Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 45: Life is an Interesting Game
Fiction Sex Story: Chapter 45: Life is an Interesting Game - 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 28, 1984, Chicago, Illinois
"I spoke to my professor about the movie," CeCi said as she, Bianca, Nicole, Deanna, and I relaxed after a light dinner. "She's amenable, though she was clear it has to be rated 'R'. We had a long back and forth about what that meant, and the bottom line is no shots of a visible erection, no spread-leg shots, and no penetration shots. I'll shoot carefully, and I'll edit after filming to make sure nothing inadvertent creeps into any frames, in addition to the usual edits and cuts."
"That kind of messes up the idea of replicating the scene from the movie," Deanna observed. "You'll have to shoot the oral stuff from behind or with an angle that didn't actually show anything."
"I know," CeCi replied. "Which is why I'm considering simply writing something myself. Maybe a riff on Sleeping Beauty or something like that. I have time to think about it because my first independent study short isn't due until the first week in December."
"How about the seduction and deflowering of a virginal, Evangelical girl?" Bianca said with a smirk. "Call it 'I Can Make You See God!' or something like that!"
Deanna, CeCi, Nicole, and I all laughed, but I also shook my head.
"Are you trying to cause trouble?" I asked.
"Always!" Bianca declared. "I even know where you can find an actual virgin Evangelical girl to be the female lead!"
"That's even more unlikely than Noel Spurgeon calling me in the next five minutes, saying he's retiring and turning the firm over to me!"
"I told you how to make that happen!" Bianca teased. "Wait about eight years, deflower his daughter, marry her when she turns eighteen, and boom, YOU are Spurgeon Capital fifteen years from now!"
"Not interested," I replied.
"Even after she turns eighteen?" Bianca asked.
"That's ten years from now, and you know my position on getting married. CeCi, what are the limitations of your rubric with regard to a subject?"
"None, really. It can be almost anything, because it will be evaluated on technical aspects more than anything, though it does have to have some coherent idea guiding it."
We didn't come up with anything, though we had a nice, quiet evening together. When it was time for bed, CeCi joined me as was usual for a Tuesday night.
August 29, 1984, Chicago, Illinois
On Wednesday morning, CeCi stayed in bed while I showered and dressed, and once I'd eaten breakfast, I headed to the office. I completed my usual morning routine, and Jack came into my office to check in. I spent about fifteen minutes with him, then began working on the daily analyst report.
The market was still in the doldrums, and nothing much had changed in the world. Everyone was waiting to see what the Fed would do, and to see the outcome of the election, which was looking more and more like a Reagan landslide. The real question would be the House and Senate, as Reagan's agenda was not something Democrats would agree to; thus it wouldn't pass if they controlled either House.
As usual for a Wednesday, I ate lunch with Violet, Bianca, and Jack, then the four of us went to the gym. The afternoon was spent researching and analyzing stocks, and I had a brief meeting with Jack after the close of the market. At 5:00pm, Bianca and I headed up to the condo. Jessica left, and Bianca and Nicole went out to dinner, taking Sofía with them. That allowed Kayleigh and me to have the condo to ourselves.
Kayleigh arrived at 5:30pm, and after a quick kiss, we went to the kitchen to make dinner together.
"What did you end up telling your parents?" I asked.
"That I was going to spend the night with a guy, have sex multiple times, and suck him and swallow!"
I laughed, "There is about as much chance of you having said that as there is of me sprouting wings to fly to San Francisco tomorrow evening!"
"You're right, of course. I simply said I was spending the night with a friend. My mom asked me who, and I said, 'just a friend'. I'm pretty sure she suspects, but she didn't say anything. I mean, not you, specifically, but a guy."
"Have you said anything to your grandfather?"
"Only that we had some very good heart-to-heart conversations. I did say that five years was a long time, but that you and I would stay in touch and see where things go."
"That's a good answer, and will avoid any awkward questions or answers."
"My grandfather likes you, and I'm not going to say anything negative about you to him."
"I wasn't worried about what you might say! How do you feel about your decision?"
"Which one?" Kayleigh asked.
"Going to Stanford; everything else flowed from there."
"I'm sure you're right, but deciding to go to college doesn't seem as momentous as deciding to lose my virginity."
"May I speak bluntly?"
"Yes."
"The Abrahamic religions all have an unhealthy virginity fetish that allows men to control women's sexuality. In your church, who is the most revered woman and why?"
"Mary, because she remained a virgin throughout her life."
"Or so the story goes," I replied. "Because of that, you put far too much value on your virginity."
"What do you mean 'so the story goes'?"
"I have an alternate theory about that claim — the religious leaders accused Jesus of being like me — a bastard. To defend him, and, by extension, his mother, they circulated the story of the virgin birth. Maybe it happened the way it's reported; maybe she made up the story herself; maybe the guys who followed Jesus made it up; maybe the guys who wrote the stories made it up. It being an invented story is far more consistent with everything we know."
"You don't think Mary was a virgin?"
"I have no way of verifying that claim, and it's not reproducible, so to speak. That means we have one or possibly two independent reports from men who were not in a position to know, and the one guy who might have possibly been in a position to know, isn't one of those two who reported it.
"The most logical conclusion is that it was a response to the rumors circulating at the time. Think about how women who conceive out of wedlock are treated in the twentieth century, and imagine how much worse it would have been in a truly patriarchal society where sex outside of marriage could be punished by the death penalty. To me, that explains it, if it even needs explaining.
"So, ultimately, your most significant decision was about going to Stanford. Rejecting Catholic teaching about sex and birth control was simply a byproduct of you asserting your independence and control over your own life, rather than bending the knee to a priest or pope or whomever. Having sex was a formal declaration of independence, so to speak. But that came only after a long train of thought."
Kayleigh laughed, "Thomas Jefferson?"
"That was the inference I hoped you'd draw."
"I like your approach better than my grandfather's. He simply dismisses it as arrant nonsense."
I nodded, "He used that phrase with me, too. And, to be honest, I would use that with certain people. You never preached, which is basically where I draw the line about being polite. Well, after asking the person nicely to stop."
"That happened?"
"Yes. Anyway, how do you feel about your decision?"
"Very good. I was wearing my faith as a straitjacket, and that really limited what I could do. I'm not going to go crazy, but I feel free to pursue a different path through life."
"Have you gone to church?"
"Yes, because not going would create serious tension with my mom. I'll decide what to do once I'm at Stanford."
"What about confession?"
"No, because I'm not ready to discuss what I've done with anyone but you, and lying would kind of defeat the entire purpose."
"You can't go and just leave that out?"
"No. Our priest always asks if there is anything we're omitting or concealing. I'm still thinking about it."
"Do you think it's a sin?"
"An interesting question that I would never have had trouble answering in the past. Now I'm not so sure. I mean, yes, the Church says it's a sin, but that's not what you mean, is it?"
"Not in this case. What matters is what you think. I don't believe in sin, except insofar as a reference to hurting someone else. Neither you nor I were harmed by what we did and what we're going to do after dinner."
"Are you sure about that?" Kayleigh smirked.
I laughed, "OK, but you are perhaps the last person I could imagine being into giving or receiving pain."
"I am Catholic, and nuns did like to smack us on our hands with rulers..."
"When you put on a nun's habit, then you can smack me with a ruler!"
Kayleigh smirked, "Most of our nuns wear plain, modest dresses with a cross around their neck, rather than like Sally Field in The Flying Nun!"
"I saw maybe one or two episodes of that when I was young, so that, and the Sound of Music, are my entire picture of how nuns dress."
"That really started changing in the 60s, and it depends on the order. I meant to ask — where are your housemates?"
"Deanna is at her studio, CeCi is out with some friends, and Bianca and Nicole went out to dinner to give us some privacy. They took Sofía with them. Misty is here, though she's sleeping in the sun right now. We leave one shade open so she has as much sun as possible."
"Is this where I make a risqué comment?" Kayleigh asked.
"That's not your usual style, but given you work with a bunch of attorneys, I'm sure you've heard plenty!"
She rolled her eyes, "They are such boys!"
I chuckled, "Yes, we are."
We continued chatting while we made dinner, and after we ate, we worked together to clean up. I wasn't at all surprised when Kayleigh wanted to go up to my room immediately after the last dish was put away.
August 30, 1984, Chicago, Illinois
"I very much enjoyed last night," Kayleigh said when we woke on Thursday morning. "Especially sleeping snuggled together."
"That is a nice added benefit!" I agreed. "Shall we shower?"
"Yes!"
I got out of bed and turned on the tap, and once the water was warm, we got in.
"I'll be home at Thanksgiving," Kayleigh said as I soaped her body. "I'd like to see you if possible."
"Call the week before, and we'll see what we can arrange."
"Great!"
When we finished in the shower, we dried off, dressed, and then went downstairs to make breakfast. When Chelsea arrived a few minutes later, she greeted us, and I introduced Kayleigh. Chelsea's eyes narrowed, and she looked as if she was about to say something, but then apparently thought better of it. She went up to check on Sofía, then came back downstairs.
When Kayleigh and I finished breakfast, we cleaned up, then I grabbed my satchel, and she grabbed her bag, and we left the condo. We went to the parking garage, where I had the overnight parking charge placed on my account, then walked Kayleigh to her BMW. We shared a soft kiss, then she got in and rolled down the window.
"I'll make sure you have my phone number and address at school," she said. "I want to stay in touch."
"As do I."
She pulled out of the parking spot and headed for the exit while I made my way to the Spurgeon offices. After my usual morning routine, I sat down and had my daily morning meeting with Jack. I'd be out on Friday, and Monday was a holiday, so we discussed strategies if something untoward were to happen overnight or during market hours on Friday. Once we had our chat, he headed upstairs, and I began working on the analyst report.
The only thing of note was that the Space Shuttle Discovery was scheduled to launch on its maiden voyage. At 7:35am, I went to the main area in the office and watched CNN. After a successful launch, I returned to my desk to complete my portion of the report. Once the report was submitted, I asked Scott Moreland to come into my office, as he'd be in charge on Friday while I was away, as Tony was still on vacation.
"I'll prepare my portion of the analyst report for tomorrow late this afternoon. You won't need to make any modifications unless something big happens overnight. If something major does occur, call me, and we'll discuss what changes to make."
"It's two hours earlier in California."
I nodded, "Yes, and if that means waking me up at 4:30am, so be it. It would need to be something major to move the needles on the graphs far enough to cause someone to alter trading strategies, and until the Fed moves again, stocks are mostly going to tread water. You got this."
"Thanks for trusting me."
"You've earned my trust from day one."
We shook hands, and he left, and I spent the rest of the morning on my usual tasks. I had lunch with Violet, Jack, and Bianca, then worked until 3:30pm, when I went up to the condo to meet Deanna so we could head to O'Hare for our flight to San Francisco.
August 30, 1984, San Francisco, California
When we walked out of the gate area in San Francisco, I saw a man of around thirty with reddish-brown hair holding a sign that read 'Kane' in large block letters, and 'Golden Gate Livery' in smaller type.
"I'm Jonathan Kane," I said to him.
"Ian McIntyre, Golden Gate Livery. Do you need help with your bags?"
"No, we have them, thanks."
"Then if you'll follow me, please."
He led us to a black Town Car, where we got into the back seat while he put our bags in the trunk. He got in and pulled away from the curb.
"Mark Hopkins Hotel, correct?" he asked.
"Yes," I replied.
"First time in San Francisco?"
"Yes. Deanna has an art show at Gallery Paule Anglim."
"You must be very good, Miss..."
"Haight. Jonathan thinks so."
"Married?"
"No. He's my friend and patron."
"Patron? Mr. Kane, may I ask what you do for a living?"
"Jonathan, please. I'm a financial analyst and hedge fund manager."
"What's a hedge fund?"
"A special type of investment fund," I replied.
"This may be out of line, but could I pick your brain about something?"
"Sure," I replied.
"I own the company," he said. "Right now, I have five other cars and drivers, and limit our services to trips to and from the airport. I could easily add ten cars just based on inquiries I've had about other trips. I went to the bank, but the interest rate they would want for a loan makes it basically impossible to expand, assuming they'd even give me a loan."
"Did you prepare a business plan?" I asked.
"Yes. A friend of mine who teaches business at Stanford helped me put it together."
"Excluding the cost of capital, would you immediately be profitable?"
"Yes. Our rates are set such that every trip is profitable, so I'd have positive cash flow, but what my friend calls 'debt service' would chew up all the profits."
"Did he propose a solution?"
"We laughed about robbing a bank or marrying money, but the first one would lead to jail, the second one to my death!"
I chuckled because he had a picture of a woman and two kids in a small frame attached to the dashboard.
"I assume that picture is your wife and kids?"
"My wife, Julie, and my kids, Raven and Robby. Julie is working on our third, who'll be born in October."
"Are you willing to give up equity to expand?" I asked.
"You mean, like taking on a partner? Sure, but I would want to run things and keep control of the company. My friend introduced me to a guy from Palo Alto, but he wanted way too much of the company and way too much control."
"So, you want a silent investment partner rather than a venture capitalist?"
"I think so, yeah; but not somebody Mobbed up."
I chuckled, "I may be from Chicago, but I'm not involved with the Outfit! Is the Mafia in San Francisco?"
"Jimmy 'the Hat' Lanza runs the Mafia here, though it's not like New York or Chicago. We also have Chinese Tongs. They're the truly dangerous ones."
"Tell you what," I said. "I'll give you my card. Send me your business plan, and I'll review it and see if there is any way I can help you achieve your goal."
"You're serious?"
"Absolutely. My main job is to analyze companies and governments and make investment recommendations to all the investment managers. I also run my own investment fund, as I said."
"How long are you in San Francisco?"
"You should know," I replied. "We booked a return trip to the airport."
Ian laughed, "I don't have everything memorized! My wife is our dispatcher, though obviously someone will fill in for her when she delivers."
"We're here until Monday."
"I'll take your card, please, but I'll drop off a copy of the business plan at the hotel reception tomorrow morning."
"Sounds good," I said.
We chatted more about his business and his family, and about Deanna's art, until we arrived at the hotel. I signed the charge form, gave him one of my broker cards, then Deanna and I got out of the car. Ian helped us retrieve our bags from the trunk and turn them over to a bellboy. I checked in at the reception desk, then the bellboy escorted us to the room Barney had reserved for us.
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