Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 46: An Unexpected Visitor

Coming of Age Sex Story: Chapter 46: An Unexpected Visitor - 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  

January 14, 1982, Chicago, Illinois

"Want to share first time stories?" Beth asked after the waiter had brought our salads.

"Not much to tell in mine," I replied. "I had known Bev since we were toddlers and we were close friends, but there was nothing romantic. Neither of us dated or had even so much as kissed anyone. Then, on her sixteenth birthday, she surprised me with a kiss and five minutes later, neither of us were virgins, something we ensured was the case several more times that night!"

"Wow!" Beth exclaimed. "First kiss to screwing in five minutes?"

"For both of us. You?"

"Fourteen with the happy recipient of my first blowjob. He and I had known each other since we started school and did the usual pre-adolescence teasing boys and girls do, but when I started developing, his teasing changed to what I'd now call flirting. One day, when we were hanging out listening to music, he asked if he could kiss me. I said 'yes', and we made out a bit, but our parents were around, so we had to be careful.

"It was like that for a couple of months, basically making out when we could and trying to avoid anyone finding out lest they try to keep us apart. Things escalated at his little brother's Bar Mitzvah, which is a coming of age ceremony, kind of like Confirmation in the Catholic church.

"David and I were bored, so we went to the basement of the house and hid in the furnace room to make out. That was the first time we touched below the waist, and he wanted to have sex, but I wasn't ready, so I offered an alternative. As I'm sure you can imagine, like any horny fifteen-year-old guy, he jumped at the chance. He lasted all of about thirty seconds, which is actually pretty good given what I've heard happens with virgin guys in that situation.

"I hadn't planned what to do, and I was afraid we'd be found out if I spit it on the floor, or whatever, so I just swallowed. I realized I wasn't grossed out, and he liked it, of course. About two months later, after I turned fourteen, I decided I was ready, and we managed to arrange for time together when we wouldn't get caught and did it. It wasn't great, but it wasn't bad, and it sure got better!"

"Did you use birth control?" I asked.

"Rubbers, which is when I developed my dislike for them. You?"

"Nothing that first night; we were lucky. After that it was rubbers and then the Pill. Most of the Catholic girls I know are on the Pill, despite the Pope telling them not to."

Beth laughed, "Telling teenagers and young adults not to have sex and not to use birth control is about as self-defeating as anything I can think of. Reform Judaism is far more practical and realistic."

"It seems like it," I replied. "What happened with David?"

"We broke up about a year later when he met another girl. It didn't bother me, because there were other guys interested in me and I didn't have dreams of marrying David. My second love affair began a day after David and I broke up. He was a virgin, and it was fun teaching him. Same with my third. Then I decided guys with experience were better, and mostly ones a year or two older. The biggest age difference was four years, when I was eighteen. You?"

"Three years."

"Pretty typical, really, even if Illinois law is completely stupid on the topic. The age of consent should be fifteen, as it is in much of Europe, and if the kids are at least thirteen and no more than two years apart, it should be an exception."

"Neatly covering your first time, too!"

"In that regard, most members of society are such busybodies! If my parents wouldn't complain, nobody else should have the right to!"

"And if they do?"

"That's my problem, not a legal problem. Or if you live in the wrong part of the country, it's dealt with by a shotgun!"

"I'd consider that the right part of the country, given that's how it was where I grew up!"

"Let me guess, you were a redneck and owned a gun?"

"Gun yes, redneck, well, I suppose that depends how you define it. I'm what you would call a lower-working class Democrat from a rural county in southern Ohio. But I was never into stock car racing, gun shows, or moonshine, and I absolutely don't own a Confederate flag."

"You've moved up in the world in several ways! Now you're a proper urbanite Democrat!"

"You're a Democrat?"

"Most Jews are," she replied. "We also mostly live in cities, and stereotypically have a higher percentage of lawyers and bankers than non-Jewish communities. Plenty of doctors, especially psychiatrists, too."

"You made those Jewish jokes before, and basically the only ones I've heard are Polish jokes, both back home and here in Chicago."

"I think this city has the largest Polish population outside of Warsaw! And a ridiculous number of Irish, too. It's about as Catholic a city as you'll find in the US."

We finished our salads and almost immediately, our steaks were brought to the table, along with mashed potatoes and broccoli.

"Good choice on the restaurant," I said after taking a couple of bites of my filet.

"Wait until you have dessert! Their cheesecake is the best in the city, bar none."

"And yours?"

"I've had rave reviews on how I taste and feel!"

"Good to know," I chuckled.

"And I love smooth and creamy things on my tongue!"

"Also good to know!"

We were mostly quiet while we ate, and when we finished our main courses, we each ordered a slice of cheesecake and coffee.

"I have to say this is not how I expected the evening to go," Beth said as we ate dessert.

"Wham, bam, thank you, Ma'am?" I asked.

Beth laughed softly, "Pretty much! And despite my burning desire to get to the main event, I'm glad I didn't talk you out of dinner. I'm really enjoying myself."

"Me, too," I agreed. "Please do not take this the wrong way, but if our date ended after dessert, I would not be upset. And no, I'm not saying I don't want to get to the 'main event', just that I value friendships and potential business relationships."

"I get how I benefit from the business relationship, but what's in it for you? I mean, besides my 'feminine charms'?"

"Most of your clientele is well-to-do, right?" I asked.

"Yes. Lawyers, doctors, CEOs, and politicians, along with the society crowd."

"When I receive my business cards in about a week, I'll give you a stack and you encourage people to call me for their investment needs. We're not a regular brokerage, and have a minimum investment of $100 grand, but our returns are double those of the market, at least."

"I wash your back and you wash mine?"

"Washing fronts is WAY more fun!" I declared. "But yes."

"Craziest thing you've done?"

"A strip 'Spin the Bottle' game with eight girls and me that did not stop with kissing."

"Eight?" Beth gasped. "Seriously? And it went as far as you're implying?"

"Seriously. And it did. You?"

"Two guys in all six possible configurations."

It took me a second to understand what she meant.

"Interesting," I replied.

"That's all I get? 'Interesting'?"

"If I can have multiple partners, why can't you? And if you're referring to the 'third option', as it were, and you enjoy that, then do it."

"I certainly didn't plan on it or expect it, it just kind of happened. A couple of guys were flirting really hard with me and implying how great they were in the sack and how they'd wear me out. I laughed and said I could take on both of them and outlast them! One of the guys said I couldn't throw out a claim such as that and not back it up. They were both cool, and I decided I wanted to see what it would actually be like. We had fooled around for about an hour in various configurations, then one guy decided to go for it, asked if it was OK, and I let him. It was, well, to use your word, 'interesting'. Of course, that led to the other guy wanting to, and I let him do that as well. You?"

"Not my cup of tea, but I've done it. I hadn't planned on it, either, but the girl surprised me. She was on top of me, and I thought she was going to do things the usual way, and instead I wound up someplace I'd never been!"

"I thought guys liked it."

I shrugged, "Some do, I'm sure. It was totally weird, and at first I thought it was totally gross, but in the end, it was just weird and didn't really do anything special for me."

"I haven't done it since," Beth said. "Though if I ever have two guys again, I might go for it again."

"As I said, whatever you want to do is up to you; I'm the last person who'll judge."

"Obviously! Is there a special girl, or are you just playing the field?"

"Yes," I replied with a grin.

Beth laughed, "So there is, but you're not ready to give up the cornucopia of pussy!"

"I'd say that's accurate," I replied with a grin.

In truth, though, there were a few special girls besides Bev — Bianca, Lily, and Ellie. And Haley was certainly trying for the top spot, as was Clara, but I felt Clara was more 'crush' than serious, though I could be mistaken.

"Why should you?" Beth asked with a smile. "At twenty, you should be banging anyone you're attracted to who is willing."

"And the same goes for you at twenty-one," I replied. "We both have a few years before we should think about settling down."

"True! Now finish eating your dessert so we can go to your place and you can eat me!"

Patience was, as it was said, a virtue, but there were limits, and I'd reached mine. I finished my cheesecake, downed the last of my coffee, then asked for the check. I paid cash for our meals, left a healthy tip, then Beth and I left the restaurant.

"I was surprised you didn't whip out an American Express card!" Beth declared.

"I actually sent in an application on Monday. I haven't needed a card, and really, didn't have the income to back up an application until recently."

"Want to know a trick of the trade?" Beth asked as we got into my car.

"I'm tempted to ask which trade, but I won't!"

"At a bar, once you can drink, just put the Amex card on the bar in front of you, to cover your tab, obviously, but it's also a chick magnet!"

"I haven't had a problem attracting girls," I replied with a grin as I pulled out of the lot and headed for Rogers Park.

"The competition is stiffer in a bar than trolling college campuses for freshman girls!"

"I believe that," I replied. "Are you staying the night? Or do I need to get you home before midnight?"

"As long as you can get me home early tomorrow, I'll stay. I need to be in Hyde Park by 7:30am so I can go to my parents' house for breakfast. We spend the Sabbath together every week. Technically, it starts Friday at sundown, but we're not that strict."

"I remember hearing at some point that Saturday is the day of rest for Jewish people. Anyway, we can be up by 6:45am and get to Hyde Park in time."

"Make it 6:30am so we can take a shower together and not have to rush!"

"Sounds like a deal!"

When we arrived at the house, I checked the fridge for a note and saw that Bianca and Shelly were out with some of the girls from the strip 'Spin the Bottle' game, and would be home after midnight. I gave Beth the nickel tour, as it were, ending in my bedroom.

"Any specific requests?" I asked.

"I'm cool with freestyle," Beth replied. "Whatever either of us wants to do, we just say it and then do it, barring any objections, which I can't imagine either of us would make."

"Sounds good to me."

"Then kiss me and we can get naked!"

"But not before?" I asked with a silly grin.

"Fine!" Beth huffed, and started stripping.

I followed suit and made a point of looking her curvy body up and down before taking her in my arms to exchange a nice French kiss, her large, firm breasts crushed against my lower chest and her pubic hair tickling my quickly hardening shaft. We kissed for a couple of minutes before Beth relaxed her arms and stepped back. She unzipped her overnight bag and took out what I recognized as a cloth measuring tape.

"My grandfather taught me to always measure my work!" she smirked.

I laughed, "Go for it."

Beth knelt in front of me, planted a sloppy kiss on my glans, then took her measurements, both length and girth.

"Satisfied?" I asked.

"Not even close! Let's get those eight and an eighth thick inches where they belong!"

I had zero objections, and we tumbled into bed.

January 15, 1982, Chicago, Illinois

On Saturday morning, we were up early as Beth had requested, and our shower involved me taking her from behind against the shower wall followed by a blowjob, before we washed each other, dried off, dressed, and quickly left the house for Hyde Park.

"I'd say that I'm sorry you had to be up so early," Beth said with a smirk. "But then you were 'up', so I doubt you're upset!"

I chuckled, "Not at all. And we got about five hours of sleep, because we basically wore each other out by 1:00am!"

"And you got a first!" Beth declared. "Nobody ever suggested that before!"

"I'm surprised," I replied. "I thought tit fucks were a thing."

"I've heard about them, obviously, but none of the guys in High School or after suggested it."

"What did you think?" I asked.

I saw Beth shrug in my peripheral vision.

"It didn't do anything for me, but you got off on it, and then you used your tongue to get me off, so I'd let you do that again! I was surprised you kissed me with your cum all over my face."

"Right, because that's a surprise after I kissed you after the blowjob last night and licked you after we screwed!"

"I suppose not, but I think a lot of guys would be squeamish. They're OK with it if it's, well, diluted, but I had some on my lips."

"I had a girl not swallow and kiss me, and I felt as if I was going to throw up. I got over it. Not my favorite thing to do, but not a deal-breaker."

"So kind of like anal?"

"Yeah, though, again, that's at the bottom of my list."

"'Bottom'! Cute!"

I laughed, "That was an accident of expression, but a fun one."

"What does a Jewish American Princess think about during sex?" Beth asked.

"I guess it depends on if she's married or not!" I chuckled.

"Good one! The answer is 'What color to paint the ceiling'!"

"I sure hope that wasn't true!"

"I was on top, except for the first time!" Beth declared. "And the color of the ceiling was the LAST thing on my mind! Next one — what does a Jewish American princess make for dinner?"

I thought about it for a second and considered the jokes she'd told and the stereotypes. It hit me what the 'funny' answer would be.

"Reservations!" I declared.

"Right the first time! What's a Jewish American Princess' favorite position?"

I thought about that one and couldn't come up with a good answer.

"No clue on that one."

"Standing in front of Marshall Field's with her daddy's credit card!"

I laughed, "Nice."

"One more — A waiter comes over to a table full of Jewish women and asks 'is anything alright?'"

"Are your mom and grandmothers that bad?"

"As I said, you have NO idea! It's all drama, all the time!"

"You seem relatively drama free!"

"I'm not married to you!" Beth teased. "And that reminds me of one more, if you want to hear it."

"Sure."

"A young Jewish boy was telling his mother about how he had won a part in a school play. His mother asked, 'What part you will play, Saul?' Saul responded, 'I get to play the Jewish husband', to which the mother replied, 'Well, you go right back to that teacher and tell her that you want a SPEAKING part!'"

I laughed, then asked, "So Jewish men are wimps?"

"Certainly with their wives and mothers. And given they spoil their daughters, I guess with them, too!"

"How badly were you spoiled?"

"Let's just say there wasn't a thing I wanted that I didn't have, and I'm very used to getting my way!"

"And yet you tolerated me insisting we have dinner first."

"I like strong «goyim» men!"

"Another Yiddish word?"

"Yes. It means non-Jew, similar to the word 'gentile'. It can be an epithet or pejorative, but I meant it simply as 'non-Jew'."

"But you're going to marry a Jew?"

"Ritual and culture are important, and there's a difference between how I would behave as a wife and as a single woman."

"Interesting."

"Jewish culture can seem strange to outsiders," Beth said. "But I can't give it up."

"So change it!"

"You might as well tell the Statue of Liberty to walk from New York Harbor to San Francisco Bay! A Jewish man who will go to synagogue and have a proper Passover Seder and observe the days of Chanukah, and so on, will be a traditional Jew, and that means accepting the other things that come with it. It's that way with life, right? You take the bad with the good, because you value the good more than you detest the bad."

"I agree, generally speaking. That said, I'd compromise on more things than I think you could, and our areas of limited or no compromise are basically the same."

"Religion and culture, though I suspect you'd just call it 'religion'."

"Yes. But that doesn't mean we can't be friends."

"I agree. And have sex! And we both know it's not leading anywhere, so it's just for fun. And may I say it was fun!"

"I agree 100%!"

Beth directed me to her apartment building in Hyde Park, and because parking was severely limited, had me pull up in front of the building. She leaned over and we shared a nice kiss.

"Call me," she said, handing me a business card. "My home number is on the back of this card."

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