Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 9: Passing the Test

Coming of Age Sex Story: Chapter 9: Passing the Test - '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  

July 18, 1981, Chicago, Illinois

“Hi!” Gudia said when I answered the door late on Saturday morning.

“Hi!” I replied. “I’m ready to go. I have the cooler with the drinks.”

We exchanged a quick, chaste kiss, I grabbed the cooler, called ‘goodbye’ to my aunt, then left the house. We walked about a block to where Gudia had parked, got into her car, and she headed for Grant Park.

“How was your week?” she asked.

“Pretty good. Mostly the same stuff as usual. How about yours?”

“Quiet and boring, really. Not much will happen until school starts towards the end of next month. Well, I mean, besides seeing you and hanging out with my friends and doing the usual stuff with my family. Have you ever been to a cricket match?”

“A what?”

“Cricket match. Cricket is a bat and ball game with some very loose similarities to baseball. It’s played in England and the Commonwealth countries.”

“I’ve never even heard of it. Why did you ask?”

“My dad and his friends are on a cricket team and they play on Sundays in Naperville. I wondered if you might want to come watch a game. I could explain how it works.”

“Tomorrow I’m hanging out with my friend Tom.”

“Then maybe next Sunday?”

I wanted to see Rachel again, so I was going to have to figure out how to juggle the situation with the two girls without lying or getting into trouble. I hadn’t made any commitments to Gudia, so it wasn’t as if I was cheating, but I still wanted to be careful.

“I’m game. Let’s talk about it when we talk during the week about our plans for the weekend.”

“OK. How’s your studying going?”

“Pretty good. I think I’ll be confident I have it memorized well enough by the end of August that I can safely approach Mr. Matheson about getting the next set of study guides.”

“How long do you think it would be before you’re out of the mailroom?”

“A couple of years, at least. In a year or so, if everything goes OK, I’ll be the supervisor. At that point, I need to demonstrate I can do that job and handle the responsibility. Once I do, then it’s a matter of a position being open and someone giving me a chance. I’ll look for the opportunity as soon as I reasonably can, but I honestly think it’ll be at least two more years. Is there an issue with that?”

“Just what I told you before — my dad would be concerned about me having a serious boyfriend who wasn’t able to support a family.”

“Won’t you make good money if you work with computers?”

She smiled, “Yes, but Dad won’t see it that way. He’s old-fashioned.”

“And you need his approval?”

“To marry? I’d want to have it, yes.”

“And if he didn’t give it?”

“I’ll marry who I choose, but I’d really like my dad’s approval and blessing. It would make life so much easier.”

I didn’t like the sound of that, at all, and wondered what would happen if I didn’t achieve sufficient success in her father’s eyes. Would she, in the end, defy her father and marry ‘outside her caste’, as it were? That concerned me, and I felt it was entirely possible to spend the next three years dating only to be told I wasn’t good enough for his daughter. And if she DID deny him, that didn’t bode well for my kids having a good relationship with their grandparents, something I hoped would be far better than my relationship with my mom’s parents.

“What would happen if he didn’t give it?”

“I’m not really sure, but let’s make sure that doesn’t happen.”

“I can’t promise any timeframes,” I replied.

“I know. But it’s not as if we’re planning on marrying tomorrow; we’re dating.”

“But going steady would be out? Because of your dad?”

“Unless I wanted to lie to him, yes. But is it a problem if we spend time together, go out together, and make love together without a commitment?”

“No, it’s just I don’t want a bad relationship with my in-laws.”

“I don’t graduate for three years, so it really isn’t an issue before then, is it?”

“I suppose not.”

“And if you do get your promotions, I think he’ll be fine.”

“I hope so.”

“It’ll be fine, Jonathan; I’m sure of it. Before I forget, I have a list of things you’ll want to get for your apartment — basic cooking utensils, and so on. It’s not long, and shouldn’t be too expensive. You can add items as you can afford them. I have a second list of those things.”

“I appreciate it,” I said. “I’ll probably buy a few of the items before I move so I have them right away. I’ll just leave them in their boxes or whatever, until my uncle helps me move my few things.”

“Let me know if you need help.”

“I will.”

We arrived at Grant Park, parked in the underground garage, then carried the picnic basket and the cooler to a nice grassy spot where we spread a blanket and had our picnic lunch. When we finished, we packed up and headed back to the car. We put everything in the trunk, then drove to North Michigan Avenue to see Endless Love, which turned out just as sappy as I’d expected it to.

“What did you think?” Gudia asked when we left the theater?

“I thought it was bizarre that a mom would watch her daughter lose her virginity!”

“That was pretty strange!”

“I suppose I could see turning psycho if I’d had a chance to make love with Brooke Shields and then couldn’t!”

Gudia laughed, “And Martin Hewitt was hot!”

“So you would with him?”

“You would with Brooke Shields if you had a chance!”

“True, and I suppose I can’t have a double standard about that! Though I’d suggest finding a guy who won’t accidentally burn down your house trying to get your attention!”

“And a girl who doesn’t have a mom who likes to watch!”

“What’s the plan for the rest of the day?” I asked.

“If there was someplace we could go...”

“My aunt and cousin are home,” I replied.

“And so are my mom and sister,” Gudia sighed. “I suppose we can go to Navy Pier and walk around. I’ll buy dinner, if that’s OK.”

“Let’s do that.”

We had a nice afternoon, and a good dinner, and then Gudia took me back to Logan Square. We shared a deep, longing kiss at the door, and after she drove away, I went inside.

July 19, 1981, Chicago, Illinois

“Come in and grab a beer and a section of couch!” Tom said when I arrived at his studio apartment. “I’m just pissed they haven’t solved the baseball strike!”

“I’m not sure who to be more pissed at,” I said. “The owners for being total dicks about money when they’re all multi-millionaires or the players for whining about free agency when they’re making hundreds of thousands, or even millions, to play baseball! I’ll play for the league minimum!”

“Me, too!” Tom laughed. “That would be double what I make at Connie’s, even with overtime! And I’d get Winters off!”

“Same here.”

I grabbed a beer from the fridge and opened it.

“Stuart is coming by in about an hour,” Tom said. “He’s bringing two girls with him. Maria will be here soon.”

“Two girls?”

“We figured it was better to have an even six so it wasn’t uncomfortable. It’s not a setup; just someone to give us an even six people. She knows you’re here stag, but she’s not expecting it’s a date or anything. Just hanging out.”

“OK. Do you know her?”

“No. In fact, I don’t know the chick Stuart is bringing. He’s got a new one every few weeks. He gets bored pretty easily. His motto is ‘Five Fs’.”

“Five Fs?”

“Find ‘em; Finger ‘em; Fuck ‘em; Forget ‘em; Fast.”

“Damn!”

“You heard us talking at Great America. I lost track of the actual body count when it went north of 75.”

“Seriously?”

“Seriously. In High School he got the entire volleyball team, which was fourteen girls; all the starters on the softball team, which was ten girls; half the cheerleaders, which was another six. And he started in eighth grade with the starters and some backups on the girls soccer team!”

“How the heck did he manage that?”

“He got the reputation of being able to fuck anyone into next week when he was fourteen. That included a couple of the moms as well. And I mean smoking hot ones, not fat, bored housewives.”

“Damn! That’s just crazy!”

“It also didn’t hurt he was hung like a horse and plenty of girls just HAD to see it for themselves. And Stuart was pretty good at negotiating to get what he wanted in exchange.”

There was a knock at the door and a pretty black-haired Hispanic girl walked in.

“Jonathan, this is my girlfriend, Maria. Maria, Jonathan.”

I stood up, shifted my beer to my left hand and shook hands with her.

“Nice to meet you,” I said.

“Same here.”

“I hear you met Stuart by him crashing into you on his bike.”

“Nearly. He swerved and missed me, but took a tumble. How long have you two been dating?”

“About two years,” she said. “We’ll get married as soon as Tom finishes his probationary period at the Fire Department.”

“I didn’t realize you were engaged!”

“We’re NOT!” Tom laughed. “Well, not officially, anyway. I can’t afford the ring right now. Once I pass the exam and get into the Fire Academy, I’ll buy the ring.”

“The wedding will be next June, most likely,” Maria said.

“Cool!”

She got herself a 7-Up from the fridge and Tom tuned the radio to a ‘Classic Rock’ station which was heavy on 60s and early 70s bands. Tom and Maria told me about them meeting at a graduation party and going out on their first date a few weeks later, about the boxing challenge, about their families, and I did the same. About forty minutes after Maria arrived, there was a loud banging on the door.

“The party can start now!” Stuart announced as he basically charged into the apartment followed by two very pretty girls — one blonde and one brunette.

“Who are your friends?” Tom asked with a wry smile.

“Lucy and Nicky,” he replied. “Jonathan, meet Nicky!”

I nodded, “Hi!”

“Hi!” Nicky, the brunette, responded.

“Grab yourselves something from the fridge,” Tom said. “We’ll get Chinese from the place two doors down at dinnertime, but there are chips and pretzels in the bowls in the kitchenette.”

Nicky got a beer from the fridge and sat down next to me on the couch.

“I hear you’re new to Chicago,” she said.

“I’m originally from Ohio. I moved here about six weeks ago for a job with Spurgeon Capital. Are you from Chicago?”

“Yes. I live in Bridgeport and work at David’s waiting tables.”

“Are you and Lucy friends?”

“Yes. She’s a bartender there. I want to tend bar, but I’m not quite old enough. She gets much better tips! What do you do?”

“Mailroom,” I replied. “First job out of High School.”

“You’re eighteen?”

“Yes. You?”

“Twenty.”

I got the distinct feeling from the way she said ‘eighteen’ that I was ‘too young’ for her, and that theory played out over the next thirty minutes or so. I hadn’t been particularly interested, and Tom had assured me that we weren’t being set up with each other, but I felt Nicky was disappointed. There really wasn’t much I could do to make her feel better, so I just did my best to be friendly and enjoy myself.

I really liked the Chinese food that Tom ordered, and when we finished, I helped him clean up by taking the empty containers out to the dumpster. When I returned, Stuart, Lucy, and Nicky were gone.

“They left?” I asked.

“I think Stuart was very interested in getting Lucy alone somewhere!” Maria laughed. “And I guess you could tell Nicky wasn’t interested.”

“I got that, but it’s cool. I didn’t come here to meet a girl, so it’s not a big deal. I actually have two girls I’m seeing.”

“Another player, Tom?” Maria asked, shaking her head.

“It’s not like that,” I replied calmly. “I’ve met a few girls I’ve gone out with, which means I’ve now dated three girls in my entire life, if you can even count hanging out with my neighbor as ‘dates’.”

“Was she your girlfriend?”

“Sort of, unofficially, I guess. We just hung out a lot from the time we were little. But we never actually went out on a date.”

“So the anti-Stuart!” Maria laughed.

“I guess so,” I replied. “It sounds like he had more girlfriends in eighth grade than I’ve had in my entire life!”

“I think he had more girlfriends in the first MONTH of eighth grade then you’ve had in your entire life!” Tom laughed. “No insult intended.”

“None taken,” I replied. “If what you’re saying is true, I’m not sure Superman could keep up with Stuart! You’re not offended, Maria?”

“By Stuart? ‘He’s a sweet-talking stud who can melt a girl’s heart with his pout; He’s the kind of lover that the ladies dream about’! Though I don’t think he owns a Mercedes-Benz!”

“‘76 Plymouth Duster,” Tom laughed. “And he’s got a long wick, alright!”

“You seem obsessed,” I chuckled.

“And you seem underwhelmed,” Tom laughed.

“Maybe he could give Stuart a run for his money,” Maria laughed.

I laughed, “As long as YOU are happy with Tom, I think that’s all that matters.”

“Nice deflection!” she laughed.

“I think the two of you have been hanging around Stuart WAY too much,” I grinned.

“Sorry,” Tom said. “It’s just one of those things we joke about in our little group. We didn’t mean to make you uncomfortable.”

“I didn’t get a lot of that kind of joking back home, really. Mostly I stuck to myself, or hung out with Bev. I had a couple of pretty good friends, but they weren’t too close because I didn’t have a lot of time to hang out, and what time I did have, I mostly spent with Bev.”

“You seem like a nice guy,” Maria said. “If neither of those girls work out, let Tom know. I have some friends who I think would like you. Heck, I might even suggest my little sister!”

“That’s high praise,” Tom said. “Maria is very protective of her little sister. The last guy spent what, six weeks in intensive care?”

“Oh, stop!” Maria laughed. “I simply told him what I’d do to him if he didn’t respect my little sister. He chose not to come back!”

“Threatening a guy with feeding his gonads through a food processor is pretty serious!” Tom laughed.

“Ouch!” I said with a grimace.

“He was a jerk and my sister deserved better! I was just looking out for her. We don’t have a Big Brother to do that. Do you have a brother or sister, Jonathan?”

“No. It was just me and my mom. My dad died before I was born.”

“Tom told me about that but he didn’t mention anything about brothers or sisters.”

“Just one cousin, and if you want her, she’s all yours!”

“How old is she?”

“Twelve.”

“She’s that bad?”

“She needs a swift kick in the butt to get on track,” I said. “If you look up ‘spoiled brat’ in the dictionary, her picture is there. I love my uncle, but he lets her get away with murder. My aunt tries to rein her in, but she doesn’t have much luck.”

“Tom said you’re getting your own place.”

“Yes, at the end of the month. It’s a garage apartment in University Village.”

“If you want, let Tom know and I’ll arrange for you to meet my sister Teresa.”

“Thanks.”

We each had another beer, and then I took the L back to Logan Square.

July 20, 1981, Chicago, Illinois

“Kane!” Mr. Nelson bellowed from the door.

“Yes, Boss!” I responded, jumping up from my stool.

“The copier company is at the loading dock. They’re here to replace that unreliable piece of shit that Laramie is always bitching about. Go meet them downstairs and bring them up the freight elevator. Stay with them until it’s running and make God-damned sure they run a hundred copies or so before they leave!”

“Yes, Boss!”

I quickly made my way to the loading dock where I met the two guys from the copier company. I took them up the freight elevator to the 34th floor and watched while they moved the old copier out of the way, set up the new one, and at my insistence, ran a hundred clean copies BEFORE they wrote down the copy count, then escorted them back down to the loading dock. I went back upstairs and went straight to Mr. Nelson’s office.

“All set, Boss! I made sure they didn’t take the copy count until AFTER they ran those test copies, They weren’t happy, but they did it.”

“See, that’s the kind of thinking we want around here. Keep up the good work, Kane!”

“Yes, Boss!” I exclaimed, then went back to the mailroom.

“God! Could you get your nose any further up his ass?” Charlotte whispered derisively.

“You do it your way; I’ll do it mine. As you said, in a year, I’ll be your boss.”

“I’ll quit if that happens.”

I shrugged, “No loss.”

“Asshole!”

I didn’t feel a need to respond, so I let her have the last word. She really wouldn’t be a loss. She did her job, barely, doing the absolute minimum to not get in trouble. That was never my way. I always made sure I went the extra mile, as it were. If there was something which needed to be done which fell into my job description, I did it. If it didn’t fall into my job description and I could do it, I’d ask the boss, and then do it. I’d always been rehired and bosses had been sad to see me go. ‘Getting by’ was not in the cards, ever.

At lunchtime I went down to the plaza and met Rachel so we could eat together.

“Would you like to go out again on Friday?” I asked.

“Of course, silly!” she said with a soft laugh. “I told you I liked you!”

“Yes, you did. What would you like to do?”

“Fly to Vegas and get married?” she replied with a silly smile.

“I was thinking something a bit less permanent,” I replied smoothly.

“Extra points for not freaking out or running away!”

“I knew you were teasing. You WERE teasing, weren’t you?”

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