Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 16: Special Assignment

Coming of Age Sex Story: Chapter 16: Special Assignment - '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  

September 7, 1981, Chicago, Illinois

On Monday, which was Labor Day, I met Tom, Maria, Stuart, Dustin, and Teresa in Grant Park for a Labor Day cookout. Stuart had a new girl with him, who he introduced as Annette. She was blonde, with blue eyes, and was ‘stacked’. I wondered what had happened to Lucy, as she’d been at Poplar Creek with us just four days previously. After everyone greeted her, we all sat down on blankets to drink Cokes and munch on chips and pretzels.

“One more week until the Academy,” Tom said. “And I’m glad to be done in the kitchen at Connie’s!”

“I’m working the rest of the week,” Stuart said. “I wanted last Friday to be my last day, but my boss talked me into working this week. They’re having trouble finding someone to replace me.”

“What do you do, Annette?” Dustin asked.

“Dental hygienist,” she replied.

“Where?”

“In Bridgeport. Stuart tells me you’re a photographer. Where’s your studio?”

“Hyde Park.”

“I know Tom is going to be a fireman, what about the rest of you?”

Maria, Teresa, and I told her what we did and further conversation led me to conclude that Annette was a basic airhead, and that Stuart’s real interest in her started and stopped with her very, very nice chest.

It was about an hour after we arrived that the three girls went for a bathroom break and I could ask Stuart about Lucy.

“I got bored,” he replied.

“More like SHE got ‘bored’ and you’re looking for new territory to conquer!” Dustin teased. “We’ve seen this movie time and again!”

“That’s true,” Tom added. “You dated Lucy for four months; that’s some kind of record. Back in High School it was a new girl every week or two, if it wasn’t two girls every week!”

“He really had that many girls in High School?” I asked.

“We weren’t exaggerating,” Tom replied. “He had more pussy in High School than any twenty normal guys get in their whole life! No female from fifteen to forty was safe!”

“Tom’s just jealous,” Stuart said smugly.

“No chance!” Tom laughed. “I was very happy with a steady girlfriend for most of High School. And I wouldn’t trade Maria for any three girls! Jonathan, are you and Teresa serious?”

I shrugged, “We see each other every weekend, but we’re not steady. Why are you asking?”

“Maria’s already planning the wedding. You saw the ring on her finger, right?”

“I did,” I replied.

“Teresa is one of her maids of honor and I wanted to ask you to be a groomsman, along with Dustin; Stuart is my best man. I know it’s a year away, but it was a question from Maria about whether you would need to bring a date.”

“Heck if I know,” I chuckled. “I’d be happy to be a groomsman, and I suspect that whatever happens, Teresa and I will be on good enough terms to sit together!”

Tom laughed, “It was more about if either of you had someone serious who would object.”

“Ask me next May about that! And about being a groomsman.”

“You don’t even want to know what goes into planning a huge Catholic wedding. May is awfully late to make changes for a late-June wedding.”

“Eloping to Vegas or wherever is sounding more and more attractive,” I said.

“That’s what I told him!” Stuart exclaimed. “The four of us, four chicks, and a preacher dressed like Elvis! Then hit the blackjack tables, the bar, and the pool!”

“If we do that, her mom will put a hit contract out on the four of us that will make us wish the Chicago Outfit was after us!” Tom declared, shaking his head.

“Where’s the wedding going to be,” I asked.

“St. Ambrose, on 47th. I’ll get you all the details once we meet with the priest on Friday.”

“Are you Catholic?”

“Sort of,” he chuckled. “I was baptized, made my first communion, and was confirmed, but I haven’t been to church in ages. Maria goes fairly often, and Teresa occasionally. You never went to church, right?”

I shook my head, “Nope. My mom wouldn’t go near a church, and the only time I was ever in one was a funeral for a soldier killed in Vietnam. The widow was one of my mom’s friends, but I never met her before that, and I think I’ve only seen her twice since, and that was a couple of years ago. Barring some bizarre occurrence, your wedding will be my second time in church in my life. Can I ask what might be a dumb question?”

“The only dumb question is the one you don’t ask,” Tom replied.

“I thought the Catholic church had a serious problem with being gay.”

“I’m not going to tell them, and Dustin won’t bring a date. Is there an issue?”

“Not with me. I was just curious. I know next to nothing about any religion except what I read in the papers or hear on the news. They have a serious problem with birth control, too.”

Tom laughed, “That rule gets ignored by just about every Catholic I know!”

Not Rachel, which was one source of disagreement between us. We were barely on speaking terms because of our disagreement about religion.

“Here come the girls,” Stuart observed.

When they came back we tossed a Frisbee around for a bit, then a football. Some other guys and girls about our age asked about playing a pick-up game of football and we agreed, our seven against their eight, with them substituting one person in and out. We had a blast playing ‘touch’ football for about an hour before the heat took its toll and we all went back to our blankets in the shade.

Stuart fired up the grill, and about forty minutes later, we were eating burgers and brats, along with chips and pickles that the girls had packed. Our only regret was not being able to have beer, but then again, we had to drink our soft drinks from cans because bottles were banned in the park. There was talk about banning grills, and that would simply ruin things in my mind.

We hung out in Grant Park until dusk, and unfortunately Teresa didn’t have a car, so I headed home alone, showered, studied, and then went to bed.

September 9, 1981, Chicago, Illinois

I was surprised when Rachel sat down next to me in the plaza while I was eating lunch on Wednesday.

“Hi,” she said.

“Hi,” I replied.

“How are things going?”

“Fine,” I replied. “You?”

“I miss talking to you. And I miss playing mini golf with you.”

“Every time we talk beyond pleasantries, or spend time together, we end up arguing about religion.”

“I know,” she sighed. “And it’s mostly my fault.”

“I don’t see anyone being at fault,” I replied. “We just don’t agree on issues which are very important to you, and I’m not sure either of us is able to compromise enough to not have that be an issue. Besides, I’m just as inflexible as you are.”

“With one major difference,” Rachel said. “I was trying to impose my beliefs on you.”

“I didn’t feel that way,” I replied. “You told me what you believed, you didn’t say I had to follow it. Sure, you would like that, and it would be a condition for a serious relationship, but that’s not imposing; that’s well, asking, I guess. And like any other question, the answer just needs to be truthful, and one which represents what I believe or suits my needs. So long as we don’t lie to each other, that’s the way things are supposed to work. If we lie to each other, we can’t even be friends.”

“Before we had our fight, you were interested, right?”

“Yes, of course. I think that was obvious!”

Rachel smiled, “It was. And you wanted to take me to bed, didn’t you?”

“That’s not a fair question,” I replied. “That’s something BOTH of us would have to agree to do.”

“You told me that you’d wait until we got married!”

I chuckled, “OK, yes, that’s true. But I was speaking hypothetically.”

“Were you? Truth now.”

“You’re a pretty girl, and yes, the thought crossed my mind. But there’s a long way from a desire to opportunity and a long way from opportunity to a decision to do it. And somewhere in there may well be a wedding ceremony.”

“But it’s not required in your mind.”

“No, it’s not. I believe I told you that if me being a virgin was a requirement, then we absolutely have no future.”

“Why did you do it?”

“Because I wanted to! And it turns out it’s fun and it feels good.”

“And that’s all it means? Fun and pleasure?”

“I never thought sex had to mean anything. I take it you do.”

“You really don’t think it’s special in any way?”

I shrugged, “You’re talking about it being only something you do with your spouse because you’re in love? And that it’s some kind of, I don’t know, religious experience?”

“So what does marriage mean then?”

“A commitment to spend your life together and to raise kids together. And a promise to only be with your spouse.”

“But if it’s meaningless...”

“My word isn’t meaningless!” I replied. “And if I make a vow, I’ll keep it. To me, the meaning is found in the vows and children, not in having sex.”

“So sex is never sinful?”

“Who ever said it was a sin? Some guy in Rome or some guy in your church? Men who never married and probably never had sex? Some book written two thousand years ago?”

“You don’t believe in sin?”

“I don’t need someone in fancy robes to tell me it’s wrong to kill or steal or cheat. But here we go again! I’m sorry.”

“No, it’s my fault. I brought it up again.”

“You keep doing that. Why?”

“It’s not obvious?”

“If it were, I wouldn’t have asked.”

“Because I like you,” she said quietly. “A lot.”

“I like you too,” I said, “but I’m not sure that’s enough to overcome the serious disagreement over religion.”

“I know. And I don’t know what to do about that.”

I did, but there was no way I was going to suggest that she simply give up her belief in God, even though I had zero use for belief in what, in my mind, amounted to an imaginary magical being. And I couldn’t imagine she’d do that, even if I suggested it. And that meant there really was no way forward as anything other than friends, despite my attraction to her, and the fact that I did like her, minus her religious beliefs.

We finished our lunch in silence, and then got up to toss our brown paper bags in the trash.

“Do you mind if we start eating lunch again?” she asked.

“Not at all,” I replied.

We headed back into the building, with Rachel using a passenger elevator while I used the freight elevator. When I arrived in the mailroom, Harry left on his lunch break, as did Nick, leaving me alone for about thirty minutes. I fielded a couple of phone calls, received a couple of couriered envelopes, but otherwise it was quiet.

Once all the lunch breaks were over, I began my usual afternoon routine, staying busy until the end of the day, when I quickly left the office and cycled home to have dinner with Lily. I had just finished showering and dressing when she came to the door, arms full of ingredients.

“Hi!” she gushed.

“Hi!” I replied. “Need any help?”

“Nope! I’ve got this! Just give me a kiss, then sit down and relax and let me get started.”

We exchanged a quick kiss, and she went over to the kitchenette and put everything on the counter. I tuned the radio to WXRT and sat down on the couch.

“How was work?” Lily asked as she began her preparation.

“Same as always, basically,” I replied. “It’s not the most exciting job in the world, but it pays the bills and I have a very good chance of being promoted next June when my supervisor leaves.”

“Do you like it?”

“I like to work, and I like to work hard, so yes, I do. But it’s only a means to an end, as I said.”

“Your goal is to make a ton of money, right?”

“Yes. That seems to me to be the path to what I really want — a family, kids, a nice house, a nice car, and most importantly, taking care of my mom.”

“That’s really important to you; that last one, I mean.”

“She struggled and sacrificed for me, so the least I can do is help her. I’m not quite sure how she’ll react to the money I sent her.”

“What do you mean?” Lily asked.

I was about to answer when the phone rang. I got up and answered it, and laughed softly.

“Hi, Mom!”

“I know we usually talk on Sunday, but I received your letter today.”

“It’s the least I could do,” I replied.

“I’m doing fine, Jonathan! You need to save your money!”

“I’m saving and investing, and I’m also paying back an un-payable debt.”

“You don’t owe me anything, Honey!”

“Mom, please let me do this. I know how difficult things were for you while I was growing up.”

“But you should save for a car.”

“I don’t need a car in the city, Mom,” I replied. “It’s not like Goshen. I can walk, ride my bike, take the bus or the L and get anywhere I need to go. The only time I really needed a car was when I bought the stuff for my apartment, and Uncle Alec let me borrow his.”

Mom laughed, “The car that cost more than every car I’ve ever owned combined!”

Truth be told, I was sure the car cost more than the house I’d grown up in, though counting for inflation, maybe not. Mom still had about fifteen years to go on the mortgage, and if I could pay that off for her, she’d be in much better shape financially. It was something I’d have to look into once I had my promotion and was making ‘significantly more’ than my current salary, whatever Nick meant by ‘significantly’.

“Just keep the money, please,” I said.

“If you’re sure, Honey.”

“I am. I have a guest, so if you don’t mind, we can talk on Sunday.”

“Is she pretty?” Mom teased.

“Very,” I replied.

“Then I’ll let you go! I love you, Jonathan.”

“I love you, too, Mom,” I replied.

We said ‘goodbye’ and I hung up.

“Very what?” Lily asked with an impish smile.

“Annoying,” I teased.

“Uh-huh.”

“Pretty.”

“Thank you! How is your mom?”

“Fine. She wanted me to keep the money but you heard what I said.”

“I did. It’s so sweet that you want to take care of her.”

“Thanks.”

“You deserve a nice kiss for that!”

She walked over to where I was standing and we exchanged a nice, soft, French kiss. She wrapped her arms around me and pulled me against her, and I put my arms around her and squeezed. The kiss deepened and Lily pressed her body firmly against mine, hugging me even more tightly, crushing her firm breasts against my chest. Her pulse began to race and I felt the stirrings of an erection.

“Whew!” she exhaled when she broke the kiss. “I, uhm, need to finish making dinner.”

I nodded and released her and she went back to the stove and I went to sit down. That kiss held a clear implication for the future, and I recalled something which Lily had made quite clear — doing that required giving up other girls. I had to ask myself, was Lily worth giving up Teresa, and what amounted to our twice-a-month sleepovers, as well as not seeing Gudia? Rachel, as just a friend, wasn’t a problem in my mind because I simply couldn’t see a relationship with her going anywhere.

Of course, the major problem with Lily, as I’d recognized when we started having dinner together, was her parents, and the fact I was renting the garage apartment from them. I wondered if she’d talked to them and decided it was better to find out now, rather than let things progress to a point where there would be a real issue.

“Did you talk with your dad about changing your curfew?” I asked.

“Yes, and he said he’d think about it, which means he wants to talk to my mom. I basically told him that when I was eighteen I’d want to be able to go out on dates that included dinner and a movie, or a concert, or whatever, and that meant I might not get home until closer to midnight. That’s the new curfew I asked for.”

“Will he be able to convince your mom?”

“I think so. He’s always been reasonable, even if I think he’s a bit too protective.”

“I think dads are like that,” I replied. “Bev’s dad was pretty protective of her, but he wasn’t crazy like some of the dads back home who liked to show boys their shotguns to make a point.”

“That’s just crazy!”

“That’s rural Ohio! Pretty much everyone had a gun, and most of the kids who drove to school had gun racks in the pickups with rifles or shotguns in them. It’s way different from here in Chicago.”

“You know you haven’t actually ASKED me on a date.”

“You haven’t actually turned eighteen!” I countered.

“I just don’t see that as being a big deal,” she replied. “You’re not even a year older!”

“I know that, but it’s only a month or so from now, and it just makes sense to wait until you’re eighteen so nobody can make an issue about it. After your birthday, if your dad allows it, I’ll take you on a date. For now, we have these Wednesday dinner dates. You enjoy them, right?”

“Duh!” Lily laughed. “But going out would be fun, too.”

“I agree.”

She finished preparation, adjusted the flame on the stove burners, covered the pots and pans, and came to set with me. We cuddled and kissed a bit, with Lily getting up to check on dinner every few minutes. When everything finished cooking, she served the meal.

“Chicken with mushroom gravy, boiled potatoes, and corn,” she said. “And some bread I bought at the store.”

After sampling everything I gave my hearty approval, and we chatted as we ate. When we finished eating, we worked together to clean up, then cuddled on the couch for about thirty minutes, kissing and talking. After Lily left, I pulled out my study materials and the Wall Street Journal and spent a few hours studying and reading before turning in.

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