Climbing the Ladder - The First Rung
Copyright © 2015-2023 Penguintopia Productions
Chapter 20: Lily’s Birthday
Coming of Age Sex Story: Chapter 20: Lily’s Birthday - '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 13, 1981, Chicago, Illinois
On Tuesday morning, I arrived at the Hancock Building at 5:00am, as Mr. Nelson had directed. We’d come close to completing everything the night before, but there were still a few things left to be done, not to mention the things which would arise as soon as the traders arrived. For some reason, Mr. Nelson believed a number of them would have trouble with the new security card system which required waving the card and then punching in a code. It seemed simple to me, and the secretaries had all understood it, he swore the Suits would not be able to handle it.
By 7:45am, he’d been proven right many times. I had to refrain from rolling my eyes and shaking my head as I showed guys who made more than a hundred times what I did how to use a simple security system with many of them requiring three or four tries to get it right. Mostly they were impatient, trying to pull the door open before the soft buzzer sounded signifying the door had unlocked, and then getting annoyed when the system reset because they’d done that. About 8:15am I went to Mr. Nelson.
“Hey, Boss. You asked about suggestions? Is there a way to disable the reset on the door if you try to pull it open too soon?”
“Probably. Why?”
“Certain people are a bit too impatient and don’t wait for the buzzer. If they pull on the door, it resets and they have to start over.”
“‘Certain people’ meaning guys who earn more money than I’ll ever see?”
I nodded, “That would be correct.”
He shook his head and rolled his eyes, “Let me call the alarm company and check. Anything else?”
“I heard some random bitching about the new phones, but the secretaries are helping their bosses with that. The other bitching is about having to use your security card to get into the john.”
“Tough! That one came directly from the Big Boss. And it’s actually easier for the women, because now they don’t have to have physical keys. Which makes it easier for us, too.”
“I just report what I hear, Boss!”
“I know. I swear, these guys are worse than my twin boys at twelve! Hell, they’re worse than my twin boys when they were toddlers!”
“I’ll be in the mailroom if you need me, Boss!” I said.
“Good job, Kane! Keep it up!”
“Yes, Boss!”
I left his office and went across the hall to the mailroom where Nick was sitting at his desk which was on a slightly raised platform.
“Anything for me to do?” I asked.
“If I give you a baseball bat will you go up to 31 and knock heads?”
“Doors?” I asked.
“No. ‘You know who’ is bitching that the copiers are ‘too far’ from his secretary’s desk.”
“Oh for the love of ... seriously? It’s like twenty feet because we centralized things so we could reduce costs!”
“I know that; you know that; I guarantee you Mr. Spurgeon knows that. But, you know the prima donnas!”
“I can’t see what we can do about it, except move his office.”
Nick laughed, “Yeah, right! He’s going to give up his corner office?”
I shrugged, “There isn’t any other solution given how things are laid out, and honestly, this saves us all work.”
“You can run upstairs and tell him.”
“No thanks! Is the morning mail here yet?”
“No. Just hang loose for the moment.”
For the next fifteen minutes I had nothing to do. Harry came in just as the morning mail delivery arrived, along with a number of packages from UPS and two couriers. That got Nick, Harry, and me hopping to get everything sorted so we could begin our rounds. I handled 32 and Harry handled 31, while Nick took care of the requests that came in while we did our rounds. Rachel smiled at me when I went past her desk, but the rules didn’t really allow any conversation, so I simply smiled back. When I went by Sharon’s desk, she winked and licked her lips; I smiled back.
We were kept hopping for most of the day handling our usual duties and numerous requests for assistance with just about every imaginable task. I ate lunch with Rachel in the plaza in front of the building, and then went back upstairs. By 5:00pm, I was beat, but Mr. Nelson was happy, so I felt good when I walked to the L for the trip home. It was Lily’s eighteenth birthday, but her parents were taking her to dinner, so I likely wouldn’t see her, a thought which was reinforced when I arrived home and the main house was dark.
I went up the outside steps to my apartment over the garage, took a quick shower, and then cooked myself a pair of pork chops and rice, sliced some bread which I buttered, and ate dinner alone. After dinner, I studied the securities regulations for about an hour, skimmed the Wall Street Journal, updated my charts, and then got into bed. As tired as I was, I was asleep almost as soon as my head hit the pillow.
October 14, 1981, Chicago, Illinois
On Wednesday morning I slept until my normal time, ate breakfast, showered, and dressed for work. It was raining, so I grabbed my umbrella and Cincinnati Reds cap and headed for the L, rather than ride my bike. The weather would be getting chilly and with more rain, so the days I’d be able to ride my bike to work would be somewhat limited until Spring. On the plus side, that let me read my Wall Street Journal during my commute, which I felt was actually a decent trade for the slight extra cost.
Things returned to what passed for normal by lunchtime on Wednesday. The problem with the doors turned out to be just an adjustment so that a magnet didn’t lose contact with a sensor. The alarm company sent out a technician, and once he’d moved the magnets slightly, the system no longer reset if someone tried to pull the door open before their code was acknowledged. That killed the grousing about the entry doors, and the whining about using a key card for the men’s bathroom had subsided, mostly because the women were equally vocal about how much better it was to not have to carry a key.
“You’re not quite as stressed today as you were yesterday,” Rachel said when I sat down beside her in the plaza.
“Things finally calmed down late this morning. Now we’re back to the usual level of insanity which is Spurgeon Capital!”
“And the inmates are running the asylum!”
“So true!” I agreed. “Once everyone got the hang of the new security system and they fixed the ‘door jiggle’ reset, complaints basically disappeared, and I believe you ladies finally shut the men up about card keys for the bathrooms.”
“The thing is, there was never really a risk of women going into the men’s bathroom like there was for men going into the women’s.”
“I can see that. I didn’t understand why Mr. Spurgeon wanted the key cards on the men’s bathroom.”
“Seriously? They’re tracking bathroom breaks!”
“No way!”
“You don’t have a card key on yours?”
“No. We punch in and out, but only for the start of the day, breaks, lunch, and the end of the day. Honestly, if Harry or I took more than a couple of minutes in the john, Nick or Mr. Nelson would come looking for us. They seriously look at that for the Suits and support staff?”
“Yes.”
“That seems a bit, uhm, I don’t even know what word to use. Authoritarian?”
“Some of the girls do take a LOT of bathroom breaks and it pisses off their bosses. This way they can prove it. And by watching the guys, too, it’s not discrimination.”
“Wonderful.”
“You know they check when you swipe your card when you come in, right?”
“Sure, but like I said, I punch in on the time clock, so it’s not a big deal, and it’s actually a way to show we didn’t cheat, at least on the start time.”
“Do you want to go out on Friday?”
“I have a date,” I replied.
“Oh.”
She sounded disappointed but I wasn’t sure there was anything I could do about the situation. The impasse over religion was insurmountable and nothing short of her god coming down through parted clouds with proof of his existence was going to change that, and even then I’d assume I was hallucinating and nothing would change. We finished our lunch in silence and then headed back into the building.
The afternoon continued the trend from the morning of a return to normal operations, though we did have the extra run on the 30th floor to make. Harry and I divided the floor which let us complete it relatively quickly, and didn’t interfere with our other duties. My rough guess was when they hired the score of new traders, their assistants, and their secretaries, the three of us — Nick, Harry, and me — weren’t going to be able to complete our work during the normal course of business. All it would take would be one special request or one moderate problem to create chaos.
I clocked out at 5:00pm, walked to the L, and once I was on the train, studied the stock pages of the Wall Street Journal It was day-old information, but I had decided to correlate my trades to information in the journal so I could show Mr. Matheson why I’d made specific trades. I knew that up-to-date information was key, but given I was doing what he called ‘simulated trading’ I had to work with what I had available. I made notes about changes I wanted to make to the portfolio, and I’d update my charts and records to reflect those changes once I arrived home.
When I walked up the driveway, I saw Lily sitting on the steps leading up to my apartment. She jumped up to greet me with a hug and a quick kiss.
“Happy belated birthday,” I said.
“Thanks!”
“Your mom and dad are out already?”
“They went to a dinner theater with my friend Mary’s parents, so they had to leave early.”
“Cool. How was your birthday dinner?”
“Good. They took me to Connie’s Pizza and then we went to Frusen Glädjé for ice cream.”
“Shall we go up and make dinner?”
“Let me get some stuff from the house, OK?”
“Sure. Just come in when you come back.”
She went into the house and I went up the stairs to my apartment. I unlocked the door, went inside, put down my bag, and quickly changed into jeans and a t-shirt. Lily hadn’t arrived, so I started copying my notes from the stock pages of the Journal into my ledger. It was another five minutes before she arrived with a bag of groceries and two pieces of birthday cake.
“Sorry for the leftovers,” she said, “but I’m not very good at baking!”
“I won’t turn down day-old chocolate cake!” I chuckled.
“There’s also some ice cream in the bag. Could you put that in the freezer?”
I did that while she set out everything on the counter for our meal. We spent the next thirty minutes preparing boneless chicken breasts, steamed broccoli, and tossed salads. Once everything was ready we sat down to eat.
“Are we still on for Friday?” I asked.
“Yes. My parents are OK with it; not thrilled, but OK. They like you and my dad said you seemed like a nice, responsible young man. But he is sure every single guy is only interested in one thing!”
“Dinner on Wednesday nights!” I replied with a grin.
Lily laughed, “I don’t think that’s what he meant!”
“It’s the highlight of my week.”
“Thanks, but I know you’ve had girls visit overnight!”
“Which doesn’t mean these dinners aren’t the highlight!” I replied.
“You’d rather have dinner with me than fool around with that pretty Mexican girl?”
“I’d prefer not to have to make a choice like that,” I chuckled.
“Aha! So this isn’t the highlight of your week!”
“It is! I just don’t want to have to choose one or the other if I don’t have to!”
“You do realize that my boyfriend is NOT allowed to sleep with other girls!”
I nodded, “You made that quite clear, and I’m pretty sure that’s a standard rule for EVERY boyfriend! We’ll cross that bridge when we come to it! We have our first date on Friday night! Well, official date, if you don’t count these dinners because you’re keeping them from your parents.”
“Do you count them?”
“That depends if you’re asking, or your parents are asking!”
Lily laughed, “No kidding! But we don’t keep shotguns around like you did back home.”
I chuckled, “Never had that problem. Bev’s dad liked me, and she and I basically grew up together, so we were always hanging out. I don’t think he ever figured it out. Before I forget, what time is the movie on Friday?”
“There’s a 7:10pm showing at Water Tower Place. That’s right by the Hancock Building, so maybe I should just meet you there at 5:00pm. There are a bunch of places around there to get food. Do you like Thai?”
“Never had it.”
“Then we’ll go to Star of Siam; my parents have taken me there and it’s good. Where should I meet you?”
“How about the plaza right in front of the Hancock?”
“Cool. You’ll have on your regular tie and dress shirt, right?”
“Yes.”
“Then I’ll wear a skirt and blouse instead of jeans. That way we basically match.”
“I’m OK either way,” I replied.
“You are pretty easy-going.”
“I try, though I’m pretty serious about work.”
“Nothing wrong with that! Dad says a man shows his character by how hard he works and how well he treats women.”
“That’s a pretty simple test, and a good one, though I would add keeping your word. You aren’t much if you don’t do that.”
“Isn’t that part of the other two?”
I shrugged, “I suspect liars could work hard, though obviously a cheater wouldn’t be treating women properly. In fact, I think I’d stick with someone keeping their word as the primary thing, because it means they’re trustworthy and will do what they say. I’m not disagreeing with your dad, by the way, just adding in something I think is really important.”
“I’d never want to date a liar because like you say, you could never trust them.”
“I agree.”
We finished our dinner and then had cake and ice cream. I gave Lily a birthday card I’d bought for her, and a small gift that I’d purchased during my break on Monday. I’d had a difficult time deciding what to get her because we weren’t a couple, and I didn’t want to imply anything, nor did I want her parents to make assumptions I wasn’t ready to deal with. In the end, I’d selected a White Sox t-shirt which was in my price range and safe.
“Thanks!” she said, and got up to give me a kiss.
“Shall we clean up?” I asked.
“If we can make out afterwards!”
“No objections!”
We cleared the dishes from the table, then I washed the dishes and Lily dried then and put them away. Once the last pot was back in the cupboard, we went to sit on the couch, with Lily on my lap. We kissed for about ten minutes before she broke the kiss and stood up. She took my hand and tugged gently. I stood up and guessing what she wanted, held out my arms. She melted into them, wrapped her arms around me and we exchanged a French kiss.
As we kissed, Lily tightened her hug, crushing her breasts against me, while my rapidly hardening erection tried to break free from my jeans and pressed against her thigh. The first time that had happened, she’d broken the kiss and pulled away; this time the kiss intensified and she squeezed her arms as much as she was able, pressing our bodies together as tightly as possible.
After a couple of minutes, Lily broke the kiss and put her lips close to my ear.
“Do you want to?” she whispered.
I absolutely did, even knowing her condition for going to bed together. I preferred her to all the other girls, including Rachel, because there were no red flags like with Rachel. So long as Lily’s parents were OK with us dating, I had no problem with being exclusive with her. And I had to let her know I knew that doing it meant I accepted the terms.
“Will you go steady with me, Lily?” I asked.
She moaned softly and ground against me, “Yes.”
The next sixty seconds were a mad scramble to get out of our clothes and into my bed. I reached over and pulled open the nightstand drawer and pulled out a box of condoms. Lily put her hand on my arm and shook her head.
“I started on the Pill in August,” she whispered.
I dropped the box back in the drawer, moved on top of her, and we began kissing. Lily wriggled under me, then wrapped her arms around my back and her legs around my lower thighs. I shifted forward slightly and the tip of my dick pressed against her slick pussy lips. I reached between us, grasped my shaft, and rubbed the head of my dick up and down until it was slick with her juices, I positioned myself, then used my hand to guide my dick as I gently pushed forward, spreading her open before me.
Lily moaned softly into my mouth as my glans passed her labia, and was sheathed in her hot, warm folds. I encountered no resistance as I pushed deeper and deeper into her, not stopping until I was fully inside her. Her pussy muscles grasped me tightly and she ground against me as we kissed. I broke the kiss after about a minute and looked deeply into her eyes.
“OK?” I asked.
“So full,” she replied breathlessly,
I smiled, kissed her, and began fucking her with long, slow strokes. Lily moved her legs further up my thighs, opening herself wider, and began moving with me, raising her hips each time I pushed into her. We developed a good rhythm as I did my best to keep my pleasure from building too fast, a difficult task given the tight embrace of her tunnel on my shaft, and the intense pleasure that created.
After a few minutes, Lily broke our kiss, panting, and squeezed her arms tightly around me. She thrust her hips upward more forcefully, her body tensed, and she groaned as spasms rippled along my shaft. Our motions became more energetic and three minutes later she tensed, groaned, and shuddered. Her second orgasm was much more intense than the first, and her pussy gripped me tightly, creating a delicious friction which I allowed to bring me over the edge. I pushed deeply into Lily, ground against her, and fired jet after jet of cum into her spasming pussy.
We exchanged a soft kiss, and I put my head down on the pillow next to Lily. She was breathing hard, and kept her arms and legs wrapped tightly around me, and continued to grind against me. A minute later she moaned softly, and once the gentle spasms of her pussy subsided, she relaxed her arms and legs, holding me loosely.
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