Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 2: You’ve Got Balls

Coming of Age Sex Story: Chapter 2: You’ve Got Balls - 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   Ma/ft   Mult   Rags To Riches   Workplace  

June 18, 1982, Chicago, Illinois

At the end of the workday on Friday, I left the office and headed to the lobby of Water Tower Place, where I met Phoebe. We greeted each other with a hug and quick kiss, and after a brief discussion, decided to head to Ed Debevic's.

As had happened the previous time, a cute, bubbly waitress flirted with me, and after she brought our drinks, actually sat in my lap while she took our orders. I knew it was part of the schtick that all the waitresses did, but I had the distinct impression that if I asked, she'd very likely give me her phone number.

"That wasn't TOO blatant," Phoebe said sarcastically, rolling her eyes.

"It's all an act," I replied. "Allyson warned me about it before she brought me here the first time. The waitress did the exact same thing."

"I have ten bucks that say she gives you her phone number, if you ask."

"I might not be completely clued in to how to have a good relationship," I replied, "but asking another girl for her number when you're on a date seems like a surefire way to mess things up!"

"That's true, though in this case, I made a wager."

"And if I take that wager and she does give me her number, then what?" I asked.

"That's up to you."

"And that seems like a very bad idea," I replied. "If I do that, it'll make you feel bad and that's not right, no matter what our relationship happens to be."

"What is our relationship?"

"We're dating," I said. "And at this point, I'm not in any position to commit to anyone."

"I thought you and Bianca were moving in together. Or at least that's the rumor."

"Shelly, Bianca, and I are renting a house together, but it's just as roommates. Bianca and I aren't a couple and probably never will be. I was seeing Huifen before she went home for the Summer, and you know I was just back home to see Bev. She's coming to visit in August, with her baby."

"You two are getting back together?" Phoebe asked.

I shrugged, "I have no idea what's going to happen. When I was home, Bev and I didn't come to any conclusions other than agreeing she would visit. Until that's resolved one way or the other, I can't make any commitments."

"You might marry her?"

I shrugged again, "I have no idea what might happen. It's confusing and, in some ways, scary, and it's weighing heavily on me, even though Heather isn't my daughter. Ultimately, anyone who might want a relationship with me has to be patient."

"So everyone plays second fiddle to Bev? She's in control?"

The conversation was confirming what I'd thought about Phoebe — that she simply wasn't as mature as Bev or Huifen, nor Anala, though my relationship with Anala was different, despite our teasing.

"I don't know what to tell you, except that I'm being as honest and direct as I'm able to be. At that point, it's up to you how you deal with it."

"And you expect me to put out while you're making up your mind?"

If I'd had any doubt in my mind about seeing Phoebe again, she'd just made it an easy decision. And that decision meant I couldn't take her back to my apartment, even if she were willing.

"I don't expect anything," I replied. "Sex is fun, I enjoy it, and do my best to please my partner, but I never expect any girl to have sex with me. If she wants to, and I want to, we do it. If either of us doesn't want to, we don't."

"But you assumed I was going to spend the night tonight."

I hadn't, at least in the way she meant, but I could turn the tables.

"I didn't assume anything," I countered. "I considered it a strong possibility based on our previous dates, but I made no assumptions. Let me ask you a simple question — did you bring an overnight bag with you?"

"Yes."

"Why?"

She glared at me before she answered, which only reinforced my feelings that things were going nowhere between us.

"Never mind," she replied flatly.

At that point, I knew we were done. If we hadn't ordered, I'd have suggested we leave. In any event, when we finished eating, the date would be over, and I wasn't going to call Phoebe again. I had a half-hearted idea of asking the waitress for her phone number, but that would be crass, and even though I wasn't interested in Phoebe as a possible girlfriend, I didn't want to be mean to her.

The problem with not leaving was that our meal was awkward, with no conversation. When we finished eating, I felt I had to put the date out of its misery.

"I think we should skip the movie," I suggested.

"Fine," Phoebe replied flatly, getting up. "Good night."

She turned and left, and just as she walked out the door, the waitress came to the table.

"I guess you're not having dessert," she said.

"I guess not," I replied. "Just the check, please."

She took out her pad, totaled the check, then handed it to me.

"Maybe your evening won't be a complete loss," she said with a smile. "My shift ends at 10:00pm. Maybe get a drink?"

I nearly laughed because Phoebe had been correct in her assessment of the situation.

"I'm not twenty-one," I said.

"College student?"

"Yes, but I work full-time and take classes at night."

"Where?"

"Circle."

"I'm at the School of the Art Institute of Chicago. Where do you live?"

"Little Italy, though people are calling it University Village. Well, for another two weeks. Then I'm moving to Rogers Park."

"I have an apartment in Armour Square. I could get a bottle and come by your place around 10:45pm."

I was attracted to the cute, blonde, blue-eyed girl, but I had a very busy Saturday, and drinking late at night, and likely being up very late, and then having to ensure she was gone before Violet arrived gave me pause. That said, until Bev arrived in August, and Huifen came back to Chicago, I didn't have anyone to go out with except the guys.

"I have a really busy day tomorrow," I said. "And it starts fairly early. How about we exchange phone numbers? I'm Jonathan, by the way."

"I'm Sophie," she replied. "What are you doing tomorrow night?"

"No plans," I said. "At least after 6:00pm."

"My shift tomorrow ends at 8:00pm. Give me your address, and I'll show up around 9:00pm."

I nodded, accepted her pen and pad, wrote my address and phone number, and handed it back. She wrote her phone number on a slip of paper and handed it to me, then I paid the check, including a tip, and left the restaurant to head for my apartment.

When I arrived home, I double-checked to make sure I had a box of rubbers in case things with Sophie ended where I suspected they might. I wasn't making any assumptions, but I wanted to be prepared. I had a full box, which meant I didn't need to make a special trip to Osco to get them. While I could easily buy them at Jewel, I didn't want to have to do that with Violet along, which she would be.

I read, listened to music, and turned in around 10:30pm.

June 19, 1982, Chicago, Illinois

On Saturday morning, I was up early so I could clean my apartment, something I hadn't done for nearly two weeks because of my trip to Ohio, my new work hours, and spending time with friends. Just after 9:00am, the phone rang, and I answered it.

"What happened between you and Phoebe?" Allyson asked after we greeted each other.

"I really shouldn't discuss it with you," I said. "What did she say?"

"That you were a total jerk, and she's not sure why she ever went out with you."

"I'm not going to get into the blame game or name-calling," I said. "All I can say is that I was completely honest with her from the very start."

"She's in love with you."

Which, if true, explained quite a bit, and I had missed it. But I didn't feel that way about her at all, and I didn't think I'd done anything to imply that I did.

"I'm not sure what I'm supposed to do about that," I replied. "You know my situation, and until Bev and I sort things out, I'm in no position to make any commitments to anyone. Huifen understands that, and that's why we specifically postponed any decisions until she comes back to Chicago. But that's all I'm going to say on the matter."

"OK. Sorry I pried; I was just worried about Phoebe because she seemed very upset. On another topic, I heard from Kristy. She's having a blast 'down under'. She said to say 'hi'."

"If you speak to her again, tell her 'hi' from me as well. That's a dream trip!"

"I think you'll have the money to do it before you know it!"

"I have so many other priorities before I even really think about that!"

"I'll let you go, but I'm planning to have a small party for Kristy when she comes home in July. I'll let you know."

"Thanks."

We hung up, and I finished cleaning, then made a grocery list, and gathered my laundry and detergent, and sat down with the Tribune to wait for Violet, who arrived exactly on time. As I was ready to go, we left for the laundromat right away.

"Where all are we going?" she asked as we walked along Polk towards Halsted.

"Venture and Sears are the most likely places I'll find what I want. I need a bed, dresser, desk, chair, sofa, loveseat, and a dinette table and chairs. Mostly I expect to find what I'm looking for at Venture or Montgomery Ward, with Sears as a backup. I do want to get some basic tools, and Craftsman are the absolute best, especially with their warranty, which lasts, in effect, forever, so we'll go to Sears no matter what. If I don't find what I'm looking for in my price range, I'll borrow a car from my uncle to check out furniture stores."

"That sounds like it's going to cost a lot of money."

"I have enough saved to cover it," I said. "And that's without dipping into my emergency reserves. I think I also mentioned that my promotion means I earn quite a bit more, and I'll be able to replenish my savings fairly quickly."

And that didn't even take into account my investments, though I wouldn't touch those unless I was in the most dire of straits and had no other options.

"How did you save so much money?"

"By carefully budgeting what I spend and putting money into savings and investment first, before anything else. Most of my increased income will go to either savings or investments."

"Your goal is to become rich beyond your wildest dreams?"

"My dreams are pretty wild in that regard!" I chuckled. "But what I really want is to be comfortable, able to afford the things I need and want, and to be able to do the things I want to do. How did things go with Doctor Lochner on Tuesday?"

"She's seriously upset with you."

"The feeling is mutual," I replied.

"She suggested strongly that I stay away from you because you're dangerous."

"What did you say in response?"

"That I was totally comfortable with you, that I felt safe with you, that you would never, ever do anything to hurt me, that you were a good friend, that I liked spending time with you, and that I thought you could help me. She tried to tell me I was mistaken, but I insisted that what I'd said was all true, and that she was wrong."

"Because it is true," I said firmly.

"She warned me that you would undo all the progress we've made."

"May I speak bluntly?"

"Yes."

"I think she likes controlling you and making you dance to her tune, and from the conversations I've had with her, she does not intend to ever let you go. I, on the other hand, think you are an adult, and ought to be free to make your own choices. Yes, you suffered serious emotional trauma, as she calls it, but you can't let that control your life. Think about all the things you've done with me that you hadn't ever done before."

"She was adamant that I'm moving too quickly."

"She's wrong. And if she tries to give you an ultimatum, don't fall for it. I'm sure there are other doctors who can help you, if you need it, in the way you need it."

"I don't want to lose you as a friend," Violet said quietly.

"That's not going to happen unless you decide you don't want to be my friend."

"What about when your girlfriend comes back?"

"What about it? She knows you and I take classes together and hang out together."

"Most girls would be jealous."

"Which is why I wouldn't accept most girls as a girlfriend," I replied. "No matter what happens with Bev, she and Heather are going to be a part of my life, and any girl who was jealous of her wouldn't be compatible with me."

"You obviously care a lot for her. Why does it scare you to get together with her?"

"You're basically the same age I am; are YOU ready to have a baby?"

"Oh, heavens no!" Violet exclaimed.

"Neither am I, and that's what is weighing so heavily on me. If Heather were mine, I'd be obligated in a way I'm not now and there wouldn't really be a decision."

"You'd marry a girl you got pregnant?"

"I'd have married Bev if I'd made her pregnant. For any other girl, it would really depend on our relationship. I'd certainly pay child support and do my best to be part of my child's life, even if I couldn't marry his or her mother for whatever reason."

The rest of the morning went by quickly at the laundromat and at Jewel, and after taking the clean clothes and my groceries home, we walked to Greek Town to get gyros. Given the amount of food they served at Mr. Greek, I wouldn't need more than a light dinner after a gyros platter.

The afternoon was busy, and I managed to find everything I needed between the three stores, arranging for everything to be delivered to my new place in Rogers Park on July 2nd. The only things we had to carry were the Craftsman tools I'd purchased — a hammer, a set of screwdrivers of various sizes, and a pair of vise-grip pliers.

We arrived back at my apartment just past 6:30pm. I invited Violet in, but she decided she wanted to go home, so after I dropped the bags from Sears in the apartment, I walked her home, then returned and ate a light meal. Once I'd finished and cleaned up, I sat down with my ledger and updated it based on the receipts for everything I'd purchased. I'd spent a bit more than I had hoped, but I had opted for somewhat better quality at a slightly higher price.

The only things left to buy were a Weber grill, charcoal, lighter fluid, and food for the Fourth of July housewarming party. I'd considered inviting Violet, but given her aversion to socializing, I didn't think it was a good idea, and the last thing I wanted to do was pressure her in any way nor make her uncomfortable. I might mention it to her when we went to the baseball game, though I'd have to think that through.

Just after 9:00pm, there was a knock at the door and I opened it to find Sophie, dressed in a skin tight black T-shirt with no bra lines, form-fitting jeans, and sneakers. Her blonde hair was pulled back in a loose ponytail, and she had on just the barest hint of makeup. She was carrying a medium-sized brown paper bag with 'Foremost Liquors' imprinted on it. I invited her in and she kicked off her shoes.

"I hope you like Jack Daniel's," she said.

"I actually haven't really drunk much in the way of alcohol except beer."

"I got Cokes, too, which is a good mixer. And a bag of chips."

"I bought some chips as well," I replied.

"Studio, just like mine, though I'm not over a garage," she said. "I take it the place in Rogers Park is bigger?"

"A house," I replied. "Three bedrooms, basically, and I'll have a couple of roommates. Grab a seat. What kind of music would you like?"

"XRT is fine, or The Loop."

"XRT it is," I replied.

I tuned the radio to WXRT, then opened the bags of chips. I got two glasses from the fridge and added ice to each one, then went to sit next to Sophie on the couch. She poured a healthy amount of the Tennessee Whiskey into each glass, then added Coke to fill them. We clinked glasses, and I had my first taste of Jack Daniel's.

"What are you studying at the Art Institute?" I asked.

"Graphic design. I just finished my Junior year. You?"

"A mix of finance, statistics, and computers, though one class at a time in the evening, as I said. I work full time."

"What job?"

"Mailroom supervisor at Spurgeon Capital, an investment firm. My goal is to move up to a position with a trading or money management team."

"Is that possible?"

"Yes. It's a fairly normal progression, though I'm trying to skip an intermediate step. I started as a mailroom clerk about a year ago. and was promoted to supervisor as of Monday. What do you plan to do when you graduate?"

"Get a job!" Sophie said with a soft laugh.

"Doing?"

"Who knows? Anything that requires graphic design skills, so it could be advertising, cover art for albums, corporate logos, book covers, or anything that requires drawing and design skills."

"How'd you get into that?"

"I started sketching when I was little and basically taught myself how to draw. I enjoyed it, and when I was in High School, I drew for our yearbooks and the school newspaper, and decided I wanted to do that for a career. I applied to the Art Institute and here I am!"

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