Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 37: A Cocky Son of a Bitch
Fiction Sex Story: Chapter 37: A Cocky Son of a Bitch - Jonathan's business life is booming, but he's also suffering from yet another loss. While he's done his best to pick up the pieces of that sundered relationship, he can't help but feel responsible. However, where two close relationships have withered, another blooms. Violet has transitioned from a badly damaged girl to a vibrant woman. Will he continue to climb this ladder, or will there be another ladder to climb in his future? No matter what, the only direction he plans to go is up.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Workplace
August 13, 1984, Boca Raton, Florida
The flight had been uneventful, and I'd spent quite a bit of it chatting with the pilots, Howard and Pete, one ex-Navy, the other an ex-Marine, both of whom had flown in the service. Noel didn't emerge from the sleeping berth until about ten minutes before we began our descent.
When we arrived at the estate in Boca Raton, a casually dressed butler, who introduced himself as Philip, escorted me to a room on the second floor. The room shared a wall with the master suite that Noel was using and was about the same size as my bedroom in the condo, complete with a king-sized bed.
I began to unpack, and had just hung my suits in the closet when a pretty girl with short black hair came to the door. Noel had mentioned her, and it didn't surprise me she was gorgeous, though if all the rumors were accurate, she was probably four or five years too old for Noel.
"Hi! I'm Rebekah Blanchard! I manage the property for Mr. Spurgeon. You must be Jonathan Kane."
"I am, and please call me Jonathan. I hear you're from Ashtabula."
"I am. I hear you're from near Cincinnati. If there's anything I can do to make your stay more enjoyable, just ask! You can reach me by picking up the house phone and dialing #20. I have a portable handset with me most of the time."
"Thanks very much."
"You're welcome! I hope you enjoy your stay."
"Thanks."
She left, I finished unpacking, then checked out all the amenities in the room — a 35" TV, a shelf stereo system with a CD player, and around fifty compact discs. The room also had an en suite bath with a whirlpool tub large enough for two, or even three, and a large stall shower. The window overlooked the pool, and I saw a gaggle of college-age girls in bikinis sunning themselves or splashing in the pool.
One of them caught my eye, and my jaw actually dropped in surprise — one of the girls was Mary Kealty, Rachel's sister! My brain rewound to meeting her when Rachel and I were dating, and later, Mary basically seducing me, and her offer to give her first blowjob if I called her. At that moment, we were both sure I would, but the next morning, in the cold light of day, I'd reconsidered what I'd done and realized it had likely been a mistake. I never called her, and had never heard from anyone in her family.
Another equally stunning girl caught my attention — a gorgeous redhead with a chest that was barely contained by her bikini. Of course, ANY of the girls would catch someone's eye, especially given they were all clad in bikinis, most of them being string bikinis. That got me to wonder who recruited the girls and if they were compensated for attending, and if having sex with Noel's clients was mandatory.
It struck me that the only way I might find out without arousing suspicion that might find its way back to Noel was to speak to Mary Kealty. I'd have to be careful, though, if I were honest with myself, she had not done anything wrong. Neither of us was in a committed relationship at the time, and she hadn't stalked me or even contacted me, except for the two visits to the apartment I rented from Lily's dad.
I decided I was going to go out to the pool, so I changed into my trunks, put on a loose-fitting cotton short-sleeve shirt, and deck shoes. I also grabbed my tam and a pair of sunglasses, then headed downstairs. I found my way through the house to the deck, and rather than wait, I cut straight to the chase and walked over to Mary.
"Jonathan?!" she gasped.
"Hi, Mary," I said. "Fancy meeting you here!"
She laughed, "It's at least partly your fault!"
"I suppose it is," I replied. "How have you been?"
"Great! I'm pre-med at Florida Atlantic. What are you up to?"
"I'm Spurgeon Capital's Chief Analyst, and I head the Research Department. I also have three securities licenses."
"That's pretty good given you worked in the mailroom when we met!"
"I've busted my ass," I replied.
"Who's the hunk, Mary?" the redhead asked.
"Jonathan Kane, this is my friend Marcie; Marcie, Jonathan Kane. I know him from Chicago. He works for Mr. Spurgeon."
"Hi!" she exclaimed.
"Hi," I replied.
"Marcie, can you give us a sec?" Mary asked.
"Don't hog him!" Marcie exclaimed, then walked over to another group of girls.
"You never called," Mary said, licking her lips.
I actually had a truthful answer that didn't require me to say something that might upset Mary, which I didn't want to do, so as not to make things uncomfortable.
"The day after we were together, I had a date with someone I'd met around the time your sister and I stopped seeing each other. It went really well, and we started seeing each other regularly."
"Are you seeing anyone now?"
The question was how much I wanted to reveal, and I decided it was best to play my cards close to my vest.
"I'm dating, but not exclusively."
She stepped as close as she could without her perfect breasts touching my chest.
"Would you like to see these ruby lips wrapped around you, sucking you until you cum?" she asked sexily.
The answer to that question was a resounding 'yes', because I did want to see it. Whether I should do it was a whole different question.
"I would, but I don't want you to mess up your deal, whatever it is."
"Deal?" she asked, taking a step back and looking confused.
I realized I might have completely misjudged the situation, thinking that the girls were compensated, and they might not be.
"Is this a job?"
"Job? No. Why would you ask that?"
"I know the man," I said with a smile. "Allow me to remove my foot from my mouth. How did you come to be here?"
"Rebekah, the girl who manages the property, just transferred to FAU from a school in Ohio after she took the job here. She put up signs at FAU and other colleges offering a chance to meet interesting, well-to-do men, hang out at the pool, have a nice meal, and go dancing. I saw the sign, called, and signed up because the chance that I'd get to go to La Vielle Maison otherwise is pretty slim. And there's no way I could get into Wildflower because I'm only nineteen. I jumped at the chance, as did some of my friends."
"Forgive my mind from running where it shouldn't, but there are no obligations?"
"No," Mary said with a smile. "That said, there weren't any restrictions, either."
"Are all the girls from your college?"
"About two-thirds; the rest are from other colleges. Well, there are two girls who are in High School; they're the ones wearing the matching black bikinis and talking to the older guy."
I glanced and saw Noel Spurgeon talking to a pair of girls who I was positive weren't a day over sixteen, and might even be as much as two years younger.
"That's Noel Spurgeon," I replied. "My boss. You haven't met him?"
"No. This is the first time I've been here, and Rebekah didn't describe him, and neither did Rachel."
Mary looked more like her oldest sister, Rebecca, while Rachel and Elizabeth looked very much alike, so there was a good possibility that Noel wouldn't make the association, and the impression was that Rebekah had made all the arrangements.
"You're going to be a Junior, right?" I asked.
"Yes. Most of the girls are either Juniors or Seniors, but there are a few Sophomores like Marcie."
"I'm going to guess Rebekah interviewed everyone?"
Mary laughed, "Because we're all hot?"
"Yes."
"I did meet her, and I did get the impression she was looking for a certain type of girl. I know one girl whom I would call plain who was disappointed she wasn't invited, but I heard Rebekah had twice as many girls call as there were available spots."
"You're staying in Florida during the Summer?"
"Yes. I live with a friend because the last thing I wanted to do was live at home, where I would have zero freedom during my Summers! I'm going to guess you moved from the apartment."
"Three times — to a rental house, to a house I bought, then to a condo in the Hancock Center."
"Then I'm going to guess 'well-to-do' applies to you, too!"
"I'm very comfortable; I'm working on well-to-do."
"Let's go somewhere so I can do what I offered two and a half years ago! Then Marcie can have her shot, if she wants it."
"Technically, you offered the pleasure of receiving your first-ever blowjob, not a blowjob."
Mary laughed, "And you would turn it down if it weren't the first? Even if I promised to make it amazing and that I'd swallow?"
"That was part of your original offer," I replied. "At the risk of being a jerk, I'm going to wager that offer isn't available!"
"That's not my fault! I wasn't with anyone else in any way — not even kissing — until after I started at FAU. You had your chance and blew it by not allowing me to blow it!"
I chuckled, "I suppose that is on me."
She stepped close again, "I want to wrap my lips around you and suck you until you cum, then wrap my legs around you and have you fuck my brains out. We have plenty of time before most people arrive."
Before I could answer, Noel walked towards us with one of the High School girls on each arm. When they came closer, I was positive they were barely fifteen. Mary took a step back.
"Enjoy yourself!" Noel said. "The girls aren't just here to entertain our clients!"
"Good to know," I replied with a smile. "I will."
He walked towards the house with the girls, and that concerned me, as there were fifteen other girls here, and by the time he finished with the underage girls, there would be clients here. I wasn't the morals police, but on the other hand, openly flaunting that he was bedding underage girls was a serious concern. There were any number of risks — blackmail or reputational risk if the information got out, and worse, the risk of criminal prosecution if he were accused of what was now being called criminal sexual assault rather than statutory rape.
My second thought was about how to answer Mary. I was absolutely positive Noel expected me to take advantage of the situation, and not doing so might actually raise questions in his mind. None of the girls here worked for Spurgeon except for Rebekah, so they weren't off-limits, and if Mary were to be believed, they were at the estate of their own free will and weren't compelled to do anything.
Mary was a known quantity and was probably the safest girl of any. There was no doubt in my mind that I wanted what she was offering, and she was one of the most beautiful girls I knew, though not the most beautiful — that was my mom's friend's daughter in Milford. But even amongst the gaggle of gorgeous girls around the pool, she was the hands-down prettiest. I was positive that if Noel hadn't had his two High School girls, Mary would have likely been his choice.
"You will?" Mary asked invitingly, echoing how I'd answered Noel's direction to have a good time.
I smiled, took her hand, and led her into the house. We went up to my room, and, as I expected, the door to Noel's suite was closed, where it had been open when I'd first gone outside. I led Mary into my room, then shut and locked the door.
"I think you'll like the tan lines," she said with a smile.
She kicked off her heels, then quickly removed her bikini, proving her to be correct. The contrast between her tan and the areas covered by the suit was striking — medium brown tan and white where the bikini covered her. The effect was stunning, and I felt the necessary stirring between my legs. I quickly removed my clothes and sat on the loveseat opposite the bed.
Mary came over and dropped to her knees, grasped my shaft with her left hand, then lowered her head. I watched intently as she opened her mouth and took my glans between her full lips, then slowly slid her lips along my shaft while swirling her tongue. She took me about two-thirds of the way into her mouth, then pulled back and began slowly stroking and bobbing, all the while sucking and swirling her tongue.
The blowjob was fantastic, and Mary took her time, clearly enjoying what she was doing, and slowly ramping up the tempo. She was clearly in no hurry, and neither was I, as I was enjoying not just feeling but watching those ruby lips slide along my shaft. Slowly, inexorably, and pleasurably, I felt the pressure begin to build.
About ten minutes after Mary had started, I reached the point of no return. I twitched, and Mary backed off to keep just my glans in her mouth. She stroked quickly, swirled her tongue, and sucked hard. I groaned and cum blasted into Mary's mouth. She continued her ministrations well past the last spurt, increasing the pleasure to a point just short of painful, then released me.
I took her hand, encouraged her into my lap, and we exchanged a fierce French kiss. After a minute, I broke the kiss, helped her from my lap, stood up, then led her to the bed. We climbed in, and I moved between her legs so I could pleasure her with my lips and tongue. She was sopping wet, and I lapped up her juices, then began teasing her clit with my tongue.
I brought her off twice before I was hard, and moved up to fulfill her request. I grasped my shaft, rubbed my glans along her labia, then drove into her. Mary gasped and groaned, then wrapped her legs around my butt, and we began fucking hard and fast. She had three more orgasms before I pushed deep into her and fired jet after jet of cum into her spasming pussy. We lay together for about ten minutes, then went to the shower to clean up.
"Amazing?" she asked once we got into the shower.
"It was!" I confirmed.
"I'll give the other girls a chance, but I'm happy to spend the night with you, if you want."
"What happens if a girl doesn't choose to participate in nocturnal activities?"
Mary laughed, "There will be cars here after dinner, and then around midnight."
"When did you decide on pre-med?" I asked.
"During my Senior year. I had thought about being a nurse like my sister, but my guidance counselor said my SAT and ACT were good enough to suggest I'd do well on the MCAT or LSAT, and I had straight A's."
"What's your actual major?"
"Chemistry with a minor in biology. That's a pretty common path, as is the other way around. It's actually possible to get into medical school with any undergraduate degree, so long as you can pass the MCAT, which is science-heavy. Are you still going to school?"
"Yes. I have one more class, then I'll finish with independent study."
"That's cool. Do you trade stocks?"
"I run my own fund, but my main focus is on research. Those things go hand-in-hand, though, as the research is necessary to select the right investments."
We finished our shower, then dressed. When we left the room, I saw the door to Noel's room was still closed. We headed outside, and I saw that a number of our clients had arrived, so I began introducing myself to them. When questioned about Noel, I simply said he was tied up and would join us shortly, which he did about twenty minutes later, but without the two girls on his arms.
When the last of the clients arrived, everyone, including the two High School girls, boarded one of three shuttle buses, which took us to La Vielle Maison, where Noel had reserved a large, private room. There were two long tables for sixteen people each, and I wasn't surprised to find that seating was assigned and alternated between male and female. That meant my 'date', if I wanted to use that term, was Isabel Martínez, the daughter of Cuban émigrés who had come to Florida about the time Castro came to power.
I did chat with her, but I also made sure to talk to the clients near me — Paul Tyson, who represented a pension fund with about $100 million in the Arrow Fund, and Bob Westergard, who personally had $22 million in the fund. I couldn't discern their attitudes, as they were more interested in the girls than in me, which, of course, was Noel's plan. That said, I was gathering a bit of information about them as they flirted with the girls.
The meal was delicious, and the wine was excellent, though I didn't think it was worth ten times what I paid for decent bottles of wine in Chicago. What didn't surprise me was that nobody carded anyone, and all the college girls, most of whom were nineteen or twenty, were served without any question, as were the two High School girls. It drove home the point Jeri had made time and again — the rules were different for the extremely wealthy.
After dessert and coffee, we boarded the three shuttle buses to take us back to the estate. When we arrived, I went up to my room so I could change into my trunks, loose-fitting shirt, and deck shoes. As I left my room, I saw the door to Noel's room was open, and caught a glimpse of a girl who was, I was sure, in her early teens, but was not one of the two from earlier in the day who had joined us for dinner. I felt he was taking inappropriate risks, and because of that, I had to do everything in my power to protect myself.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.