Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 21: Eminently Practical, Miss Clemmons!
Fiction Sex Story: Chapter 21: Eminently Practical, Miss Clemmons! - 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 14, 1984, Chicago, Illinois
"Please don't take this the wrong way," Piper said as we dressed, "but that sounds like a TV soap!"
"I know," I replied. "But every word of that is true. When we go downstairs, you'll certainly see Bianca and her girlfriend, and probably my daughter. You know I was in Ohio for my friend's funeral, and I can show you a painting of my wife. The condo is obvious, and if you insist, I could show you the paperwork."
"Sorry; I wasn't saying I didn't believe you, just that it's pretty far outside what I'd expect to hear from a guy who is only a few years older than I am."
"Someone recently said I had a lot of baggage, and they weren't wrong. There is even more than I just related, though that would only matter to a girl looking for a committed relationship. Despite what we just did and what we'll do again after dinner if you're still interested, a committed relationship is the last thing that ought to be on your mind right now."
"I'm curious to hear your thinking on that."
"By your own admission, you've lived under your parents' thumbs for eighteen years. You have your freedom, and you shouldn't give it up before you have a chance to discover who you are, who you want to be, and what you want from life. Being in an exclusive, committed relationship is not the way to do that."
"You think I don't know who I am, who I want to be, and what I want from life?"
"Honestly? No, I don't believe you do. You haven't even scratched the surface of experiencing life. You haven't held a job, you haven't lived anywhere except your parents' house, you haven't had a serious relationship, and you've suffered no real adversity except for your parents' control-freakery.
"Given all of that, and please take this as observation, not criticism — you're not ready for a serious relationship with a widower who has a three-month-old daughter. I'm not saying we can't be friends, and I'm not saying I don't like you. You're intelligent, personable, and cute, and the sex was awesome.
"I'm more than happy to mentor you if you're serious about working in the financial services industry, and I'll absolutely consider hiring you when the time comes. But in the short term, I think you need to move out of your parents' house and see how your life unfolds. I'll be here when you move to Chicago, and I'm positive I'll be here when you finish your Master's degree. Neither of us knows what the universe has in store for us."
"I'm not saying you're wrong, I'm just not sure you're right."
"Let's try a different way," I said. "Was your plan to marry and have kids before you finished your Master's?"
"No."
"Then you have seven years to explore the world and, as they said in the sixties, to find yourself. You need to discover your own path through life, not the one your parents, or anyone else for that matter, want. Are you a fan of Frank Zappa?"
"I don't know much about him; my parents didn't like him."
"Which is why something he said is completely on point for the conversation we're having — 'If you end up with a boring, miserable life because you listened to your mom, your dad, your teacher, your priest, or some guy on television telling you how to do your shit, then you deserve it'."
"Harsh," Piper observed.
"Perhaps so, but I prefer blunt, direct talk, and generally don't pull my punches. A lot of people can't deal with that; those are not people with whom I'm ever likely to be close. May I suggest a course of action?"
"I don't think it would be wise to say 'no'."
"Is that a 'yes'?"
"Yes."
"Move to Chicago, start classes, make new friends, hang out with my friends and me, and see what life brings your way. All I'm able to offer at this point is friendship and fucking, if either or both of those interest you."
"I don't really have a choice, do I?"
"That's not the case; we always have choices. Sometimes, we have to make suboptimal choices because the optimal choice isn't available. Sometimes, we don't know the optimal choice; sometimes the obvious choice is sub-optimal, and we don't realize it. The goal you should have is that for each decision you make, you choose the option that has the highest likelihood of success for achieving your goals.
"It's also incumbent on you to constantly evaluate your goals and ensure they're aligned with what's most important to you. The one constant is change, and you have to adapt. A perfect example was when you asked about a job — you adapted to the situation. I'm positive that prior to about three hours ago, working for me was not on your agenda or even a remote possibility in your mind."
Piper had a look of consternation, then nodded, "I think you're right, though I feel a bit ... discombobulated."
"Being confused or out of sorts is not uncommon when you cross the threshold from childhood to adulthood. That's what you did today."
"You mean because I lost my virginity?"
"A symbolic declaration of independence, an assertion of self-determination, and a common rite of passage. The most important thing you did today is prove to yourself that you, not your parents, are in control of your life. One thing that didn't come up was church — do you attend?"
"Every Sunday, but not because I want to. Mom insists. I would have stopped attending when I was fourteen or fifteen if I'd had a choice."
"What church?"
"Loveland Presbyterian. You?"
"Atheist. I never attended any church. Do you not believe, or do you just not want to go to church?"
"I'm not sure what I believe, but the fact that my parents made me go is the problem."
"As I see things, it's absolutely impossible to force someone to believe something against their will, and it's a very bad idea to try. You can attempt to persuade them, but you can't force them. Everything I've said to you today should be persuasive, but if it hasn't been, there is nothing I can do to force you to agree with my analysis."
"What if I don't agree?"
"That actually doesn't interfere with anything unless you had designs on a long-term, committed, exclusive relationship. I can't do that now and can't say when I could, if ever. As I said, all I can offer at this point is friendship, mentoring, and, if you're still interested, sex. The future is an open book, but, as I said, I'm unlikely to marry again."
"Don't you think you should have disclosed that before we had sex?" Piper asked.
"I'm of the opinion that if a young woman believes sex is a commitment to an exclusive relationship, it's incumbent on her to state that clearly up front. If she doesn't do that, the guy has no ethical obligation to her, except to take responsibility for any baby they conceive."
"Do you think I believe that it's an obligation?"
"I don't know what you believe, which is the basic point of this conversation. I'm going to ask a direct question — what do you think I should have done? Consider the facts — a girl I had just met asks for a kiss and almost immediately asks to have sex. There are three options — say 'yes', say 'no', or have a two-hour discussion about his complicated life, completely spoiling the mood. Which option should I have chosen?"
"Er, you think I'm upset that we had sex?"
"Again, that goes right back to the point that I don't know you well enough to know what you're thinking. Consider that when you consider why I didn't try to have this discussion first. It would have been very different had you asked me to have sex to begin a committed relationship. And I'm not trying to impute that thinking to you; I'm simply trying to explain why I didn't try to tell you beforehand.
"I'm going to point out that when you came here today, I was prepared to go out and do something before dinner, have dinner, and then invite you here if you wanted to come. Instead, shortly after you arrived, you asked if I wanted to finish what we started in Goshen. Again, consider my options — 'yes', 'no', or a two-hour discussion. It would have been different had we gone out, but trying to have the conversation immediately would have been a mood killer."
"You're upset," Piper said, frowning.
"No, I'm not. I'm being my usual self, and you don't know me well enough to know that. I'm totally not upset, or bothered, or annoyed, or anything like that. I'm simply responding logically and analytically to what you've said and how our relationship developed. It's what I do, because it's who I am, and that's why I'm so good at what I do."
"I'll say!" Piper smirked.
I laughed, "I meant at work!"
"Obviously. I guess this is the 'getting to know you' part we should have done first, right?"
"Yes and no. A lot depends on what you think having sex means. That's the question I'd like you to answer."
"You mean, do I think having sex means we're a couple? No, but it should be a possibility. Do you agree?"
"In my mind, the two aren't necessarily linked. It is entirely possible to have sex just for fun with no intent of having a relationship — what people call 'casual sex'. Given how we met and the events that led to us being in bed together, the most logical conclusion for me to make was that it was casual sex. That does not preclude any specific future, but it absolutely does not guarantee one, or even guarantee exploring the possibility of having one. To be blunt, it was just sex. That said, it's also the case that I agreed to mentor you and consider hiring you. My question to you is when you decided it was more than 'just sex'?"
"To be honest, I'm not sure I ever thought that. You were tall, good-looking, lived in Chicago, and obviously successful. You're implying I would have sex with some random person just to have sex."
I nodded, "I am, because that is what it looked like to me. Remember what I asked?"
"If I had a habit of asking random guys in barns to kiss me."
"Yes. Nothing you said after that indicated to me that it would have been anything more than, to be blunt, fucking purely for pleasure. If that wasn't your intent, then it was incumbent on you to make that clear in advance; otherwise, it looks like a trap. At this point, I believe I have to ask a VERY pointed, insensitive, and perhaps even insulting question — are you really on the Pill?"
"What kind of question is THAT?" Piper spluttered in outrage.
"One I had to ask given the circumstances and the conversation we've just had."
"You know what? I think I'm just going to go back to my hotel."
"I would like an answer to my question, please."
"That question doesn't deserve an answer!"
"Actually, it does," I said firmly.
"Drop dead!"
That response indicated to me the possibility she had lied, and if I put all the pieces together, she saw me as a way to escape her parents. She might well be on the Pill, but there was a chance she wasn't, and that could have dire consequences. At this point, there was nothing I could say or do, and I'd just have to wait for time to pass and see what happened.
"Then I'll walk you out," I said.
We left my room and went downstairs. As I expected, Bianca and Nicole were sitting on the sectional sofa, and Bianca was cradling Sofía. I said hello, then walked Piper to the door. I opened it and decided I had to say something.
"Call me if you need to," I said.
She glared at me and walked the short distance to the elevator. She jabbed the call button, and I waited until the elevator doors opened, and she got in before I closed the door to the condo and walked back to the conversation pit.
"Mind if I borrow Bianca for a moment for a private conversation?" I asked Nicole.
"Not at all! I'll take Sofía."
Bianca handed Sofía to Nicole and followed me up to the loft.
"That did not appear to end well," Bianca observed. "What happened?"
"I'd say either I misinterpreted her intentions, she misled me, she didn't communicate clearly what she wanted, or she had ulterior motives. It's entirely possible it's a mix of all four."
"I don't think you can use 'either' for more than two options," Bianca said with a goofy smile.
"According to my writing class, in informal speech, it's widely used and accepted. In formal writing or a formal speech, you would use a different construction to convey options which might be mutually exclusive! Satisfied, Miss Pedantic?"
Bianca laughed softly, "You're always so accurate in your speech and writing at work that it's almost jarring to hear you use language informally. Anyway, what happened?"
"Everything was fine until we started talking in the whirlpool after we'd fooled around, and I said my situation was complicated. She took that to mean I had a girlfriend and was possibly cheating. After I explained about Keiko, Sofía, and Bev, Piper said that it sounded like a TV Soap. Then, after a bit of back-and-forth, she said she felt I should have disclosed all of that beforehand. To me, that meant she had designs on me as a boyfriend."
"The girl who asked you to have sex less than five minutes after meeting you, left you a note saying she wanted to get laid, then called you, came here, and suggested right away that you should go to your room to fuck?"
"That's exactly my point. I don't see how I could have misinterpreted her words and actions, but it's possible I missed some clues."
"Or she changed her mind when she saw the condo," Bianca suggested.
"That may well be, and I consider it to be a real possibility. I also remember telling her, when we were together in Ohio, that I was a securities analyst and fund manager and I had my securities licenses. That's what caused me to think of the possibility that I was not only a target of opportunity, but a way to escape extremely controlling parents. I had an idea that her mom was overprotective, but in talking to Piper, both her parents are complete control freaks."
"How bad?"
"According to her, they watched her like a hawk, controlled everything she did, who she was with, and so on. When I challenged that because she was here in Chicago without them, she claimed one of her grandmothers had intervened on her behalf. As the conversation continued, she had a number of chances to agree that it was just sex, but she never did. Her answers to my questions made me suspicious, so I asked her point-blank if she was actually on the Pill."
"Jesus, Jonathan! You called her a liar to her face!"
"I did, though I prefaced it with the comment that I knew I was being insensitive and insulting. She was outraged and refused to give me a direct answer. When I asked a second time, she told me to 'drop dead'. That makes me VERY suspicious."
"When did she tell you she was on the Pill?"
"In the barn; I obviously wouldn't have agreed to have sex with her otherwise, as I didn't have rubbers with me. She indirectly confirmed that when we talked about her parents being control freaks when she said she went on the Pill right after she turned sixteen."
"Are you sure she wasn't just offended by the question?"
"No, I'm not sure, but given the entire conversation, I think the question was both logical and warranted, despite the fact that it offended her."
"What are you going to do?"
"All I can do is wait and see what happens. When she chose to leave, I said she should call me if she needed to do so."
"That would be very bad," Bianca observed.
"Yes, it would, but there's not much I can do about it now. If I had to bet, I'd say she was just offended, but I could also read outrage at being caught in her response."
"I'm curious if you'd suggest she have an abortion."
"I'd certainly point out that it was an option. This has done one thing, and that is, that combined with what happened with Leslie in LA, it's convinced me that simply graduating from High School isn't enough. I think I'm just going to stick to the Art School Girls and girls with whom I have a developed relationship. None of them has caused even a slight amount of trouble, and that includes Claire and Britney, both of whom I turned down."
Of course, there was Alyson's party, but in my mind, that was different from randomly meeting someone, or girls like Jennifer.
"That does make some amount of sense. The last thing you need is drama."
"No kidding."
"Does that mean not fucking on the first date?" Bianca smirked.
"The Art School Girls are different," I grinned.
Bianca laughed, "So true! What are you going to do tonight?"
"It would appear I have no plans. I can watch Sofía if you and Nicole want to go out."
"We were planning on ordering Chinese and watching Star 80, a movie about Playboy Playmate Dorothy Stratten. You're welcome to join us."
"I'll do that. Dinner is on me. Did you go to the video store?"
"Yes, while you were with Piper. I took Sofía for a walk, and we stopped to rent the tape."
"OK. I'm going to spend about ninety minutes on homework."
"Sounds good."
Bianca went back downstairs, and I sat down at the Mac in the loft to work on a creative writing assignment for my English composition class. This was our final paper, and it was to be between 2500 and 3000 words. I had decided to write a story about an eighteen-year-old Dungeons & Dragons player who was transported into his game world.
It fit with the times, as there was a complete moral panic over the 'satanic' nature of the game and the supposed negative psychological effects. I made my short story very positive, with the guy becoming very successful because of his modern knowledge. I didn't think the story was great, but with proper grammar and spelling, I'd receive at minimum a B+, which I felt was sufficient for this paper, as I'd had either an A or A-minus on every paper so far.
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