Climbing the Ladder 5 - Reaching New Heights - Cover

Climbing the Ladder 5 - Reaching New Heights

Copyright© 2026 by Michael Loucks

Chapter 14: Oh, I Suppose I'll Behave

Fiction Sex Story: Chapter 14: Oh, I Suppose I'll Behave - 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 23, 1984, Chicago, Illinois

"I'm not upset, just surprised," I replied.

"Please don't be upset with Mom," Jennifer pleaded. "She told me there were more paintings upstairs in the loft and the halls, and the door to the room with the paintings was open, so I went in."

"That room is intended as a gallery, and I'm not upset with your mom. The art on the walls is meant to be viewed, and suggesting you see it wasn't out of line. Had you gone through a closed door, that would have been different."

"I'll say!" Jennifer smirked. "If I could go through a closed door, I'd be a ghost!"

"And, of course, you know what I meant!" I retorted.

"Of course, but I also heard what you said! And I was just doing what I did with the word 'sleeping' — being literal when what was said wasn't meant literally. Which YOU seem to like to do!"

"Touché!" I chuckled.

"Are there going to be more paintings in that series?"

"At three months, six months, a year, and two years. Deanna wants to keep going, but I'm not sure that's wise beyond toddler age."

"It's art, right?"

"Yes, but that doesn't mean someone at DCFS or the State's Attorney's office will see it that way. Not to mention that, at some point, Sofía has to have autonomy to decide. And that's a tricky question."

"At this point, it's not really different from all the dumb bathtub pictures every parent takes, and nobody has a fit about."

"So far. But parents stop taking those pictures around age two. What's your take on nudity?"

"I think the best way to answer is to say that both my guidance counselor and the nurse I talked to when I went to visit Loyola on a career day said that if you couldn't handle naked bodies in non-sexual situations, then you shouldn't be a nurse or doctor. They mentioned a number of procedures that are done in the Emergency Department, like catheters that are used to drain urine."

"I'm aware of that one," I said. "Keiko had a catheter. Let's just say the concept alone is discomforting!"

"No kidding! They talked about other stuff that is pretty gross and were blunt about it. At first, I was like, no way I can do that, but then, as I thought more about it, I decided I could and went ahead with my plan to be a nurse."

"That is pretty much the only option. If I understand correctly from a nursing student I spoke with, you have to do all those things as part of your training, no matter where you choose to work, be it a part of the hospital or a doctor's office."

"That's right. Medical students do the same thing, but not until they finish two additional years of classroom work after an undergrad degree."

"Did you ever think about being a doctor?"

"Briefly, but that's basically eight years of school and then at least a year as an Intern before you have a license, and even then, you have to finish a Residency. That's nine years, minimum, and more like ten or eleven. As a nurse, I'll be fully licensed and working full-time in three years. Once I looked into it, being a doctor didn't really interest me. Did you ever think about being anything other than what you are?"

"I didn't even think about being what I am! When I called my uncle to ask for help finding an entry-level job, I didn't put any restrictions on that request except that it had to have a chance for advancement. Once I started in the mailroom at Spurgeon, I got the idea of getting my securities licenses and taking it from there, but I figured I'd go the traditional route. Instead, I kind of made my own way by sheer determination. That's how I became the youngest licensed securities professional at Spurgeon and one of the youngest ever in the US to have three licenses, including the one that allows me to manage people."

"Nice horn you're blowing!" Jennifer teased.

"If I don't promote myself, nobody else is going to. I mean, do you think I should stand in front of a group of potential clients and give them an 'Aw, shucks' attitude like Gomer Pyle?"

"No, of course not! I'm positive you knew I was teasing."

"I was, but I like to give straight answers to teasing because it's fun!"

"Do you play any instruments?"

"No. I never had the time to learn, and at this point, I certainly don't. Do you?"

"Piano. I played in the concert band at school starting in eighth grade. It's fun, but it's not something I'd try to do professionally. Did you play sports at all?"

"No. I worked from the time I turned fourteen and had two jobs from the time I turned sixteen. Money was very, very tight, and I had to contribute to the household budget so we could make ends meet."

"That's changed, obviously."

"Obviously. From that, I learned the value of hard work, the value of a dollar, and the value of saving. I learned responsibility and self-sufficiency from a very young age. I want to instill all of that in my daughter, but it'll be difficult because she's basically been born with a silver spoon in her mouth."

We reached Little Italy, and I found a parking spot about two blocks from the restaurant. As she had at Miller Meadow, Jennifer slipped her hand in mine as we started walking along the sidewalk to Pompeii. When we reached the restaurant, we had to wait about ten minutes for a table, which wasn't bad given it was late Saturday afternoon. We were seated at a table for two near the front windows, and a waiter appeared immediately.

"If you're going to order beer or wine, I'll need to see ID from both of you," he said after greeting us.

I wasn't surprised that they would card us, given the proximity of the university.

"I'm twenty-one, but she isn't, so we won't order alcohol. Jennifer, what do you want to drink?"

"Coke, please."

"Make that two Cokes," I replied.

The waiter left to get our drinks.

"What if I have a fake ID?" she asked.

"Do you?"

"Well, no, but what if?"

"Well, then the thing to do was mention that before we were seated! That said, with UICC just down the street, I bet they're good at spotting fakes."

"You look like you're about twenty-five; do you get carded?"

"Almost never, but you look like you could be fifteen, so you're going to get carded a long time after you turn twenty-one. Your mom looks younger than she is, so I expect that'll be true for you."

"You think I look that young?"

"I said 'could be'. It's honestly tough to tell from fifteen to twenty because it depends so much on makeup and clothing. You don't wear anything other than lip gloss, so you look younger. A bit of eye shadow and lipstick, and you'd probably look eighteen or so. But I'm not a great judge in that regard. Your mom told me you had just graduated from High School, so I knew you were eighteen. Well, technically, you could have graduated early, but that's pretty rare."

"So, if you saw me without knowing how old I was, would you have been interested?"

"My personal rule is that girls have to have graduated from High School. Before I turned twenty-one, I would have said they had to be at least Seniors because that would have been, at most, a three-year difference. Now that I'm almost twenty-two, graduating is a minimum, mainly because of maturity level."

"I know plenty of kids who have graduated who are immature, and most of my friends were mature at fifteen or sixteen."

"Well, once I turned eighteen, dating someone under seventeen was frowned on by the government here. It was sixteen back home, which I think is more reasonable, but it's not up to me. And while what you said is true, setting the limit makes sense, and I can weed out the immature girls. Let me ask this — what would your dad have said if you wanted to date a twenty-one-year-old when you were fifteen?"

"He'd have locked me in my room and obtained a restraining order!" Jennifer declared.

The waiter brought our drinks, and we asked for a few minutes to review the menus. We both decided on Fettuccini Alfredo with chicken, with minestrone soup to start. The waiter took the order and left the table.

"As I was saying," Jennifer continued, "Dad wasn't happy with ANY guy I dated."

"Including me?"

"Mom talked you up, and so he's neutral."

"Overprotective?"

"Actually, no. He let me mostly do what I wanted, and I had a lot of freedom; he just disapproved of the guys. My curfew was reasonable — 10:00pm when I was a Freshman or a Sophomore, 11:00pm as a Junior, and midnight as a Senior. I did get until 1:00am for Prom, but Dad was up waiting to make sure I was in the house by 1:00am. Was your girlfriend's dad like that?"

"Not really. I didn't have a car or much money to spend, so we didn't go on dates; we just hung out together, mostly in a barn on some farmland behind our houses. The farmer was cool, and from about age ten — she was nine — we hung out in the hayloft most evenings."

"The scene of the crime, so to speak?"

"Yes. My mom was OK when she found out about it; Bev's dad not so much."

"What happened with her, if it's OK to ask?"

"I made a grave error in not inviting her to come to Chicago with me, though that would have had to wait a year for her to graduate. She started dating, got pregnant, had a baby, and then her life spiraled completely out of control when the father was revealed. Things went steadily downhill, she lost custody of her daughter, and she took her own life about three weeks ago."

"Oh my! Is the baby with the father?"

"The father is going to be in prison for about thirty years. He was a High School teacher who had a preference for girls who were fourteen or fifteen. My friend was seventeen when they were together, but at least six other girls weren't."

"Wait! Mr. Rodgers, right? The math teacher?"

I hadn't even thought about the fact that Glen had taught in Oak Park and that Jennifer might know him.

"Yes. I suspect you know more than I just told you."

"You mean about him trying to flee to Canada with the baby and the baby's mom?"

"Yes. I was involved, but it's a really long story."

"Did you know they think he slept with two Freshman girls, but both girls denied it, so the police dropped the investigation?"

I couldn't suppress the groan.

"That would fit everything else I know about him from talking to the police," I said. "What's your take?"

"I think they did," Jennifer replied. "I think fourteen is too young, but if he didn't force them and they aren't complaining, is it really anyone else's business?"

"I tend to agree, but the government disagrees vehemently. I also agree fourteen is probably too young, but that's a very private decision that has to be up to each individual."

"That sounds libertarian. What do you think about pot?"

"That it's no different from alcohol or tobacco or caffeine and ought to be legal. I'm not interested in smoking pot or using coke or anything like that, but what other people do ought to be up to them, so long as they aren't hurting someone else. And pretty much anything consensual should be legal.

"The idea that my gay and lesbian friends could be jailed for having sex, despite being consenting adults, is insane, but some states have laws against it. Oh, and technically, in Illinois, fornication is illegal if it's open and notorious, meaning living together is a crime. Think about THAT one! Can you imagine what would happen if they tried to enforce it?"

"The Second American Revolution. That law is still on the books?"

"As crazy as it sounds, yes. There's an adultery statute as well. Supposedly, it hasn't been used in a long time except in a nasty divorce case in the 70s, but the prosecution was dropped after charges were filed."

The waiter brought our soup, and we began eating. We chit-chatted while we ate, sharing stories from High School, though neither of us had much more than a typical High School experience, minus me not going out on dates. We continued after our main dishes arrived and discussed movies we'd seen, concluding we had similar tastes. The same was true for music, though our TV tastes diverged, mostly because I didn't watch much TV.

"Dessert?" I asked once we finished our Alfredo.

"Absolutely! Tiramisu?"

"That sounds good."

We ordered dessert and coffee, and the waiter brought them quickly. The Tiramisu was fantastic, and the coffee was strong. When we finished our dessert, the waiter refilled our coffees and brought the check.

"So, now what?" I asked once I handed over my Amex card.

"We both know where this is going, so we can just cut to the chase!"

I was more than a bit surprised, given this was our first date, but Deanna's observation flashed into my mind — that every girl who laid eyes on me thought about having sex. I was positive that was what Jennifer had just implied, but I decided to temporize a bit.

"Do we both know that?" I asked.

"Seriously? Isn't that the goal of every dating relationship?"

"Ultimately, yes."

"Tell me with a straight face you didn't at least think about it."

"I did."

"Me, too. I mean, if I look at a guy and think I'd never kiss him, let alone go to bed with him, I wouldn't go out with him. I'm not saying that has to happen, but you can't tell me it's not the goal of dating."

"You're right, of course, and I recently said that to someone — several someones, actually. That said, I'm not ready to move into any kind of long-term, committed relationship."

"Talk about a leap!" Jennifer exclaimed. "I suggest going to bed together, and you're thinking of a white picket fence, 2.3 kids, two cars, and a cat! Are you picking out china patterns, too?"

"I'll counter with your same basic argument — isn't that the goal of every dating relationship?"

"Eventually? Sure. But I'm not ready to get married, and I doubt I will be for years. Who knows, maybe you suck in bed, so it won't be an option!"

"Maybe you don't, and so it won't be an option!" I retorted with a grin.

Jennifer laughed, "Nice way to turn that one around! You'll have to take your chances!"

The waiter returned with the credit card and flimsy. I added the tip, totaled the bill, signed the flimsy, and removed and tore up the carbons.

"You have me at a disadvantage," I said with a grin once I'd finished with the check.

"Not my fault you 'let it all hang out'!"

"A reasonable point," I replied. "And I could have closed and locked the door."

"So?"

"I suppose it really does come down to what you're looking for. What I said before is absolutely true — there is no chance I'm going to be in a committed relationship in the near future. And longer term, well, it's complicated, but the bottom line is while I expect to have a long-term, committed relationship at some point, I doubt I'll ever marry."

"Well, that does present a potential problem. May I ask why?"

"Yes, of course," I replied with a smile.

Jennifer rolled her eyes, "Why?"

"Before Keiko died, I committed to being cremated and interred in her family's crypt as husband and wife. My name is already next to hers on a stele, though it indicates I'm still living. Given that, it's hard to see how someone would agree to marry me, given we'd be buried apart, and the implication is that I was still married to Keiko."

Jennifer nodded, "OK, I can see how that would be a concern."

"I'm positive it would be, but not just that. There is also something inside me that says remarrying would somehow replace Keiko in my heart and in my life, and I simply can't do that."

"That sounds definitive," Jennifer observed.

"I can't say with absolute certainty, but I'd say what I described is the most likely outcome. That doesn't mean I wouldn't make a commitment to someone; it just wouldn't be as husband and wife. And that person, whoever she is, would need to accept that my final resting place would be next to Keiko."

"I appreciate you answering the questions," Jennifer said. "Based on what you've said, whatever this would be, I would have to accept it would never end in marriage."

"Never say 'never', but that would be the safest assumption and the most likely outcome. May I ask if you had some particular path in mind?"

"Besides the obvious one?" Jennifer asked with a smirk.

"Yes, besides that!"

"Well, as I said, marriage is probably four or five years down the road, but that doesn't mean not looking for the right guy. You kind of check all the boxes; well, I'm going to assume one of them."

"Mind if I get a peek at the scoresheet?"

"Good-looking, in great shape, a great personality, successful, and could easily support a family. That pretty much checks every box except 'great in bed', which I'm going to assume is true."

"A pretty big assumption."

"From a guy who is pretty big!" Jennifer said lightly. "But I think it's a safe assumption from your confidence to pose nude."

"A reasonable inference, though one that is actually very subjective. It's possible for both of us to be good in bed but not good together."

"How the heck is THAT possible?"

"It's entirely possible our sexualities and libidos are incompatible, and while the mechanics might be good, it wouldn't fulfill our needs. I'm not saying that's the case, simply that it's possible for sex to be extremely pleasurable but unfulfilling. If it's just fucking, then pleasure is what really matters. If it's a long-term, committed relationship, fulfillment, whatever that means to each of us, is far more important."

"An interesting take, and not one I'd have expected to hear from a guy."

"Let's just say I've learned some lessons over the last four years, mainly from having made several mistakes."

"Isn't that what dating is all about?"

"Absolutely. My first girlfriend in Chicago called me a 'starter boyfriend', and she was not wrong!"

"I've dated, but nothing serious. Part of that was my dad, but part was me being picky."

"There's nothing wrong with that at all."

"May I sum up what I drew from this talk?" Jennifer inquired.

"Yes, of course."

"If what I suggested was in the cards were to happen, it would have to be casual. I couldn't count on any specific outcome, and marrying is, for all intents and purposes, ruled out, even in four or five years, when I expect to be ready to seriously consider marriage. The most I could hope for would be a committed relationship, but even then, you'd still consider Keiko to be your wife."

"A reasonable summation," I replied.

"That presents a serious conundrum — I want to go to bed with you, but I also want any guy I'd consider doing that with to at least be open to getting married in three to five years."

"May I make a suggestion?"

"What's that?"

"We go see a movie — I'm OK with Karate Kid or Star Trek III — and we see each other on Saturday, two weeks from today. That way, you have time to think about what you want to do."

"I assume you're interested?"

 
There is more of this chapter...
The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.

 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.


Log In