I Learn About The Hot To Trot Club

This is an adult sex story.

All the characters are of the age of consent or far over it!

Any children named are not involved in anything sexual.

This story follows "Have You Ever Changed a Diaper?"

Enjoy and thanks for the views and votes.

I've edited this since first posting on 8/27/2018.

****

End of February

It was about a month since Catherine and I had spent the long weekend in Hawaii, getting things figured out for our family and the businesses.

About a week after we returned, I had a three-day meeting at my country club.

I flew in all the out-of-town people in management from the various locations and businesses and posed these challenges to them:

1.How should we be organized for rapid growth and scaling (adding revenue and profits without adding people and overhead)?

2.Are you in the right position? What position should you be in? What is your next position and when will you be ready to take it?

3.Do you have the right people working for you? What do they need to improve and when will they be ready for more responsibilities?

4.What support and tools do you need to hit your financial and other goals?

5.What are your monthly goals for this year, and what are the goals by quarter for the following two full years?

I wanted a rough draft presented at the end of the second day and a better one by the end of the third day.

To avoid any ego centered arguments and all that went with that, I shared my overall plan for Catherine and me, and laid out a five- and ten-year overview that made everyone in the room a multi-millionaire within a decade but they needed to be a genuine team to be part of that and I didn't want any bullshit.

I said to everyone: "Set your egos aside and make fucking money. The only arguments I want to hear about are the differences between how much we will make and how we will make it. Notice that "who" is not in that sentence."

Also, I had made the decision to add my long-time business friends to a formal advisory board for the company and gave them a list of the areas I needed additional expert input on: real estate, human resources, technology and franchising; they had the job of finding me more experts to join them on the advisory board.

In the meantime, Catherine and I continued to look at hotel properties for sale and we would do short out and back day trips using the company plane. Down to San Diego or over to Palm Springs; up to Pismo Beach, Cambria or over to Phoenix. Catherine almost always fell asleep on the return trip. Her belly was swelling as the baby grew.

There were a lot of irons in the fire. Plenty to do. Life was far from boring.

****

Janet (The MILF) and her two children had practically moved in with us; they were with us all the time.

Both Catherine and Janet's daughters were excited at the pregnancies and that they would be having baby brothers.

Of course, they had no clue that I was the responsible party for both babies and all the adults were sworn to secrecy not to reveal anything.

As far as Janet's two daughters were concerned, their dad Tony was the father of their unborn sibling yet, within just a few weeks of Tony moving to Las Vegas, both girls started calling me "Dad."

My wife Catherine said she thought it was cute, and appropriate.

****

I started getting up at 5:00am each morning and going upstairs to workout.

It was the only way I could faithfully and regularly stay in shape and get everything else done in my life.

So, I made working out a priority.

Catherine slept in and did her laps in the pool with Janet once the kids were off at school.

Janet, on the other hand, was an early riser like me and she would often join me in my workout room just after 5:30am. Her bedroom was down the hall on the second floor. Everyone else slept downstairs.

I'd be working out on the Elliptical and she'd silently enter the room, close the door behind her, lock it, strip her night clothes off, put a towel down and then lie down on the workout pad in front of my machine and start masturbating.

She was my Private Dancer, just like in Tina Turner's song.

We didn't speak; our eyes connected, and we smiled at each other.

A lover's smile, a knowing, intimate smile.

Her legs spread wide, with her fully shaved bare pussy and her puffy labia only for my viewing pleasure, I waited patiently for her extraordinarily long clitoris to rise and be visible as I continued my workout.

Once Janet lay down on the mats, whatever I was watching on television quickly became boring and for 15 minutes she'd play with herself all the while looking up at me huffing and puffing and sweating like crazy.

Janet really liked watching my flaccid cock rise in my shorts as she finger-fucked herself and pulled on her long nipples.

I don't mind saying that Janet was a horny lady; this pregnancy had her hormones going crazy and she needed dick daily. I was happy to provide it.

In a box in the closet of this room Janet had stashed a small dildo that she often used on herself while I was finishing my workout.

She slid that thing in and out of her wet pussy, making that sloshing sound of fucking that I loved.

I was fine if she came from her own efforts, and often she did, our eyes locked as she shuddered and came, her hips pumping in the air, moaning softly.

When I finished my workout, I would wipe my face and still dripping, walk over to where Janet was spread eagle on the mat, covered in her own sexy sweat.

Janet would sit up, pull down my shorts to reveal a fully erect, dark pink and sweaty cock, have me step out of my shorts and then she would lay back down, legs obscenely spread and whisper "Good morning Jack."

Hot and dripping from my workout, I did the deed.

Janet loved my size and always said something complimentary, which only made my ego grow.

"You're so big this morning!" or "My God you're so hard!"

She took my cock by the hand and guided it right into her tight wet snatch and I pushed in, so I was balls deep.

Janet would always groan at my initial penetration, and we'd kiss a deep French kiss, and she'd whisper "Now, fuck me, Jack. Hard."

I always came when I fucked Janet, she made sure of that.

Janet loved me coming inside of her. She said it made her feel loved and needed.

She didn't mind me dripping out of her either.

She'd often come too, her legs around my neck as I pounded her hard, missionary style.

When she got larger around the middle, she wanted it doggy, and I delivered.

It was a great way to start my day; those mornings when I came inside of Janet's welcoming pussy, I was unstoppable.

What made it extra special for me was that once I had come, and fully dripped everything I had into her pussy, she would get between my legs and clean my cock with her tongue.

Between licks and sucks she would whisper "Thank you for fucking me Master ... Thank you for fucking me Master ..." and she was sincere in her comment.

Janet was very grateful to me, and to Catherine, for all we had done for her.

And, during the middle of each business day, after lunch, my Executive Assistant Sabrina scheduled sufficient time in my busy calendar so she could come into my office and suck me off, swallowing my load.

Life was good and just like that Beatles song, "Getting Better."

****

I finally got around to calling Dianne, the Assistant Principal at my youngest stepdaughter's elementary school.

As you recall, she handed me a business card after the Valentine's Day dance my wife Catherine and I put on.

On the back of the card, she wrote "Call me for coffee ... and more!" which made me wonder what she was thinking as she knew Catherine well.

Did Dianne want to have an affair?

That was out of the question. Off the table. No way Jose. El Paso.

Catherine had said that Dianne was "on the prowl" which meant to me she wanted to get laid.

I had Sabrina set an appointment for a late afternoon the week following the dance.

****

Dianne showed up dressed to the nine's as they say.

She showed a lot of skin, a lot more than you would expect to see from a management employee at a public elementary school.

I greeted her with a smile, and she came up and gave me a big hug and a kiss on my cheek.

Another balloon smuggler: what was it with the ladies in this town?

I took it all in as we shook hands: styled hair; white blouse under a dark blue business suit; four-inch heels on her Ferragamo's.

Dianne said, "I hope you don't mind but I want to take off my coat" and I helped her do so.

There was a method to her madness; she had on a tight white silk blouse, and it did nothing to hide her balloons.

I smiled, trying hard not to stare at her ample chest but she knew what she was doing, and she sat up straight and in doing so, thrust her bust out, which was all just fine with me.

We chatted for a few minutes about the dance, and she passed on the regards and thanks from the principal and the PTA for what Catherine and I had done for the sixth-grade class.

Dianne asked me if we had any thoughts about hosting some sort of graduation dance in late May or early June and I replied that we hadn't discussed it, but it was certainly something we could do.

I followed that with "Do you have any thoughts on a theme?" and she replied that she and the principal wanted something where the kids had to dress up; the boys wearing shirts and ties and the girls wearing dresses.

Dianne said that she was sure that not all the kids had these types of clothes and I told her that we would set something up so that all the kids would have appropriate clothes. I had in mind gift certificates for each child for $150 at three or four different places around town. The local merchants would appreciate the business and having new clothes would make the kids feel good about being dressed up.

At that, Dianne's eyes filled with tears, and she got up, I stood up, and she came over and gave me a huge tight hug, those titties really smashing into me, and she kissed me on the cheek and whispered, "You are such a wonderful man."

She wiped her tears away, smearing her makeup, but she still looked fucking hot.

When she finally smiled at me, I asked her "What's the purpose of your visit today? How can I help you?"

Dianne smiled at me and said, "I am wondering if I can help you."

I returned her smile; "Please go on, I'm all ears."

She said to me "I understand you have a company that recruits people for your businesses."

I said "Yes, we do."

"How are things going?" she asked me.

I looked at her and said "Not very well, I'm afraid. We haven't been able to get the right people to become our recruiters."

Dianne smiled and said, "I believe I have a solution for you."

And with that, Dianne pulled out a single sheet, a succinct business plan, outlining how she could recruit a cadre of Assistant Principals who could do their day jobs during the week and head out of town on Friday late afternoon, then recruit on Saturdays and Sundays, getting back into town Sunday with plenty of time to get ready for work on Monday.

These would primarily be divorced, widowed or single women who wanted more income and didn't mind travelling. The ladies could travel alone, in pairs, or larger teams depending on the situation and need.

I thought it was a brilliant idea and said so.

I followed that with "What's in it for you?"

Dianne took a sip of water, a giveaway she was nervous, and stated "I just want a one-time "finder's fee" for each Assistant Principal I bring in. You will only pay me if you hire them and they work out. I also want first dibs on each recruiting assignment."

That was fair, I thought, and with that I went to the office door and asked Sabrina to find Cynthia, the CFO, and ask her to please join us.

We spent another hour working through the possibilities and options.

I was late coming home for dinner, but Catherine understood the reason why and wasn't upset.

****

Cynthia and I agreed that what Dianne proposed made good sense, but our first hire had to be someone inside the company who was technologically savvy, understood what we wanted accomplished and could work on weekends because that was when the recruiters would be having the most issues.

In baseball, this is the catcher, the individual who organizes and facilitates things.

When Dianne walked out the door, we quickly agreed on promoting Maria, a young woman who had just graduated from college with a degree in History. She had been working on the sales floor helping the salespeople close deals, take care of our customers, and all that.

Maria was young, engaging, energetic and tech savvy. She was well liked and a fast learner. Most importantly, she understood the need to get things done quickly, quietly, and correctly.

As we were getting Maria situated and oriented, Dianne did not waste any time bringing by prospects for us to interview. Dianne did not just put us in touch with these folks (every one of them female by the way) but she personally introduced each one to Cynthia and me before we interviewed them.

Sometimes she had two candidates come in on the same afternoon, which was fine. There were plenty of positions for us to fill. We were talking to everyone that Dianne brought in.

The job, pay, travel and work appealed to most of the ladies and that was good; we lined up a couple of attorneys to do some classes on the correct (and legal) way to conduct job interviews.

We also had each candidate take a couple of personality profiles because our college grad job seekers would also be taking those same assessments.

Once she got her desk set up, we sent Maria on the road, visiting some colleges, and working out details for when we could conduct interviews on the weekends, because that was when our prospective employees would meet with our recruiters.

It was a little unorthodox, but it set us apart from all the other companies recruiting and it made sense because even if one of our candidates worked a full-time gig on a Saturday, we could interview them during that evening after work or on Sunday morning.

And remember, we weren't interviewing at Stanford, USC or the University of Washington. We were out in the hinterlands, going to places like Flagstaff, Olympia and Santa Fe, where the smaller, lesser-known colleges and universities were located.

Our recruiters could meet with candidates at Starbucks at 10pm on a Friday night or at IHOP at 11am on Sunday if need be.

We didn't care what they candidates wore; we did not expect business suits, white shirts, and ties. We did care that they were on time, clean, appropriately dressed, and nice.

We explained to our Assistant Principals that our new hires were hungry to start a "professional job" with good pay and benefits. We needed to be open to adapt to these candidates' schedules as they were likely working their way through college.

After we had met with about ten possible recruiters in a few days, I called Dianne up and said "Please explain something to me: how do you know all these people?"

Dianne replied that there was an organization of Assistant Principals in the region, and they met for dinner once a month as an industry group to discuss common problems and challenges.

I replied back "Every one of the women you have brought in to meet me is, forgive me, a knockout. Surely not all the Assistant Principals in this organization look like you or your friends. The female Assistant Principals I had in school were all frumpy, overweight and downright mean, especially to the boys."

Dianne laughed asked me "Can you keep a secret?"

I said I could and that I would.

"Jack, I am only bringing to you the best-looking women from the association because that will get you more people to interview. Once the word gets out that hot babes are the recruiters, people will really want to talk to us."

What Dianne did not tell me, but I found out later through a friend of a friend, was the women Dianne brought in to meet me had their own little club that they called "Hot to Trot."

These were single, divorced, and widowed professionals on the prowl for man meat.

Cougars.

Looking for young studs to fuck just for fun.

Nothing long term, just flings. Lots of them.

In my town most of this Hot to Trot group had joined four gyms in the area and they rotated their visits in order to maximize visibility to be seen and to meet the most number of available hunks.

The latest thing was for these cougars to take after work yoga classes because most of the women attending were married but most of the men who attended were not. While there were not many men in any given class, the ones that were took care of their bodies and were fuckable.

Some of the ladies attended night school, working towards an MBA because that was a place where the odds were in favor of meeting smart men who were interested in bettering themselves and making more money.

I found out that one lady in the group had gotten her MBA and was able to teach nighttime and weekend business classes, allowing her the pick of the litter each semester, selecting a "teacher's pet" so to speak.

Several became flight attendants and worked weekend flights only, meeting many eligible men. Within an hour of landing in a new city, these ladies were being pounded by either a young stud pilot (usually a former Top Gun with the Navy) or were picking up a hot passenger in the hotel bar.

It all made sense to me later when I learned the details, but I was initially satisfied with just knowing how Dianne was working to bring us potential recruiters.

I didn't know any of this when one of the prospects for a recruiter position came into the dealership with Dianne one Friday afternoon late in the month.

I was beat, it had been a long week, with out-of-town trips for me on both Tuesday and Thursday, and I was dying at my desk, trying to get a few last tasks done before I left for home.

Sabrina, my Executive Assistant, had left work early and without performing her usual and customary blowjob. I was both tired and horny.

In my last story "Do You Know How to Change a Diaper?" I mention a lady that was the new star of one of my porn sites.

That Friday afternoon, as beat as I was, I immediately recognized the lady that Dianne was introducing me to, it was the lady who was "dating" my father-in-law, Tom; the lady I had been videoing for months and marketing her sex tapes on one of my subscription pay sites.

She was better looking in person than on tape; I knew everything about her physically, but I did not know her name or her personality (I had some idea based on what she said during her sexual escapades).

I had guessed her age on the video to be 38 to 40; she was actually 36.

She was a fine 36. Very fine.

Nor did I know her profession, but Dianne introduced Darcy as an Assistant Principal of a smaller private K through 12 school in a wealthy area of Los Angeles.

Darcy gave me a firm handshake with a beautiful smile and was dressed impeccably.

I already knew the carpet matched the drapes, although she didn't have any carpet. Her blonde mane was thick, shoulder length and her clothes fit well.

Dianne left us and Darcy and I talked.

Once I found out how the "Hot to Trot" club worked, it was easy to get background information on all my recruiter candidates.

Darcy opted for the did the gym route, which is how she found her way to my house for those poundings by my father-in-law, but she also spent summers on a cruise ship as one of those "Directors of Fun" which meant she met different guys (single and married) each week and often had a different guy each night while onboard the ship.

Darcy also made sure that she was far enough away geographically from her employer, the school, so that she would not run into any students, parents, fellow teachers or administrators or former students as she laid the bait for her would be sex partners.