Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 4: A New Home and an Old Flame

Coming of Age Sex Story: Chapter 4: A New Home and an Old Flame - 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 30, 1982, Chicago, Illinois

After I invited Ivy in, I got two glasses, put ice in them, then got two cans of Coke from the fridge. I used the open bottle of Jack Daniel's to prepare Jack and Coke, and handed one glass to Ivy.

"What else did Sophie say?" I asked.

"That she'd met a guy who was tall, good looking, great in the sack, understood hooking up with no drama, and was hung like a horse! Importantly, you didn't call begging to see her. You're just what any aspiring art student needs to take her mind off studying! And all it cost was a bottle of Jack!"

"What are you studying?"

"I'm working on my BA in Fine Arts. I'll end up with a Master's and then I'll teach High School."

"I'm curious — what about guys at the School of the Art Institute?"

"Gay, wimps, or both! Not to mention having to see them in class, which can make things awkward."

"So you just show up at a guy's house willing to fool around?"

"Not much different from band or cast parties in High School, or college parties."

"And, hypothetically speaking, if I weren't interested?"

"Then I'd go back to my apartment disappointed, but not upset. I think you are interested, but in case you're on the fence, I'm pretty sure I hit the sweet spot! You can see the bod, obviously, and it's toned and tight in all the right places! I swallow, you can put it anywhere, and I'm on the Pill. So, how about it? Finish your drink and I'll make you cum so hard you'll nearly pass out!"

The crazy amount of sex available to me boggled my mind. Going to work at Spurgeon had given me numerous opportunities, and I'd taken advantage of a few of them — Charlotte, Sharon, Nickie, and Kristy. Meeting Kristy had led me to Allyson, who had offered my first threesome, which had basically opened the floodgates, and led to me having eleven different girls, including Kristy and Allyson. Meeting Sophie, who, if I traced things back, was due to Phoebe, who was a result of meeting Allyson. And now Ivy.

Never in my wildest dreams before I moved to Chicago could I have imagined anything like what was happening. And really, with the exception of Lily and Phoebe, none of the girls I'd been with had created any real drama. There had been minor drama with Gudia over her need for her dad's approval, and the situation with Jeri was complicated. And even with Phoebe, the drama had come because she'd apparently read more into our 'prize' date than I'd understood.

Even Bianca, who had hoped for a possible relationship, hadn't created any drama. In fact, she'd basically simply gone with the flow, and, in my mind, ended up in a better place, as she'd discovered something important about herself — that she liked having sex with girls as much as she did with guys. I was happy she'd discovered that at a point when I could participate, as I didn't think that was viable in the long term, given my goals.

And that made me think about Huifen and Bev, and the decisions I'd have to make in August. If I was honest with myself, and I tried to be, the most important thing I'd discovered in the year I'd been in Chicago was that I was not ready to be tied down. That discovery created a serious dilemma because it meant I could lose both Bev and Huifen. That was a difficult question and was the one I had to answer in August. In the here and now, though, there was a hot girl sitting on my couch who wanted to have sex.

"Go for it!" I replied with a grin.

Ivy downed the last of her Jack and Coke, and I did the same.

"Stand up!" Ivy commanded.

I did as she requested and she knelt in front of me, pulled down my shorts and briefs, then grasped my quickly hardening shaft and took my glans into her mouth, and swirled her tongue around it. As I hardened, Ivy slowly took more and more of my dick into her mouth, breathing heavily through her nose. When I was completely hard, Ivy released me and stood up.

"Raise your arms," she said.

I did, and she stripped off my t-shirt, though I had to lower them for her to pull it completely off, as I was about five inches taller than she was. Ivy quickly stripped off her t-shirt, shorts, panties, and socks, revealing a perfectly toned body, moderate breasts, and a neatly trimmed V of pubic hair.

She gently pushed me back onto the couch and I sat down.

"Sophie said you had stamina and control. Don't cum until I say, OK?"

"I'll do my best!"

Ivy straddled me, grasped my shaft, then rubbed my glans along her labia, which were slick with her juices until I was coated with them as well. Ivy kissed me, then slowly sank down on me, moaning softly as she did so. She was very tight, though not as tight as Allyson, and the pleasure of the embrace of her tight, silky walls was intense.

"Oh, God!" Ivy moaned when her triangle of pubic hair meshed with mine.

Ivy slowly rocked back and forth, then began moving up and down, squeezing her muscles as she moved up, and grinding against me each time she had me fully inside her. I let Ivy control the pace and simply relaxed and enjoyed the feel of my dick in her pussy. It didn't take long before Ivy groaned deeply and shuddered while her pussy spasmed around my shaft.

"God damn!" she gasped as her entire body shook.

She had two more good orgasms before she lifted off and knelt in front of the couch.

"Cum in my mouth," she said with an inviting smile, then slowly took me more than halfway in.

Ivy grasped my shaft with one hand and began short strokes while she bobbed, licked, and sucked, and used her other hand to cup my sack and squeeze gently. I watched as she gave me an amazing blowjob, savoring the feel of her tongue and hands, and enjoying her gentle sucking. Despite the intense pleasure, I felt no urgency, and after about five minutes, Ivy released me.

"Not close yet?" she asked

"No."

She smiled, stood up, straddled me, and impaled herself on me again.

"Tell me when you're close," she said as she began sliding up and down my shaft.

Ivy moved with more urgency and had an orgasm fairly quickly. When she had her next one, which was intense, I let her know I was close. Ivy quickly lifted off and resumed the excellent blowjob. She bobbed and stroked faster than she had before, and brought me right to the edge. I twitched and Ivy began sucking hard, and squeezing both hands more tightly around my shaft and sack. A few seconds later, I groaned and my head spun as cum blasted into Ivy's mouth. She sucked and bobbed and stroked and squeezed, intensifying the pleasure almost to the point of pain.

When my orgasm had passed, Ivy released me, stood up, straddled me, and impaled herself on my still hard shaft. She moved her lips to mine, and I didn't resist the deep French kiss as she ground against me, quickly bringing herself off once again. She slumped against me, and put her head on my chest, not moving until I softened and slipped from her tight tunnel about five minutes later.

"I want you to suck my nipples, lick my pussy, then fuck me however you want — pussy, butt, tits, mouth; and cum wherever you want — pussy, butt, tits, face, mouth."

I scooped Ivy into my arms, stood up, moved to the bed, and carefully laid her down. I got into bed with her, French kissed her, then feasted on her breasts and pussy, bringing her off twice before electing to simply fuck her tight pussy as hard and as long as I could. Ivy had four good orgasms before I slammed as deeply into her as I could and blasted her spasming pussy full of cum.

As I expected, Ivy didn't do 'overnights', but she did ask me to shower together, which resulted in a second exquisite blowjob. After the shower, we dried off, dressed, and I walked Ivy to the door.

"One favor, please," I said. "Call next time."

She smiled, "I took a chance because I was positive if I was here, you'd say 'yes', but over the phone, you might have said 'no'. Sophie mentioned that you're moving to Rogers Park this weekend. That works better because I live in Ravenswood with my sister and her boyfriend. OK to call your new number in, say, two weeks?"

"Sure," I replied. "I had a great time."

"Me, too! And if you're interested in Sophie and me double-teaming you, I'm positive she'd go for it!"

I didn't believe in heaven, but I sure felt as if I'd died and gone there. A Summer of threesomes with Bianca and Shelley, and Sophie and Ivy was beyond any fantasy I could imagine, short of the two parties Allyson had thrown.

"That sounds great!" I replied enthusiastically.

Ivy gave me a quick peck on the lips, then left. I was tired and had to be up early for work, so I went right to bed.

July 1, 1982, Chicago, Illinois

Thursday at work was busy, and I had to deal with several special requests, which were time-consuming but not difficult. There had been no fallout and nothing more said after the meeting with Matheson, and Monroe's new secretary would start on Tuesday after the Fourth. I'd seen her when she interviewed, and she had the primary characteristic for being hired — an impressive chest.

Someday, I was sure, that was going to come back to bite Spurgeon Capital. I'd read in the Journal about a lawsuit by a woman, Mechelle Vinson, against Meritor Savings Bank, which claimed that her boss had forced her to have sex as a requirement for continued employment. The case was working its way through the courts, but the Journal felt that the novel claim, that a 'hostile work environment was a violation of the Civil Rights Act of 1964, had merit and that she had a very good chance to prevail. If that happened, and it would take several years before the case was resolved, likely going to the Supreme Court, it might force Spurgeon to rein in his staff.

The rumors about him, which Jeri had basically corroborated, and which his wife had effectively confirmed, were a different problem. That was already illegal, and at some point, I suspected he'd be caught. I had been with Jeri, though I was nineteen and she was sixteen, which was, in my mind, far different from Noel Spurgeon at forty-one being with girls who were fifteen. And after I'd succumbed to Jeri's machinations, I'd resolved not to be with any girls under the age of consent, no matter what. It simply wasn't worth the risk.

I ate my lunch at a spot I'd found in a small grassy area away from the building which, thankfully, the secretaries didn't seem to know about. If the weather was poor, or when it got too cold, I'd have to find another private spot. I took a short walk after I ate, then headed back to the mailroom for the usual afternoon routine.

I worked right up until 5:00pm, then quickly left the building, walked to the L, and rode north to Rogers Park. I arrived at the house about ten minutes early to find Kasia Pucinski sitting on the front porch. We greeted each other, then she used her key to let us into the house. We did a quick walk-through, and I checked to make sure there were no obvious problems, which there weren't.

"Everything looks good," I said.

"Here are three sets of keys, as we agreed," she said, handing them to me.

"Thanks, My roommates should be here shortly. They're going to move in, though I won't move until Saturday."

"OK. Is there anything else?"

"Not that I can think of."

"You have my number in case there are any concerns. If you mail the rent check, please make sure you do that by the 25th of each month, or a few days before that in February, to make sure it arrives by the 1st."

"Will do," I said. "I really appreciate you renting us the house."

"You're welcome! If you haven't eaten, we could grab a bite at Giordano's, if you like."

I was a bit surprised at the offer, but I did need to eat, and Giordano's had great pizza. The only question was when Bianca and Shelly would arrive, and if they'd need my help moving their things.

"I need to wait for my roommates so I can give them their keys. I expect them sometime in the next ten to fifteen minutes."

"I'm OK with waiting," she said. "How's your new position working out?"

"Just fine," I replied.

"You seem to be pretty successful, given you only moved here a year ago."

"I've found that if you work hard, follow the instructions you're given, and have some basic common sense, things tend to go fairly well. Then it's a matter of seizing opportunities when they arise."

"Carpe diem?" Kasia asked.

"That is the exact phrase my mentor used to encourage me to not sit back and wait, but to aggressively go for what I wanted."

"I suspect that works well in your field, but in others, a bit of subtlety goes a long way."

"I've also found that being direct has far more pros than cons. I'd rather someone was upset and knew where I stood, or I was upset and knew where they stood, rather than beating around the bush. That just doesn't work for me."

"Do you approach everything that way?"

"Pretty much. I try to always speak my mind and hope that people do the same with me. It eliminates a lot of confusion and avoids having to make assumptions which are often wrong."

"A little tact can go a long way."

"In the right circumstances, I'm sure," I replied. "But sometimes being polite makes things worse or doesn't achieve your goal. Remember when I called you? I told you exactly what I wanted, laid out my circumstances, and explained everything I thought was relevant. What would have been served with what my friend's mom back home called 'embroidery'?"

"OK, in business, that can make sense. But for relationships? Or asking someone out?"

"Which is better," I asked, "to not say something or to have the person gain a false impression? In my mind, it's better to just lay your cards on the table so that the other person knows where they stand. I'm not talking about being impolite, but about being honest and upfront."

"How would you ask a girl out?"

I smirked, "The same way you asked me out five minutes ago!"

"And you think I asked you on a date?"

"You just proved my point!" I declared with a friendly smile. "I could have taken it in a number of different ways, and you don't know for sure how I took it because I don't know for sure what you meant. That's not a problem, per se, unless our individual understanding of what you meant is at odds with the other's. And even then, only if we took it personally, which I try not to do, no matter what. If someone doesn't want to be a friend or turns down a date or whatever, it's no skin off my nose and there are plenty of options."

"So you don't care?"

"I do care; I just don't let it bother me to the point where it makes me upset or depressed or whatever."

"How did you take it?"

"Do you want a blunt, direct answer?"

"That's what you're going to give, isn't it?"

"Usually, but I'll freely admit that sometimes the best approaches are indirect. I just don't prefer them."

"So?"

"Any answer I give runs the risk of offending you if I misread you," I replied. "The truth is that you surprised me by asking me to have dinner with you and I wasn't sure what you meant by it, so I simply took it as you having no plans and wanting some company for dinner. We haven't spoken much, and don't know much about each other, so you might well have a boyfriend or even be married. But I assume nothing, so I'm surprised by nothing and disappointed by nothing."

"And if you were attracted to someone and asked them out or to dance at a party and they said 'no', then what?"

"Then I find someone else, or find something else to do."

"You know some girls play hard to get, right?" Ms. Pucinski asked. "Some guys, too."

"That's not going to work with me," I replied. "If someone says 'no' to a date, I might ask once more if it appeared they were interested but unavailable or whatever. A second 'no' would certainly mean I would give up."

"My dad had to ask my mom for a date eight times before she would say 'yes'."

"Maybe that's how it worked in the 50s, but I'd give up after two, as I said. At that point, if she was playing hard to get, she'd have to come to me."

"Some girls won't do that."

"Then there isn't much I can do," I replied. "If a girl says 'no' when she means 'yes', she's playing games and that right there is enough for me to lose interest."

We were interrupted by the doorbell ringing and I went to answer it.

"Hi!" Bianca exclaimed, giving me a quick hug. "Where should we park the truck?"

"Go into the alley behind the house," I said. "Then just back up into the driveway. Do you need help?"

"Dad brought three of his friends, so I think we're set."

"OK. Here are your keys."

I handed her two sets of keys, and she handed me two checks for Shelly and her portion of the rent.

"I'm going to head out, if that's OK. And I'll see you tomorrow evening."

"That's fine. Anything I need to know about the furniture?"

"Not really. The bed goes in my room, obviously, the desk and chair go in the attic bedroom, the sofa and loveseat in the front room, and the dinette table in the kitchen."

"What do you plan to do with the other rooms?"

"No clue! For right now, they'll just be empty until I figure it out and have the money to spend to furnish them."

"OK. See you tomorrow, then!"

She left, and I went back to Ms. Pucinski and said I was ready to go. We left the house, and I followed her to her car, which was parked about a block away.

"What do you like on your pizza?" she asked as she pulled away from the curb.

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