Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 26: Easier Said Than Done

Coming of Age Sex Story: Chapter 26: Easier Said Than Done - '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  

November 13, 1981, Chicago, Illinois

Even as a ‘starter boyfriend’, I could quickly work out that Lily wouldn’t approve of ‘hanging out’ at Nickie’s place, even if all we did was ‘hang out’. I had the clear impression, after working with Nickie for four hours, that what she was suggesting was something more than that. She was, as I’d noticed when I first met her, ‘smoking hot’, and that made her offer tempting, but even if I were inclined to be a cheater, the fact that I lived in an apartment over a garage owned by Lily’s dad would have given me pause. But I wasn’t inclined to cheat, and I really liked Lily, which made the answer to Nickie’s question simple.

“I would,” I replied. “But I have a steady girlfriend who most definitely would not approve of me being at your place.”

“I missed the steady girlfriend part,” Nickie said.

“The topic never came up,” I replied.

“You just moved here in June and you’re already steady? How’d you meet her?”

“She’s my landlord’s daughter. And that provides a double-whammy of why not to take you up on your offer.”

“That might be awkward,” Nickie said with a laugh. “Renting a room?”

“An apartment over their garage in University Village.”

“College girl?”

“Senior in High School. I’m only nineteen, so we’re only a year apart in age. She’s going to Circle next year.”

“What major?”

“Undecided. She’s planning to take the core courses for a BS degree, and figure it out after her first year. I take it you went to nursing school right out of High School.”

“Yes. Well, I guess I’ll see you in the morning. The offer is still open.”

“Thanks. See you in the morning.”

We left the building and walked to the L, though we ended up on opposite platforms as she was heading north and I was heading south. When her train came, I waved just before it pulled into the station and she waved back. My train arrived a few seconds later and we waved once again from the windows of our trains. Twenty minutes later, I climbed the steps to the apartment, and found a note tacked to the door asking me to knock on the door of the house if I was home before 10:00pm, which, checking my watch, I easily was.

“Hi!” Lily greeted me when she answered the door. “How was work?”

“Fine. I have to be back in the morning.”

“Mom and Dad said we could hang out until 11:00pm, if you want to come in.”

“I probably should take a quick shower,” I replied. “But I’d like that.”

Lily leaned forward and whispered, “I’d offer to help, but my parents are home.”

“I wish!” I whispered back, then spoke a bit louder, “See you in about ten minutes.”

I quickly went up to my apartment, showered, put on jeans, a t-shirt, and a sweater, and went back to the house where Lily was waiting to let me in. Her parents were in the den, so we went to the front room where we could sit together on the couch.

“Sorry about missing our date.”

“It’s OK. I ended up going to dinner, but not the movie. You and I can see it together, and I wanted to see you when you got home.”

“I’m glad we knocked off at 9:00pm!”

“What time do you think you’ll be home tomorrow?”

“I’m not sure, but let’s just plan for our shopping and laundry trip at 2:00pm. If I’m home earlier, we can go as soon as we’re both ready.”

“How many people were fired?”

“Twenty. Mostly it was the lowest-performing traders and their assistants and secretaries. The mailroom lost one position.”

“So the other guy was fired?”

“No, he moved to a runner’s position. I think Mr. Matheson saw an opportunity to move his guy up and pulled the right strings. Even if it wasn’t on my account, and I don’t think it was, it helped.”

“So what does that mean?”

“That for at least couple of months my supervisor and I have to run the mailroom, and that’s going to keep us really hopping because it’s a three-person job. Worst of all is that someone has to answer the phone, so only one of us can be out at a time, and that likely means I have to deliver all the mail and stock all the supply cabinets. And that doesn’t take into account all the special requests. It’s going to be crazy.”

“But they’ll replace him eventually, right?”

“What my boss said was ‘at least until January 1st’ but he didn’t say that was the date.”

“Well, you still have your job.”

“I wasn’t complaining,” I replied. “Just acknowledging reality. And I may well get some overtime out of it, which will let me build up my reserves for the future.”

“So, in the end, you come out better off, right? You have your job, more income, better reserves, and you’re still on track?”

“For the promotion to supervisor when Nick leaves? I believe so, yes. For my true career path? No idea. It’ll be a few weeks, at least, before I can talk to Mr. Matheson.”

“I think you ended up in a pretty good position, considering.”

“I agree.”

“My parents won’t object if you kiss me,” she said quietly.

We spent the best part of an hour kissing and cuddling, which only made me look forward even more to Wednesday night.

November 14, 1981, Chicago, Illinois

On Saturday morning, I showered, dressed, and headed for the L. It was just above freezing, so I was wearing a Winter coat, hat, and gloves, but according to the forecast in the paper, it would be in the mid-50s when I left the Hancock Building. Nickie was waiting for me. I used my badge to get us into the building, and my key to operate the freight elevator.

When we arrived at the 30th floor, we hung up our coats and I admired Nickie’s firm butt, which was encased in very tight jeans, and her equally firm breasts which her fitted t-shirt clung to, making it obvious she wasn’t wearing a bra. I felt a slight pang of regret for not agreeing to ‘hang out’ with her, but it passed quickly when I remembered that Lily was not just pretty, but also my steady girlfriend. The only downside was living over her parents garage, which limited our chances to ‘hang out’.

I did my best to push those thoughts from my mind while we worked to properly address all the boxes, and fill out the necessary forms for the courier companies which would deliver the boxes. Nickie flirted lightly, but didn’t push, and I didn’t object, though I wasn’t willing to risk Lily for what would obviously be an enjoyable roll in the hay. The final courier which Mr. Nelson had arranged departed just before noon, and as we were done, Nickie and I left the Spurgeon offices and rode the freight elevator down to the ground floor.

“Let me give you my number,” Nickie said. “If things change, give me a call!”

I decided there was no harm in accepting her phone number. so I accepted the piece of paper with her phone number and shoved it into the pocket of my jeans. As we had the previous night, we walked to the L, climbed the stairs to opposite platforms, and I waved as her train pulled out of the station. Thirty-five minutes later I was showered, changed, and at Lily’s door so we could go to the laundromat and Jewel.

“Did you hear from Tom?” Lily asked as we walked hand-in-hand towards the laundromat, with me pulling the cart with my laundry behind us.

“No. I really need one of those machines that answers the phone and takes a message on a cassette tape. I have no idea what they cost, so I’m not sure one fits in my budget.”

“You could check at Jewel. The one we go to is a Jewel/Osco which means they have general merchandise on the Osco side.”

“We’ll take a look.”

“Do you need anything else for your apartment?”

“Not really. It’s not like there’s a lot of extra room. I have what I need until I get my next place.”

“What are you thinking?”

“Probably a two-bedroom townhouse. I’d love to be able to buy, but that’s years off, but once I get my promotion, and I’m comfortable with my reserves, I’ll do that.”

“So, then, what? Eighteen months?”

“Something like that.”

“You could do it sooner if we lived together and I had a part-time job and contributed.”

“What about school?”

“My parents are paying.”

“And you think they’ll do that for sure if you move in with me?”

“They like you a lot.”

“And will they still like me a lot when you tell them we’re going to be sleeping together? Or if they figure out about our Wednesday night dinners?”

“We’ll find out in May when I ask if I can move in with you!”

“Then I need to be prepared to find a new place,” I replied. “Just in case.”

“You’re afraid they’ll kick you out?”

“If your dad objects to us sleeping together, wouldn’t that be a logical thing for him to do?”

“I guess it would. Would you break up with me over that?”

“No, of course not, but your dad might not allow us to see each other.”

“I’m eighteen!”

“And living in his house. Seriously, if you’re going to tell him, we have to be prepared for the worst.”

“Just like you did with your job?”

“Yes. So, let’s talk in the Spring before you say anything.”

Lily squeezed my hand and kissed my cheek.

November 16, 1981, Chicago, Illinois

“This is going to be fun,” I said to Nick when I walked into the mailroom on Monday morning.

“I’ve been wracking my brain all weekend about how we can do this and the one thing I can’t overcome is the phone. We’re absolutely required to have someone man the phone the entire business day, and that basically means you have to do your job as well as Harry’s.”

“The same conclusion I reached on Saturday.”

“I wonder if we can get a temp. They’d only make minimum wage and that might fit into Mr. Nelson’s budget.”

“Not to tell you what to do, but I’d ask him. Otherwise, things are going to fall apart the minute there are two tasks which have to be done at the same time outside the mailroom.”

Nick nodded, “You’re right. Let me do that now. Watch the phone.”

“Will do!” I said.

He left and I saw there were stacks of memos marked ‘Urgent’ and ‘First Thing’ which meant extra rounds, and something I’d need to do immediately upon Nick’s return. I put all of them into my cart, as I was certain I’d need to make the deliveries, which would make it take twice as long, and would ensure complaints. I moved my cart close to the door so I could leave as soon as Nick returned.

“He’s going to see if he can get someone here tomorrow,” Nick said. “It might only be half days, but that would still help a lot.”

“It would. I need to get these memos out.”

“Right. When the morning courier deliveries and the mail arrive, I’ll start sorting.”

“Did I mention this was going to be fun?” I asked as I pushed my cart out of the mailroom.

Nick laughed and I headed for the freight elevator. I decided the best plan was to deliver the memos on 32 first, then work my way down back to the mailroom, because complaints from 32 carried much more weight, and there were now several empty offices on 31. The memo detailed all the changes which had occurred on Friday. In addition to the layoffs, the management team had been juggled and some assignments shifted. It didn’t mean anything to me, nor did it really affect anything that mattered to me.

“The courier deliveries are ready to go,” Nick said when I returned. “I sorted them by floor, but not by the chart.”

“How many are there?”

“Fourteen.”

“I can do it on the fly,” I replied. “Let me take those now and then come back.”

The rest of the morning was like that, and I didn’t have a chance to sit down, nor did I get my usual morning break, and I ate my lunch in fifteen minutes in the break room, rather than taking the time to go downstairs to eat with Rachel. The afternoon wasn’t much better, though I did get to take a short break, which was long enough to drink a can of Coke I bought from the vending machine. Nick and I both stayed until nearly 6:00pm to finish all the tasks, and after the long day, I took the L home.

When I arrived, I made dinner, read the Wall Street Journal, and updated my practice portfolio. I was just about to turn in when the phone rang. I glanced at the clock-radio and saw it was 10:20pm, and wondered who’d be calling me. I got up and answered the phone.

“Jonathan Kane,” I said into the phone, having adopted the Spurgeon Capital standard way of answering.

“Hi, Jonathan. It’s Jeri; Jeri Lundgren. Do you have a minute to talk?”

“Sure,” I replied, wondering what Lisa’s fifteen-year-old friend could possibly want to talk to me about. “What’s up?”

“I haven’t seen you at your uncle’s house. I wanted to ask what happened, but I was afraid Lisa would wig out if I did.”

“I’ve been busy,” I replied, hoping she’d accept the little white lie.

“It’s because of Lisa, isn’t it? Because she was treating you so badly? I promise I won’t say anything if that’s true.”

It was true, but I had no clue what Jeri was trying to do by calling me. She seemed nice, but she was only fifteen and I was nineteen, not to mention I had a steady girlfriend. And even if I didn’t, dating one of Lisa’s friends, even if she had been eighteen, would be a non-starter because the last thing I wanted was to have any kind of ties to her beyond her being my cousin. But, given the fact that my aunt, uncle, and Lisa all knew, there was no point in denying it to Jeri.

“Let’s just say she and I do not get along and leave it at that.”

“Obviously. Lisa can be a real bitch, and her dad lets her get away with murder, but you seem like a really nice guy. Most guys I talk to are either society dweebs, or older men who want to get into my pants. You talked to me like a normal person.”

“I’ve found it’s much easier to be nice to everyone. Life is way simpler if you do that.”

Jeri laughed softly, “You would think so, but if I were nice, all it would do is encourage them. It’s much easier to just pretend to be a ‘shy, frigid bitch’. But I know when to turn that off. Lisa doesn’t. Well, the bitch part. She’s obviously not shy.”

“Obviously,” I replied dryly.

“Would it be OK if I called you to talk? You’re the first guy I’ve met in a long time who treated me nicely and wasn’t a total dork.”

I was about to protest that I had a steady girlfriend, but realized that was absolutely not what was on Jeri’s mind. I was the nice guy who didn’t want to have sex with her. Bringing up a steady girlfriend would send exactly the wrong message.

“I’m assuming Lisa shouldn’t know about us talking?”

“You assume correctly!” she replied. “How do you like working for Noel Spurgeon?”

“I don’t really see him very often,” I replied. “Mostly I only talk to my supervisor, his boss, and a couple of secretaries. I take it you know him?”

“He’s one of the biggest contributors to my mom’s fund-raisers. He also hits on every teenage girl who goes to the galas.”

“You?” I asked.

“Since I turned fourteen. But I just act cold and uninterested and the guys mostly leave me alone. My mom is always trying to fix me up, but I’m not interested. Can I ask if you have a girlfriend?”

“I do. She’s the daughter of my landlord.”

“Very convenient!”

“Well, except that means ‘my place’ is actually her parents’ place.”

“Well, putting it that way sounds more like my house. My mom is a total control freak.”

I was starting to get a good picture of why she wanted to talk to me — everyone else in her life was either a bitch, a control freak, or trying to have sex with her. She was really cute, and I could see why the guys were attracted to her, but she was only fifteen. If I were sixteen or seventeen, and not dating someone, I’d be interested, but a four-year gap at this point was huge; I’d even been a bit wary with Lily before she turned eighteen and she’d had to point out that we weren’t much more than a year apart.

“I’m happy to talk to you if you want,” I replied. “I can always use more friends.”

Which reminded me I needed to try to get hold of Tom before the weekend. I’d ended up purchasing an answering machine and so now if he called, he could leave a message.

“Cool! I need to go before mom finds out I’m on the phone after 10:00pm, but this was the first chance I had to call after I didn’t see you yesterday. Good night!”

“Good night”!

We hung up, and I went about my bedtime routine, climbing into bed about 10:35pm and almost instantly falling asleep.

November 17, 1981, Chicago, Illinois

“We get a temp for the afternoon, to answer phones,” Nick said when I arrived on Tuesday morning.

“Well, that’s something,” I replied. “Mornings are still going to suck.”

“Given the mood on 32, we’re lucky we got that. The Big Boss is in a severe cost-cutting mood. According to Mr. Nelson there will be a memo going out about controlling expenses.”

“So, no overtime, then?”

“Mr. Nelson will still be able to approve it. He will just have to justify it. But that’s not really any different from how it is now, just that there might be a bit more pushback. Fundamentally, every penny we spend comes right out of our clients’ pockets. When everyone is making money, it’s not a big deal.”

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