Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 57: Eminently Practical

Coming of Age Sex Story: Chapter 57: Eminently Practical - '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  

March 19, 1982, Greater Chicagoland, Illinois

On Friday afternoon, Allyson met me in front of the Hancock Building and we headed for the subway so we could take it into the Loop.

“We can grab something to eat at Union Station and eat on the train,” Allyson suggested. “The 5:40pm train is an express to Naperville, and we’ll get off at the Eola Road station. Kristy will pick us up. She’ll stay tonight, if you want.”

“I think it’s really up to you,” I replied. “I suspect this weekend will be our last one together, so it really has to be your decision.”

“Hannah or Bianca?”

“That is the question,” I replied with a slight smile.

“What happened with Phoebe? She was so up before your date, and after, she seemed down.”

“If she didn’t tell you, I’m not sure I should say anything other than that it probably won’t work out.”

“So similar to me?”

I shrugged, “Every girl is different, just as every guy is different. But the same end result, I think. I like you, you like me, but we both agree we don’t click the way we should in order to be a couple.”

“Great sex is important, but it’s not the most important thing. And trust me, the sex is awesome!”

“I think so, too.”

“I think I’ll have Kristy stay tonight, we’ll have a wild and crazy threesome, and then tomorrow I can have you to myself for the night.”

“Not being a complete idiot, I have no objection to that plan!”

Allyson laughed, “Nice.”

“I wanted to ask you about your birthday — is there someone else you’d rather invite?”

“I want you there. All the girls from school will be there, and about an equal number of guys. My parents are taking my little sister out, so we’ll have the house to ourselves for pizza, dancing, or games. I’m positive Julianne will want to dance with you ... horizontally!”

“We’ll see what happens,” I replied. “Have you heard about any developments with the cops?”

“According to Lucy, they found a security camera at a business across the street that shows someone coming out of the garage who is a suspect.”

“My supervisor at work said the cops would latch onto anyone they could, even if the evidence was flimsy.”

“Supposedly this guy matches the description of a guy who raped a UICC student last year. She was strangled, but survived.”

“That actually sounds like a real suspect. Hopefully, they’ll catch him.”

We reached the subway station, dropped our tokens in the turnstile, and walked down the stairs to the platform. A train arrived about four minutes later, we boarded, but there were no seats, so we stood, holding the overhead rail for balance. We rode into the Loop, then walked to Union Station. We bought burgers, fries, and Cokes from a fast-food place in Union Station, then went down to the south platforms to board the Burlington Northern train for the far west suburbs.

“What kind of doctor do you want to be?” I asked as the train pulled out of the station.

“I don’t know for sure. I only have classroom work for another five years, then I’ll get basic hands-on training. That’s when I’ll decide.”

“How does it work? Do you just apply for the position?”

“Not the way you mean. There’s something called the National Match, where students and hospitals indicate their preferences, and a mainframe computer matches everyone together, based on lists that both sides make.”

“So you get assigned?”

“To one of the places I list, yes, assuming they list me, too. If you don’t get Matched, then you apply directly for any open spots.”

“Weird.”

“They developed this system because the old way, where people applied directly and were chosen, fell apart when students would accept a position, but then be offered a better one and take it, causing a chain reaction. This prevents that, because you have to take whatever the computer assigns.”

“The new system seems a bit crazy, but I suppose I can see the problem it solves.”

“You have to pass exams to advance, right?”

“Yes. I’ll need a license from the SEC to act on behalf of other people. I can do my own thing without a license, but if I manage assets for someone else, then I have to have a license.”

That wasn’t quite true, because I was investing money for Jeri, and that was allowed, because we were, in effect, pooling resources and neither of us was officially acting in a professional capacity.

“How long will that take?”

“I figure about four years from now, maybe sooner, possibly a bit longer. It all depends on when the guy who is mentoring me decides to move me up. I’m trying to show him I know my stuff and see if I can cut into that four-year timeframe.”

“Have you started looking for a place yet?”

“No. I’ll start next month. I’ll check out University Village, Pilsen, Bridgeport, and Greektown. From what I can tell, those are all in my price range, and close enough to bike to work, plus they have good bus or L service.”

About forty-five minutes after we’d boarded the train, the conductor called our stop. When the train pulled into the station, we got up, got off the train, and saw Kristy waiting for us on the platform. She greeted Allyson and me with hugs, then the three of us walked to her car.

“We want you to stay tonight,” Allyson said.

“Love to!” Kristy declared happily.

We stopped at Kristy’s house so she could pack an overnight bag, then headed to Allyson’s house. The girls opted to use the Jacuzzi, so the three of us went to the basement. Allyson turned on the tap, waited for the water to warm up, then closed the drain. We all undressed and got into the tub, with me between the girls. When the tub was full, Allyson closed the tap and pressed the button to start the water jets.

After the whirlpool, we went up to Allyson’s room and got into her bed for a threesome that lived up to Allyson’s billing of ‘wild and crazy’.

March 20, 1982, Greater Chicagoland, Illinois

The three of us slept late on Saturday morning because we hadn’t fallen asleep until nearly 4:00am. We showered individually, then went downstairs to have lunch. Kristy left after we ate, and Allyson and I decided to go to Fox Valley Mall in Aurora and check out the stores. She specifically wanted to go to Spencer Gifts, which she said carried ‘adult’ items, in addition to posters, games, and novelty items.

“Are those for real?” I asked, pointing to the ‘edible panties’ on display.

Allyson laughed and nodded, “Those are made of something like cherry licorice, or maybe the gelatin they use to make Gummy Bears. And the body paint next to it is flavored as well.”

“Things I never knew about,” I chuckled. “I don’t know where I’d buy something like this in Ohio. The Cincinnati area is really conservative, though maybe across the river in Newport. They opened a mall not too far from my house about two years ago, and I don’t recall seeing a store like this there.”

“Want to get some?” Allyson asked. “It might be fun to play with tonight.”

“It’s up to you,” I said.

“Handcuffs?” she smirked, pointing to a display.

“That might be a bit much,” I chuckled.

“Some people get off on that,” Allyson said.

“You?”

“I’ve never tried bondage, so I don’t know, but it doesn’t really appeal to me. Last night was exactly what I think great sex should be — me and another girl with a guy.”

And that was different from Bianca and Shelly, because Kristy and Allyson actually had sex with each other. When I’d been recovering, they’d enthusiastically engaged in sixty-nine, and I’d enjoyed watching.

“Is that common?” I asked.

“I don’t know, actually. I know a couple of lesbians, but that’s different. I only know one other girl who does that stuff Kristy and I do with each other who is really into guys.”

“Do you consider yourself bisexual?”

“I suppose, because I really like threesomes the way we did last night, though I’ve never been with a girl without a guy involved. Kristy has at least twice. I’m not sure if I’d do that or not. Anyway, should we get the body paint and edible panties?”

“Sounds like fun.”

Allyson picked what she wanted from the display, and we took them to the register where she paid, refusing any cash from me. We left the store, and stopped at Mrs. Fields, where I bought us each a chocolate-chip cookie. We walked around the mall, checking out the stores, then discussed what to do. We ended up seeing Porky’s at a theater close to the mall, and then going to Fuddruckers for dinner. After dinner, we stopped at Oberweis Dairy for ice cream, then headed back to her house.

When we arrived back at the house, we watched TV for a couple of hours, cuddling on the couch, and then went up to her room. I undressed, put on my robe, then went to the bathroom to brush my teeth and empty my bladder. When I opened the bathroom door to return to Allyson’s room, her little sister Clara was blocking my exit. She winked, then reached for the cloth tie on her robe and pulled on it, which caused the robe to open, barely concealing her breasts, but showing off her flat stomach and neatly trimmed pubic hair.

“See anything you like?” she asked impishly.

“I don’t think your sister would approve,” I replied, though mentally acknowledging she was sexy, and I did like what I was seeing.

“I’m positive I’m better,” she said saucily. “And you can have my cherry!”

“Let’s ask your sister what she thinks about that idea,” I said with a grin.

“She’s not your girlfriend! Come to bed with me and I’ll do anything you want!”

She spread her robe wide, revealing pert breasts with hard, pink nipples, and I was sorely tempted, but there was no way I was going to get involved with another sixteen-year-old. Jeri had been a very special case, and I’d taken a risk that I was unwilling to take again.

“Sorry,” I said, stepping past her and quickly walking back into Allyson’s room.

“Your sister just propositioned me,” I said after I closed the door.

“She’s jealous,” Allyson said.

“She did open her robe to entice me and suggested she’d do anything I wanted.”

“Tempted?” Allyson asked with an arched eyebrow.

“No. She’s sixteen, and while that’s legal back home in Ohio, I know seventeen is the age of consent in Illinois. That’s trouble I don’t need!”

“You’re nineteen, so I seriously doubt they’d come after you if anyone ever found out, but I totally understand being careful about that. If she was seventeen?”

“I’m here as your guest,” I replied. “I’m not that much of a dog!”

Allyson laughed, “No, you’re not. Come get in bed and I’ll paint you and lick the paint off, then you can eat the panties from me!”

“Sounds like a fantastic plan!”

March 21, 1982, Greater Chicagoland, Illinois

“One last time?” Allyson asked on Sunday morning. “With me on top?”

“I won’t refuse!” I declared.

She used her mouth to get me hard, then rode me for nearly thirty minutes, her very tight tunnel squeezing and massaging me the entire time, but having cum six times the previous evening, I could probably have gone even longer if I’d made a determined effort. She had five good orgasms before I came, then she stretched out on top of me. I wrapped my arms around her and we lay together for about ten minutes before we went to the bathroom for a very enjoyable joint shower.

After our shower, we had breakfast, and then Allyson and I got into her car and headed into the city. She dropped me at my apartment, and I quickly got my laundry and headed to the laundromat. I did my shopping and returned to the apartment, having just enough time to call Bev to chat before Huifen arrived. Bev was doing fine, but starting to be uncomfortable. I had just hung up when there was a knock at the door, signaling Huifen’s arrival.

“What are we doing today?” Huifen asked after I greeted her.

“Meeting my friends Tom, Stuart, and Dustin and their dates at Connie’s Pizza.”

They had a rare common Sunday off, and Tom had left a message while I’d been at Allyson’s.

“That sounds great!” Huifen declared. “What time do we have to leave?”

“About 4:45pm,” I said.

“Then we have an hour we can spend in bed!”

I took her in my arms, we kissed, and that led to one of her amazing ‘French kiss’ blowjobs, and then a slow, pleasurable screw. When we finished, we showered, dressed, and headed to meet the guys, Maria, Kelly, and Archie. I’d mentioned Archie before we’d left the apartment and had been very happy when Huifen had simply taken it in stride. I hadn’t been worried, but I knew the majority of people didn’t approve of Dustin’s choice of partners.

“This is Huifen,” I said when we met the gang at Connie’s. “She’s a math major at Loyola.”

Everyone greeted her, and about ten minutes later, we were seated. We ordered two large pan pizzas immediately, as they took at least forty minutes to bake.

“How are things at the Fire Department?” I asked once we had our pitchers of root beer.

“Busy,” Tom replied. “We’re under-manned and a lot of equipment needs to be replaced. The city is not spending enough on firefighting and paramedic response. On the plus side, being under-manned means a lot of overtime for us, especially Stuart, but that creates a budgetary problem.”

“How about you, Dustin?” I asked.

“Wedding season is starting, and I’m doing a spread for an architectural magazine on a house in Hyde Park that’s being completely restored to how it was in the 1920s. How about you?”

“Not too much ever changes in the mailroom,” I replied. “Though I am on track for the supervisor’s position in June. I’m also going to start looking for a new place in May. Something a bit bigger than my one-room apartment over the garage.”

“How did you guys meet?” Dustin asked.

“At a party about six weeks ago,” Huifen replied. “We just clicked immediately, and have been seeing each other since. Maria, Jonathan tells me you’re getting married in June.”

“Yes. Jonathan should get his invitation in the mail in the next week or so. My Mom and sister are taking care of that.”

That presented a dilemma, because I’d have to decide whether to invite Bianca or Huifen, and relatively soon. I really was torn between the two girls and wasn’t sure how to make the decision. I wondered if it might be possible to continue the current situation indefinitely, but I suspected, at some point, most likely soon, one of the girls would force the issue. In one sense, Bianca already had, by suggesting we move in together, with the added sweetener that I’d be allowed to have sex with any of the girls who had been at either party.

Making the decision based on that benefit, knowing Shelly, Sally, and Julianne were all still interested in fooling around with me, and suspecting that Sylvia and Lucy might be available, seemed wrong. Yes, I would love that situation, and most guys would kill for it, but I wasn’t sure giving up on Huifen was worth it. Similarly, deciding based on finances — Bianca would pay half the rent and expenses — while practical, didn’t seem right, either.

I realized that despite all the ‘extras’ that Bianca offered, I was still strongly considering Huifen, and that, at least in my mind, was a very important factor. If, even with everything Bianca offered, I still considered Huifen a potentially better match, that was a pretty strong indicator that I should choose her. But I wanted to think about it, and talk to both of the girls.

“Where are you going on your honeymoon?” Huifen asked.

“The Bahamas,” Maria replied. “A friend of my dad’s has a vacation home there, and he’s letting us use it for a week. That’s all the time Tom could take off because of what he said before about the department being under-manned.”

We had a great meal, and I really enjoyed my time with my friends, though it was becoming more and more difficult to get together because of Tom’s and Stuart’s schedules. When we finished our pizza, Tom suggested we head to the bar where we could all get served, and we had beers, though Huifen ordered a Coke instead. Once we finished our beers, we said ‘good night’ and Huifen and I headed back to my apartment.

“Did Maria’s comment about the wedding invitation make you uncomfortable?” Huifen asked once I’d made green tea for us.

I liked the fact that she was direct, which was another plus in her column.

“No, it didn’t make me uncomfortable, but it did make me realize I have to choose who to invite.”

“Bianca or me, right?”

“Yes.”

“Except I’ll be in California, and probably couldn’t fly back for the wedding. You can safely take Bianca.”

“It’s not quite that simple,” I replied.

“You mean because you have to decide between us?”

“You do cut to the chase!”

“You like people to be direct, and trust me, there is nobody more direct than my grandmothers, so I learned from the best! I also know enough about you to know you did an analysis of pros and cons of each ‘investment’ and, I’m pretty sure I know how the balance sheet worked out.”

“Oh, you do, do you?” I asked with a grin.

“I do! I think, on balance, you prefer me, despite Bianca’s willingness to let you play around with other girls because SHE likes to play around with other girls! And as attractive as that is to you, you’re actually inclined towards true monogamy, at least once you make a commitment to someone. So, as much fun as you could have with Bianca and the girls she likes, that’s not your long-term future.”

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