Climbing the Ladder 5 - Reaching New Heights - Cover

Climbing the Ladder 5 - Reaching New Heights

Copyright© 2026 by Michael Loucks

Chapter 35: Want To?

Fiction Sex Story: Chapter 35: Want To? - 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 11, 1984, Chicago, Illinois

Krissy's flight was about twenty minutes late, and when she came out of the gate, she greeted me with a quick hug.

"I have two large bags and a box, in addition to my carry-on," she said.

"Then let's go to the baggage claim."

We began walking towards the escalator that would take us down to the baggage claim.

"How was your flight?" I asked.

"Other than leaving a few minutes late, fine. There was no turbulence, and the seat next to me was empty."

"Did you enjoy your Summer?"

"I worked and hung out with friends who were home from college; I really enjoyed being back in Ontario for the Summer. How about you?"

"Work, obviously, and school, as well as taking care of my daughter. I think the big news is one of my housemates got a cat who seems to have imprinted on me."

"Cats are weird, and nobody can explain them! My dad says dogs have owners, but cats have staff!"

"A friend said, 'servants', but same difference. Neither your dad nor my friend is wrong. Misty basically gets what she wants when she wants it."

"She's obviously an indoor cat; ours is indoor, but we let him outside when he asks. When he wants to come back inside, he climbs up on a fountain outside the side window so we can see him from the kitchen."

"My biggest concern is her rubbing against my legs when I'm trying to walk, especially up the stairs."

"Cats rub their faces on you to tag you as part of their territory. I'm not sure the exact mechanism, but some kind of oil on their fur is transferred. Have you seen her blink slowly when looking at you?"

"Yes. Does that have some significance?"

"If you repeat the gesture, it's a signal of love and acceptance."

I laughed, "Seriously? She's a cat!"

"You don't think animals can have emotions? I can tell you exactly what your cat is thinking or how she's feeling just by looking at her! For example, if she's happy and wants attention, she'll hold her tail straight up to make herself more noticeable. If she's scared, her back will be arched. If she's angry or threatened, her tail hair will spread out, and she'll hiss. And so on. Cats are far more sophisticated than dogs, which tend to be dumber than a box of rocks!"

I smiled and said, "Perhaps that's a bit of an overstatement, as I've seen trained police dogs and hunting dogs."

Krissy smirked, "Nobody had to train your cat to hunt! She'll do it naturally! In fact, you should get some squeaky toys and a ball, as well as some string to play with her. I'm sure you know you can leave your cat alone for a long time without her destroying your condo! Try that with a dog! Or try leaving a dog a week's worth of food and going away. The dog will eat it all on the first day and get sick, then starve for the rest of the week. The cat will only eat what he or she needs to for a given day."

"You must be what they call a 'cat person'!"

"Obviously!"

We reached the baggage claim, and I retrieved a cart for her bags and box, as that would make it easier to get everything to my Saab.

"Are we having dinner?" Krissy asked.

"We certainly could," I said. "We can go out, or we can eat at my condo with Bianca and her girlfriend. They rented Willy Wonka & the Chocolate Factory, so we could watch with them, if you wanted. I'm OK either way."

"Dinner at your condo sounds great," Krissy said. "I saw that movie at the theatre, and it's a good one, so I'll watch it."

"Let me call Bianca and let her know we'll join them. We'll probably get Chinese takeout, as it's our default choice when cooking seems like too much effort. Is there anything you don't like?"

"Not really."

"Let me make the call."

I walked over to the bank of pay phones and dropped in a quarter. I dialed the condo, and Bianca answered.

"Krissy and I will join you for dinner. She said she's OK with whatever we want to order from the Chinese place."

"I'll order four different things to share, plus egg rolls and hot-and-sour soup."

"Sounds like a plan," I said. "We're at the baggage claim, so we'll be home to eat at 6:00pm with no problem."

"See you then!"

After we said 'goodbye', I hung up and returned to where Krissy was waiting.

"All set," I said.

A light flashed and a buzzer sounded, and the baggage belt began to move. Ten minutes later, we had Krissy's two large suitcases and a sturdy box on the cart. We made our way to the parking garage and loaded everything in the back of my Saab.

"Nice car!" Krissy exclaimed when we got in.

"Thanks. I bought it at the beginning of June after my car was stolen when I was in Cincinnati."

"That stinks, but this car is better, right?"

"Yes, though the original car was a reward for being right about a particular stock's rise in value."

"Your company gave you a car for that?!"

"Not the company; my boss."

"Gave you a car? For doing your job?"

"Yes."

"Do you know how crazy that sounds?" Krissy asked, shaking her head.

I stopped to pay for parking, then set out for the Loop to take Krissy to her dorm.

"Outside the financial services industry? Yes. Inside it? It's not uncommon. My new watch was a gift for proposing a solution to prevent one of our funds from taking a loss for the year."

"What kind of watch?"

"A Rolex," I replied.

"Those are super-expensive! And your boss gave you one?"

"The owner of the firm did, yes. If my plan works, and it should, it'll save him millions."

"And all you got was the watch?!" Krissy asked.

"I'll get a taste of the profits, but it isn't my money, nor is it money I raised. I get a significant percentage of the fees and profits from money in my fund that I convinced clients to allow me to manage."

"How much do you manage now?"

"Either directly or indirectly, about $700 million, but only about a third of that is in my fund."

"Seven. Hundred. Million. Dollars!"

"Yes."

"At age twenty-one?"

"Yes.

"Unreal," Krissy said, shaking her head. "I'm going to ask a totally rude question that is none of my business, but how much are you worth?"

"If you factor in the mortgages on the properties I own, and allow for taxes on money that is considered long-term capital gains, it will be around $1.5 million by the end of the year."

"And you were basically dirt poor when you arrived in Chicago?"

I nodded, "I had about $800 to my name, and nothing more than my clothes and a few personal items, like my inexpensive Timex watch."

"What I said at your condo is still true," Krissy said.

"Which part? That you want to be my girlfriend? That you seriously considered asking to spend the night? That you aren't mercenary or a gold digger? That you seriously offered to move in? That you have trepidation because of my situation? That the best path was to go home, come back, go on a second date, and see where things led?"

"You have a really good memory!"

"I pay very close attention to what people say and do, both for work and in my personal life. Which thing?"

"The girlfriend part," Krissy replied. "What would that take?"

Displacing Violet, which was not going to happen, unless Violet changed her mind, which was in the area of so improbable as to discount it.

"You mean exclusively, rather than just dating?"

"Obviously! That's what 'girlfriend' means."

"First, I'm not ready to get into an exclusive relationship because I haven't figured out what that would look like. Second, I have commitments that I would have to break to do that today. Third, we haven't even had our second date as yet!"

"Will you explain? I mean, obviously, you don't have to, but I'm not sure what you mean by figuring out what it would look like."

"I think the simplest way to explain is that I committed to being cremated and interred next to Keiko when I die."

"Not next to your wife?"

"That right there is exactly the point — Keiko is my wife, and didn't cease to be when she died. I mean, sure, OK, legally, she's not, and I'm free to marry, but that doesn't change our relationship. To be frank, I don't foresee changing that decision."

"That says a whole lot," Krissy observed. "I mentioned when I was at your condo that you're still grieving."

I nodded, "I am. The commitment I made was out of respect for Keiko, her parents, her grandparents, and the Shinto tradition we followed. There's already a stele with my name on it, though painted red so as to show I'm still living. But, in the end, grieving or not, that is what I intend, and it's written into my will and other end-of-life documents."

"I'm not sure what to say about that."

"You're not the only one," I replied. "That is part of the reason I'm not ready to enter into an exclusive relationship."

"You mentioned commitments."

"For one, I'm taking a female friend to Hawai´i after Christmas. In my mind, it would be tacky to tell her I couldn't take her."

"You're not leaving many options."

"All I can say at this point is that I'm dating, and the future is open. If I can turn the question around, why ask about an exclusive relationship on the first date? Most people date for a bit before they become an official couple. The same is true with moving in together. That's how it worked with Keiko — we started off dating, and it was just casual, but then, over time, we grew closer, she moved in, and we decided to marry. To me, that makes the most sense."

"You think I'm a gold digger, don't you?"

I shook my head, "No, I think you saw an opportunity and went for it. Unless you were lying to me about not being one, that is. You did say I was 'good-looking, dressed to the nines, successful, and friendly' and wondered what more a girl could ask for? The money is, if you will, icing on the cake. The only flaw in your thinking, if there is one, is assuming you understand my personality from our one date and our brief phone calls. I'm pretty sure determining that is the point of dating."

"This is going to sound ... trite, I guess, but girls know if guys are phony."

"If that were true, there wouldn't be so many failed marriages. And I'm not saying women are perfect, just that I'm positive some guys are not what they purport to be, and the girl doesn't find out until he beats her or cheats on her or whatever."

"I think a lot of girls know, but convince themselves that either it's not a problem or the guy will change."

"But they would have to know they were engaging in self-delusion, or they wouldn't realize they were doing it. Honestly, as I see it, if a girl goes into a relationship with her eyes wide open expecting the guy to change, she doesn't actually have her eyes wide open. But even setting aside those scenarios, isn't part of dating to see if you can get along in the long term? And living together is a sort of trial run?

"In my mind, it goes in stages where you date casually to make sure there aren't any big incompatibilities; you date exclusively to make sure there aren't any minor ones that you can't accept; you live together to make sure you can, well, live together. Then you marry. But even that last step isn't required, at least for me, because the commitment to live together is pretty much permanent unless you set some sort of time limit in advance."

"You have that all laid out in perfect logic, but love isn't logical."

"If you tell me you're in love with me, I'm going to question your judgment, given we haven't even had a second date!"

"Wow! You shut THAT down fast!"

"My love for Keiko developed over time; it wasn't a lightning bolt like Michael Corleone and Apollonia in Sicily."

"I recognize the name, but I never saw The Godfather."

"Call it 'love at first sight' or 'thunderstruck', though I'd argue it was lust at first sight. Love came later, if you follow the story. Are you telling me it was the 'thunderbolt' and you're impossibly, madly in love with me?"

"No, but ... I just have a really good feeling about you."

"That's certainly cause to explore the future, but to go from that to moving in together?"

"That might not have been the wisest thing to say," Krissy admitted.

"I prefer direct talk, as we discussed, so if that's how you were feeling, it was better to say it than to keep it as a putative hidden agenda, or whatever you want to call it."

"Putative? Why qualify it that way?"

"It's not really hidden, even if it's not said, assuming you were serious about being my girlfriend. That is the logical conclusion of a successful relationship, either before marriage or after. But it is kind of putting the cart before the horse, given you offered to move in with me after saying you didn't, to use your words, 'put out' on the first or second date."

"Those two things did kind of contradict each other," Krissy admitted. "I didn't think it through, obviously, but I don't sit down and consider if each thing I do is logically consistent. You seem to."

"Or, at least, not obviously inconsistent," I replied. "In any system, there are grey areas, and we can change our minds when presented with new information."

"I'm not used to having these kinds of conversations. I think the only thing that ever came close was an introductory philosophy class in High School. It seems like that's all you do."

"I can have as much fun as the next guy, and I can joke and jest and tease, but that's mostly with people with whom I'm close. At work, I need to be calm, cool, collected, and professional, and basically emotionless. The way to lose all your money is to fall in love with a position and not act when the indicators tell you to buy or sell. That does leak into my private life, but I'm not Mr. Spock. If you still want to come to dinner, you'll see, so long as I let Bianca know it's OK to let her hair down in front of someone new."

"If?"

"I'm sure I've given you sufficient reason to decline my invitation."

"I haven't changed my mind about dinner and a movie."

"OK."

We arrived at the dorm, and I pulled up near the door, turned on the emergency flashers, and quickly unloaded Krissy's bags and box from the Saab. She waited there while I drove around the corner to park, and together we moved everything into the lobby. She checked in, and about five minutes after we arrived, we used the elevator to take her things up to her room on the 3rd floor.

"I'll unpack when I come back," she said.

"Sounds good," I agreed.

We left her room, walked to where the Saab was parked, then headed for the Hancock Center, which was about six minutes away. Nine minutes later, after traversing two elevators, we walked into the condo. We took off our shoes, then walked to the conversation pit.

"Krissy, please meet Bianca and her girlfriend Nicole. That young lady in Bianca's arms is Sofía, our daughter. Bianca and Nicole, my friend Krissy, a student at the School of the Art Institute."

They all greeted each other, and we sat down.

"The food will be here in about twenty minutes," Bianca said.

"Can I get anyone something to drink?" I asked. "We have Burgundy, Cabernet, Chardonnay, Zinfandel, Old Style, Jack Daniel's, vodka, a couple of other bourbons, Coke, Sprite, Dr Pepper, and Orange Crush. We also have OJ, grapefruit juice, apple juice, and, of course, water. Krissy?"

"Chardonnay, please."

"Same for me," Nicole said.

"Sprite for me," Bianca requested.

I went to the kitchen to get the drinks and poured myself a glass of Burgundy. I brought everything on a serving tray and handed each girl their requested drink. I sat down, and Misty immediately climbed into my lap.

"I forgot to introduce Misty," I said. "I believe she's letting me know!"

Krissy reached over and stroked Misty's head.

"What are you studying, Krissy?" Bianca asked.

"Photography," she replied. "My goal is to be a photojournalist. What about you?"

"I switched to night school for computers so I could work for Jonathan as a data analyst. Nicole is a French major. We're both at Loyola."

"What does a data analyst do?" Krissy asked.

"Mostly I write computer programs and develop spreadsheets to aid the research team and the traders."

"And you can do that without a degree?"

"Yes, just as Jonathan can do his job without a degree."

"It just seems crazy you can make that kind of money without a college degree," Krissy observed.

"Mike Schmidt of the Phillies will earn nearly $2 million this year for playing baseball," I said. "Earlier this year, Pedro Guerrero signed a five-year, $7 million contract to play for the Dodgers, and Steve Young signed a ten-year deal worth $40 million in total to play football for the LA Express in the USFL. Wayne Gretzky will make at least $1 million next season playing hockey for the Edmonton Oilers."

"OK, besides athletes!" Krissy responded.

"Any number of Hollywood stars," I replied. "Or, perhaps closer to home, Peter Jennings, the ABC News anchor, does not have a college degree. In fact, he dropped out of High School after tenth grade because, in his words, he 'loved girls and comic books'. Or, in business, JD Rockefeller didn't have a degree, nor did Andrew Carnegie.

 
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