Climbing the Ladder 5 - Reaching New Heights - Cover

Climbing the Ladder 5 - Reaching New Heights

Copyright© 2026 by Michael Loucks

Chapter 51: A Different Look

Fiction Sex Story: Chapter 51: A Different Look - 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 12, 1984, Chicago, Illinois

On Wednesday morning, I showered with Allyson, who had come home with me after dinner at Jeri's, and, after breakfast, I called a car for her. Chelsea said nothing and didn't even give me a look, so I said nothing to her.

My trip to the courthouse had a different outcome, and I was selected for a case in which a landlord was suing a woman for damage to a rental unit and seeking to have her evicted. They had asked a few potential jurors about being landlords, but not me, most likely because I was so young. I had been asked about my job and whether I could render a fair verdict, and that had been it.

The only thing I could say after both sides had presented their cases was that I wanted the three hours of my life back. There was no question in my mind that the woman had caused the damage, and the landlord had Polaroid pictures to prove it. Her claim that it was damaged when she moved in was laughable because the landlord had a signed 'move-in' sheet showing very minor damage to the enamel on the stove, and a small amount of corrosion around a bathroom faucet.

Thankfully, the other eleven members of the jury saw things exactly the same way. It took us longer to fill out the verdict sheet and damage award sheet than it did to deliberate because there was literally no deliberation, just three quick votes — electing a foreman, who was my new acquaintance Albert Ball; the verdict, which was a voice vote that he was right and she was wrong and that she could be evicted; and the award, which was everything the landlord had asked for, including court costs.

Mr. Ball let the bailiff know we were ready, and I could tell by the look on his face he wasn't surprised we had finished quickly. He notified the judge, and ten minutes later, Mr. Ball read out the verdict, which surprised nobody in the courtroom, except the woman who had lost, who threw such a fit that she had to be escorted from the courtroom by a Sheriff's Deputy. The judge dismissed us, and I left the courthouse to head back to the Hancock Center.

I arrived just before 1:00pm, greeted Chelsea, held Sofía, then went upstairs to change. Ten minutes later, I walked into the office.

"You're later today," Violet said.

"Your powers of observation serve you well," I replied.

She rolled her eyes.

"Did you serve on a jury?"

"Yes, and it was a complete waste of just over three hours of my life that I can never get back."

"What kind of case?"

"A dispute between a tenant and a landlord. He was suing her for damages and to evict her. Slam dunk. The only person in the entire courtroom who was surprised was the woman who had trashed the apartment and was being sued for doing so."

"You're a landlord, and they let you sit on the jury?"

"It was Small Claims, so the judge asked the questions proposed by the plaintiff and the defendant. She had asked for a jury trial with twelve jurors, so I suspect she was hoping for one sympathetic person to hang the jury. It didn't happen. Around $2500 in damages and court costs, and the lease was terminated so he could evict her immediately."

"Crazy!"

"Anything important happen this morning?"

"No."

"Then I'm going to get to work. Dinner at your place as usual?"

"Yes! But no pie afterwards, correct?"

"Correct."

I went into my office and, despite having been out all morning, had a very typical day. At 5:00pm, Violet and I left together to have dinner at her house, and after dinner, we walked to UIC for our classes. In class, I took copious notes on the discussion about Bēowulf, and answered the question I'd randomly received to the professor's satisfaction.

At the end of class, I reminded myself that I needed to send a copy to Elaine Burroughs in the morning, then headed home, where Tara was waiting for me. She suggested we go right upstairs, and because Sofía was already asleep, we did that, with Misty padding up the stairs behind us.

"Finally, I get you alone again!" Tara exclaimed. "I was SO pissed at my parents making me go to a dumb party when you were in the city!"

"Daphne let me know," I replied.

"I had kind of hoped I could steal you on Sunday, but you had the art show thingy here."

"I am pretty busy," I said. "And we're keeping this casual."

"Uh-oh," Tara said with a frown.

"I thought that's what we agreed," I said.

"It was, but something in your voice made it seem, I don't know, final, like there was no chance of it ever being more."

"I don't think I was doing that, but even so, I'm pretty sure I explained everything to you, including the strong likelihood I'd never marry."

"I think I like you more than you like me," Tara observed.

"I'm not quite sure how to respond to that statement," I said.

"I want to ask you something straight up and would like a totally honest answer."

"That's pretty much the only kind of answers I give."

"Are you done with me because you got your intro to my parents?" Tara asked.

"It was never about that," I replied. "In fact, you offered the contacts; I didn't ask. Yes, I'm very happy with that, but the two things aren't related except insofar as I don't want you to have trouble with your parents. I wasn't using you, if that's what you're asking."

"I guess it was, and I believe you, but I think we're pretty much over because I asked the question."

"I'm not upset in any way that you asked; it's a completely legitimate question. I know people who get bent out of shape by uncomfortable or blunt legitimate questions, but I'm sure not one of them. I have people question me all the time, especially about investing and the stock market, and my boss can push me pretty hard. I don't take it personally. What do you want to do?"

"Well, I'm here, it's late, and it would be kind of tacky to go home."

"Not if that's what you want to do," I countered.

"Sorry, I was trying to be flip, but it clearly didn't work. I like fooling around with you and want to, though..."

"You're reconsidering. Tell me what you want to do, and I promise I will not be upset, and you will be welcome here on Sundays, no matter which way this goes."

"I want to stay."

September 13, 1984, Chicago, Illinois

Tara's reaction hadn't really surprised me, though something about it felt off, and I couldn't really place what it was. I finally figured out what made me feel something was off late on Thursday morning — Stefi, Daphne, and Skyler. Tara had been more than willing to share, and while she had hinted at something long-term, sharing me with Daphne didn't seem to fit the way she'd spoken the previous night.

What it told me was that, to put it crudely, fucking the Art School Girls was not a problem, but seeing any of them on a regular basis could lead them to believe that more was possible, and if I was honest with myself and them, it wasn't. January wasn't that far off, and barring some completely unforeseen event, Violet and I would discuss and define the shape of our relationship.

After lunch, I photocopied my notes for Elaine Burroughs and had them couriered to her, rather than risk the Post Office delaying them or, worse, losing them. Ellie arrived as planned for our mentoring session, which lasted an hour. Later, at 4:50pm, Violet let me know that Ms. Burroughs was on the phone.

"You didn't have to do that!" she exclaimed.

"I could send the courier to take them back," I teased.

"No, I'll keep them! Thank you very much!"

"You're welcome. I'll see you in class on Monday."

After I ended the call, I shut down my computer and trading systems and locked my notes in my desk, then left the office to meet Erin Laning and her dad to discuss her business plan and a possible investment. We met at Szechuan House, a Chinese restaurant on Michigan Avenue just south of the Hancock Center.

Erin's dad, Paul, was very laid back and friendly, though I did get the vibe he was slightly uncomfortable with the fact I was fucking his daughter, but Erin had made it clear he was fairly cool and had never said anything to her. I'd found dads generally fell into one of two camps — unhappy or resigned — about their daughters having sex. I'd yet to run across a dad who was comfortable with the idea, or — crazy thought — happy about it.

"Where are you from, Jonathan?" Paul Laning asked.

"Goshen, about thirty miles northeast of Cincinnati."

"You graduated in '81?"

"Yes."

"There's a guy who works for us at Nuvatec named Steve Adams who's from your area."

"I don't know him, but I know of him. He lives down in Kenwood, and we have a few mutual acquaintances, but that's it."

"Erin gave me a bit of background on you, but would you mind telling me more?"

I gave him the short version of the story — longer than the elevator pitch but without too many details. Erin mostly sat quietly until it came time to talk about her business proposal — Omega Graphics. She'd chosen the name because it was the last letter of the Greek alphabet, and she wanted to imply her business was the 'last word' in desktop publishing.

She'd thought of using 'Alpha Graphics', but her dad had paid for a trademark search and found it was in use by a Colorado company, AlphaGraphics, which franchised desktop publishing. I'd discovered that as well during my due diligence, but rather than putting me off, it validated the idea, and there was no reason multiple desktop publishing businesses could not thrive.

"The business plan is solid," I said. "I'm ready to invest if you're comfortable with my proposal."

"I read it over, and just to be clear, although you'd have an ownership interest, you wouldn't have any control?"

"Correct. I would be a silent partner and would provide advice or guidance when asked, in exchange for 25% of the quarterly distribution from the S Corp. That's required by IRS regulations, and is calculated after all expenses, including salaries and retained reserves. After five years, Erin can buy me out, if she chooses, at 25% of an independent third-party valuation. You choose the company, and I pay for the valuation, as noted in my proposal."

"I don't see any problem if this is what you want to do, honey," he said to Erin.

"It is."

"Then you should sign the deal."

"Thanks, Dad."

We had a very nice dinner and left the restaurant together. I waited while the valet retrieved Paul's car, then shook hands.

"I'm going home with Jonathan," Erin said to her dad when the car arrived. "I'll be home in the morning."

Paul did a good job of mostly hiding his disapproval, but I could see it in his eyes.

"OK, honey," he said. "If that's what you want to do."

She hugged him and kissed him on the cheek, then got a bag from the back seat of the car. She stepped back, and her dad got into the car and drove off.

"I hope you don't mind," she said.

"I don't mind at all, though I could tell that your dad was uncomfortable."

"Do you know any dads who are happy their unmarried daughters like to fuck?" Erin asked.

"Nope!"

"Then don't worry about him. Let's go to your condo, get naked, and fuck all night to celebrate!"

"Half the night?"

"Fine," she said with a theatrical sigh. "But at least once in the morning!"

"If you insist," I said with faux resignation.

We both laughed, then I took her hand, and we began walking back to the condo.

September 14, 1984, Chicago, Illinois

The look Chelsea gave Erin and me on Friday morning was different from all the others, and telegraphed her answer to the question I'd posed. Rather than disdain, it was pure jealousy, and I was positive it was only a matter of time before she asked me to take her to bed. Erin noticed, too.

"Did she lose her Bible?" Erin asked quietly.

"She's battling the same forces every teenager or young adult battles almost constantly. You should know!"

Erin laughed softly, "I was ready at fifteen, but you know how introverted I was."

"That's changed," I said.

"I was so tempted to write a paper for my psych class on how swallowing cum is a cure for introversion, but I don't think the professor would have approved!"

"Probably not, though these days, you never know!"

"It kind of depends, really," Erin said. "In some ways, things are less prudish, but in others, even more. Even though the 60s had a sexual revolution, things people didn't freak out about then, they freak out about now."

"An example?" I requested.

"Other than dads, nobody really blinked if girls who were sixteen or seventeen dated guys in their twenties, or if the age gap was bigger when she was eighteen or older. It's not everyone, but the idea that it's wrong is spreading. I read an article about increasing penalties for statutory rape and changing the name."

I nodded, "Ohio did something like that, and the criminal charges for having sex with an underage girl were increased significantly, even if she consented."

"See, that's the problem — the government says she can't consent, period. In Illinois, a sixteen-year-old can't legally have sex with her eighteen-year-old boyfriend."

"Isn't it technically the other way around? The law doesn't prevent her from having sex; it punishes him for having sex with her, even if she initiated it."

"Sure," Erine agreed, "but practically, it works the way I said."

"True, and why I've drawn a hard line at graduating High School. That removes any and all questions because not knowing she was under seventeen is not a defense. It also, generally speaking, implies a certain level of maturity."

"I suppose that makes sense," Erin agreed. "Can I ask you a question?"

"Sure. Always."

"I know you have a ton of girlfriends, or whatever you want to call them; aren't you afraid of a girl trying to trap you?"

"That thought has crossed my mind on occasion. There was one specific case where I actually suspected it, but the concern turned out to be unwarranted. I mean, I suppose it's possible, but most of the girls I'm with are artists, and that just doesn't fit their worldview. Now, if it happened by accident, that's a different thing altogether, and we'd work it out. I suspect most of the girls would simply terminate the pregnancy."

"You don't have a problem with that?"

"When men can become pregnant, then men can have a say!" I replied. "I mean, seriously, I can't see telling someone they had to carry a baby to term against their will. I'm happy my mom chose to, but it had to be up to her, not anyone else."

"I obviously agree, but your nanny might not."

And suddenly, I understood Erin's point about pregnancy risk or entrapment.

"Something I hadn't even thought about," I said. "Thank you."

"What are fuck and suck buddies for, if not good advice?" Erin asked playfully.

"Uhm, fucking and sucking?" I asked with a grin.

"I hope we can get together again sometime," she said.

"I'd like that very much."

We finished breakfast, and after I walked her to the lobby, I headed to the Spurgeon offices to begin my workday.

September 15, 1984, Chicago, Illinois

"You have your dinner with Keiko's grandparents tonight, right?" Violet asked as we showered together on Saturday morning.

"Yes. This morning I'm modeling for Claire's public drawing class."

"But not like the other ones, right?"

"It's open to the public, and the lower age limit is fifteen, so no."

"Would you mind if I showed up to watch?"

"Watch me sit in various poses for four hours? If you want to, sure, but it'll be boring. Or are you trying to head off me being hit on?"

Violet laughed, "I think I'm going to have to deal with that for the rest of our lives. But I also know you'll never break your word to me, no matter what."

"Does it bother you?"

"Girls hitting on you? Or you taking them up on it?"

"Either? Both?"

"No. Why be jealous when I've already won?!"

"What is 'winning' in your mind?"

"We'll discuss that in January," Violet said with a smile. "You have to take Deanna to Hawai´i before we have that conversation. If we have the conversation beforehand, you might decide not to take the trip depending on what we decide about the future. I don't think that's fair. Before you object, I know you well enough that you would consider canceling the trip. So, stop worrying about January and worry about now!"

"Yes, Dear," I said with a grin.

Violet simultaneously kissed my chest and lightly smacked my arm.

"You are just a goofball!"

"I know!"

We finished our shower, dressed, then went downstairs for a quick breakfast before heading to the School of the Art Institute. I was surprised at the number of students, with the large studio having forty seats and all of them filled. The attendees were mixed, though with a slight majority of women, and a slight majority older than thirty. There were, as Alexa and I had suspected, six or seven girls who appeared to be teenagers, and that group skewed the overall balance towards females, as there were no teenage guys. I greeted Alexa, then walked over to Claire, while Violet stayed with Alexa.

"Hi, Jonathan," Claire said. "This is Glenda Hartley, a graduate student. She'll take you to the dressing room so you can change. You brought your shorts, right?"

"Yes."

"Just shorts, then. Just put on the robe to walk back here from the dressing room."

"Got it."

I followed Glenda out of the room.

"New to Chicago?" I asked.

"Yes. I'm from Ohio, same as you, though north of Columbus."

"Where'd you go for your undergrad degree?"

"William Howard Taft in McKinley. You're at UIC?"

"Part-time," I replied. "I'm a financial analyst and investment advisor."

"Here's the room," she said. "I'll wait outside."

"OK," I agreed.

I went in and quickly changed into my shorts, put my clothes in a locker, attached my lock, put on my robe, then went back into the corridor.

"What do you think of Chicago so far?" I asked.

"It's not nearly as repressed as McKinley."

"I can believe it. The closer you get to Cincinnati, the more conservative the social values become. I'm sure you know all the stories."

"Yeah, I thought the radio station refusing to play Olivia Newton-John's Physical was just about the dumbest thing I've ever heard, but SO Cincinnati."

"Chicago is a great place to make friends," I said.

"It seems like it so far," she agreed.

 
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