Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 8: A First Driving Lesson
Fiction Sex Story: Chapter 8: A First Driving Lesson - 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
June 6, 1984, Chicago, Illinois
"Jonathan, I have David Finch on the phone for you," Violet said over the intercom on Wednesday after we returned from the gym.
I asked her to put him through, which she did.
"Jonathan Kane," I said.
"Good afternoon, Jonathan," David Finch said. "I'd like to take you up on your offer to pitch your services."
"Did you have a day in mind?" I asked. "I'll need about two hours of your time, at most."
"Either the 14th or 15th, or 20th or 21st."
"One moment," I said.
I turned to my computer, signed on to the mainframe, and brought up the schedule for the Gulfstream. I saw that flying out on the evening of the 14th and returning on the afternoon of the 15th would be possible, and I wouldn't miss any classes.
"How about the morning of the 15th?" I asked.
"9:00am in our office on the 27th floor of the Crocker Center at 333 South Grand Avenue."
"I'll be there. May I ask who will attend?"
"Me, of course, along with Jonathan Ford, one of the other name partners. I'm also going to invite Morris Stoller from the William Morris Agency, as well as someone from RKO Pictures."
"Then I'll see all of you on Friday, June 15th, at 9:00am."
We ended the call, and I immediately called Julie to reserve the Gulfstream. Because it was an overnight stay, she needed to confirm with Noel Spurgeon, and he asked me to come up and explain. Two minutes later, I was in his office.
"What's the play?" he asked.
"Entertainment," I said. "I'm not having much luck with pension funds, and as you know, ultra-high-net-worth individuals are difficult to contact and even more difficult to pitch. Athletes worked, and now I'm trying for producers, directors, or studio execs, but I won't turn down talent. The firm I'm working through probably has attorneys similar to the ones at Hart-Lincoln who have investable assets in the range I'm targeting."
"Approved. Your options are John Wayne in Orange County or Van Nuys; I'd suggest John Wayne because even though it's about twenty extra minutes by car, it's not nearly as busy as Van Nuys. I've had to stay in a holding pattern for as much as thirty minutes at Van Nuys, but never at John Wayne."
"Thanks for the suggestion."
"Are you taking Clemmons with you?"
"That's the plan, yes, based on your advice for the trip to Ohio."
"Speaking of Ohio, Murray tells me the LeBaron was stolen."
"Out of the parking garage next to the Carew Tower in downtown Cincinnati. That said, I pulled in more money from MTB, including some of Marvin's own, totaling about $2 million. That should be on board by the end of next week. How was the race?"
"It's more about the parties because even from the balcony of our condo, which has a good view, it's hard to see more than a small part of the course. Pretty much every celebrity you can imagine shows up in Monaco at some point, and the race weekend draws the most. The one major downside was the rain. Back to work-related topics, I saw the memo about J. William Oldenburg."
"We dodged a bullet there," I replied. "Pete dug further, and from what we can tell, Oldenburg is not going to be able to cover the cost of owning the LA Express. This morning, Pete discovered that Oldenburg told league officials that he could no longer afford to pay the bills, and they tapped into a $1.3 million line of credit the league requires each team to carry.
"There are rumors the league is looking for a capital infusion to keep the team alive through the end of the month, when the playoffs will finish. The problem with that is that the team has a ridiculously high payroll and doesn't have the revenues to support it. I wouldn't buy it for a buck. The USFL is a perfect example of the joke I heard from Murray — 'How do you make a small fortune? You start with a large fortune and buy a hockey team'."
"That's been said about restaurants, winemaking, and a host of other things," Noel observed. "Trump seems onto something with the Generals."
"Yes, and his hope has to be a merger with the NFL. Bring four teams — two each for the AFC and NFC — and dump the rest, similar to hockey in '79. The teams in LA and Chicago are easy ones to drop, as they can't compete with the NFL teams. I don't know enough about the league to know which other teams would be chosen. I'd bet that's Trump's play."
"That makes sense. Did you buy a new car?"
"A black Saab 900 Turbo," I replied.
"Interesting choice. Why?"
"A practical, entry-level luxury car with good performance and handling. And one I could afford to buy for cash right now."
"Keep me posted on the LA deal."
"Of course."
I left his office, confirmed the details with Julie, then returned to my office, where I called Barney at Windy City Travel to give him the details of my trip to Los Angeles.
"Your best bet is the InterContinental Hotel, which is across the street. With your permission, I'll sign you up for their Six Continents Club. You get a number of privileges, including a guaranteed room, room upgrades, and other perks."
"Do that, please, and book two rooms. Violet will be traveling with me again."
"This is business, right?"
"Yes. So Violet and I cannot share a two-bedroom suite even if it's cheaper. Adjoining rooms are fine."
"Understood," Barney said. "What flight times are you looking for?"
"We're flying on the corporate jet. I will need a car to pick us up at John Wayne Airport and get us to the hotel, but I won't know the timing until I hear the flight plan from the pilot on Friday."
"That's easy enough to take care of. Return trip to the airport on Friday?'
"Yes. Call it 1:00pm. The flight back should depart around 2:00pm, but I'll confirm with you on Friday."
"What about on this end?"
"I'll drive to Meigs."
"OK. Call me when you know your arrival time at John Wayne. Can I ask you a question?"
"Sure."
"Could you arrange a meeting with whoever it is who manages your firm's travel?"
"Each Desk arranges their own travel," I said. "If you want to pitch, we can set a day, and I'll invite all the Desk heads to hear the pitch. You obviously have mine, though I'm pretty much the only one on my team who travels regularly. Well, Violet, but only with me."
"That'll work. I'm free any day for the next two weeks."
"Let me set it up, and I'll get back to you with that and the arrival and departure times."
"Thanks, Jonathan."
"You're welcome."
I let Violet know about the trip, then returned to my usual afternoon research. At 5:00pm, Violet and I left the office to head to her house for dinner before my class.
"Are we sharing a suite?" Violet asked.
"No. We have to keep the business relationship professional. Given I'm going to file for reimbursement, we don't want to raise any additional questions. And yes, before you say it, everyone will assume we're sleeping together, but we need deniability."
"Does anyone actually care?" Violet asked.
"Probably not, but I want to maintain propriety. Even if everyone here thinks we're sleeping together, I don't want my clients to think that's the case for what I hope are obvious reasons."
"Don't you think they might suspect?"
"Possibly. But let's not allow other people's assumptions cause us to do something that could backfire badly. Besides, if we have adjoining rooms..."
Violet laughed, "Plausible deniability?"
"Something like that. My biggest challenge is going to be my coursework."
"We're flying on a private jet, so there are no restrictions on luggage, right?"
"Right."
"Get a carrying bag for your Macintosh and bring it along. You could work on your paper in the hotel room."
"You're brilliant, Miss Clemmons!"
"I am, aren't I?!"
I laughed and realized just how much I appreciated Violet's true personality, which was no longer suppressed by the abuse she had suffered from her parents.
Dinner was beef stew Violet had put in the crockpot that morning, and after we'd eaten and cleaned up, I headed to class.
When I walked into the lecture hall, I put my rough draft on the small pile on the professor's desk, then sat down in the same seat as I'd used on Monday. I wasn't surprised to find Missy waiting for me, and she sat down next to me.
"You don't mind, do you?" she asked.
"Not at all."
"Still cool to exchange papers on Friday morning?"
"Yes. Fortunately, the next two are essays of between 350 and 500 words. I have to be in California on business next Thursday and Friday, so I'll have my paper to your dad Thursday morning next week. I can get yours on Friday evening — just have your dad leave it on my desk."
"OK," she agreed as Professor Messier stood up to begin class.
The material covered in class was a mix of topics, some relevant to the papers we had due in the coming weeks and others that were more generally about the writing and editing process. After the break, the professor handed out copies of several short essays and led the class in reviewing and critiquing them. From that, I picked up a few hints on how to ensure I turned in writing that would pass muster with her.
When class ended, I bade Missy 'good night', then headed to my car. I had agreed with Violet that I wouldn't stop in after classes, given we'd had dinner together, and I needed the extra time to write. I drove home, parked, and was in the condo about twenty-five minutes after class ended. Natasha had arrived, but she was hanging out with Deanna, which let me start work on my next paper — a short essay on our hometowns. It was reasonably easy to write 350 to 500 words on Goshen, and I knocked out a rough draft in just under forty minutes.
Sofía was awake when I finished, so I held her for about fifteen minutes, then Natasha and I went up to bed.
"Another satisfied customer!" Natasha declared as we got ready for bed. "Erin was positively ecstatic when we left and happier than she's ever been."
"Glad to be of service!" I said with a smile.
"Do you have rules?"
"If you mean regarding sex, I pretty much make it up as I go along, though I won't be involved with anyone who is cheating. Why?"
"Erin would like to see you again."
"I certainly wouldn't mind, but I'm up to my eyeballs in stuff for the next few weeks, maybe even the next two months, because of class three days a week and homework. Or are you volunteering to cede your time?"
"No chance!" Natasha declared.
June 7, 1984, Chicago, Illinois
Thursday was a typical day at work, and at 5:00pm, Teri arrived in the office so I could show her the paintings Deanna had done, as we'd missed the previous week due to my car being stolen. Once we'd looked at the paintings, we headed to Gene & Georgetti on Franklin, one of the best — and oldest — restaurants continuously operating in Chicago.
"Going all out?" Teri asked when we were seated.
"I haven't been here before and wanted to check it out. Thursdays are a much easier reservation than Fridays or Saturdays."
"Think they'll let me drink wine?"
"I'll order a bottle and see what they say. You look like you could be twenty-one."
When we ordered, the waiter didn't blink at my order of a bottle of Chianti Classico. When he returned with the bottle, he poured for both of us without any hesitation.
"I know you prefer frank conversations," Teri said, "so I'm going to ask directly — what would happen if I transferred to a school in Chicago?"
"I think things would more or less be the same, at least in the short term."
"You mean seeing you only once a week?"
"Most likely, given my other commitments."
Teri smiled, "Code for fucking other girls?"
"While it's true that I am seeing other girls, it's more than that."
"I know! I smiled because it wasn't an accusation, simply an acknowledgment. You have work, school, and friends. I think my first question is, was it good enough?"
I chuckled, "I'm not even sure what that means."
"Isn't good sex part of a good relationship?" Teri asked.
"Yes, and if that's your question, the answer is a definite 'yes'."
"Serious question then — if that's true, do you still need other girls?"
"I think the answer is somewhat complex," I replied as the waiter brought our salads.
We began eating, and I continued.
"Part of it is I'm not interested in any kind of exclusive relationship right now. It's also the case I'm not emotionally ready to have that kind of relationship. And to be blunt, I like the variety. Given the first part, I have no reason to limit myself to one girl. You know I don't adhere to any specific moral code, so from my perspective, there's nothing wrong with it. Before you ask about monogamy, I can do it if I choose to, as witnessed by my marriage to Keiko; I simply choose not to, at least not in my present circumstances."
"Then there's only one thing to do," Teri said.
"What's that?" I asked.
"Have great sex, and hope for the best in the future!"
June 8, 1984, Chicago, Illinois
"So, was the sex great?" I asked Teri when we got into the shower on Friday morning.
"I should have fucked you on our first date!" Teri declared.
"Until you worked through your concerns about the context, you couldn't have. We met in January last year, and you weren't ready until March this year when you made the decision that you were willing to fuck without any pre-conditions and went on the Pill."
I finished soaping her, and she rinsed off, then took the soap from me and began lathering my body.
"It's almost impossible to argue with your analysis of anything."
"It is what I do for a living," I replied. "I'm really good at it."
"Modest, too!" Teri exclaimed.
"I'm really good at fucking and eating pussy, too. Care to object to THAT statement?"
Teri laughed, "It's not in my best interest to do that! And you know I think you're very good at both of those things!"
When she finished soaping me, I rinsed off, and we got out of the shower. We put on underwear and robes, then went downstairs to have breakfast. Forty minutes later, Teri was on her way home, and I was in the Spurgeon offices to begin my day. I checked with Rich, as I usually did, left a copy of my paper in a folder on Monroe's desk, then went to the Research Office. I made a pot of coffee and sat down at my desk.
The morning was routine, except for Monroe dropping off a copy of his daughter's paper, and just after 11:00am, Julie called to let me know the flight plan for the following Thursday. We'd leave Chicago at 2:00pm Chicago time and arrive in California at about 4:00pm local time. That flight plan would let me work until noon, which meant only missing one full day in the office. The return flight would leave at 2:10pm. I thanked Julie, then called Barney to let him know our arrival and departure times for John Wayne Airport. Once that was accomplished, I let Violet know, then called Tony in to bring him up to speed.
"Get me a date with Phoebe Cates," he said with a grin.
I chuckled, "You're married; I'm not."
"Yeah, but what a last time THAT would be!"
"I'll see what I can do!" I replied with a grin. "I'm partial to Jennifer Jason Leigh, but I wouldn't throw Phoebe Cates out of bed for eating crackers!"
Tony laughed, "Yeah. How much is on offer?"
"No idea. This is prospecting. To use a cliché, thar's gold in them thar hills. I just have to find it and mine it. I'm actually targeting directors, producers, and studio execs, but I sure won't turn away actors and actresses."
"Looking for a whale?"
"You know the saying about banks, right? That if you owe the bank $100,000, the bank owns you; if you owe the bank $100,000,000, you own the bank. Too much money from a single source poses a grave risk to the stability of any fund. At this point, I could survive losing any single client, even the pension fund.
"On the other hand, if I had someone who invested, say, 25% of the money in the fund, they'd be in control, not me. That's Noel Spurgeon's biggest challenge. He has three clients who control about half the money in his fund. That's why he took his two biggest investors to Monaco for the Formula One race. It's also the case that it's more difficult to land those bigger clients, and I don't have the track record."
"Makes sense, and then you're not competing against Spurgeon or Matheson."
"At least for clients."
"Are you going to beat Spurgeon's returns?"
"I'm sure as heck going to try!"
He left, and as was the norm for Fridays, I had lunch in the break room with Violet and Bianca, then the three of us went to the gym to work out. The afternoon was busy with my usual review of my positions ahead of the weekend, and I didn't feel I needed to make any adjustments. Just after the market closed, Joel Steinem called me.
"I have a bid of 9⅛ on your block."
"I think it has enough room higher. My 9⅜ is firm."
"That's what I told them, but I felt I should present it to you."
"They'll be back next week or the week after, at the latest. It's going to hit $10 before the end of the month, but that's our rough estimate of the immediate upside. It has more long-term upside, and as I said, I'll sell it piecemeal over the next month if necessary."
"Got it. I'll let them know."
"Any idea who it is?"
"No. Whoever it is, they're being fronted by the Bank of Hawai´i, which makes sense. It could be the airline itself."
"Let me know when they up their offer."
"Will do. Have a good weekend."
"You, too."
Nothing else interesting happened before 5:00pm when Bianca and I went up to the condo. I changed, took Sofía from Jessica, and sat down to proofread Missy's paper. I made a few notes one-handed and, when I finished, handed Sofía to Bianca so Sofía could nurse. I sat with them, and about thirty minutes later, Deanna came in. We both changed, then headed to the parking garage for the drive to Noel Spurgeon's house.
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.