Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 39: Allyson

Coming of Age Sex Story: Chapter 39: Allyson - '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  

January 10, 1982, Chicago, Illinois

Because it was -20°F, I asked Phoebe to drop me at Tom’s so I wouldn’t have to walk. Allyson was driving, so she’d have her car to drive me home. When we arrived, we exchanged a quick kiss, then I got out of the car and went to the door and pressed the button for Tom’s apartment. He buzzed me into the building, and I went in, then climbed the stairs, walked down the hall to Tom’s apartment, where the door was ajar.

I was a bit early, but that wasn’t a problem, and let me explain to Tom and Maria that a different girl was joining me.

“You’re as bad as Stuart!” Maria teased.

“Not everyone is ready to get married or even be tied down,” Tom said. “Jonathan is only nineteen, so cut him some slack! And unless his list of girls is as long as the phonebook, he’s not even close to Stuart!”

I wasn’t anywhere near Stuart’s reported total, but in the past month, I’d been with six different girls, seven if I counted Bev. I’d basically doubled the number of girls I’d been with in the space of four weeks, and had a threesome, which boggled my mind, but I certainly wasn’t objecting.

Stuart and Kelly arrived about five minutes later, along with Dustin and Archie, and shortly after that, Allyson. I introduced her to everyone, and we all settled down in front of the TV to watch the Bengals play San Diego in the cold, though Cincinnati was ten degrees warmer than Chicago. Of course, that still made it -10°F, and that made me like Cincinnati’s chances.

“The wind chill is -60°F!” Stuart declared, reading the on-screen graphics.

“How many points can I get if I take the Chargers?” Tom asked me.

“I’ll give you a touchdown,” I said. “But actually, make it six-and-a-half so we don’t have a tie.”

“Make it seven-and-a-half and I’ll take it.”

I laughed, “If I lose, I pay you with your own money, so sure, why not!”

“Sucker bet,” Stuart said.

“For me or for Jonathan?” Tom asked.

“You. It’s colder than a witch’s tit and there is no way that Dan Fouts is going to be able to throw in that weather. Anderson will, because he’s the king of short passes into the flat. The only way San Diego has a chance is if they can establish a running game and keep possession of the ball.”

Stuart’s comments proved to be correct, as Cincinnati got out to a 10-0 lead on a field goal by Jim Breech and then a touchdown with an eight-yard pass from Anderson to M. L. Harris after San Diego had fumbled the kickoff.

“Well, shit,” Tom said. “I should just pay you now!”

Things looked better for the Chargers after that when they had a good kick return and a 21-yard pass, but the Bengals held them, and Rolf Benirschke missed a 37-yard field goal. One possession later, the Chargers scored when Fouts, under heavy pressure and about to be sacked, managed to get the ball to Kellen Winslow at the line of scrimmage, with Winslow running 33 yards along the sideline for the score, making it 17-7, which is where the first half ended.

The pizzas arrived and we all dug in, waiting for the second half to start. It was all Bengals for the rest of the game, which ended 27-7, with San Diego unable to score despite being inside the Bengals 40-yard line five times. The only worrying thing was that Anderson was injured in the fourth quarter, and was replaced by Jack Thompson. It didn’t look serious, and he’d have two weeks to heal.

“Remind me not to bet against the Bengals in two weeks!” Tom declared, handing me another ten-dollar bill.

The second game was decided in San Francisco’s favor with just 51 seconds remaining, when Dwight Clark made an amazing catch to tie the game at 27-27, and with the extra point, 28-27. The Cowboys drove down the field and nearly scored, but San Francisco sacked Danny White, who fumbled, with San Francisco recovering the ball to end the threat.

“It’s going to be a good game in two weeks,” Tom observed.

We all agreed, and then I thanked Tom and Maria, and Allyson and I headed out to her car. It had ‘warmed up’ to -8°F, and the car was very cold. We had a short drive, and the car didn’t have time to warm up before Allyson pulled into the driveway.

“Want me to come in for a bit?” she asked.

“Sure,” I replied. “Park in the street, please.”

She backed out of the driveway, and found a spot to park the car. We got out, locked the car, and quickly headed to the apartment.

“I have powdered hot chocolate,” I said.

“Yes, please!”

Allyson sat down on the couch while I put on some water to boil and then turned on the radio.

“Have fun last night?” she asked.

“You’ll have to get your report from Phoebe,” I replied.

“You’re right; I shouldn’t have asked that question. Sorry.”

“It’s OK. I will say that we had a nice dinner and the hotel was really nice as well. That must have set your dad back a pretty penny.”

“He can afford it! Thanks for inviting me to watch the game. It was fun and your friends are really nice. If you need a date for the Super Bowl, I’m available.”

I’d hoped to avoid that decision until Allyson and I’d had a chance to talk, but there really wasn’t a way to do it. I had thought about inviting Nickie, but if I were forced to decide between the two girls, Allyson would win for sure. Part of it was that Nickie had set a clear limit on dates at two or three, and while I wasn’t looking for a long-term relationship, Allyson was certainly the kind of girl I’d look for, at least based on my experience.

I thought back to what had happened with Lily, and realized that she wasn’t as mature and open-minded as I had thought she was, and in the end, things had become too serious, too fast. I’d misread her, and probably didn’t understand my own feelings and motivations well enough to have asked her to go steady, which had led to what amounted to two breakups. On the other end of the spectrum were Nickie and Kristy, both of whom were basically too casual. Allyson, on the other hand, seemed ‘just right’.

I almost laughed at the comparison to Goldilocks and The Three Bears, but also realized I hadn’t answered Allyson’s question. A date for the Super Bowl couldn’t hurt, so the answer was actually easy.

“I do need a date,” I said. “I don’t have any details about what Tom is planning, though.”

“Cool!” she gushed. “I’ll be back at Loyola then, so I can be super-flexible. I won’t have my car, though. I leave it at home because I usually don’t need it. That’s not a problem, though, because it’s super-easy to get to your friend’s place on the L.”

“I’ll need your phone number at Loyola.”

She got up and went over to the phone and wrote her number on the pad I kept by the answering machine. While she did that, I poured packets of hot chocolate into two mugs.

“Do you go home on weekends?” I asked.

“Sometimes. It all depends on what’s going on with my friends at Loyola and with my friends out in the burbs. I also hang out with Sally sometimes. Most of my friends who have graduated go to school further away, so I only see them on breaks. From the people at the party, only Phoebe and James are still in High School, and they’re both Seniors, of course. The rest are all in college. Did your friends go to college or are they working like you?”

“I had one close friend, my next-door neighbor, Bev. There were a couple of guys I hung out with occasionally, but we weren’t close and I worked so much that I never really did much with them except play football or baseball a few times each Summer.”

“I guess you think we’re all spoiled rich kids.”

I almost laughed again, because compared to Jeri, Allyson’s family was as poor as mine, they just had nicer things and didn’t have to struggle to make ends meet, though I had heard some of the Suits complaining about having no money because they were leveraged to the hilt — mortgages, fancy cars, and all the other trappings of being ‘rich’, but leaving them with a barely positive cash flow.

“ARE you a spoiled rich kid?” I asked with a silly smile.

“Probably,” Allyson admitted. “I mean, my dad pretty much gives me anything I want, I have a nice car, go to a very good university, and have more than enough spending money.”

“But you don’t act like one,” I countered. “Which is the entire point. I know someone who is like that, and she’s a complete and utter bitch.”

I was referring to Lisa, of course, though Jeri was on the edge. The difference was, Jeri and I could work together, so to speak, while I couldn’t stand to be in the same room as Lisa.

“I know a few girls like that,” Allyson said. “Kristy’s little sister Marie is pretty much the epitome of the spoiled brat bitch. She’s also the biggest prick tease I’ve ever met.”

“Kristy implied they don’t get along.”

“They don’t. My sister and I get along really well. Clara can be a pain in the butt, but she’s also really sweet and a lot of fun.”

“Having never had a brother or sister, and only one cousin that I’d only seen twice before I moved here, It’s tough to relate to having a brother or sister.”

“We come from totally different worlds, don’t we?” Allyson asked.

I nodded, “Yes, but if you think about it, other than money, you and I seem to think a lot alike.”

“Money is the class differentiator,” Allyson said. “But what’s different here is that it’s basically the only differentiator. Once you move up at Spurgeon, nobody will give two figs about the fact that you grew up without much money.”

“Tell that to blacks,” I observed. “Oh, wait, there aren’t any at Spurgeon despite the city being like a third black! And no Latinos, either, despite being about a quarter of the city population.”

“Were there a lot of black or Latino people where you grew up?”

“Not really, no.”

“How much do you know about race relations?”

“You mean like Martin Luther King and Malcolm X?”

“As examples, but in Chicago, there’s a pretty strong divide. I’m not saying it’s right, but most law firms, investment firms, and accounting firms are basically all white. Sure, there are some blacks, but nothing like the percentage of the population would suggest. And mostly, that’s about money, not race.”

I shook my head, “I don’t think that’s true. Well, I think the money part is directly related to them being black or brown, not white. When I was on the IIT campus, I saw more kids from India or Asia than I saw black kids or Mexican or Puerto Rican kids. I bet it’s the same at Loyola or Northwestern.”

“Fewer Indians and Asians because IIT is a tech school. But you’re right — in my pre-med classes it’s almost all white guys; girls are a serious minority, though that’s changing.”

“A friend mentioned that IIT is something like ninety percent guys, and having been on campus a few times, that sure looked to be the case.”

“So what would you do?” Allyson asked.

“Everyone should be given the opportunity to succeed. Strangely, I actually am part of the problem, not the solution.”

“Huh?”

“I got the job because I knew someone, and that seems to be how the system works, and THAT would normally exclude blacks and Latinos. Of your friends, besides Bianca who is from Puerto Rico, how many are not white.”

“Uhm, none,” Allyson admitted.

“And so in your circles, when it’s time to hire someone, and your friends recommend someone, you hire them. And they’re almost guaranteed to be white, right?”

“Yes. You’re making me sound like a racist!”

“If you are, then I am! All my friends were white, though as I said, it was a small group. And that’s true here, too, with my friends Tom, Stuart, and Dustin. Maria’s family originally came from Mexico, but everyone else is white. And really, Maria might as well be, because it’s really only cultural differences tracing to Southern Europe rather than Northern Europe.”

“You belong in college,” Allyson said. “I mean, you’re at least as smart as all my friends, maybe smarter.”

“I start my first class tomorrow. But college was never in the picture because I had what amounted to a C average in High School because I couldn’t spend a lot of time studying. Not to mention the cost. And yes I know about scholarships, but getting one with a C average and what probably would have been average SAT or ACT scores would have been difficult if not impossible. I chose the best route to change my future, and so far, it’s working out better than I’d hoped in pretty much every area.”

The kettle whistled so I turned off the gas, poured hot water into the mugs, and then got spoons from the drawer. I put one in each mug, then carried them over to the couch and handed one to Allyson.

“Girls?” Allyson teased.

I laughed, “Beyond my wildest dreams!”

“All your fantasies fulfilled?”

“What fantasies? I didn’t know enough to HAVE fantasies! The idea of a threesome never even crossed my mind until you and Kristy suggested it!”

“I could give you some REAL fantasy ideas,” Allyson smirked.

“Phoebe mentioned one.”

Allyson laughed, “The Valentine’s Day Cherry Popping Party?”

“That did seem a bit over the top! Of course, being a clueless guy, I asked why girls would give their virginity to a random guy and she reminded me that I was basically a random guy!”

“I’ll let you in on a secret, but once girls start talking about how great it is, girls who are still virgins can’t stop thinking about it and often end up doing it because they get so horny just thinking about what it’ll be like.”

Which was exactly what Rachel had said — that she couldn’t stop thinking about it.

“I suppose that does make sense,” I replied.

“And now YOU are thinking about it, right?” Allyson asked with a smirk.

“Guilty as charged!” I declared.

“My brother managed three at the same time, well, you know, as a foursome, though I don’t think the girls did stuff with each other the way Kristy and I did.”

“Can I ask you about that?”

“You mean, am I like bisexual or lesbian?”

“Yes.”

“That’s only the second time I’ve done that, and obviously only with Kristy. The guy in Majorca dared us to do it, and we were so hot and bothered, we did. It turned out to be fun, but it’s not something I’d do often, or with anyone but Kristy. She’s open to being together again, if you want. Or I could actually set up the party...”

“I got the impression you liked me a lot, so why?”

“Phoebe and Kristy need to keep their mouths shut!” Allyson groused.

“Why? It’s true, isn’t it?”

“It’s, well, complicated,” Allyson said, sipping her hot chocolate.

“I said that to someone last week about my situation. You go first. And be honest, please.”

“Well, you obviously know I like you a lot, and I don’t want to mess things up. I suppose I should just tell you what I think.”

“That would be best,” I replied, taking a sip of my hot chocolate.

“I dated some after I turned sixteen during my Sophomore year, but nothing serious. We had parties like the one you attended, but they never got beyond kissing and a bit of touching. I had my first serious boyfriend when I was a Senior, and he got my cherry at Prom, which is kind of traditional. If I had to do it over again, I’d probably make a different decision, because we had a fight right after that. I had the trip with Kristy planned, and he didn’t like it, because she had the reputation as a party girl. It actually both was and wasn’t true.”

“How can it be both true and not true?” I asked.

“You know Kristy lost her virginity to my brother, right? After that, she was with a couple of guys, both of whom talked, and she immediately had the ‘school bicycle’ reputation.”

“‘School bicycle’?”

“Everyone gets a ride,” Allyson replied.

“Ah, OK. It was ‘doorknob’ in my High School — everyone gets a turn.”

“Anyway, tons of guys asked her on dates, thinking they’d get their ride or turn, but she wasn’t that easy. The guys, though, couldn’t let their friends think that they’d failed to score with her, so the reputation grew and grew. She stopped dating High School guys at that point, and dated one of my brother’s friends until we went to Europe last June.

“And that takes us back to the fight with my boyfriend. Once we’d fooled around, he was even more concerned about me going to Europe with Kristy and when I wouldn’t change my plans to be with him during the Summer before college, he broke it off with me. That gave me the freedom to do whatever I wanted in Europe. I ended up being with one guy in Italy, and then the threesome in Majorca.

“Before that, I’d only done it twice — once with my boyfriend, and once with the guy in Italy. It was OK, I guess, but Majorca kind of flipped a switch and I REALLY liked sex, rather than it just being OK. Kristy taught me how to give a blowjob, and that’s when the guy dared us to kiss. It wasn’t a big deal, really, because it was about sharing his cum, not us kissing, if that makes any sense at all.

“From there, he just dared us to do other stuff, and we did. It was fun, and pleasurable, but it’s not something I’d do with anyone but Kristy, and even then, only in limited circumstances. I felt really good and life seemed more exhilarating after Majorca, and I wanted to have sex a lot, but didn’t want a reputation.

“About a week later, I came home, while Kristy stayed and added to her total, which before I left was eight guys. She felt free to do what she wanted because she didn’t have to worry about her reputation back home, and could just have fun. There were a few more after I came home, and I’m pretty sure she told you she plans to do the same in Australia and New Zealand.”

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