Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 44: Destination, Deflowering, and Discussion

Coming of Age Sex Story: Chapter 44: Destination, Deflowering, and Discussion - How do you maintain your personal integrity and loyalties to those you care for in the face of unbelievable temptations? Is it even possible, or will Jonathan's principals be compromised as much as the ones of those whose fortunes he seeks to match? The only way to truly find the answer is to keep climbing up.

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

January 8, 1983, Chicago, Illinois

Author's Note: This chapter has been modified to comply with site guidelines as of 2025-03-29

I left the law offices just after 11:00am, having spent about an hour with the two attorneys from Cincinnati. I was convinced, as was Nelson, that their goal was to develop information to interfere with Bev moving to Chicago. It made perfect sense, and as Nelson had said, they could have hired a private investigator to gather the information, so the fact that I'd said it was, in one way, immaterial. That fact aside, I still felt bad, but I didn't know if there was any way it could have been avoided, except if I hadn't moved into the house with Bianca and Shelly. The die had been cast the previous Spring.

There was literally nothing I could do now except fly to Cincinnati for the hearing, and that meant driving down to Hyde Park to the offices of Windy City Travel. I parked in the lot behind the building, and then walked around and went in the front door.

"Can I help you?" a young man sitting at a desk near the door asked.

"I'm here to pick up some tickets from Barney Evers," I said.

"Jonathan?" a black guy in his late thirties called out from an office. "Come in."

I walked past a few desks and into the office, shook Barney's proffered hand, then sat down.

"Nice to meet you," he said. "I have your tickets printed, and also an application for an American Express Card."

"Thanks. I'll pay by check."

"Great. I'll need to see your driver's license. Does the address on the license match the check?"

"It does."

I filled out the check, signed it, then handed it and my driver's license to Barney. He wrote down the number and expiration date of my license on the check, then handed me my license and the envelope containing the tickets and my itinerary.

"Protect these like cash," he said. "Airline tickets are considered negotiable instruments."

"That's not something that was covered in any of my securities classes."

"I don't think it means the same thing as 'negotiable security'. Basically, you can get your money back, or, if your flight is cancelled, use the ticket on another airline. In the past, you could resell it, but with every airline now checking ID, that no longer works. Do you have a passport?"

"No."

"I'd suggest applying for one immediately. They're good for ten years, and that way, you have it if you need it at a moment's notice. You can use your driver's license to go to Canada and northern Mexico, and a few islands in the Caribbean, but otherwise, you need a passport. They aren't expensive to obtain, but it can take as long as six to eight weeks, so I recommend all my customers have one. It also serves as a second piece of photo identification, should you ever need it."

"How do I do that?"

"Go to a photographer who offers 'passport photos', then take those photos to the Passport Office in Chicago and fill out an application. There are a couple of photographers less than a block from that office, which is on Congress Parkway. You'll also need your birth certificate."

"OK. Any other advice?"

"Do you know the process at the airport?" Barney asked.

"No," I admitted. "I've never flown before."

"You go to the departure hall at Midway, present your ticket booklet, check any bags, and receive a boarding pass and luggage check receipts, if necessary. They'll tear out the ticket for the leg of the journey and return the rest to you. Once you've completed that, you go through security where they'll X-ray your carry-on bag and have you remove any metal from your pockets. Then you walk through a metal detector, and if it pings, they'll use a wand to find the spot, which can be a large belt buckle or something similar. It's also possible they'll frisk you. You can refuse, but then you'll be denied access to the gate area and won't be able to board the flight.

"From there, you find your gate, have a seat, and when the flight is called, check in with the gate agent, who is an airline employee, often a steward or stewardess. Follow their directions, board the plane, find your seat, stow your bag, and listen to the crew for instructions. Once you arrive in Cincinnati, you leave the plane, walk through the concourse to the arrivals hall and meet your party, then collect any checked baggage. They can also come to the gate if they're willing to go through security. For your return flight, just repeat the process."

"Got it. Thanks."

"Do you have any fears about flying?"

"Should I?" I asked.

"Some people do, and you can't always predict who. How long have you been in Chicago?"

"Since May 1981. Why?"

"Then you weren't living here when the accident occurred at O'Hare. That caused quite a bit of fear."

"I remember seeing that on the Cincinnati TV news. That was 1979, right?"

"May 25th. I had booked several people onto that flight."

"No survivors, right?"

"None. They lost an engine on takeoff and crashed into a field just off the airport. A super-rare occurrence. Most people won't ever even have a minor problem on a flight."

"My dad was killed in a plane crash in 1962."

He glanced down at his paperwork, "Before you were born."

"Yes. He was on Continental Airlines Flight 11 from Chicago. It was blown up by a crazy with a bomb."

"I know about that, but I only started working here in 1968. The owner of this agency had booked someone on that flight."

"Maybe I should find a different travel agency," I said with a slight smile.

"Of the millions of miles flown by our passengers, those were the only two flights with reported injuries, let alone fatalities. And that's tens of thousands of flights. Airline travel is safer than your drive back to Rogers Park."

"I was joking," I replied. "The way I see it, everything has risks, you calculate the risk, decide if you want to take it, then do the thing or don't do the thing."

"Up and coming stockbroker, right?"

"Most likely I'll focus on currency trading to start, along with related products such as precious metals and gold stocks, but I'm licensed for all securities."

"Somebody gave you a leg up the way the owner of this agency gave me in 1968."

"Somehow, if I know my history, the owner here took the far bigger risk."

"Hiring a black nineteen-year-old who had only ever bussed tables and washed dishes at a diner was pretty gutsy, especially given all the stuff that went down in 1968."

"Assassinations, right? And riots?"

"Doctor King and Robert F. Kennedy, plus the Democratic National Convention. Throw in the resulting riots, and white folks were even less interested in hiring black folks for anything other than manual labor."

"Crazy times."

"Yes, they were. Thankfully, things are better, and Chicago is likely to elect a black mayor, which in 1968 would have been unthinkable. On a positive note, the Boeing 747 debuted in 1968."

"A great plane, according to everything I've read."

"And a great company, run by engineers and aviation enthusiasts. If you fly internationally, you'll probably be on a 747, and if you're anything like Murray Matheson, you'll fly first class and be pampered during the entire flight."

"That might be a few years away," I replied with a smile. "Buying a house comes first."

"That was a pipe dream for me at your age! We finally bought our first house in 1978. With two kids, an apartment just didn't cut it."

"I can believe that."

"Anyway, back to your trip. On the itinerary are three phone numbers — the agency number, my direct number, and an emergency 800 number which is answered twenty-four-hours a day, every day, including Christmas. If you can't reach me or someone here for any reason, call that number and they'll help you."

"Thanks."

Barney and I shook hands, and I left the travel agency to head back to Rogers Park. When I arrived home, Bianca and Shelly weren't there. A note hanging on the fridge said they had done the weekly grocery shopping, and would be out the rest of the day, as they needed to buy their books for the new semester, then were hanging out with some of the girls from Loyola, and going to a party on campus.

I went upstairs, stashed the tickets in the drawer of the computer desk, changed into comfortable clothes, changed the sheets on my bed, then went downstairs and started a load of laundry. Once the washer was running, I had a quick bite to eat, washed the plate I'd used, then went back upstairs to update my portfolio spreadsheets. Just before 1:00pm the doorbell rang, so I saved my work, shut off the Apple II, and went downstairs.

"Hi!" Clara Crowley exclaimed when I opened the door.

"Hi," I replied. "Come in."

She walked into the house carrying an overnight bag, and I closed the door behind her. As soon as it clicked shut, she launched herself into my arms, pressing her body against mine and giving me a searing French kiss.

"It's already thirty-seven hours since I turned seventeen and I'm still a virgin!" she exclaimed when she broke the kiss.

"Something which you could have remedied at any point in the past couple of years," I replied with a grin.

"Unh-uh!" she protested. "You said I was too young and I want YOU!"

"Not to be ungrateful, but why me?"

"Tall, dark, handsome, successful, and a man, not a boy!"

"And it has nothing to do with me dating your sister for a time?" I asked with an arched eyebrow.

"Duh!" Clara exclaimed. "She thinks she's hot shit, but I'm better in every way!"

"As I said when you made that statement earlier, it's a bold claim!"

"I guarantee I'm better!" Clara declared forcefully. "I'll do anything you want, and I'm positive you'll not only like it, but it'll be the best you've ever had!"

"I don't think you need to do a sales job at this point!"

"Then why are we standing by the door instead of screwing in your bed?"

"Why indeed?!"

I took her hand and led her up to my bedroom. I closed the door and turned on the stereo to WXRT, and turned up the volume, though not too loud.

"Birth control?" I asked.

"I'm on the Pill! I have been since I turned sixteen! I wanted you then!"

"Well, you have me now!"

"Wait here!" Clara declared, going into the bathroom and closing the door.

...

"I take it you want to do it again?" I asked.

"Again and again and again!" Clara declared. "All night, if we can!"

"I do need to get a bit of sleep," I replied. "But I'll do my best!"

"I am SO glad I waited for you!" Clara declared. "Kelly's first time, which was with a High School guy, sucked, but then she started seeing a college guy and it was way better."

"Kelly seems to have given you all the information you needed."

"She told me all kinds of stuff that they didn't cover in health class! And somehow I don't think the nuns would tell us about blowjobs and pussy eating!"

"Do you go to church?"

"No. I quit going when I was fifteen. I don't think taking the Pill is a sin and, well, only the good die young!"

I laughed, "Virginia was Catholic, and of course, her name conveys that she hadn't had sex."

"You liked it enough to want to see me again after today, right?"

"Top 5, for sure," I replied, my voice conveying I was teasing.

"TOP 5!" she screeched in what was obviously mock outrage.

"Well, the sample size is limited," I replied. "The rating might improve if you work hard enough!"

"I know you're teasing, but I'll do anything you want. I meant that, too. Anything."

"What we did was great," I replied. "Next time you can be on top, and there are other positions, too."

"Kelly told me about a bunch of position, plus what she called sixty-nine, which I want to do, and some other stuff I'm not sure I want to do, but would do if you wanted."

"I want you to say what you want, and if I ask for something you don't want to do, either at that time, or ever, I want you to tell me."

"Well, next we should sixty-nine, then me on top, then whatever you want to do."

"And what's your plan after tomorrow morning?"

Clara smirked, "That you like me enough to ask me out and keep asking me out!"

"And your parents will be OK with you dating a guy who's twenty?"

"You're only three years older, which Mom specifically set as the limit when I turned sixteen. She'd be OK if you were my boyfriend. I'm not sure dad will be OK with any guy, but Allyson and Kristy both like you, and that will make him at least accept it, even if he doesn't like it."

"Do you have a plan for the future?"

"College, but I don't know what I want to study, then marriage and three or four kids. Interested?"

I chuckled, "It's a bit premature to go from a casual screw to marriage and kids."

"I was teasing about marrying, but I absolutely wouldn't mind having a tall, handsome, HUGE, older guy as a boyfriend! Just think, blowjobs whenever you want, warm, slick, tight pussy whenever you want, and a smart, fun girl to hang out with!"

"We don't really know each other well enough to make any decisions like that," I replied.

"Duh! Isn't that the point of dating? To get to know the person? And I think you'll like my personality at least as much as you like having sex with me!"

"You're putting a lot of effort into marketing yourself!"

"Dad says you only get what you want if you work hard and are persistent. Kristy says you're like that. And that's another thing, though not as important — Kristy says you're successful and will make a ton of money. I'm not mercenary, but if it's a choice between two similar guys, it would make sense to pick the one with the better career."

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