Climbing the Ladder - Climbing Higher - Cover

Climbing the Ladder - Climbing Higher

Copyright© 2023 by Michael Loucks

Chapter 63: It Could Also Be a Lot Worse; a Whole Lot Worse

June 20, 1983, Chicago, Illinois

"That was the weirdest thing I've ever done!" Katy exclaimed when we finished.

She had, as I'd suspected she would, not requested I wash before we engaged in sixty-nine to get me hard so that I could fulfill her request, which I'd done with slow, deliberate strokes, not prolonging it given she'd never done anal before.

"That was my reaction the first time I did it," I said.

"I want to try it," Taya said. "But I also want to screw again. Could we do that in the morning, before our shower?"

I looked at the clock, and because it was just before 11:00pm, I felt I could get enough sleep, even waking up thirty minutes early.

"Yes," I replied, getting out of bed and going into the bathroom. I decided the best thing to do was take a quick shower to ensure I was completely clean. I used a copious amount of soap, rinsing and repeating, to ensure I removed any remnants of what Katy and I had done, then after drying off, went back into the bedroom.

"Can I change my request?" Taya asked.

"Nobody is compelled to do anything," I replied.

She laughed softly, "I still want to, but after you give me an orgasm with your tongue, we screw until I have an orgasm, then do me in the butt. But still once more in the morning, and it should go as long as possible."

"Whatever you want," I replied. "No objections, Katy?"

"No. I'm OK if she gets something extra!"

Taya and I began by kissing, but rather than immediately move to sixty-nine, I kissed, licked, and sucked on her nipples for several minutes, worshiping her perfect breasts. Given what I knew would be a longer recovery time, I slid down and used my mouth to bring Taya off. I was sorely tempted to ask her to give me a blowjob because her mouth felt that good, but, as always, it was about what the girl wanted because there was no chance of me not cumming, no matter what we did.

I was hard by the time Taya had her orgasm, and at my encouragement, she turned and mounted me, slowly sliding down my shaft, then grinding against me until she had an orgasm. She lifted off, then lay on her stomach. I used the lube Katy had brought with her to liberally coat my shaft and glans, then spread her firm, toned butt cheeks with my hand to expose her rear entrance.

I rubbed my glans along her rear, had her take a few deep breaths and relax her muscles, then pushed forward. Taya groaned loudly when my glans popped past her tight ring, so I stopped and waited.

"OK," she gasped about thirty seconds later.

I used short, slow strokes to work myself into her, with Taya grunting each time I pushed forward. A dozen strokes later, I was fully embedded in her very, very tight butt and once again simply lay still, waiting for her to relax and become accustomed to the invasion.

"Go slow," she gasped.

I pulled back a bit, then pushed forward again, repeating the motion, and pulling back a bit further each time, until about twenty strokes later, I was pulling back so that just my glans was in her butt, then slowly pushing forward until I was fully embedded. Taya snaked her hand under her and began rubbing her clit, just as Katy had done when she and I had done this same thing.

"Don't ... cum ... too ... soon," Taya requested, breathing heavily.

Whereas Katy had, in my estimation, tolerated me being in her butt, Taya appeared to be enjoying it. And if she was enjoying it, I was going to do my best to increase her enjoyment, despite my own desire to finish relatively quickly, as I had with Katy.

"Go harder," Taya requested about five minutes later.

I did, though it was still slow and gentle compared to the athletic screwing we'd done earlier in the evening. Taya had three very good orgasms over the next ten minutes, and to my surprise, the sensations for me were extremely pleasurable, though different from being in her pussy.

"You can cum any time," she gasped after her third orgasm.

I stopped trying to control my pleasure, changed my motions a bit, and two minutes later, pushed deep into Taya's butt and groaned as I blasted her full of cum. When my orgasm had passed, I stroked five more times, then carefully pulled out and went straight to the shower to clean up.

When I returned, I changed the alarm clock, then asked the girls to help me change the sheets. After we had fresh, clean sheets on the bed, we climbed in, with one girl snuggled on each side of me.

"You really got into that, Taya," Katy observed.

"I surprised myself!" Taya exclaimed. "I'm pretty sure I'll do that again. You?"

"At least once," Katy said. "It didn't do much for me, but I want to try it with two guys, one in front and one in back. I'm pretty sure that's what Jonathan had expected I'd done."

"Given you've had threesomes with two guys, it was a logical conclusion," I replied.

"As I said, it was about trust, and I knew you wouldn't react badly if I'd asked you to stop or had changed my mind at the last minute. I didn't realize you'd done it and weren't into it."

"Oh, he was 'into it' alright!" Taya teased.

Katy and I both laughed.

"Yes, he was!" Katy declared. "And I absolutely made the right decision, both the first time with him and tonight. Giving him all my cherries was exactly the right thing to do!"

"For sure," Taya agreed. "Giving him all my cherries was absolutely the right thing for me to do, too!"

The only word for the feeling I had was 'shock' because nothing about Taya had said 'virgin' — not her comfort with the situation, not the way she screwed, and absolutely not the way she gave blowjobs. I almost couldn't believe it, but she had no reason to lie, so I was positive she was being truthful.

"Then I am the most privileged man on the planet!" I declared.

"You don't have to answer," Katy said, "but you couldn't tell?"

"No, I couldn't," I replied. "The physical evidence is pretty rare after age fifteen from what I've read and heard, and Taya wasn't nervous or tentative, and she clearly knew what she was doing."

"Katy gave me pointers," Taya said. "She knew, but I asked her not to say anything because I didn't want you to behave differently."

"I reassured her you wouldn't," Katy said. "But she decided it was best not to say anything."

"As I've said to others, it's not my business, and all that matters is being truthful about anything the girl chooses to reveal. She doesn't have to reveal anything, though I'd be very upset if she didn't reveal she was in a committed relationship. I don't brook infidelity at all."

"Does Keiko know we're here?" Katy asked.

"Yes. This is my last fling, so to speak, before we commit to each other. Keiko had no objection because of the way our relationship started and how it progressed."

"Mind telling me?" Taya inquired.

"A circumstance similar to this one. A friend told her about our encounters, and Keiko decided to take the opportunity. What was supposed to be a purely casual encounter turned into something special."

"Three years from now, that might have been me," Katy said. "But no way before I graduate from college!"

"A common sentiment," I replied. "And a wise one for anyone who wants to go to college."

"You don't have a degree?" Taya asked.

"No. I've taken evening classes, but securities licenses are far more important than an undergrad degree in my field. I hold Series 3 and Series 7 licenses, which means I can broker anything except real estate and life insurance."

"Katy said you did research and analysis."

"That's my primary role at the moment because I'm learning about the industry. I also trade my own account and have a fund I manage, mostly for friends, but I also have a few other clients."

"I don't know, Katy," Taya said, "if he weren't effectively taken, I think I'd consider it, even though I'm only eighteen!"

Katy laughed softly, "A big dick and a big wallet? Not to mention being a great guy? I hear you, but I am not ready to settle down!"

"Because you're having so much fun at Princeton," I said. "And it's going to be even MORE fun with Esme and Taya there!"

"Truth!" Katy declared. "We should probably get to sleep."

She reached over and turned off the bedside lamp, then snuggled close, and the three of us fell asleep fairly quickly.

June 21, 1983, Chicago, Illinois

We woke with the alarm on Tuesday morning, Taya used her mouth to get me hard, then mounted me and rode me gently, giving herself two orgasms, before we switched to the missionary position and had a long, slow screw. When we finished, the three of us went to the shower, where Katy and Taya washed me, and then I washed each of them in turn, something I very much enjoyed doing.

"I know it's unlikely," Katy said as we dressed, "but feel free to call anytime over the Summer."

Taya expressed the same sentiment when she sang...

Call me on the line
Call me, call me any, anytime
Call me, I'll arrive
You can call me any day or night
Call me

"Jonathan's Stud Service?" Katy teased.

"Anytime, anyplace, anywhere, any day, any way!" Taya exclaimed.

We went downstairs, I grabbed an apple, a banana, and a Pop-Tart, and then the three of us left the house with Bianca and Jack. Taya and Katy each gave me a hug and kiss, then got into Katy's car. Once they'd pulled out of the driveway, Jack, Bianca, and I got into my car and headed for the office.

"Is that girl American Indian?" Jack asked.

"Cherokee," I replied.

"Smoking hot!" he said, shaking his head.

"Does Jonathan have any that aren't?" Bianca asked with a smirk.

"Now that you mention it," Jack chuckled. "Including you!"

"Kristy is pretty hot," I said.

"Hey, that wasn't a complaint, just an observation! Just because the store is closed doesn't mean I can't window shop!"

Not to mention occasional threesomes with Allyson, about which I was positive he'd never complain! I wondered how Allyson would react to the news about me and Keiko, but I suspected she already knew, given how close she and Kristy were.

"Fortunately for us," I said, "neither Kristy nor Keiko is the jealous, overly-possessive type."

"I'd say, given Keiko gave her blessing for you and Bianca to have a baby! It's going to be totally weird having a baby in the house!"

"More for me than you!" Bianca declared mirthfully. "And it's not like we place an order and 'presto' a baby shows up!"

"I very much enjoy the ordering process," I chuckled.

"Who doesn't?!" Bianca asked.

When we arrived at the office, I quickly completed my usual morning routine, eating my makeshift breakfast as I worked. The morning was occupied with currency research, and at 11:30am, I left to meet Marcia for lunch.

"I decided to apply for a job with Charles Hayes' office," Marcia said after we had ordered and she'd asked about Keiko.

"I think that's a wise idea. Can you do anything before the election?"

"I spoke to the woman who's going to be his Chief of Staff, and she expressed interest, but no promises can be made before the election."

"What role did you express interest in?"

"Manager for his legislative office," Marcia said. "I think I have a decent shot, given my experience and education. I also have a strong recommendation letter from Mayor Washington, which he wrote after he was elected, but before I was offered my current role."

"Do you think he'd be bothered by you leaving?"

"I doubt he cares, really," Marcia replied. "I mean, given all the other stuff that's going on, housing is not his biggest concern, not to mention we're basically under federal control."

"Then I think that's a very good move on your part all around. I'd have suggested it even if it caused problems with the Mayor, simply because you have to look out for your own best interests and let him worry about his."

"That does make sense," Marcia agreed. "Changing topics, could we go out sometime?"

"We could, but it would be just as friends because I ordered rings for Keiko and me."

"You asked her to marry you?!"

"Informally, yes. The rings will be exchanged at a Japanese ceremony where we'll formally get engaged."

"Not to be negative, but her diagnosis is unclear, so why?"

"Because there are never any guarantees, and we don't ever know what will happen in the future. Remember, my dad got on a routine flight from Chicago to Kansas City, and the plane was blown up by a crazy person hoping his wife would collect insurance."

"OK, but in your case, you know there's a good chance of a negative outcome."

"Which doesn't mean no chance of a positive outcome. I can't change how I feel about Keiko simply because she's sick. Think about the vows used in most weddings."

"OK, but ... no, never mind. You make a good point. It's just ... well, no, forget that too. Congratulations."

"Thanks."

"Who knows?"

"My housemates and a few close friends, which now includes you. We don't know the exact timing of the ceremony because the rings are coming from Japan."

"Already flaunting your wealth?" Marcia asked though she said it in a friendly way with a smile.

"I will not apologize for using money I've earned to make Keiko happy, nor, to be honest, for using it to make ME happy. And while I don't feel I have to justify this to you, I will say that the two rings certainly cost less than even a small diamond engagement ring, which she doesn't want."

"Sorry," Marcia said quietly. "I was out of line."

"I understand your general point, but what you don't seem to accept is that my tax burden will be significant, and I pay it on all realized gains. If you don't think it's enough, that's for Congress and the President to fix. Maybe the number should be higher, and if our elected representatives change it, I'll pay it because I need public services and feel it's my obligation to pay my fair share. If I were cheating, that would be a different thing altogether."

"I know," Marcia replied. "I was being catty because ... well, I'm sure you know I wanted to keep seeing you and thought we might find a way."

"What?" I asked with a smile. "And participate in my quest to gain piles of filthy lucre and fill my basement with gold coins in which we would swim?"

Marcia laughed softly, "OK, I deserved that. And you are not Scrooge McDuck."

"I'm sorry if things didn't work out the way you had hoped, but my hope is that we can remain friends. And if it doesn't offend your progressive sensibilities, I'd like you to start investing, which you can do with as little as $500 and then $100 a month in my fund. You can get filthy rich in the process!"

Marcia laughed, "I don't think that small of an investment will make me filthy rich!"

"Want to bet?" I asked.

"No, because I wouldn't bet against you on anything financial."

"If you started with $500, then added $100 a month, and did so for thirty years, at the passbook rate, you'd only have around $90,000. If, on the other hand, you earned 20% returns, which is typical for Spurgeon but not guaranteed, you'd have just under $2,000,000 when you're ready to retire."

"NO WAY!" Marcia gasped.

"It's basic investment math with compound interest. Granted, it discounts inflation and taxes, but the worst-case scenario there would be having about a million bucks. And all you have to do is put away $100 a month. Granted, we might not earn 20% every year, but if that's the average, the numbers hold. Even at 15%, you'd have over half a mil."

"Wait! 5% makes that much difference?"

"Yes, because of compounding. But either way, you only put away $36,500. And if you increase your monthly investment, it's even better. But seriously, even putting it in a passbook at 5¼%, you'd double your money by retirement. And that would supplement Social Security or any other pension or retirement plan."

"That's just crazy!"

"It's math, and if more people understood it, retirement would be better for nearly everyone. As I was taught in school, Social Security was meant to supplement your own savings and investment and any pension, but it hasn't worked out that way. And no, I'm not advocating to privatize it or anything like that, just advocating for a way to ensure you have a comfortable retirement."

"I've been pretty strident about it, haven't I?"

"There's nothing wrong with being a strong advocate for your beliefs," I replied. "My only objection is when you impugn my motives and suggest that making money is somehow evil. It's not. Remember, compared to my childhood, you lived in the lap of luxury. I don't hold that against you, nor do I think it was 'unfair' or 'evil' or whatever."

"Getting on your case constantly probably wasn't the best strategy for success."

"Probably not," I agreed.

"I'll get you a check for $500," she said.

"I'll fax you the forms you need to fill out, and you can give them back to me with the check."

"OK. Have you and Keiko set a date?"

"No. We'll do that once we exchange rings."

We had a nice lunch, then I headed back to work. There was nothing too exciting going on in the world, and most of our trades were on behalf of clients or arbitrage between exchanges, but my gold and silver positions were approaching the point where I'd close them out. They weren't quite to my price target, and I didn't see any risk of holding the positions open for the time being.

I was happy with my stock holdings, as they were performing well, though none of them had reached a point where I was ready to lock in the profits. According to my spreadsheet, my projected annual return, if my gold and silver plays worked as I expected them to, would be 22%. I felt that was a respectable annual return, especially given the comparatively limited assets I controlled.

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