Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 56: Harsh Truths and a Work In Progress

Coming of Age Sex Story: Chapter 56: Harsh Truths and a Work In Progress - 'Climbing the Ladder' is the story of Jonathan Kane, a young man from rural Ohio, who begins a new life in Chicago in the mailroom of Spurgeon Capital. This is a story in the 'A Well-Lived Life' universe, and provides history and backstory for Spurgeon Capital, the Spurgeon family, the Glass family, the Lundgren family, Anala Subramani, Tom Quinn, and others from the 'A Well-Lived Life' series. The story stands on its own, and does not require reading any other stories in the universe.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Rags To Riches   Workplace  

March 13, 1982, Chicago, Illinois

“Morning,” I said when Phoebe woke up on Saturday morning.

“Morning!” she exclaimed.

“Did you sleep OK?” I asked.

“Absolutely! Just like last time after I was thoroughly, completely, and expertly fucked! And, just like last time, ready to do it again!”

“Four times last night wasn’t enough?” I asked with a grin.

Phoebe laughed, “No! Know what I want for breakfast?”

I chuckled, “I can guess.”

“Lick me while I suck you?”

“Love to!” I declared.

Phoebe turned, straddled my face, and lowered her extremely plump labia to my lips while taking my glans into her mouth. We pleasured each other for about twenty minutes, and Phoebe had two very good orgasms before I came hard in her mouth. After the last spurt, she carefully licked me clean, then turned so we could exchange a sexy French kiss. We got out of bed and I pulled on shorts and a t-shirt so I could make breakfast.

“After we eat, will you fuck me as hard and as long as you can before I go home?”

“I will,” I said. “If you want, you can come with me to the laundromat and grocery shopping, or I can take you to Union Station before that.”

“Spending more time with you is good!” she declared. “Allyson said you guys aren’t really seeing each other at this point.”

“That’s true.”

“I graduate in three months, and I’ll have more freedom. And when I get to Northwestern in August, I’ll have complete freedom, because I’ll be living in the dorms! I really like being fucked by you and I really like sucking you! I want to keep doing that!”

“Full disclosure,” I said. “I’ve been dating Bianca, who you know, and a girl from Loyola, Huifen, who the girls call Hannah. Nothing serious at this point, just casually dating.”

“Allyson mentioned you were dating, but she didn’t say who. What does ‘at this point’ mean?”

“Exactly what it sounds like, I hope,” I replied. “The future is open, and I haven’t made any promises to anyone. That means we could see each other, but right now, and at least for the near future, I’m not going to make any commitments to anyone. My one attempt to do that turned out badly because I didn’t know the person as well as I thought I did.”

“Not Allyson?”

“No. A girl I was seeing before I met Allyson. Basically, we were a couple, but our views on important topics diverged such that it couldn’t work out, so we broke up. In my mind, it’s better to take my time, date casually, and figure out as much as possible before thinking about a commitment.”

“Why buy the cow if you can get the milk for free?”

“Not even close!” I protested, turning from the stove. “In the case of the girl I just mentioned, I wasn’t getting the milk, so to speak, before we were a couple. And sex, or not having sex, had nothing to do with breaking up. It was about church, if you must know.”

“Sorry,” Phoebe said softly. “That was wrong of me to say.”

“Is that how you feel, though? That I’m delaying making a decision so I can get laid with multiple girls?”

Of course, I thought, if I did decide to accept Bianca’s suggestion, I could still get laid with multiple girls, though from a limited, but awesome, group.

“I’m not sure why I said that,” Phoebe replied. “Maybe it’s just how I see things working in High School.”

“That might not be the best measure,” I counseled. “I never went through the whole ‘going steady’ or ‘class ring’ thing. The one relationship I did have kind of just developed out of a close friendship, and we never really discussed it. My ex here in Chicago called me a ‘starter boyfriend’ and I have to say she was right, because I was trying to figure it out as we went along. The mistake, if you will, was not understanding her desire for a church wedding, and what that would entail for someone who was an atheist.”

“Can we forget the past five minutes, please?” she said, her eyes pleading with me.

“Sure,” I replied, turning back to the stove, though I wasn’t sure I could.

To me, the conversation showed that Phoebe wasn’t as mature as Bianca. Huifen was, I believed, even more mature than Bianca. Maturity was part of the problem with Lily, though I didn’t think I needed to reveal that to Phoebe.

“Did I just blow it?” she asked about a minute later.

I turned, smiled, winked, and said, “You did, and it was awesome!”

She laughed softly, “That is NOT what I meant!”

“It’s a learning process for both of us,” I said. “Learning about each other, learning to have a relationship, learning about life. My mom never had a relationship with a guy, and the only actual model I had was my next-door neighbor’s parents. Not living with them meant I didn’t see a lot of the interaction. So I’m basically flying blind here, except for what I’ve learned in the past ten months or so.”

All of that was true, but I kept coming back to the maturity question. Jeri, who was two or three years younger than the other girls, was way more mature than Phoebe, though Jeri was not the right girl for me by any stretch of the imagination. As much as I liked Phoebe, she’d have to mature pretty quickly for her to be a true consideration. I decided the best thing to do was see her again, perhaps in a month, and reassess.

I finished making bacon and scrambled eggs, along with toast and coffee, then sat down with Phoebe to eat. We ate, cleaned up, and then I fulfilled Phoebe’s request. We showered and headed to the laundromat, and followed my usual practice of doing my shopping while my clothes were in the dryer. When we returned to the apartment, I put away the groceries and clean laundry, then I walked with Phoebe to the L so we could go to Union Station.

“Are you going to call me again?” she asked hopefully when we arrived at the doors to the platform where her train was waiting.

“Yes,” I said. “I’m busy for a few weeks, but I’ll call and we can arrange another date, if that’s what you want.”

“It is!”

We exchanged a quick kiss, then she walked down the platform and boarded the train. Once she was safely aboard, I realized that I could walk home in about the same time as it would take to get to the L, wait for a train, and then walk home. I walked quickly and arrived about twenty minutes before I expected James to arrive. I showered, dressed, and ate an apple, then watched for James. When he arrived, I grabbed my bag and went down to the car.

“Hi!” Jeri exclaimed when I was shown into the great room twenty minutes later.

“Hi!”

“I hope you still have some energy after your date!”

“I do,” I chuckled.

“Do you need something to eat?”

“Just you?” I chuckled.

Jeri laughed, jumped up, took my hand, and led me up to her room, where I feasted on her, and she on me, before we did our best to fuck each other unconscious.

“You’re really going to stop having sex after Monday morning?” I asked when she moved on top of me and rested her chin on her forearm.

“A tactical decision,” she replied.

“Playing the shy, innocent virgin to gain some advantage?”

“Yes,” she said, laughing. “You’re on to me!”

“Let’s just say at this point, with me, you’re pretty much transparent.”

“So you think you have me figured out?”

“I think you’ve made it clear that you’ll use every resource available to gain what you want.”

“As will you,” Jeri said. “It’s only a matter of what you and I consider resources.”

“Except,” I said carefully, “I don’t believe in manipulation or coercion.”

“I call ‘bullshit’! You do things to get people to do what you want just as I do!”

“There’s a difference between negotiation and manipulation,” I replied. “I think, sometimes, they might even look the same, but it’s the intent and the outcome. You want to win, as it were, and deny the other person an equitable outcome. You tried that on me, and I actually let you get away with it at first. May I make an observation?”

“Sure.”

“If you had tried being sweet and sexy, not only would you likely have convinced me to go to bed with you, but I probably would have considered an actual relationship with you. The sex is awesome, our overall goals are similar, and we’re totally compatible. The manipulation killed any chance of that.”

She frowned and was quiet for a moment.

“That’s not me,” she replied.

“But it could be,” I replied. “We can’t go back and change the past, and to be honest, there would always be some doubt in my mind, but you certainly can do it in the future. When you decide you’re ready for a relationship, try it my way. I think it’ll work out far better.”

Jeri shook her head, “I think that’s for people who believe in love and romance and all the bullshit in the novels I read.”

“If you don’t believe it, why read them?”

“Amusement. Don’t you do things that entertain you but have no intrinsic value?”

“Actually, not very often. Growing up I had little time for entertainment, and while I occasionally go to movies, most of what I do has a reason — bettering myself, whether that’s intellectually, financially, physically, emotionally, or whatever. But not at the expense of another person.”

“You’ll be taken advantage of with an attitude like that.”

“The way you did?” I asked with an arched eyebrow. “At least until I caught on and figured it out.”

“And now?”

“This is to our mutual benefit, with mutual satisfaction, both in bed and in business. But only because I upended your plan.”

“Why are you being so hostile?”

“Remember my desire to have people speak bluntly to me and say clearly what they want? That’s who I am. Fundamentally, I don’t have any patience for what my friend Bev’s mom called ‘embroidery’. Say what you mean, mean what you say. Give your word and keep it. Work hard, care for your friends, and be kind to everyone.”

“Like now?” she asked skeptically.

“I am being kind by telling you the truth. Perhaps nobody has spoken to you plainly, the way I am now, and I suspect they haven’t and THAT is your problem. Well, I told you.”

“You did. Now what?”

“I intend to fuck your brains out for the next two days, then reset our relationship to purely business, where we both gain relatively equal value from the relationship. If that isn’t OK with you, have James take me home right now. And by ‘OK’, I mean you do not even THINK about trying to manipulate me, ever. If you do, I’ll return your money and walk away.”

“You realize I could crush you, right?”

“You probably could. And I’ll find a way to start over. I mean, I had nothing when I came to Chicago except a small amount of money in my pocket and a few changes of clothes. You see, you can’t hurt me, at least not the way you mean. YOU losing everything would ruin your life; me losing everything would simply put me back to square one, but I’d still have my integrity and work ethic. It’s your call what happens now, but the relationship is going to be exactly as I’ve defined it.”

“I didn’t realize you were like this.”

“You mistook naïveté and inexperience for weakness; they’re actually strengths.”

“Huh?”

“There is much to be said for being a ‘self-made man’ and I get to make myself. You, on the other hand, were made by your mom and the circles in which you travel. In a sense, you couldn’t do what I said before — be sweet and try for a relationship — because you didn’t know how and had no way to learn unless you could throw off sixteen years of what amounts to brainwashing or conditioning.”

“I think I seriously underestimated you,” Jeri said thoughtfully.

“I think you did, too. And, going back to what I said earlier, you missed a chance.”

“You are awfully full of yourself!”

“It’s not about ME,” I replied. “It’s about YOU! What I’m trying to say is that I am positive that inside Jeri Lundgren is a wonderful young woman, if only she were allowed to show her face. That young woman would be desirable beyond just someone to fuck because she has a nice body and is willing to do anything I ask in bed.”

“But not the other way around.”

“You have to recognize that other people have limits, and accept those limits. That’s part of having a good, equal relationship. I’m no expert, and I’ve screwed up twice with regard to relationships — once back home and once here. But I’m learning from my mistakes, and I won’t make the same mistake twice. You, on the other hand, don’t think you CAN make a mistake. Well, you’re wrong, because you did, with me.”

“And yet I got what I wanted.”

“What you SAY you wanted, and maybe what you THINK you wanted, but I wouldn’t be so sure about that. I mean, sure, it’s possible that the true Jeri Lundgren is a selfish bitch who doesn’t care about anything except her own gain, but I don’t think so.”

“I don’t think you understand.”

“Actually, I do. I’m not religious at all, but one phrase I’ve heard before that I think rings true is that the love of money is the root of all kinds of evil.”

“You love money as much as I do!”

“And there you’re mistaken. It’s a means to an end, not an end in and of itself. Money, in and of itself, is neutral. How you use it is what determines good or evil. You see money as power, plain and simple. I see money as one tool among many. Love is just as powerful, and probably more important in the long run.”

“Bullshit!” Jeri said.

“And that response shows our fundamental disconnect. It’s why we can fuck for fun and do business, but I could never have a romantic relationship with you.”

“It’s as bullshit in real life as it is in the books I read.”

“You’re mistaken again,” I replied. “But I don’t think I could convince you of that any more than a Catholic girl I know could convince me that there is a god. So, fucking and finance. Your call if I leave now or stay until Monday morning.”

“You’d seriously give up two days of what you’ve said is great sex?”

“It’s your call, Jeri. You promise to never try to manipulate me, ever again, or I leave. And you better mean it, because I wasn’t kidding about walking away forever.”

She lay quietly for several minutes before she responded.

“Stay. Fuck my brains out.”

“Your wish is my command!”

March 15, 1982, Chicago, Illinois

Jeri and I had one last fuck in the shower, standing up, with her back against the tile on the wall and her legs wrapped around my waist. Because of that, we had to hurriedly dress and eat, so that she wasn’t late for school and I wasn’t late for work. We went out to the car, and Jeri had James raise the privacy shield when he got into the driver’s seat.

“How do you see this working in the future?” she asked.

“As I said, no changes, except we stop having sex. More than likely, I’m going to ask one of the two girls I’m seeing to move in with me when I move to a new apartment. And I really don’t want to have to hide our relationship from either of them.”

“Dinner once a month? My treat, at any place you can name?”

“That would work. I assume you’re going to continue to keep your parents in the dark?”

“Other than you being a friend? Yes, of course. So long as Mom doesn’t think I’ve given it up to a commoner, she won’t care if we’re friends.”

“Do YOU feel that way?”

“Does it matter?” Jeri asked. “It was just sex. It doesn’t have to mean anything. I am positive you’ve fucked other girls just to fuck.”

“Except you DO assign it meaning,” I replied. “It was part of the business transaction, and as such, it did have value beyond physical pleasure. And I honestly don’t think you’re as emotionless as you represent yourself to be.”

“You’re wrong about that,” Jeri said firmly.

“I don’t think so.”

“My world is so different, that I don’t think you understand.”

“I could say the same exact thing!” I countered.

“You’ll see once you have the kind of money I expect you to have.”

“And the day it corrupts me is the day I go back to work at the lumber yard. I’d rather be poor than live in the world you live in.”

“We’ll see.”

“Yes, we will.”

We dropped Jeri at school, and then I asked James to swing by the apartment so I could leave my bag before he drove me to the Hancock Building. When we arrived, he drove to the loading dock where he let me out right by the freight elevators.

“Thanks, James,” I said. “I appreciate it.”

“You’re welcome, Sir! See you next time!”

The ‘next time’ would be a business dinner, not spending the night together, but I fully expected James to drive us to whatever restaurants I chose for our dinners.

“Have a great day,” I said.

“You, too, Sir.”

He got back into the car, and I pressed the button to call the elevator. When I got in, I used my key to access the 30th floor, the doors closed, and the elevator surged upwards.

“Kane!” Mr. Nelson bellowed as I walked past his office.

“Yes, Boss?” I asked, sticking my head in through the door.

“I have a memo that needs to be on every desk immediately.”

“Let me get my jacket and badge, and I’ll get right on it.”

“Don’t bother with your cart; that just makes it take longer.”

“On it, Boss!”

I quickly went to the break room, hung my windbreaker and baseball cap in my locker, put on my jacket and ID, then put the lunch Karolin had made for me in the fridge. I went back to Mr. Nelson’s office, where he handed me a stack of memos. I hurried to the freight elevator and rode up to 32, then began distributing the memos. I took the opportunity to read it, about a sentence at a time, as I put one on each desk, or handed it to the individual if they were in their office.

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