Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 45: Lifestyles of the Rich and Famous

Coming of Age Sex Story: Chapter 45: Lifestyles of the Rich and Famous - '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  

January 29, 1982, Chicago, Illinois

"Good evening, Mr. Kane," James said when he came to the door of the apartment. "Miss Lundgren sent me for you."

"Then let's go," I replied.

"May I take your bag, sir?" he asked.

The whole chauffeur and manservant thing was not something I appreciated, though I knew he had a job to do, just as I had mine in the mailroom. I was perfectly OK with carrying my bag and doing all the other things Jeri's servants did for her. But I didn't want to disrespect James, so I handed him my bag. He carried it to the car, and after he opened the door for me to get into the back seat, he placed the bag in the front passenger seat, then walked around to the driver's side and got in.

Fifteen minutes later, we arrived at Jeri's house, and it did not surprise me when James walked with me to the door and handed my bag directly to the butler when he answered the door. I thanked him, he left, and the butler, Karl, stood aside so I could come into the foyer.

"Good evening, Mr. Kane," he said. "Miss Jeri is in the great room."

"Thank you," I replied.

"Shall I take your bag upstairs?" Karl inquired.

"Yes, please."

He walked me to the great room and announced me, which I felt was silly, and Jeri hopped up to give me a hug and kiss on the cheek.

"I don't know if I could get used to someone waiting on me like that," I said. "What's wrong with me just walking in and saying 'hi'?"

"This is how it's done," Jeri replied. "It's what I've known since I was little, so it's normal and automatic, like breathing."

"It seems ... oppressive, I guess. I mean, could you make dinner yourself? Or get a drink from the fridge?"

"I could, but why would I want to?"

"I guess for me, doing that is normal, though it takes a bit more effort than breathing! Will they be here all weekend?"

"They have Saturday off, from 9:00am until 9:00am on Sunday. They usually spend that in their townhome in Wrigleyville."

"The whole thing is very strange," I replied.

"Different worlds. Someday, you'll have the resources to live this way, if you choose."

"I doubt I will," I replied. "Live this way, I mean."

"Dinner is in about fifteen minutes. Come sit with me."

I sat down next to her, she drew up her legs onto the couch, and leaned against me, so I put my arm around her shoulders.

"How was your week?" she asked.

"Good. My boss had some heart problems, so things are a bit different at work. He'll be back late next week, as they don't think it's anything serious. On the plus side, I get a bump in pay for acting as the supervisor for the time he's away, and my supervisor is filling in for the boss."

"Cool."

"Oh, before I forget, I have a report for you on the investments. I'll send one to you each month."

"How do you prepare those?"

"By hand on graph paper, using a calculator. Why?"

"Just curious. Is there a specific time you need to be home on Sunday?"

"Not really. I just need a few hours to review my textbook."

"How is your class going?"

"Great. I've had A's on my homework and quizzes. Some of it is review from the study material I have from Spurgeon, which makes it easier. What about you?"

"High School is pretty easy. I've had straight A's since first grade. Have you talked to your uncle recently?"

"Not in a couple of weeks. They did invite me for dinner the week after next, but I'll be in Ohio. Why?"

"Natalie is pregnant," Jeri said.

"Oops."

"Yeah. She's like four months along and she's going to have the baby."

"She's fifteen, right?"

"Yes. Her sixteenth birthday is in late July. She's due the week before her birthday."

"I take it her parents didn't freak out?"

"Oh, they did, but not quite as bad as your grandparents, from what you said happened to your mom."

"I'm almost afraid to ask what Lisa's reaction was."

"That Natalie was stupid to not go on the Pill and even more stupid for not having an abortion."

"That sounds like Lisa," I replied.

"Lisa also thought Natalie was stupid for giving it to a High School kid rather than someone who would have showered her with gifts."

"You haven't revealed anything, have you?

"No way! Nobody but you and I know, and I'm keeping it that way."

"Karl and Karolin?"

"Black holes, as I said. Servants who would reveal a secret would lose their jobs in a second and never, ever be hired again. The same with James."

"Doesn't he keep logs?"

"Sure, but the company keeps those totally private. I have my own account now, so nobody can see my logs."

"That's an awful lot of trust."

"When your livelihood depends on discretion, there's no upside to violating it. Trust me, I could invite a dozen girls here and have a lesbian orgy in the great room, and my parents would never, ever know."

"Is that something you would actually do?" I asked.

"No way! I was trying for the most outrageous thing I could think of!"

"Miss Jeri, dinner is served," Karl announced.

"Thank you, Karl," Jeri said.

We went to the dining room and Karl and Karolin served us, basically waiting on us hand and foot. The food was excellent, and when we finished, Jeri invited me to the backyard where the Lundgrens had a hot tub, which was heated and illuminated.

"The fence is high enough we can just undress and get in," she said. There are robes for when we get out."

"It's like 30°F!" I protested.

"And the water is really warm, and once we're in the tub, the air above the water will be plenty warm. Strip!"

I laughed and did, and it was COLD, cold enough so I shriveled! I quickly followed Jeri into the tub, which was very warm, and she was correct about the air being plenty warm above my exposed shoulders.

"I bet you never fooled around in a hot tub," she said, sliding along the seat so our bodies touched.

"You bet correctly," I said. "I've been in a Jacuzzi, but never a hot tub, and never outside."

"Then we'll both do it for the first time," she said, moving her hand to grasp my flaccid dick.

Jeri turned her head for a French kiss and she stroked me until I was hard, then had me scoot forward on the seat, straddled me with her legs behind my back, then lowered herself slowly onto my erection. She moaned softly several times, and when I was fully inside her, she put her head on my shoulder and began grinding.

"God, this feels SO good," she moaned, moving her shoulders so her erect nipples rubbed my chest as she continued to grind her mons against my pubic bone.

She felt good, but she wasn't as slick as when we'd done it in her bed, and I wondered if the hot water had something to do with it. I just let her grind and she gave herself three really wonderful orgasms before she started moving more forcefully, but only back and forth, not up and down. She was plenty tight and squeezed her muscles, which worked perfectly to bring me off. When the first jet of cum spurted into her, Jeri lifted her head for a searing French kiss and two spurts later, she came for the fourth time, groaning into my mouth.

"That was awesome," Jeri breathed, resting her head on my shoulder again. "We don't have to be up any specific time tomorrow, so I want to fool around all night, then tomorrow afternoon do it in front of the fire. In fact, once we get up, I want to stay naked until Sunday!"

"Any particular reason why?"

"Just because I think it'll be fun! If you're up for it, you could fuck me on the dining room table!"

"Seriously?"

"Sure! I want to play around with you as much as possible before you decide to be exclusive with someone! I'm a horny teenage girl, and I can only see you once every five or six weeks when my parents are away."

"And after that happens?"

"We'll see. I have my public persona to maintain."

"And that's worth not having sex?" I asked.

"Yes."

I totally didn't get it, but I was sure there was some method to her madness. To me, it would have made sense to change my public persona, but obviously, she decided that acting shy and introverted was a better plan, though I wondered why she hadn't been that way with me. She'd claimed to be OK one-on-one, but it felt like there was more to it.

"Are you really shy?" I asked. "Or is it a complete act so you can manipulate your parents and others?"

Jeri lifted her head and looked directly into my eyes, answering the question for me without words, before she spoke.

"Promise to never, ever reveal what I'm about to tell you?"

"Yes."

"And promise not to get angry with me?"

"That you manipulated me? I knew that, but went with it because the arrangement you offered worked for me. I could have said 'no' at any point."

Jeri nodded and said, "You'll go far! So no, I'm not shy at all. Not even a little bit. But, it works to keep people away from me who I don't want around, and means my parents don't pressure me too much about getting together with one of the society guys who are a few years older. I'm so totally not interested in them, or, for that matter, the older guys.

"What I am interested in is someone who will do what I want, when I want, how I want. Lisa told me about you and, here's where you might be upset, I decided you were perfect for what I wanted to do. It was just a matter of getting you into my bed, which was more difficult than I expected. But you saw the advantage of a relationship with me, and chose to accept the partnership I was offering. In one sense, all it cost me was all three of my cherries, and now you'll work with me for the rest of our lives, and I know I can trust you completely."

"And if I ever say 'no' to you?"

"I'm sure it'll happen, but you'll have a perfectly valid reason. But, as I said, you cannot say anything to anyone, because if it gets out that I'm a manipulative bitch, which I am, it'll make it impossible for me to get away from my mom, which is what I really want."

"And here I thought Lisa was the most manipulative person I knew."

"Ha! Not even close! The difference is, I'm nice once I get what I want. She's not! The day she gives up her cherry, she'll become an even bigger bitch to the guy who got it because he'll want her again and she'll make him really work for it."

"She's not even thirteen," I protested.

"And spoiled rotten."

"That's rich, coming from you!"

"Actually, I'm not spoiled the way Lisa is. Your uncle lets her get away with murder, hell, I suspect he'd literally let her get away with murder. My parents set pretty firm rules and I'm breaking them right now. No guys in the house when they're away."

"I say again, that's some serious trust you're putting in Karl and Karolin."

"And it's not misplaced. They know the code, so to speak. Heck, we could go in and fuck on the rug in front of the fireplace, and if one of them came in, they'd ask if I needed anything, I'd say 'no', and they would leave as if nothing was happening."

"I truly find that hard to believe."

"Trained butlers, and there are schools for them, are masters of discretion. They have been for centuries, and if you look at history, it wasn't strange to have a butler or maid, or in Roman times, slaves witness their bosses or masters having sex. And think about this, most people lived in small, one-room houses. Kids would see their parents have sex. It's only in modern times that we've become so private about it."

I wondered what she'd say about what had happened the previous weekend, but I wasn't going to reveal any confidences. Allyson had obviously spoken to Kristy, but that didn't surprise me, and it really was Allyson's business what she told her friends.

"Interesting. Do you plan to manipulate me for the rest of our relationship?"

"I won't need to! I got you where I needed you, and then you saw the wisdom of a business relationship that also involved fucking a sixteen-year-old virgin! From now on, it's business."

"And sex is a commodity to be traded, right?"

"Exactly! And I clearly judged correctly that first day, though I did get more than I bargained for! You're VERY well endowed."

"You decided that first time we met to seduce me and manipulate me into a relationship?"

"Yes. Your Uncle was absolutely convinced that you were going to be very successful, and my timeline is college graduation, so I wanted someone a bit closer to my age, but who was going to be very successful, to be a partner in crime, so to speak. Well, minus committing any actual felonies!"

"You mean besides having sex with an underage girl?"

"Actually, once I turned sixteen, they'd never prosecute anyone who was under twenty. The law has some exceptions for being close in age, and it would be nearly impossible to get a conviction if they tried, which they wouldn't. Not to mention, I'd have to complain, which I won't. Now, someone like Noel Spurgeon who has a thing for fifteen-year-olds, they might bust, but he'd buy his way out of it."

"How did you know I wouldn't become angry about being manipulated?"

"I didn't know for sure, but I figured I could smooth it over. The thing is, anyone who wants to make it as a trader has to be willing to take advantage of anyone and anything, pushing it right to the limit. If you don't, you get beat."

Which was basically what Murray Matheson had said when we discussed the yen trade he'd executed. He'd found an advantage and used it to make a very nice profit. Some would, I was sure, say he exploited the system. I didn't see it that way. He followed the rules and when presented with an opportunity, he seized it without thinking about it beyond making money. Pure capitalism at its finest. And that, actually, was what Jeri had done. She'd seen an opportunity, made an offer, and I'd accepted, because, in the end, it worked to my advantage to have extra money to run. The more money, the more opportunities I'd have, and she was basically doubling what I had to play with, and I also got to play with her!

"Pure capitalism," I said. "With sex as a commodity as we said before."

"Exactly. Lisa, if she were to ever find out, would suggest the price I demanded for my cherries wasn't high enough; I obviously disagree."

"Well, I've learned a few lessons from you and because of you, so the transaction was worth it!"

"You're referring to everything other than sex, obviously."

"Yes."

"Shall we get out and go watch a movie? We have quite a few tapes."

"Sure."

We got out of the tub, put on the long white robes, gathered our clothes, and went into the house. Jeri led me to the den, which had a cozy couch and a pair of recliners in front of a huge 35" color television with a videotape player.

"Have you ever seen M✶A✶S✶H?" she asked.

"The TV show? A few episodes. Why?"

"I meant the movie."

"I didn't know there was a movie!"

"Then I'll put it on, unless you'd rather see something else, like Patton."

"M✶A✶S✶H is fine," I said. "There's always tomorrow."

"True."

Jeri turned on the TV and the videotape player, inserted the tape, and came back to sit next to me, a remote with a cord that led back to the machine in her hand. Before she started the movie, she pressed a button on a box on the table next to her, and almost instantly Karolin appeared.

"Yes, Miss Jeri?"

"Popcorn and two Cokes, please. Then that will be all for the evening."

"Right away, Miss."

I wanted to roll my eyes because I could have gone to the fridge and got the two Cokes and popped some Jiffy Pop, but that wasn't how things were done, and I suspected that Jiffy Pop was too 'common' for the Lundgren household. I was right, of course, because about fifteen minutes into the movie Karolin returned with two bottles of Coke and some freshly popped popcorn with real butter drizzled over it and with a dash of salt.

The movie was hilarious, and I really enjoyed it, discovering that the theme song actually had words, something I hadn't known, because they only used an instrumental version for the TV show. Some of the characters were different, but I recognized 'Radar' who was played by the same actor.

"You and 'Painless' have something in common," Jeri smirked as people lined up to spy on him in the shower. "And I've seen yours 'angry'!"

I laughed and shook my head.

"And I guarantee you I had a smile on my face that first night!" she said later when Nurse 'Dish' had a huge smile on her face after at first being reluctant to have sex with Painless.

When the movie finished, Jeri suggested we go up to bed.

"What about the bottles and bowl?"

"Karolin will take care of them in the morning."

"Seriously? We can't just bring them to the kitchen?"

"We could, but that's their job, and they're well paid for it."

I let it go and decided not to say anything more about it. We headed up to Jeri's room where my bag had been unpacked, with my robe hanging in the closet and my other things in a dresser drawer or on the counter in the bathroom. We shed our robes, brushed our teeth, then took turns using the toilet. When I came out, Jeri was on the bed, on her stomach, and I admired her cute butt.

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