex he just knew he would have based on the attraction factor of the ladies, but to try to reconcile with Catherine, to save their marriage. "This whole thing was her idea," Jack swore to me.

After "breeding" (his term) with about 20 or so women, Jack said he found out that Doctor Tina and Catherine emptied his bank account via outbound wire transfer, the day after the large inbound payment was wire transferred in, leaving nothing for Jack as compensation.

That was the end of his so-called marriage to Catherine (although they had never legally married) and in addition to suing both Catherine and Doctor Tina in civil court, Jack quickly got the criminal justice system involved, and both ladies were indicted by grand juries on such interesting crimes as money laundering, wire fraud, and conspiracy to commit fraud.

They were both out on bail awaiting further investigation, and Jack was able to get most of the money back from Catherine and then he got the criminal charges dropped. Catherine got off lightly. A few years of probation and a financial fine.

As for Doctor Tina, she was under house arrest, living in an upscale apartment in scenic Woodland Hills, California. Her medical license had been suspended by the state of Hawaii, her assets frozen, and she was certain that her once fairytale life was over. She wore an ankle tracking bracelet and lived off the financial gratitude of her friends. More on that in a few minutes.

Jack shared with me that he would have dropped the civil charges and worked with the government and the other agencies to get the criminal charges against Tina dismissed but for two little things: she never let him see their love child and she never said she would pay back the money.

You see, the day after they first met, Tina wanted Jack to show her (demonstrate to her, do to her; fuck her, impregnate her) what he was going to do with her clients. You know, fuck the shit out of them and drop a load or two of his overactive baby batter in fertile pussies.

Jack said Tina had not only the tightest pussy he had ever been in, but he gave her three huge loads, doggystyle, assuring that Tina was pregnant with a baby boy.

Sure, as shit, she gave birth about 8 months later to a baby. She named him Jackson.

I assumed that the legal stalemate was continuing between Jack and Tina.

I was so busy with my business trips and the pussy I was getting I didn't think any more about it.

Until someone brought it to my attention that there was a business opportunity in it for me. Sometimes I am slow on the uptake, and I soon figured out that what your friends are for, letting you know when you're missing out on opportunities.

*******

It was October, about eight weeks following the end of The Reunion at Lake Tahoe. It was Monday, and I was working at my home office on a bunch of stuff.

I was finding it increasingly difficult to juggle my job, my law business, and my lady friends. Oh, and my retired parents are now living in Nevada near Lake Tahoe; I never see them in person anymore.

I was home alone. My next-door neighbor, Leeann, (aka LA) and number one fuck buddy had warmed my bed over the weekend (we had some serious sheet stains to prove it!) and left for the airport that morning to see her folks in Atlanta.

LA's dad was not doing well. And even though she had purposely kept me away from meeting her parents, LA had shared with me that her mother was delighted that I was "dating" her daughter and LA's college age girls sang me praises as well.

There was no way LA was going to marry me, her alimony and child support were golden handcuffs to staying divorced and single. But, for as long as it lasted, we could rut (fuck) together, bringing each other pleasure in and out of bed. She appreciated my stability (and my big cock) and I appreciated her perspective and insight to push me out of my comfort zone in business and life.

I didn't mind being alone doing my work. Without the distraction of a hot 45-year-old MILF, I was quite productive and profitable, I might add. I missed LA but there were other females in my life to empty my balls into.

Trying to stay on my workout schedule and stay in shape, I had hit the gym early, before 6am, and had a nice post workout session with Laura, my real estate agent and number two MILF fuck buddy, in the back seat of my large truck.

The sex with both LA and Laura was getting better and better and so far, neither one knew about the other.

I had lunch plans; someone was coming to my house at noon. I was looking forward to seeing what she wanted to talk about. "She" was Barbara. More about her and our relationship in a minute.

If you go back and read my story "Pt. 26 - I Find New Love in Tokyo", you will remember that during the week I was in North Shore Lake Tahoe at Jack Colton's Reunion, I spent some time with some of the women that Jack had impregnated.

Let me be clear what I mean when I say, "spending time." It means we had sex. We fucked. I made damn sure that lady was satisfied, fully, and I dropped nice loads of baby batter deep into their tight, warm, and wet pussies.

Those ladies, all wealthy, and either divorced, widowed or single, had been approaching the end of their childbearing times, or had difficulty getting pregnant.

Each of the ladies wanted a male child. Not just any male baby, but one that would be tall, healthy, handsome, intelligent and if the Gods of DNA were pleased, to further bless these baby boys that they would each be hung like horses.

Having a large penis in every culture is considered a sign of male masculinity, of strength, of virility, of power; a sign of leadership and bravery (or so I was told).

One of Jack's ladies, Barbara, rose to the occasion and served as the unofficial leader of this pack of ladies. While they were all Alpha females, this was a vacation and a reconciliation of sorts for these ladies with Jack, and so when Barbara took command, no one disagreed. They were happy to have her lead.

I ended up hooking up three times in a few short days with Barbara, and each time we were naked together, I came into her welcoming pussy twice. When you are 28, you have zero recovery time.

We never discussed birth control, I assumed she had that under control or was post-menopausal, which explained her wanting to have such vigorous sex with me. Freed of the possibility of becoming pregnant, she was as horny as a 20-year-old.

I wasn't complaining, she had an awesome body: she stood five feet eight, weighed about 120 pounds, had a magnificent pair of 36 DDs, had a waist of 26 inches and 34-inch hips. She was simply a beautiful woman with shoulder length dark honey colored hair, a great smile and blue eyes that looked into your soul.

As for the sex, Barbara loved sex. But to be clear, it was either oral sex or vaginal sex. Her ass, she made it quite clear, was off limits. Barbara did enjoy some gentle teasing and probing of her very tight rosebud but as for my dick disappearing into what I assumed was a virgin Poop Shute, no way Jose.

It's kind of weird to have sex with women, especially wealthy, beautiful, horny women that you know next to nothing about, so when we finished our final sex bout, she made it clear that she wanted to meet with me, one on one, for coffee. Barbara made no promises about future sex romps, and she also made it clear that she needed to be very discreet in where and when we met.

She wasn't wearing a wedding ring and she never made mention of a husband, either past or present, but I accepted her terms and she said she'd reach out to me.

It took a while to get a meeting set up but when I returned from Tokyo and Hong Kong, we connected for a cup of coffee in downtown Sacramento. I was just getting home from a long trip, and she was headed to Los Angeles for business.

We opened to one another, and I learned about her family business and more importantly, about her. Her grandparents started out as farmers in the Sacramento Valley but got tired of the ups and downs of drought, wind, flood, and fire. They sold their land and started buying apartment buildings. Originally sticking to the Sacramento area, over time they expanded all over California and into Nevada.

Barbara and her siblings were now running the company and she was the CEO. She was in the process of buying out her brothers and sisters and setting them up for nice retirements. She was the baby of the family, and the others were glad she was up for running the show. They were burned out and wanted nothing more to do with the business. They just wanted the money and no further headaches. Oh, and monthly dividends!

So, during that first cup of coffee we learned about each other and did some laughing about some of the mistakes we'd seen in business or some that we'd made ourselves. Gradually, we became friends, having already been lovers.

I know that sounds funny, usually you open to another person and then have sex, but we had sex first and then learned about one another. Love the one you're with seemed to be okay by both of us.

Of course, the issue of both sex partners and spouses came up and I was candid with her. I wasn't looking to get married for a few years and I was playing the field until I found "the one." Barbara smiled and replied that she was seeing someone but that it wasn't serious.

The subject of Dr. Tina came up and Barbara was open with me. She pretty much gave me a lot of semi-useful and somewhat-useful information which I absorbed and then she asked me if I wanted an introduction to Tina.

That opened a can of worms, so I bluntly asked Barbara, "Where are you going with this?"

*******

Even though we were sitting in a quiet part of the coffee place, away from prying eyes and ears, Barbara looked around and being satisfied that no one could hear us, asked me, "At The Reunion, do you remember anything Janet said to you of personal significance?"

Barbara had a huge, shit eating grin on her face.

I smiled and nodded, sharing that Janet had told me, "I have a bigger and longer cock than Jack Colton and I use it much better to pleasure my partners than Jack. She also said she'd never come as many times as she did when we were fucking."

Barbara smiled back at me and responded with, "Every single one of those ladies you were with in Lake Tahoe, including me, agrees with what Janet told you. And that brings me to a business opportunity for you to think about. But I don't have the time to discuss it now. Next time we meet, okay?"

*******

Barbara and I met two more times following that first time, in short order, and then she went radio silent on me. Tina was only briefly discussed.

During our meetings, we never kissed, held hands, or sat any closer together than if we were attending a business conference. There were no PDAs (public displays of affection) although we did do a quick hug like business colleagues when we parted.

Her tits felt great pressed against my chest. She said she liked the way I hugged her, nice and tight.

I enjoyed spending time with Barbara and would have liked to ask her out, like to dinner, but she was talking a mile a minute, always with a smile and a laugh, so I knew she was enjoying herself, but it never seemed there was a good time to ask her, so just I smiled and laughed back.

And of course, I took it all in, visually: she was a fucking beautiful lady, all woman, and even though she was dressed in business attire when we met, there was no hiding the fact that she had a great body and as I knew from experience, Barbara loved to fuck.

Of course, I also replayed the video in my head of the times we fucked at The Reunion. She particularly enjoyed me taking her from behind, my hands on her hips, controlling the speed, tempo, and depth of my thrusting. Some women are silent, some are screamers, she was a groaner, letting me know how she felt when my hard cock finding places inside her pussy that had maybe never been touched before.

While she was an active participant, getting into primitive rhythm with me, she also quickly surrendered to my fucking. As wet as she was, it took me no time at all to start pounding her, hard and fast, bringing her to orgasm after orgasm, her head down on the mattress, her hands gripping the sheets to stay in place, her ass up in the air, her female fragrance quickly filling the suite.

It was one I was quite familiar with: the sexual aroma of a woman who hadn't had strong, deep, subordinate sex in a long time.

Unlike some women, who loved it doggy style but found it necessary to play with their clit while getting pounded, Barbara was occupied just hanging onto the sheets for dear life.

Her hands had a death grip on those silk sheets leaving her love button free for me to play with. I just teased her enough for her to first groan in response and then start begging me in a husky voice of a woman who knew she was being well ridden.

My deep thrusts brought her to heaven a few times, quickly, and even though I had not yet emptied into her, I pulled out and rolled her over on her back, spread her shaking legs and went to town on her pussy with my tongue, lips, mouth and fingers.

I mere seconds she was bucking against my tongue, coming again and again, soon pleading with me to stop as she couldn't take it anymore.

Did I stop? Fuck no!

I licked her to three orgasms, each one bigger than the next, the last one using my thick, long fingers on her g-spot, driving her nuts, until she went limp, her body covered with sweat, her legs shaking, her hands holding her ample breasts as she came down from her sexual high.

All those visuals got me hard as I listened to Barbara, in our prim and proper meetings and each time, I had to discretely shift my slacks a bit as my hard cock was making me quite uncomfortable. I didn't think she noticed.

I found it fascinating that I could take a woman of this caliber, education, beauty, and wealth, and turn her into a near-slut begging for my cock and tongue to satisfy her.

After not hearing from her for about a month, which I thought was odd, given our level of intimacy, Barbara broke radio silence when she called me out of the blue to ask if I wouldn't mind her bringing a picnic lunch to enjoy on my patio, and oh, by the way, would I be willing to give her a massage when lunch was over? Plus, she had some things to talk to me about, business-wise.

Finally, I thought, we'd get back to having sex. We set a date and she told me what she was going to bring to eat. I in turn, promised to give her a great massage.

*******

I started having my female visitors park in the third stall of my garage. And then I closed the garage door to any prying eyes in the neighborhood. I was a little paranoid that a neighbor would see that someone other than Leeann was at my house and use it to extort me. I have an overactive imagination, but I didn't need to deal with a naughty neighbor, so I dealt with it in a way that worked for me.

Barbara drove up in the new Tesla, the most expensive model. Pulling into the garage, I closed the door and greeted her with a hug which wasn't enough for her, she wanted a big, wet, deep kiss, the one I had been wanting to lay on her for two months!

*******

She brought in the food and asked me to grab a file box for our business discussion.

Barbara wasn't in her traditional business attire, she was wearing a dark blue and white summer like dress, no hose, and sandals, showing off her shapely and tanned legs and a great (recent) pedicure with bright red toenails to match her perfectly manicured fingernails.

She was wearing her hair in a ponytail, something I had seen her in at the hotel swimming pool at The Reunion. But she changed her hair color from a dark honey blonde to a soft very light red. She looked stunning in that new color, and of course, being the horn dog that I am, I wondered if her dark blonde pussy bush was the same or if she had dyed it too.

So, enjoying lunch and having nothing but lecherous thoughts of having her naked on the massage table, Barbara dropped a bombshell on me by asking me if I had some time each month to devote to working for her in her company.

"I need an advisor, Rick, someone who I trust, someone I like, someone who isn't afraid to tell me that I am full of shit when I am full of shit, and someone who will compliment me when I do a good job. Right now, I am getting no feedback and I need some. Badly."

I nodded and replied, "You know I am pretty well booked up time wise. What are we looking at? How much time are you thinking?"

She smiled and said, "I'd like to have a three hour in person meeting with you once a month. And between those sessions, talk on the phone, or text or email. So, four hours a month. Max."

I responded back with, "Are you open to where we have these sessions? I may have to fit you in before a flight or when I land. Is that okay?"

Barbara reached over and touched my hand. "If you are in a place where we have facilities, I just might meet you there. If time permits, we might have an extended meeting. How does that sound? Maybe even an overnight session."

Before I could answer, she reached into her purse and pulled out an envelope.