Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 53: You're One Cool Customer
Fiction Sex Story: Chapter 53: You're One Cool Customer - 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
September 20, 1984, Aboard the Gulfstream en route to Chicago, Illinois
Because there had been five of us, Golden Gate Livery had provided two cars, with Noel and Murray in one, and Jack, Violet, and me in the other. That had given me a chance to speak with Ian McIntyre, and we'd agreed I would transfer the money to his bank on October 19th.
"Excellent job, Kane," Noel said once we boarded the plane at SFO.
"Thanks. What do you think?"
"I'd like to hear your impression first," Noel said.
"They were, at best, neutral until Murray mentioned Keiko, which moved the room decidedly in our direction. If I had to handicap it, and I have to because you asked, I'd say they'll give us half, monitor, and then give us the other half early next year. If we perform, they'll double up in another year. That's more or less their limit because their asset allocation guidelines require them to keep the majority of their reserves in government securities or high-grade municipal bonds."
"Murray?"
He was interrupted by the flight attendant informing us the pilots were ready to taxi.
"I'd say Kane's analysis is sound. Sierra Nevada Re is conservative by nature, like most insurance companies. They see massive potential gains, so despite the natural conservatism, they'll bite, but one bite at a time."
Noel smiled, "You're both wrong. Danforth will call on Monday and give Kane $100 mil."
"Your read on rooms is almost never wrong," Murray observed. "This is one of those times when it is. I believe Kane is right."
"We'll see," Noel said. "Kane, was that one of Deanna's paintings on the wall of the conference room?"
"Yes. That's Daybreak; it was the best of the works she showed at Gallery Paule Anglim."
"If he bought one of her paintings, I'm even more convinced he wants to move the full amount, and he'll convince his Board."
"Care to put your money where your mouth is?" Murray asked. "$25 grand on Kane's analysis against your $25 grand on yours?"
"Done," Noel said.
Of course, for those two, $25 grand was pocket change, though the way things were going, it would be pocket change for me, too, though the chance that I'd make such a wager was near zero.
I was just as surprised on the flight home as I had been on the flight to SFO that Noel hadn't taken the flight attendant into the sleeping compartment. I wondered if that was because of Jack or Violet, or because this flight attendant didn't provide that form of in-flight hospitality.
September 20, 1984, Chicago, Illinois
"How did it go?" Bianca asked when Violet and I walked into the condo just before 11:00pm on Thursday night.
"I think we'll get some of their money," I replied. "Maybe half, with the balance in three to six months."
"Even $50 mil is huge! That's about 15% of your current AUM, not counting the Arrow Fund."
"Yes."
"That'll take you to something like $6 million in fees, and if next year is anything like we predict, around $18 million in carried interest."
"I can do basic math," I chuckled.
"Those numbers are just insane!" Nicole observed.
"That's not all mine, not even half," I replied. "But it's still a ton of money."
"Would you keep more if you were on your own?"
"Not really, because I'd have to cover 100% of the costs, rather than a pro-rated portion. I'd need compliance, legal, research, a pair of executing traders, office space, computers, and on and on. I might make a bit more, but that's a lot of headaches to make an additional 10% or so, not to mention losing things I wouldn't be able to have anytime soon, including a corporate jet."
"How much does that cost?"
"The plane itself is around $35 million. Operating costs with a crew run $400 to $600 per hour, and that doesn't include scheduled and emergency maintenance. I once estimated I'd need a personal net worth of around $600 million to afford that without it seriously impacting my lifestyle. There are sharing arrangements, though they aren't cheap either."
"Spurgeon doesn't own the plane personally, does he?" Bianca asked.
"No, it's a corporate asset, and I believe there's a leasing arrangement. Anyway, has Sofía gone down for the evening?"
"About twenty minutes ago."
"Then we're going up to bed."
Nicole and Bianca said 'goodnight', and Violet and I went up to my room.
"Bonus night!" she exclaimed.
"For both of us!"
September 22, 1984, Chicago, Illinois
Friday had been a typical day at work, and not much had happened. After work, Violet and I had joined Jack, Kristy, and the Boys for dinner at Golden Bull, then seen Amadeus. As was the norm for Friday nights, Violet had spent the night, then had gone home after breakfast.
Once she'd left, I'd spent the rest of Saturday morning working on the paper due on Monday in my English class. After finishing that, I did the grocery shopping with Bianca. Once the groceries were put away, I drove to Oak Park to pick up Jennifer for her overnight.
"How did things go in California?" she asked after she got into the car.
"I should know sometime next week, but I have a good feeling about it. How is nursing school?"
"A ton of reading and studying. I'm looking forward to next Summer when I start my practical training. You started classes again, right?"
"Last week. It's a ton of reading, but I managed to read for about three hours each way on the plane."
"What happened with your jury duty?"
"Half a day of my life I can't get back! A landlord sued a tenant for damages and to terminate the lease. He had a slam dunk case. It took longer to elect a foreman and fill out the verdict and monetary award forms than it did to reach the verdict. I think she was hoping her sob story would hang the jury because in Illinois, civil juries have to be unanimous. Most states only require a majority or super-majority."
"I thought juries always had to be unanimous?"
"Only in criminal cases," I replied. "I meant to ask, are we going right to my place or doing something first?"
"I'm OK either way; we could go to the Museum of Science and Industry if you want to. We'll have all night and tomorrow morning to fool around."
"True!"
September 23, 1984, Chicago, Illinois
"I could get used to this!" Jennifer declared as she snuggled close after we woke up on Sunday morning.
"Me, too."
"How long can we stay in bed?"
"The Bears game is in Seattle, so it's the 3:00pm game. The gang won't be here until after lunch, so we have a few hours."
"Do you mind if we just snuggle for a bit?"
"I don't mind at all."
She sighed deeply and snuggled even closer, her body firmly pressed against mine, and her head on my shoulder. We lay quietly together for about fifteen minutes before she spoke.
"I know what you said about playing the hand we're dealt, but I wish I could discard a card and draw a new one."
"I hear you, but if I discarded a card and drew a new one, we'd most likely never have met, and we absolutely wouldn't be lying in bed together naked after fooling around last night."
"Keiko," Jennifer said.
"Yes. Whatever else might be true, that has colored my views on life and the best way to live mine."
"Which doesn't include marriage."
"I certainly don't believe it does, and as I've said, nobody should count on my opinion on that changing. I'm not ruling it out definitively, but I don't think it will happen for the reasons we discussed."
"A friend of mine suggested that the more time I spend with you, the less chance I'll meet someone."
"I suppose it depends on whether you're seeing other people or not."
"Not. The problem is, I don't think I could sleep with another guy while we're still sleeping together. No judgment about you; it's just I don't think it's right for me."
"This is one area where I cannot give you advice, except to say be true to yourself and your values."
"But if I had done that, I wouldn't be here right now. I kind of put myself in a strange position because I had thought I'd only do it with someone with whom there was a real possibility of a future. Even the guy at Prom, while I said he left me cold, if he hadn't, we'd have dated exclusively, with the obvious destination in mind. That was how I saw the world until I met you. I do not regret having sex with you in any way, but it did go against my views on when it was OK to do it."
"I think we all struggle with whether there should be exceptions to our rules, and if there are, what would qualify for an exception. I have some rules where there are no exceptions and others where I'd consider an exception on a case-by-case basis."
"Mind telling me?"
"No girls who haven't graduated from High School. Period. No exceptions."
"Given our conversation that included discussing Mr. Reynolds, I can totally understand that. I guess you won't be banging the babysitter!"
I chuckled, "Right now, that's your mom!"
Jennifer laughed, "I think my dad might take more exception to that than he would to finding me in bed with you."
"And with good reason! That's another inviolable rule — no cheating."
"I agree with that one, for sure. No exceptions. What would be one where you might?"
"A client or someone who works for a client," I replied. "It's not against firm policy, but my default is not to become intimate with a client because of the potential risks. That said, if I felt there was minimal risk, then I'd consider it. An example would be a secretary at a law firm for whom I managed investments."
"OK, I can see that, too, and yeah, so long as it wouldn't cause a problem, it wouldn't be a problem, though you'd have to be really sure."
"Exactly. Beyond that, I don't have too many rules other than doing my best not to hurt anyone. What are you going to do?"
"You mean about my dilemma?"
"Yes."
"I like this too much to stop," she said, sliding her hand down to my groin. "Would it bother you if I went on dates?"
"It won't bother me, so long as you don't lie to anyone. I'm not saying you have to come out and tell the guy you're sleeping with me, but you should let him know you're seeing me unless you choose to end it."
"That was what my friend said I should do, but I don't think I want to. At least not today."
"I understand. Given what you said about the end of our relationship being inevitable because I don't want to marry, I knew that might happen at any time. Every time I get to see you is a bonus."
Jennifer kissed me, then slid down and gave me a very sexy blowjob while I watched in the mirrors. That led to her being the recipient of oral attention from me, and an energetic screw before we snuggled again.
"Are you staying for the Bears game?" I asked.
"Yes. There's no reason I have to be home at any specific time; it's not like being out would give away where I spent the night, or even that I wasn't home last night."
"What do you think would happen if your parents discovered you spent the night here?"
"Mom would be OK because she really likes you; well, at least until she figured out it wasn't going to last. Dad would be pretty upset, but I don't think he'd do anything other than express disappointment. In the end, it's more about avoiding grief than anything else. You said your mom was cool with it, right?"
"Yes. Bev's dad, not so much. He wouldn't have been nearly so upset if Bev and I had been a couple, as he, her mom, and my mom had expected we would be. I messed that up by not talking to Bev before I made my decision to come to Chicago. I didn't even invite her to move to Chicago with me; well, to move after she graduated."
"Your life would have been completely different."
"Maybe. I have no idea what Bev was thinking when she decided to sleep with Glen Rodgers while she was dating steady. That might have happened with the same results, and given the timing, things would probably have developed along the same lines, with the exception of my relationship with Lily, whom you've met.
"The big turning point was when I met Kristy, which was after I found out Bev was pregnant. Kristy introduced me to Allyson, and it was through Allyson that I met Bianca, and eventually Ellie, and then Keiko. I honestly don't see how that sequence of events would have changed."
"But would you have helped Bev if she had cheated on you?"
"See, that's just it; I'm not sure it would have been cheating. In my mind, we were never actually a couple. I mean, we were, but neither of us acknowledged that, and we sure didn't discuss it. At least from my perspective, in hindsight, having sex was kind of the logical progression, even if it was as friends. I don't know for sure what she was thinking when she kissed me and unbuckled my belt."
"One kiss and she was already unbuckling your belt?"
"Yes. Her intent was clear the moment our tongues touched, and her hands went right to my belt."
"And who were you to object?" Jennifer teased.
"What else would a red-blooded, seventeen-year-old American male confronted with a gorgeous, horny, sixteen-year-old who clearly wanted to fuck, do?"
"Unless he was gay? No chance of anything but sex!"
"Of course, the problem with her approach and my consequent lack of planning was no birth control. We were extremely lucky. She wasn't on the Pill, and my brain had short-circuited, so I didn't even think about it until afterwards. That led to a delay of about six weeks before we had sex again, and sex wasn't our regular activity even though we had plenty of opportunity."
"If I’d met a guy like you in High School, I'd never have let him go!"
"See, I'm not the guy I was in High School. I was an introverted loner who had one close friend and no ambition other than finding a way to have a comfortable, middle-class life. Everything changed after I moved to Chicago, or if you want to push it back a bit, when I decided to ask my uncle for help finding a job here. Even then, when I first moved here, I was pretty much a loner until Stuart nearly ran me over with his bike."
"That's your firefighter friend you don't see very often, right?"
"Yes. His schedule is a mess due to the way firefighting shifts are scheduled and his side jobs. The other firefighter — the paramedic — basically dropped out of our group when he married, and I haven't seen him since he divorced after being married for only a short time. Through them, I met Dustin, who's pretty much a fixture, along with the rest of the Boys, though I met Rick when I was modeling, and Costas is Lily's brother."
"Rick's the one who hit on you, right?"
"Yes. I told him I was straight, but more than happy to hang out. Pretty much every guy or girl I've met at the School of the Art Institute is cool except one militant feminist who had a hissy fit about her grade because she didn't follow the rubric."
"I missed that story."
"She drew a certain part of my anatomy at something like half scale when the rubric called for reality."
Jennifer laughed, "There's one girl I met in nursing school who thinks all heterosexual sex is violence and dicks are weapons."
"Given I had a friend who was raped and murdered, I can see how someone might come to that opinion."
"When was that?"
"February 1982, about nine months after I moved to Chicago. She was friends with Allyson, Lucy, Sylvia, Sally, and a few of the other girls who occasionally join us for football and parties."
"Given a comment you made before we fooled around the first time, you've slept with most of them."
"I will agree I've slept with a lot of girls, but beyond the four obvious ones, I can't comment."
"Four?"
"Bev, Bianca, and Keiko are three I've mentioned. The fourth is in bed with me at the moment. Other than my housemates, nobody knows you and I are sleeping together, and they only know because you've come here and we've spent time alone in my bedroom."
"Not!" Jennifer declared. "Misty is on the loveseat!"
"Deanna's cat doesn't count in that regard!"
"At this point, I'd say she's your cat."
"It does seem like it."
"Once more before we have to get out of bed?" Jennifer requested.
"Absolutely!"
About twenty-five minutes later, we went to the shower. After our shower, we went downstairs so I could make breakfast. Deanna and CeCi joined us for breakfast and helped us clean up. There was no rush to set up for the Sunday gathering, so I took some time to read more in The Canterbury Tales, with Jennifer cuddled next to me.
As usual, we had a great time with our friends, though the result of the Bears game put a damper on the mood, given the Seahawks blew them out 38–9. Most people stayed until between 8:00pm and 9:00pm, and just after 9:00pm, I drove Jennifer home.
September 24, 1984, Chicago, Illinois
On Monday morning, I got up about an hour early, leaving CeCi in bed, because I had to appear for my IRS audit at 9:00am, and wanted to complete my portion of the daily Analyst Report beforehand. I did that, and at 8:50am, I met Nancy King and Robert Black in the lobby of the Kluczynski Federal Building at 230 South Dearborn.
"Remember, I will probably answer better than 90% of the questions," Robert said. "This is clearly adversarial, and the less you say, the better. They cannot take any action against me for what I say, so long as it is not aiding or abetting tax fraud. Anything you say could be considered 'material misrepresentation' if it's not 100% accurate, even inadvertently."
"Our Head of Compliance warned me about that, with regard to speaking to the SEC, though there, I can be compelled to speak even without formal legal process."
"Yes, your license gives them, in effect, carte blanche, because it can be suspended for failing to coöperate with an investigation. Of course, that's very subjective, and they decide, not you. Today is all about the statutes. You are in compliance with the tax code, but Jacoby is going to imply, or even state outright, that you are not, in an attempt to provoke you or force an admission. Our job is to ensure that doesn't happen."
"You can, in effect, ignore anything he says that is not a specific question," Nancy added. "And even then, as Bob says, allow one of us to answer."
"Got it," I said.
We entered the building and took the elevator up to the floor where Terrence Jacoby had his office. Unsurprisingly, he kept us waiting until almost ten minutes after the scheduled time, when he came to the waiting room to usher us to his office.
"Mr. Kane, you are legally entitled to one representative; who is it?"
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