Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 63: Confusion
Fiction Sex Story: Chapter 63: Confusion - 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
November 1, 1984, Chicago, Illinois
CeCi had left Chicago as planned on Tuesday and had arrived safely in California. She'd called from her efficiency apartment near the studio to say she was settled in, and that she'd begin working on Wednesday morning. The only truly negative part was that we wouldn't see each other, as she couldn't reasonably come home for Thanksgiving, given they had a full day on both Wednesday and Friday of that week.
On Thursday morning, Chelsea and I got out of bed with my alarm and went to the shower, as was the norm for the nights she spent with me.
"I have a question for you," I said as we got under the spray.
"What's that?"
"It's been a month, so you've had some time to consider the situation. What's your plan?"
"What do you mean?"
"Career? Marriage? Kids?"
She hadn't been to church in a month, and I was curious, but I didn't want to do anything that would prompt her to start going, as I felt that would only impede her progress into turning into the person she needed to be, rather than the one her dad and pastor wanted her to be.
"I don't want a career," she said. "I want to be a stay-at-home mom."
"How do you propose to do that if you aren't dating?" I asked.
"I ... uhm..." she started, but then fell silent.
"Just say what you're thinking, please," I requested, keeping my voice gentle.
Chelsea turned and stepped close so that her nipples were touching my chest.
"I'd marry you," she said timidly.
"Setting aside my thinking on that topic in general, how do you see that working, given you and I disagree on nearly every fundamental principle and our worldviews are almost diametrically opposite?"
"Because I'm in love with you," she said quietly.
I nodded. "I'm aware."
"You knew?!" she asked in surprise.
"Yes. I actually mentioned it to someone about ten days ago, and made the same comment about our worldviews."
"You don't love me, do you?"
"Romantically? No. But there are kinds of love besides romantic love."
"I ... well ... is it OK to say something from church?"
"Sure."
"There are three types of love mentioned in the Bible — romantic love, brotherly love, and self-giving, self-sacrificing love, which is called «agápē». I think that's the word I would use to describe your feelings for Sofía, Bianca, CeCi, and Deanna. I think, based on what you've said, only your wife would have experienced romantic love, but even then, it was both kinds of love, according to the girls. You were in love with her, but it was «agápē» that caused you to care for her the way you did."
"I don't know much about the Bible beyond a few specific stories and parables, or about Greek for that matter, but that sounds about right. I absolutely care about you and want to help you. I'm curious how you think being in love could solve your challenge with my worldview and how I live my life."
"You mean because you casually have sex with lots of girls?"
"Yes, but that's simply one facet, and for you, perhaps the most obvious one. I'm sure you remember all the conversations we've had."
"I do."
"Ignoring all other impediments, could you actually deal with that?"
"I have been for a month," Chelsea said.
"Except for when you've been offended, and for the several days you moped around after our last conversation. I don't mean to cut this short, but let's shower, and we can continue at breakfast, because I do have to get to the office."
Chelsea agreed, and we both quickly washed ourselves, dried off, and dressed. We went downstairs with Misty padding behind us, though she went to her bowl to drink and eat, while we went to the kitchen so I could make breakfast.
"The point I was trying to make was that something I do or say is going to trigger a negative reaction. The only way to stop that is to change your worldview and your approach to life, which you have to do for yourself. I've done my best not to tell you how to live your life. Yes, I've challenged your assumptions and beliefs, but other than asking you to have an open mind, I've left it to you to decide.
"The question I asked in the shower was intended to get you to think about the future, and to come up with some kind of plan. That plan doesn't have to be specific, either. I didn't have a specific plan when I arrived in Chicago, except to start an entry-level job that would offer opportunities for advancement, leading to a comfortable life, rather than a daily struggle to ensure basic necessities like food, shelter, and clothing. I had no idea I would end up where I am right now, as a research analyst and hedge fund manager."
"You don't think being a stay-at-home mom is OK?"
"It is, if that is what you want to do, and you'll be fulfilled by doing it. If that is what you truly want and you think it's the right thing to do, then you need to take the steps necessary to achieve it. I do want to ask a question — what happens when the two or three or four or five kids you have graduate from High School? What will fulfill you at that point? I ask because you expressly said 'stay-at-home mom'."
"I, uhm, hadn't thought about that, but I think at that point, I become a grandma and do grandma things, kind of like «Abuela»."
"If that will fulfill you, then you need to take concrete steps to find a guy to marry. Do you remember what I said about our relationship?"
"That it would just be about sex and would end, and you had no intention of marrying."
"Correct. I haven't said it expressly to you, but there's a good chance Deanna and I will be lovers for our entire life, no matter what other relationship I might have, including one where I was basically committed to another girl."
"You would cheat?"
I shook my head, "No, it would be an agreement between the girl and me, and it would have rules or guidelines or whatever you want to call them that defined the relationship. Maybe that doesn't happen, and maybe I commit to one girl to be with her for the rest of my life, but even in that situation, there isn't a realistic chance I'll get married."
"Because of Keiko, right?"
"Given I committed to Keiko to be cremated and interred next to her, and my name is already on the stele near the vault, it means I could never be buried next to a future partner. It's also the case that Keiko is my wife, and I don't want to replace her. That doesn't mean I won't have a partner for the rest of my life, but it does mean that partner would not be a wife. I'm fairly certain marriage is important to you."
"It is, because of ... er ... never mind. I can't say that."
"Because of having kids?"
"Yes, but ... well, Sofía."
"You do realize that nothing about being born out of wedlock has harmed her in any way, shape, or form, right?"
"I, well, you know how I feel about that."
"I do, and so long as you only hold yourself to that standard, you're free to believe and even express it, but you can't look down on Sofía, Bianca, or me because we chose a different path, or my mom and me because she chose a different path. Being a bastard, using the technical sense of the word, has literally no bearing on Sofía or on me. Fundamentally, if you don't agree with having children out of wedlock, don't. What other people do is their business."
I put the eggs, bacon, and toast on the counter, poured juice and coffee, and we both began eating.
"Uhm, are you saying you want to stop having sex?"
"No, but eventually, that is what will happen. Either you'll begin a relationship with someone, or I'll settle down with someone. I doubt that happens in the next few months, but, then again, I didn't see marrying Keiko happening as quickly as it did. I'm not referring to moving up the wedding dates because of her leukemia, but knowing she was the girl I wanted to marry. Something like that could happen at any time, though without the government paperwork, as it were."
"I'm not sure what to say or do," Chelsea said.
"You don't need to answer right now, or even next week, but you do need to think about it, and you do need to make a plan, even if it's general. May I suggest something?"
"Sure."
"You enjoy being a nanny, and you're good at it. Have you considered starting your own nanny agency?"
"No. I don't know anything about running a business or anything like that."
"How much do you think I knew about research, analysis, and investing when I came to Chicago?"
"I don't know, but from your question, I'd have to say very little."
"Exactly. The mailroom job was straightforward, requiring only the ability to follow directions, read, and work efficiently and reliably. Everything else I've learned since starting at Spurgeon Capital is a result of my desire to learn and taking the initiative. That included the training materials Spurgeon offered, taking classes at Circle, and finding a mentor.
"It's not just me, either. Jack started in the mailroom and is following a similar path, though I'm his mentor instead of Murray Matheson. Violet worked in a daycare, and within six months, she'll have a securities license. I've invested in the futures of a number of people — Bianca, Deanna, CeCi, Erin, and others. If you want my help, I'll happily provide it, but the least likely outcome would be marriage."
"Can I think about it?"
"Absolutely. Sofía will need a full-time nanny at least until she's in full-day kindergarten, and that's four years from now. She clearly likes you, and we're happy with how you care for her, so four years is a rough timeline. That said, I'm certain you know as well as I do that things could change due to external circumstances. It's also the case that if you want to marry and have a large family, you probably can't wait five years."
"You're sure you won't ever change your mind?"
"The practical answer and the real answer are different," I said. "The practical answer is that I'm sure. The real answer is that no, I'm not sure, because I can't reliably predict the future. What happened with Keiko proved that definitively. It's improbable, not impossible. That said, I've made it clear to girls in the past that it would be foolish to base their future on something so highly improbable. In other words, the real answer implies the practical answer — you cannot count on me changing my mind, therefore, you should assume I won't."
"That's ... convoluted."
"It's Jonathanland!" Deanna exclaimed as she walked over to the kitchen area. "What he said is how his mind works, and while it seems totally convoluted and crazy, the analysis is logical and consistent, and he follows it."
"Why not just say you won't change your mind?" Chelsea asked.
"I'll answer," Deanna said quickly. "Because it's inaccurate, and if anything, Jonathan is precise and accurate, and his job and investing success depend on it. If someone asks him to present an analysis of something, he has to report all the possibilities, no matter how remote. He assigns probabilities to them, and it's up to the person hearing the analysis to decide what to do.
"He did that, then added a suggested course of action, which is not what he does at work, because that's not his job. In other words, you can hold out a remote hope, like winning the lottery, that the infinitesimal probability will come to pass, but that's an awful wager to make with your future. When you lose that wager, he can safely say that he warned you, and that it's on you, and your poor choice, not on him.
"He doesn't do that to say 'gotcha' or whatever, even if it seems like it. It's like someone putting up a warning sign and barricades to say a bridge is out, but you choose to drive around the barricades and ignore the sign. Who's to blame for driving into the flooded river? Is it the person who put up the sign and installed the barricades? Or is it you?"
"It would be me," Chelsea replied. "It makes sense, but it's just ... different."
"That's why we call it 'Jonathanland'!" Deanna declared. "If you listen to him and heed his advice, he can do a lot more for you than just give you amazing orgasms."
Chelsea blushed and laughed nervously, "Uh, yeah."
"I hate to eat and run," I said, "but I need to get to the office. I'll see you both later."
I went upstairs, grabbed my satchel, and left the condo to head to the Spurgeon offices. When I arrived, I went through my usual morning routine of talking to Rich, making coffee, and reviewing Bloomberg for overnight news. Indira Gandhi's assassins had been identified as two Sikh bodyguards, and there were reports from India of anti-Sikh riots and violence.
That had the potential to destabilize India, and I needed to work that into my analysis, ticking the Asian risk factors up by several points, though they'd have little real effect on US markets. It might affect Singh, as he traded in Indian shares, but they were a small portion of his portfolio. I had just submitted the report when Violet came into my office.
"We never discussed how we're going to handle Cynthia," Violet said. "She's in her orientation, by the way."
"I'll leave it to you, but it makes sense to have her handle anything to do with the Desk, and for you to handle anything to do with the Research Department until it's time to swap. You should ask Phil to move my broker line to Cynthia's desk upstairs, so she can take those calls. Most of them will go to Jack first, anyway."
"That's probably the best approach," Violet agreed. "If you plan to move upstairs next September, we should probably begin the transition in August."
"Agreed," I replied. "Make it happen, Miss Clemmons!"
"That's what I do on Friday and Monday nights!" Violet smirked.
I chuckled, "It is!"
"When Cynthia finishes her orientation, I'll get her settled."
"Thanks."
That happened just before lunch, and after briefly chatting with Cynthia, I left to meet Beth for our first lunch since her wedding.
"Stopped having sex yet?" I asked with a smirk when we met at the kosher deli near the tailor shop.
Beth laughed, "Despite the stereotype, no!"
"I assume everything is good?"
"It is. We do need to fill out the paperwork to add him to my account at Spurgeon."
I nodded, "I'll have Cynthia fax over the form."
"Cynthia? What happened to Violet?"
"Nothing! I believe I mentioned I'd be transitioning to running my fund full-time next September. This is part of that transition. Cynthia will work with Jack until that transition. It was Violet's choice because she wants to keep working closely with me. She's also seeking a securities license."
"That's cool!"
It was our turn to order, and once we had our food, we sat down to eat.
"Anyway," Beth said, "as soon as I receive the form, we'll have our signatures notarized, and Josh can drop it off, as Allen & Baker's offices are just down Michigan Avenue from the Hancock Center."
"That sounds good. How are things otherwise?"
"Great! Of course, both our moms are out of wedding mode and into wanting grandkids mode."
"That didn't take long!" I chuckled.
"It never does!" Beth declared. "It's part of the DNA of Jewish mothers! They're going to have to wait, though, because we're thinking that three or four years from now will be the right time. Josh will be a Senior Associate by then, which will give us enough time to plan how we're going to handle the tailor shop. At some point, my grandfather will retire, or at least mostly supervise the younger tailors, and I'll run the shop day-to-day."
"I never asked, but do you have much competition?"
"A decent amount, but we're one of the few shops in the city with the ability to custom-make suits and shirts. There are plenty of off-the-rack shops in the city and suburbs, but they also don't have the same quality tailors we have."
"What about the trend towards business casual?"
"There will still be plenty of doctors, lawyers, stockbrokers, and bankers who will need our services, at least for the foreseeable future. Obviously, we'll watch the trends, but I don't see any massive change in the next five to ten years. What happens after that, who knows; my crystal ball isn't nearly as good as yours!"
I chuckled, "I can't see that far into the future, either. My timelines are almost always no longer than a year, because calculating accurate probabilities beyond that is nearly impossible in a way that would matter for my investment strategy."
"Well, I'm sure not complaining, given you're projecting 25% returns for this year and you keep saying you expect next year to be even better."
"If the Fed follows through on rapid cuts to the Fed Funds Rate, and the Prime Rate comes down significantly, the market will take off like a rocket ship."
"How good could it be? Unofficially, of course."
"Realistically, you could double your money over the next two years, possibly even close to triple it."
"Crazy!" Beth declared.
"That assumes, of course, I have it right and only time will tell if I do."
"I have faith in you!"
"Thanks."
We finished our sandwiches, chips, and pop, and I walked Beth back to the tailor shop, where we exchanged a hug before I headed back to the Spurgeon office. When I arrived, I had a trio of messages – one from Marlena; one from Maja; and one from Isabella, the girl I'd met at Allyson's party. I decided the best order to return the calls was to start with Maja, the woman who had sold me my Saab.