Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 19: A Sticking Point
Fiction Sex Story: Chapter 19: A Sticking Point - 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
July 12, 1984, Los Angeles, California
"The way you said that, it sounds like a long story. Are you willing to share it?"
I didn't know Leslie very well, and that meant I didn't know how she'd react, or whom she might tell. It most likely wasn't a problem, but I did have a reputation to protect. That was my major concern when thinking about CeCi's request to take photos that would be beyond risqué, as well as shoot what amounted to a short, pornographic 8mm movie. I had no real moral or ethical concerns about her request, but reputational risk was something I had to consider.
Taking Leslie on a date and having her spend the night, which was very likely, wasn't a concern, given David Finch had given his blessing for the photo and hadn't reacted negatively to the sexy, inviting kiss I'd received from Leslie. I doubted he'd even taken any real note, and if he had taken note, he had no objections because he'd agreed to invest and had instructed Leslie to set up the meeting.
"I'll tell you the short version if you wish," I replied, "but I believe the story would put a serious damper on the evening."
"It's that bad?"
"It is."
"I suppose, at this point, you should, because otherwise, I'm going to spend the entire evening wondering."
"I think the best is just to tell you the end of each part of the story. I fell in love with a girl in Chicago, was sure she was my life partner, and we talked about marriage. She was diagnosed with leukemia, we married, and she died last December."
"Oh, my gosh!" Leslie exclaimed. "That's so sad."
"In addition, a girl I was involved with in High School, and who was very close to me, and whom I would have married, committed suicide."
"I don't even know what to say!" Leslie exclaimed.
"It's even more complicated, actually," I said. "I have a three-month-old daughter with a lesbian friend who conceived before I married; intentional, mind you."
"All of that, and successful in your career, too," Leslie observed.
"All three stories are even more complicated, especially with the girl from High School."
"I have a sympathetic ear if you need to talk about it, but I think you're right about putting a damper on the evening."
"Sorry."
"It's OK. I more or less insisted you tell me what it was. You seem to be doing OK."
"I had some pretty bad times in the first few months of this year, but my friends helped tremendously."
"We should probably change the subject," Leslie suggested. "What sports do you like?"
"Baseball primarily, then hockey, and football. I'm not a huge football fan, but a bunch of friends get together to watch every Bears game. I go to six to eight baseball games a year, both the Cubs and White Sox, and several Black Hawks games each season. Spurgeon has tickets for all the teams, including the Bulls, and I can make use of them, but I also go on my own. You?"
"Lakers and Angels; I never got into hockey, and I don't like football. Do you have any hobbies?"
"Art," I replied. "Collecting, patronage, and modeling."
"Modeling?"
"At the School of the Art Institute. I have some very close artist friends and did it as a favor for one of them, and I've been invited back a few times. You?"
"I did needlepoint when I was in grade school, but haven't done it since I was about thirteen. I like going to the beach."
"There are beaches along Lake Michigan, but nothing like the ones in California, I'm sure."
"You haven't been?"
"No. This is my second time in California. My entire experience before tonight is John Wayne Airport, the InterContinental Hotel, and your firm's offices. I can add Yamashiro after we have dinner."
"What kind of art do you collect?"
"Paintings, mostly. My entire collection is from students at the School of the Art Institute of Chicago."
"So, nobody famous, right?"
"Nobody famous yet," I corrected.
Leslie pulled up to the restaurant, and two valets came to the car and opened the doors so we could get out. We went into the restaurant and discovered there would be a twenty-minute wait, which actually didn't surprise me.
"What's your typical day like?" Leslie asked.
"Mostly research and writing reports," I replied. "Probably similar to your paralegals. As I said, managing my fund is only a small part of my role. I manage a dozen researchers and data analysts. I assume your role is similar to Violet's — administrative tasks?"
"Yes, though I haven't taken a trip on a private jet!"
"It is very convenient, but I don't get to use it all the time."
"Yes, but you do get to use it!"
"True. Going back to a question you asked me — you don't have a boyfriend?"
"I dated a guy for Junior and Senior Year of High School, but he's at Texas A&M, and we decided it was foolish to try to stay together for four years while he was away most of the time. I dated some while I was at Harbor College, but nothing serious. I also went out with one of the new associates a few times, but I decided dating someone from work was a bad idea."
"I agree with you completely on that," I said, though there were two obvious exceptions in Violet and Bianca. "There are simply too many potential problems."
"I assume that rule doesn't apply to employees of clients?"
"I felt it was OK, given Mr. Finch was amenable to the photos and didn't object to the kiss you gave me."
"He'd never say anything, so long as I'm doing my job well, which I am. There are no rules about dating at Ford, Jackson, and Finch, either employees or clients. The only thing to consider is the ethical rules enacted by the Bar Association, which means attorneys cannot date current clients."
"We don't even have that limitation. The SEC and CFTC only care about fiduciary and reporting duties."
After about fifteen minutes, the hostess let us know our table was ready and led us to it. We ordered green tea, and when Leslie suggested we order saké, I agreed. Our waiter brought those and took our order.
"What's your favorite type of food?" Leslie asked.
"That's not really something I've thought about," I replied. "But I'd say I prefer Japanese, Thai, or Chinese. Of course, Chicago-style deep-dish or pan pizza is pretty awesome."
"I've never had Chicago pizza. What's it like?"
"About an inch thick with plenty of sauce, cheese, and toppings; you have to eat it with a knife and fork. If you ever happen to be in Chicago, I'll take you to Connie's, Lou Malnati's, or Giordano's; all of those are excellent."
"Just send your plane, and I'm there!"
"If only it were my plane!" I said with a grin. "First off, operating costs with a crew run $400 to $600 per hour, and that doesn't include the price tag of around $35 million. I'd need a net worth of around $300 million to even consider owning a jet. That's fifty percent more than I have in my fund, and most of that money belongs to my clients."
"As quickly as you've advanced, I could see it."
"I wasn't ruling it out, but if you want me to send my jet, it'll be ten to fifteen years or so!"
Our food arrived, and while we ate, we talked about High School, college, and work. When we finished our meal, I paid the check, and we left the restaurant to drive back to the InterContinental Hotel. We chatted amiably during the drive, and I wondered what Leslie's intentions were. So far, everything had been platonic, though the French kiss on my previous visit had seemed inviting. My question was answered when, instead of dropping me off, she parked in the parking garage and grabbed a bag from the trunk of her car.
I took her hand and led her back to the hotel, where we got into an elevator to go up to my junior suite. It wasn't quite as nice as the suite I'd had in Minneapolis, but I also didn't need two bedrooms.
"This is nice," Leslie observed.
"There's a whirlpool tub," I said.
"Cool!"
We exchanged a soft kiss, which turned into a fierce, urgent French kiss.
"Birth control?" I asked.
"I'm on the Pill," she replied.
That was all I needed to know, and we kissed once more before I led her to the bedroom.
July 13, 1984, Los Angeles, California
Leslie and I had used the whirlpool, then fucked twice before snuggling together to sleep until my alarm went off at 6:30am. We got out of bed and went into the bathroom for a joint shower.
"You know, you could have warned a girl!" Leslie said lightly as I soaped her body.
"About?"
"Your huge dick!"
"Right," I chuckled. "How exactly does one work that into a conversation?"
Leslie laughed softly, "I suppose that would be as difficult as it was working it into me!"
"It was a nice, tight fit," I replied.
"And boy did it fit well!" Leslie declared. "You certainly know how to use it! Your tongue, too!"
"After last night, I think I can give a different answer for my favorite thing to eat," I chuckled.
"Pussy?" Leslie asked.
"Yep!" I chuckled.
"You aren't upset that I'm not a big fan of giving blowjobs?"
"As I've said to a number of girls over the years, you talk to your partner about what you like and don't like, and work it out. For a casual thing, slight incompatibilities aren't a big deal; it would be different in a long-term relationship."
"I'm not trying to criticize or pick a fight, but you'd reject a girl who won't blow you?"
"Sexual compatibility is a very important part of any successful long-term relationship. It's not the most important, nor is it a litmus test, but if one partner is frustrated, even a little bit, that can cause significant problems. I'm not saying blowjobs are mandatory, just that they are one factor in an overall decision."
"I suppose if it's that important..."
"The opposite problem is one partner doing something they don't prefer to keep the other partner happy. That could work, but it could also lead to resentment and frustration. Don't get me wrong — I truly enjoyed last night, and I'm not making any complaints, and I would be happy to see you again when I come to Los Angeles."
"But..." she prompted.
"No 'buts'," I replied. "This is casual, right?"
"Yes, though, obviously, I like you."
"And I like you, too, but I'm not even close to being ready for a long-term relationship, not to mention the distance."
I finished soaping Leslie, and she rinsed off the suds under the spray, then picked up the bar of soap to use on me. As she did, I wondered exactly what she wanted and decided to ask directly.
"Did I misinterpret your offer of a raincheck?" I asked.
"I'm not sure what you mean."
"After the kiss, I had the impression you were just interested in some fun. Your reaction to my comments about oral sex leads me to believe I might have misunderstood or misinterpreted your request to get together. Now it seems, at least to me, as if you're contemplating some kind of relationship."
"Are you writing off a relationship because we fucked on our first date?"
"I wasn't thinking about it one way or the other," I replied. "My mind was still on the first date, not the future. We spent time getting to know each other over dinner, and things obviously went well enough for you to follow through with your implied offer and for me to agree. As for a second date, I'd worry about that if and when the opportunity presented itself."
"But you just said we're not sexually compatible."
"No, I pointed out one thing that might be a concern. The only way it's a serious concern at the moment is if you're thinking much further down the road, and assuming nothing would change between now and some hypothetical point in the future. I'll also point out you raised the topic by asking if it bothered me when I hadn't said a word or, as far as I'm aware, done anything to indicate I was unsatisfied or that I felt something was lacking from the sex we had."
"Was there and you didn't say?"
"No. I didn't even think about it until you mentioned it. I perform oral sex because I like doing it, and at least before the first fuck, it ensures the girl is wet enough because, as you noted, I'm bigger than average. It also gets me hard, so I didn't even think about a blowjob."
Leslie simply looked at me without saying anything, so I took the soap from her and finished soaping myself, then rinsed off. We got out of the shower and dried off, then went to the bedroom to dress. My estimation of Leslie had changed, and I no longer felt she was as mature as I had thought before.
Every indication was that she had several partners before me, but had what Bianca had once referred to as a 'Junior High' attitude towards oral sex. Her approach to sex hadn't been like Marcia's, but I did see a bit of the same thinking. The true source of the problem was Leslie's reaction to my comment about communication and determining sexual compatibility. If she couldn't have that conversation, this was our first and last date.
As I dressed, I concluded that my best approach, at least until I was ready emotionally to have Violet move into the condo, was to stick to the Art School Girls and their friends, all of whom were fun, adventurous, and uninhibited partners. None of them, so far, had indicated any interest other than casually dating. Of course, that didn't include Deanna and CeCi, but I didn't consider them Art School Girls despite the fact they were girls who attended The School of the Art Institute.
"You're unhappy," Leslie observed.
"Only about your reaction to my observations about communication. You seemed bothered by what I said when, from my perspective, I didn't say anything critical. Fundamentally, to have any kind of relationship at all requires communication. All I did was point to a potential concern about our sexual compatibility, and suggested that it had to be taken into account and that everything had to be communicated, discussed, and agreed."
"That almost sounds like a contract."
"Whatever you want to call it, it's a meeting of the minds. Honestly, you've blown something I've said completely out of proportion to what I intended. And then you clammed up. Right up until then, I was sure I wanted to see you again."
"But not now?"
"That all depends on your willingness to communicate, which means both expressing your feelings and desires and listening to mine. That is literally the only way forward. I will also point out that whatever else is true, you live in California, and I live in Chicago. One date is nowhere close to being enough for either of us to consider anything other than agreeing to see each other again at some point in the future, assuming you still want to."
"I think you've already decided."
"And that means nothing I can say will disabuse you of that erroneous thought. Let's go have breakfast."
She agreed, and we left the hotel room. As we made our way down to the ground floor to the hotel restaurant, I considered the situation. As I did that, I realized that it was as bad an idea to date a girl from a client as it was to date someone from Spurgeon Capital. Violet and Bianca were different, as I had a pre-existing relationship with each of them, but the rule was a good one, and also allowed Violet her plausible deniability, which she felt was important.
The question lurking in the background was whether or not the minor tiff with Leslie would negatively affect my client relationship with Ford, Jackson, and Finch and the Hollywood investors. I didn't think it would, but if something was said, I needed a strategy to recover, but one that didn't involve ruining Leslie's reputation. In the end, the sex had been OK, but no girl was worth wrecking my career, and that meant exercising extreme caution with clients and staying away from Spurgeon employees except Violet and Bianca.
We reached the restaurant and were seated. We both asked for coffee, then perused the menu. As I contemplated what to have for breakfast, I wondered if I should say something to Leslie about my concerns, but decided, in the end, raising those concerns risked her doing something she hadn't considered. Based on that, I felt it wise to simply try to make small talk while we ate.
The waitress returned, and Leslie and I both ordered our breakfast.
"How long is your commute?" I asked.
"About forty minutes, mostly using surface streets to avoid the freeways. What about you?"
"My condo is in the same building as Spurgeon Capital. Five or six minutes via three elevators, including waiting time."
"That's convenient!"
"It is. Do you live alone?"
"I have a roommate who works at an accounting firm in the same building as Ford, Jackson, and Finch. I'm guessing your daughter and her mom live with you?"
"Yes. We have two other housemates. One is the artist for whom I'm a patron, and the other is her friend from Ohio."
"Your housemates are all girls?"
"Yes. And they all have their own rooms, including my daughter."
"Wait! How many bedrooms does this condo have?!"
"Six. It's laid out like a townhouse."
"It's unreal how much you've made in just three years."
"A combination of skill, aggressiveness, self-confidence, and being in the right place at the right time. I suspect there are some young hotshot attorneys who make the kind of money I do. Granted, they're about four or five years older because of the requirement that they go to law school and pass the bar."
"You can actually get a law license in California without going to law school — you basically apprentice to an attorney and learn by doing paralegal work, then take the Bar exam."
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