Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 22: Obstacles

Coming of Age Sex Story: Chapter 22: Obstacles - '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  

October 19, 1981, Chicago, Illinois

My lunch with Rachel had depressed me a bit, but it had also made me think about how I’d left things with Anala the night before. By quitting time, I’d decided to stop at the Mandel Building which was about ten blocks south of the Hancock Building on Michigan Avenue, and was on my way home. I rode the mile or so, locked my bike outside the building, and went inside.

“I’m looking for a book,” I said to the clerk at the desk, a woman who was probably about fifty.

“You’ll have to be a bit more specific,” she said with a smile. “We have a few hundred thousand books here.”

The Art of War by a Chinese general,” I said.

“Sun Tzu,” she replied. “You’ll find that in the 350s. Do you know how the Dewey Decimal System works?”

I nodded, “From High School. How do I get a Library card?”

“Do you live in Chicago and have a driver’s license?”

“Yes.”

“Then it’s just a matter of filling out a form and we’ll issue you a card today. Let me show you how to find the correct shelves.”

She picked up a map from the counter, circled the shelves, and directed me to them. I easily found them, and after a minute of searching, found the book on the shelf. I followed the signs to the desk where I’d check out the book. It took less than ten minutes to have my card issued, have the book stamped with a return date, and walk outside to my bike. With the book safely in my satchel, I headed home.

At home I saw Lily in the window, waved to her, put my bike away, then went up to my apartment over the garage. I took a quick shower and started making dinner, and wasn’t surprised by a knock at the door.

“Hi!” Lily said. “Mom said I could come up and say hi! I’ll take a kiss if you have one!”

I nodded, took her in my arms and kissed her deeply.

“I like that greeting!” I said when we broke the kiss, though I kept her in my arms.

“I need to get back to the house for dinner. What are you doing tonight?”

“Reading,” I replied. “Someone recommended a book called The Art of War and said I could apply it to business.”

“War and business?”

“Supposedly it’s Chinese philosophy that works for both. I didn’t buy it — I checked it out from the library, so if it’s no good, all I did was waste about twenty minutes getting it.”

“OK. I need to run. I do not want my parents uptight about us! I’m looking forward to Wednesday dinner and our date on Friday!”

“Me, too!”

We kissed again, she slipped from my arms, and left the apartment. I finished making dinner, ate, and after I cleaned up I pulled out the book. The first chapter, in fact, the first few paragraphs, showed that Anala had been correct.

Command is a matter of wisdom, integrity, humanity, courage and discipline.
All regulation entails organizational effectiveness, a chain of command, and a structure for logistical support.

As I read further, I saw more and more how the advice in the book could be applied to my life, and it dawned on me that I might have been too harsh on Anala.

October 21, 1981, Chicago, Illinois

“Hiring forms for Norman Monroe and an Emily Coghlan,” Mr. Nelson said, coming into the mailroom on Wednesday afternoon. “Looks like you called it, Kane!”

“Thanks, Boss! The other name is the receptionist. A smoking-hot redhead.”

“She’s going to be his secretary, according to Personnel. Monroe will be in the empty office on 31 next to Nichols.”

“Not on 32?” I asked.

“New blood almost never starts on the top floor. But you can be sure Matheson will do his best to get his guy up there as soon as possible. Monroe starts Monday, so we should have no trouble. I already called for the trading terminal, which willl be set up tomorrow. Foulkes, make sure the office and the secretary’s desk are stocked with supplies.”

“Yes, Boss!” Harry replied.

“Kane, I gave the terminal installers your name. I’m out tomorrow.”

“I’ll make sure everything is working before they leave.”

“Good.”

He left and Nick called me over and handed me a stack of memos to deliver.

“Green eyes?” he asked.

“Yes.”

“If only...”

“Yeah,” I agreed, “if only we made six figures base and more than that in bonus!”

“What are you complaining about? You have that cute secretary you eat with almost every day!”

“Guess who’s a sucker for redheads!”

“Aren’t we all!” Nick laughed.

I looked at the memos which announced the Christmas party, and was surprised that everyone was invited and that everyone could bring a spouse or boyfriend or girlfriend. It was being held in the restaurant at the top of the Hancock Building on December 18th, which was a Friday. I made a mental note to ask Lily, or rather, ask her parents. Even though she was eighteen, I didn’t want to do anything which might upset them, given where I was living.

When I made my afternoon rounds, Sharon smiled at me, licked her lips, and made it very obvious she was interested in getting together. I’d need to find a way to talk to her outside the office and let her know I had a steady girlfriend. Rachel smiled at me as she always did, but I was sure I detected sadness in her eyes, but there really was nothing I could do about it.

At the end of the day, I left the second the clock showed 5:00pm and rode home as quickly as possible so I could shower before my dinner with Lily. She was waiting on the steps for me and when I mentioned I was going to shower, she giggled and followed me up to the apartment. I really enjoyed the shower, even though we didn’t actually fool around. I also enjoyed working together on dinner, and after we ate, we cleaned up, then got into bed.

“I wish we could do this more than once a week,” Lily said as she gently rode me.

“Let’s not upset your parents,” I replied.

“I thought about asking them if I could move up here, but decided that was a bad idea. To ask, I mean. Maybe once I graduate from High School.”

“Uhm, won’t that make it clear...”

Lily laughed softly and squeezed her muscles, “That we’re screwing? Yeah!”

“Your dad doesn’t seem like he’d approve.”

“He won’t,” Lily sighed, leaning down so we could kiss.

As our tongues danced, Lily ground against me, squeezing her muscles around my dick, and after about a minute moaned softly into my mouth. She gave herself a second orgasm then began moving more forcefully back and forth and up and down until I groaned and came hard. Lily continued moving until my orgasm passed, then stretched out on top of me.

“How is your book?” she asked a few minutes later.

“Interesting,” I said. “And I think the advice will be useful.”

“Such as?”

Opportunities multiply as they are seized.

“So like what you’re trying to do?”

“Yes. If I don’t seize an opportunity when it presents itself, I may never get another. But each one I seize opens up more possibilities. He also wrote ‘Ponder and deliberate before you make a move’.”

“So like your studying?” Lily asked.

“Yes. Or my relationship with you. I thought a lot about it before I asked you to go steady.”

“Wondering if I was worth it?”

“More like wondering if I could be a good boyfriend.”

“For a rookie, I think you’re doing a good job! Though you obviously weren’t a rookie at sex!”

I chuckled, “You knew that because of Teresa!”

“Your first time was the girl back home, right? The one you were never steady with?”

“Yes.”

“Will you see her when you go home at Christmas?”

“Probably. She lives next door to my mom. And there’s nothing to worry about — she found a steady boyfriend as soon as I left. And even if she hadn’t, I do know the most important rule!”

Lily laughed, “You do, and I trust you.”

“Speaking of Christmas, Spurgeon Capital has a Christmas Party on the 18th of December and I’m allowed, well, actually, encouraged, to bring a date. Would you like to go?”

“Yes!”

“I’ll ask your dad, just to be safe.”

“Unfortunately, that’s probably a good idea. What are we doing on Friday?”

“Whatever you want,” I replied.

She wiggled her hips and ground against me.

“I wish!” she exclaimed. “Dinner and a movie is probably the best we can do. How about Chariots of Fire? It’s supposed to be really good.”

“What’s it about?”

“About two British guys who are trying to compete in the 1924 Olympics.”

“I’m game,” I replied.

“We could see something else if you wanted.”

“No, it’s fine. I’ve seen so few movies except old ones on TV that I couldn’t really tell you what I like and don’t like. But I do know one thing I like!”

“Sex!” Lily giggled. “Ready to go again!”

“Absolutely!”

Lily moved so I could be on top, and after sucking on her nipples for a bit, I gently slid into her silky pussy and we began fucking, slowly increasing our tempo. Lily had two good orgasms before we shared her third, kissing furiously as I pumped her full of cum.

“One day,” she sighed as we got out of bed, “I want to sleep in your arms.”

“I’d like that, too,” I said as I led Lily to the shower.

Twenty minutes later I walked her to the door of her house, we kissed, and I went back up to my apartment to read for an hour before bed.

October 22, 1981, Chicago, Illinois

On Thursday evening after dinner I picked up the phone and dialed Anala’s number.

“I owe you an apology,” I said after I greeted her.

“For?”

“The way I left when we had coffee.”

“Religion seems to really bother you.”

“I’ve never had a use for it, nor do I think it makes sense, and it feels like every time I turn around, it’s there. I guess I didn’t realize because back home I never really spent time with anyone who went to church.”

“You only had a few friends right?”

“Yes. And Bev was the one I spent the most time with by far. May I be honest?”

“Of course.”

“I enjoy talking to you, but I don’t enjoy talking about religion.”

“What about philosophy?”

“I read the book you suggested — The Art of War.”

“And?”

“It has some good advice which I think I can apply to my life. And honestly, that’s what I want to focus on — how to give myself the best chance for success, without resorting to magic incantations, magic lamps, or magic beings.”

“You never went to church?”

“One funeral, when I was ten, for the husband of one of my mom’s friends. He was in the Army and died in Vietnam. And my mom read Bible stories to me when I was little, but she quit around the time I was five or six, and basically never mentioned it to me again. And I’m fine with that, seriously.”

“You don’t think there are things to learn?”

“If the lessons are so important, they’ll be pretty obvious without some god being involved. I don’t need a god to tell me to be nice, especially if he’s going to torture me forever in hot lava if I curse using his name or have sex or pick the wrong god to pray to or whatever!”

“Didn’t you say your girlfriend goes to church?”

“Sure, but she doesn’t talk about it, beyond what I said, and offered a compromise I can live with. And it’s not like I’m getting married tomorrow! If I see bad signs, I’ll have a chance to deal with them. For now, at least, Lily is good company and we enjoy our time together. What happens in the future, well, I’ll worry about it then. The only thing I’m worrying about right now is ensuring I get promoted next Summer and making sure I learn everything I can about the markets.”

“You seem very focused on your goal.”

“I told you about my life, and I was given a chance to change it. I’m going to do that one way or the other. I’m not going to blow this chance.”

“And nothing else matters?”

“Not right now. I remember hearing a song on the radio...

They say there’s a heaven for those who will wait
Some say it’s better but I say it ain’t
I’d rather laugh with the sinners than cry with the saints
The sinners are much more fun

... that pretty much sums things up.”

“You have a lovely singing voice.”

“Thanks. I used to sing along with the radio while I was working. Of course, mostly it was bad transistor radios, so I can’t say I’m getting it right. I did have some tapes Bev made for me that I could play in a cassette recorder, too.”

“I suppose I can understand your point. What you’re trying to do would never be possible in India.”

“Then it’s a good thing I’m not in India! May I ask a question?”

“Sure.”

“Why are you so determined to talk to me?”

“I told you — I like meeting people and making friends. You approached me, and that intrigued me. And when I spoke to you further, you seemed intelligent and interesting. I like intelligent, interesting people. Perhaps we can have lunch once a month and coffee once a month. I promise to be careful about talking about religion. What do you have to lose?”

“My sanity?”

Anala laughed, “Nice. But given where you’re working and what you intend for a career, I think that might happen anyway.”

“No,” I said, shaking my head, even though she couldn’t see it. “I’m not like most of the guys who work there, and I never will be.”

“If that’s your goal, then you need friends like me more than you think you do.”

“Why?”

“To help you resist the impossible pressure to ‘fit in’. Huge sums of money have a way of corrupting even the best men. I wonder if you can even understand the risk?”

“What risk? That I become an asshole? Why? Jonathan Kane with money is the same as Jonathan Kane without money, except he has the things he wants from life.”

“I can’t imagine you’re that naïve.”

“Do you really think I can forget what it was like growing up?”

“You wouldn’t be the first. Let’s have coffee next week. Would Tuesday work?”

“Sure. 7:30pm?”

“That’s fine. See you then.”

October 25, 1981, Chicago, Illinois

“Hi, Jonathan,” Jeri said when I arrived at Uncle Alec’s townhouse on Sunday afternoon.

“Hi,” I replied. “I’m almost afraid to ask, but where’s my cousin?”

“She’s at Natalie’s. They’ll be here in fifteen minutes. You can stay and talk with me.”

Jeri was cute, and was being nice, and my aunt had said she was very shy and quiet. It couldn’t possibly hurt me to be nice and talk to her, Lisa be damned. I sat down on the couch.

“Jonathan, did you want a Coke?” Aunt Wendy asked.

“Yes, please.”

She left and came back with a Coke a minute later.

“Where do you go to school?” I asked.

“Maria. It’s an all-girls Catholic school. What High School did you go to?”

“Goshen. It’s east of Cincinnati.”

“And you moved here to work?”

“Yes.”

“What do your parents do?”

“My mom is an office worker; my dad died after I was conceived but before I was born.”

“I’m so sorry!”

“It’s OK. I never knew him, obviously. What do your parents do?”

“My mom runs our family foundation, and my dad helps her.”

“Foundation?”

“Basically a charitable organization. My grandparents made a lot of money and started the Lundgren Foundation to try to help people. My mom does fundraisers to increase the money they have and decides who to help.”

“Like?”

“Mostly liberal organizations.”

“I don’t know much about politics.”

“Groups like the Sierra Club who are concerned about the environment.”

“Is it rude to ask how much money?”

“A few hundred million.”

“Whoa!”

“And I’m supposed to take over from my mom.”

“Do you want to?”

Jeri looked around then whispered, “No! I want to study computers and that’s what I want for a career.”

“So do it, then,” I replied.

“My mom will have a fit if she finds out.”

“I promise not to say anything to anyone.”

“What are your plans?”

“To find my way to the 32nd floor with the top traders, brokers, and money managers.”

I heard the front door open and a few seconds later Lisa came into the room.

“Stay away from my friends!” Lisa growled.

“Well, hello to you, too.” I said.

“If you think you’re going to get any of us, you’re insane!”

“Lisa Catherine!” Aunt Wendy exclaimed, coming into the room.

I didn’t wait for things to unfold. I got up and went into the kitchen and sat down at the table. Aunt Wendy reprimanded Lisa who I was sure was rolling her eyes. A minute later, Aunt Wendy came into the kitchen.

“I’m sorry, Jonathan.”

I shrugged, “It’s no big deal. I have a steady girlfriend and like I told you, Natalie and Jeri are too young. Lisa, well ... I just ignore her.”

“That’s probably for the best, but it doesn’t excuse her behavior.”

“Jonathan?” Jeri said quietly from the door to the kitchen.

“Yes?”

“I’m sorry.”

“You didn’t do anything wrong,” I replied. “Thanks for talking to me before.”

“You’re welcome,” she said, and left.

“She likes you,” Wendy said quietly. “She barely says two words to most people. Her parents are very domineering.”

“So the opposite of Uncle Alec?” I asked.

Wendy nodded, “A happy medium would be better in both cases, I think. I’m curious, and you don’t have to answer, but how much freedom did Linda give you growing up?”

“Infinite, I suppose. I could do whatever I wanted and go wherever I wanted. Of course, I started working basically full-time at fifteen, and before that I had done odd jobs to help make ends meet. So I really never had any time or money to get into trouble and the freedom didn’t much matter.”

“And now?”

“I’m focused on work and figuring out how to be a good boyfriend to Lily.”

Aunt Wendy laughed, “Usually easier said than done!”

“She says she’s ‘low maintenance’ and so far I have to agree. We have dinner together on Wednesdays and go out on Fridays. On Saturdays she usually goes grocery shopping with me and hangs out while I do my laundry. She seems happy and I’m happy. So I guess, so far, so good.”

“I think you’re balancing things quite well. Want to help with dinner?”

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