Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 29: I love you, Jonathan!

Coming of Age Sex Story: Chapter 29: I love you, Jonathan! - 'Climbing the Ladder' is a story in the 'A Well-Lived Life' universe, and provides 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. Follow along as the adventures of Jonathan Kane continue!

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Mult   Rags To Riches   Workplace  

November 20, 1982, Chicago, Illinois

"What do you want?" Lisa demanded when she answered the phone.

"To speak to your dad," I replied.

"He's not here. And I told you to stay away from my friends!"

"You don't decide for me or for anyone else," I replied. "Please let your dad know I called."

"Drop dead," she replied, and hung up.

I'd have to call back, as I felt there was no way she'd deliver the message. I expected my uncle to invite me for dinner and to bring a date. Lisa was such a bitch that I'd consider inviting Jeri just to mess with Lisa. And given how much of a bitch she was, I'd even pay the price I was sure Jeri would demand for a date. Of course, it wasn't that sex with her had been bad, just that I'd felt a business relationship, as I defined it, was better for both of us.

As I thought about it, I realized that would be me being a dick in the same way Lisa was being a bitch, and it would cause tension at dinner and ruin it, though I was sure Lisa would do her best to make the few hours I was at my uncle's house a living hell if she could. I felt it would be wise to speak to Aunt Wendy in advance so she could deal with Lisa.

I didn't have anything to do for the rest of the afternoon, so I went upstairs, got Stranger in a Strange Land, the book Anala had recommended but which I hadn't started reading, from the shelf and went back to the front room to sit with Bianca and Shelly while they studied. I'd read for about thirty minutes when the phone rang, so I went to the kitchen to answer it.

"Kane," I said reflexively.

"Jonathan? It's Katy Martin!"

"Hi, Katy. How's Princeton?"

"Awesome! I'm having a great time and making good grades! I'm coming home for Thanksgiving and wondered if you wanted to get together with Esme and me."

"I'm leaving for Ohio on Wednesday night and I won't be back until late on Sunday."

"Bummer! What about during my Christmas break?"

"I'll be in Ohio from the 24th to the 27th, but otherwise, I'm here. Either call when you get home or have Esmeralda call me to set something up."

"Awesome! See you in December, then!"

We said 'goodbye' and I decided to try my uncle's house again. Thankfully, Aunt Wendy answered and called my uncle to the phone.

"Hi, Jonathan!" Uncle Alec said. "How are you?"

"Good! I wanted to let you know I passed the Series 3 test and Murray Matheson offered me an analyst position starting March 1st."

"Congratulations! I knew you had it in you, but now the real test begins. You should come for dinner in December."

"I'd like that," I replied.

"Bring a date, if you want. I'm sure you have a wide selection to choose from!"

I chuckled, "Perhaps. There is one other thing I wanted to talk about, if you have time."

"I do. What?"

"I'm thinking of buying a house in Rogers Park or somewhere close next year, probably in April or May. Could you help, or refer me to someone who could?"

"Aren't you being a bit hasty? You shouldn't deplete your savings and reserves and be illiquid."

"I won't be," I replied. "I'm bringing in some new business to Spurgeon, so I'll have enough to put twenty percent down and Spurgeon will hold the mortgage."

"What the hell?! How?"

"I was asked to manage a trust fund," I replied. "I get half of the two and a quarter of the twenty."

Uncle Alec was quiet for a few seconds.

"Lisa knows, right?" he asked. "That's why she's in such a foul mood?"

"I suspect so. Were you home about thirty minutes ago?"

"Yes."

"I called, Lisa told me you weren't home, told me to stay away from her friends, then told me to drop dead before hanging up."

"I'll speak to her."

I considered what I'd decided earlier and changed my mind.

"Please don't," I requested. "That'll only make things worse for dinner, unless she's not there."

"Good point. Just don't bring Jeri as your date, please."

"I actually considered doing that, but being a dick isn't the correct response to my cousin being a bitch."

"Thank you. Let me work out a day with Wendy and let you know. Congratulations again!"

"Thanks. About the house?'

"Oh, sorry! I don't deal in single-family residential property, but I know a guy who'll help you. His name is Bill Wyatt, and he'll find you exactly what you want."

"Thanks, though I wouldn't be able to even think about closing before March 1st, because I'm not eligible for a mortgage from Spurgeon until then."

"When does your lease expire?"

"The last day of July," I replied.

"Give Bill a call and let him know you'll be looking in February or March, which, with a sixty-day closing, would put you in April or May. If it goes long, ask your landlord about a month-to-month extension. If she's reluctant, offer a premium over your current rent so you don't have to do something silly like move twice."

"Got it. Thanks. I'll call him next week."

I'd also need to call Miranda's dad and the attorney Nelson had recommended, as I'd need a CPA and a tax expert sooner than I'd originally thought.

"Good. You know what, let me speak to Wendy. Hang on."

He put the phone down and was back three minutes later.

"How does December 15th work?" he asked.

"That's fine," I replied, making a note on the calendar. "See you then!"

We said 'goodbye' and I hung up, then went back to the front room to continue reading. When the girls finished their homework, I put the book down and chatted with them until it was time for them to get ready for their night out. I went upstairs, showered, then dressed. I was downstairs in time to say 'goodbye' to Bianca and Shelly, and about fifteen minutes after they left, the doorbell rang.

"Pizza delivery!" Ivy exclaimed.

I chuckled, "I know that trope from the guys at work! Come in!"

She did, followed by Sophie, and surprisingly, a third girl.

"Jonathan, Deanna Haight; Deanna, Jonathan Kane!"

"Nice to meet you," I said.

"Same," she replied.

"She was bored, so we invited her along," Sophie said. "I hope you don't mind."

Deanna was tall, thin, and had long, braided dark hair which reached her waist. She wore no makeup and was dressed in what I'd call 'ratty' clothes and a hoodie. Her entire look screamed 'starving artist', and I wondered if it was an affectation, or just who she was.

"I don't mind," I replied. "Let's take the 'za to the kitchen. I have pop, beer, or red wine."

"Let's open a bottle of wine," Ivy suggested. "We have the price of admission with us!"

I chuckled, "A bottle of Jack Daniel's, of course."

"Of course!" Sophie declared. "Deanna paid for the bottle!"

That was Sophie's way of confirming that Deanna was a willing participant in their plan for casual, occasional sex. I got plates and glasses, then opened a bottle of red wine. Ivy took it from me and poured wine for each of us, then we dug into the thin crust pizza.

"What's your major, Deanna?" I asked.

"Fine Arts; I paint oils on canvas."

"When did you start?"

"With fingerpaint around age four!" she said with a silly smile.

"And oils on canvas?"

"Junior High. I experimented with watercolors, but thought they weren't bold enough. I like bold, abstract art."

"Sold any paintings?" I asked.

"I wish! Most artists die poor and THEN a single painting can sell for more than the artist made in their entire life!"

"What year?"

"Freshman; I just started in September."

"From?"

"A place I'm sure you've never heard of — Milford, Ohio."

I started laughing, then said, "I'm from Goshen. I only moved here about eighteen months ago. Did you go to Milford High?"

"No. McNicholas. Good Catholic girl, don't you know!"

"Not anymore!" Ivy declared.

"I might have decided that only the good die young after I met Ivy and Sophie when I came to the Art Institute!" Deanna said mirthfully.

"I have news," I said. "I have my securities license and I'm moving to an analyst position as of March 1st."

"So you'll have plenty of money to buy art!" Deanna declared.

"Well," I said with a silly grin, "you just told me it's a great investment. I buy it ultra cheap from you, hang onto it until you starve to death, then sell it for a major profit!"

Deanna, Sophie, and Ivy all laughed.

"You did basically tell him that, Dee!" Sophie declared.

"Me and my big mouth!" she said, rolling her eyes and sighing theatrically.

"You'll need it," Ivy smirked. "There's one thing about Jonathan we failed to mention! He's hung like a horse!"

Deanna had a wide mouth with full lips, and the thought of them wrapped around my shaft was enticing. The same was true for her long legs, which I imagine wrapped around my waist.

"Birth control?" I asked.

"I followed Ivy's advice when I got to Chicago and I'm on the Pill," Deanna said.

"She also followed my advice at the first party she attended, and now she's going to Hell with the rest of us sinners!" Ivy said gleefully. "Because the sinners have much more fun!"

"Jonathan," Sophie said, "when we finish the pizza and the bottle of wine, you and Deanna get to know each other Biblically, then the three of us will do our best to fuck you unconscious. Deal?"

"Deal!" I agreed.

"What do you do now, Jonathan?" Deanna asked.

"I'm the supervisor in the mailroom, and I'm taking classes at Circle, in addition to working on two securities licenses, one of which I have, and the other I should have in January."

"How'd you get that job, if it's OK to ask?"

"It is. My uncle called in a favor with a friend to get me a job as a mailroom clerk. I worked my way up to supervisor while going to school and studying for my securities license."

"That's totally cool."

"Do you work?"

"At Venice Café on Wacker. Basically, every artist, actor, singer, and songwriter waits tables to put food on the table. I'll basically work whatever jobs I can to support my painting. It's who I am. Did you always want to be involved in the stock market?"

"No. I had no idea what I wanted to do except get out of Goshen. My uncle provided the means, and I honestly didn't care what the job was, so long as there was a way to advance and at least make a comfortable living."

"I'd say you're there already," Deanna said. "You have a nice house, a good job, and according to Sophie, you're drowning in pussy!"

I couldn't help but laugh, "All true, but my sights have changed a bit. Comfortable is no longer enough. Oh, sure, I could settle for that if I had to, because it's a huge step up from where I was before I came to Chicago, but I don't feel I have to settle."

"Mansion in Glencoe or someplace like that?" Ivy asked.

"Ask me in five years. I'm not looking that far out just yet. Right now it's getting settled into the new job, learning the business, and making contacts. Sophie, have you started looking for jobs?"

"I will in February," she replied. "Firms that hire graphic designers recruit on campus."

"Ivy, you're starting a Master's next year, right?"

"Right. I hope to teach in the area, but I have two more years of school before I have to actually act like an adult!"

"Finish your pizza and you can do all kinds of adult things!" Sophie teased.

"That sounds like an excellent idea!" Ivy declared.

We finished our pizza and wine, and went upstairs to my bedroom.

"What do you like?" I asked Deanna.

"Orgasms! Duh!" Deanna exclaimed. "Lick me while I suck you, then you fuck me, but cum in my mouth!"

"I can do that," I replied, and began getting undressed.

Deanna quickly stripped off her clothes. She was about an inch shorter than me, but was skinny to the point of her ribs showing, with narrow legs and a small butt. The thing that was out of proportion were her breasts, which were nice, and appeared large on her waif-like body.

"Nice!" Deanna declared, looking me up and down.

I pulled her to me, we French kissed then fell into bed. We did what she'd asked for, starting with sixty-nine, then fucking hard, and me pulling out when I was close, and Deanna taking me in her mouth, sucking and stroking me until I came. She released me, and we exchanged a fierce French kiss.

"Play time!" Ivy declared.

She and Sophie stripped off their clothes and got into bed.

November 21, 1982, Chicago, Illinois

The girls had left at 1:45am, adhering to Sophie's 'no sleepover' policy. I had been, as a phrase I'd once heard said, ridden hard and put away wet. The girls had, as Sophie had promised, done their best to fuck me unconscious, and had come close, not giving me a moment's rest, with one of the girls taking me into her mouth as soon as I'd cum, and I'd been offered breasts and pussy for my tongue and fingers. When I eventually couldn't get it up again and was tired to the point of exhaustion, the girls had each given me a kiss, dressed, and let themselves out, promising to call after New Year's.

When I got out of bed on Sunday morning, the first thing I did was shower, the second thing I did was wash the sheets which were soaked with sweat and other fluids, the third thing was to open the window of my room to air it out, despite it being below freezing, and finally, I went down to the kitchen to have a bowl of cereal, given our friends would arrive in less than an hour for football.

"Have fun?" Shelly asked.

"I did! Did you guys have fun last night?"

"Twelve girls out on the town! But nowhere near as much fun as you had, I'm sure!"

I finished my cereal, then drove to the White Hen to get ice and filled the coolers just before people started to arrive. Everyone joined us except Tom, Maria, Stuart, and Melinda. That included Sally, her date, Will, Allyson and her boyfriend, Tim, along with Costas, Trevor, Dustin, Archie, Jack, Kristy, Lily, and Violet, who I'd drive home after the late game.

Things didn't start out well for the Bears, and they were trailing 14–3 at the end of the first quarter. From there, they played better defense, and outscored the Lions 17–3, winning the game 20-17 with a 4th quarter field goal. Walter Payton had a decent game with 87 yards rushing and, and Jim McMahon had a great game, passing for 233 yards.

"Not an auspicious start," Jack said. "But I'll take it."

"Agreed," I said, "though I was happy to see the Bengals beat the Eagles."

"What's the second game?" Archie asked.

"Seahawks at Broncos," I replied.

That game ended 17–10, with the Seahawks coming out on top. As soon as the final gun sounded, Violet and I left so I could drive her home.

"So you can legally manage my money now, right?"

"Yes. It will need to go into my fund, though, because you don't have enough to have your own account at Spurgeon. I'll combine it with money from nine other people, and you'll get your percentage of the profits."

"That's cool. You said there were fees, right?"

"Yes, but I'll waive the buy-in fee for you."

"Does that come out of your pocket?"

"Yes, but I'll still take ten percent of the profits over the hurdle, but I won't make you pay the 1% to get into the fund."

"Are you doing that for everyone?"

"No, just for you."

"Thanks. You won't get in any trouble?"

"No. I'll just add enough to your buy-in to cover it, and nobody will know the difference except you and me. It's not illegal, and I'll give you the money so that when you transfer it to Spurgeon, the numbers will be correct."

"How much?"

"It's a 'one and ten' fund, which means the buy-in is one percent, or about $750 in your case. Of that, half goes to Spurgeon and the other half to me. I'm basically refunding my half and covering the other half. I just don't feel right taking the fee from you."

"You're really sweet."

"Thanks."

"You're going to call on Sunday, right?"

"Yes, when I leave Goshen."

"Cool!"

At Violet's house, I walked her to the door and received the usual hug and a kiss on the cheek. Once she was inside, I walked back to the car and headed home, where everyone had left except Lily, who was staying until 11:30pm, as her mom wouldn't be happy if she spent the night.

"Interested in chocolate covered Lily?" she asked.

"I am indeed!" I replied.

We went to my room, then took turns licking chocolate from each other before we had a long, slow, sensual screw. We lay in bed together cuddling and talking until 11:00pm, then showered, dressed, and I walked her to her car.

"You're gone next weekend, right?"

"Yes."

"OK. Do you want to go out the following Friday or Saturday? If so, I won't make a date."

"How about Friday?" I suggested.

"Great! Pick me up after work?"

"Yes."

We hugged, kissed, and I went back inside, changed the sheets, and got into bed.

November 22, 1982, Chicago, Illinois

On Monday morning, something I'd expected to happen happened — Theo Lipari was on 29 when I went down to speak with Marcus.

"Hey, Kid," he said.

"Mr. Lipari," I said evenly and with a nod.

"Relax, Kid," he said. "Your boss squared everything in advance. My guys are working and I'm just making sure there aren't any non-union guys on the job."

"Mr. Brown wrote into the contract that he'd only use union labor."

"He's a straight shooter, but we still check union tabs."

I checked with Marcus and there were no problems or potential delays, so I went back to 30 and stopped in to see Mr. Nelson.

"Theo Lipari is here," I said. "Supposedly checking union tabs. He did say that you had squared everything with him."

"No attempted shakedown?"

"No. He seemed to be happy."

"Guys like him are never happy, but he doesn't want to lose out on the box at Soldier Field next season. Everything's good, right?"

"Yes. I'm not an expert, but it looks like they're making progress so that they'll finish on schedule. The real question is the furniture and new terminals and phones."

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