Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 28: Are You Doing Her, Too?
Fiction Sex Story: Chapter 28: Are You Doing Her, Too? - Jonathan's business life is booming, but he's also suffering from yet another loss. While he's done his best to pick up the pieces of that sundered relationship, he can't help but feel responsible. However, where two close relationships have withered, another blooms. Violet has transitioned from a badly damaged girl to a vibrant woman. Will he continue to climb this ladder, or will there be another ladder to climb in his future? No matter what, the only direction he plans to go is up.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Workplace
July 29, 1984, Chicago, Illinois
On Sunday morning, after showering together, Violet and I went downstairs to make breakfast. Bianca joined us, and nursed Sofía while Violet and I made bacon, eggs, and waffles. I held Sofía while we ate, and after breakfast, Violet and Bianca cleaned up. When they finished, I called a car for Violet, and she headed home. Deanna came downstairs about ten minutes later.
"Morning!" I said. "How did it go?"
"Great!" Deanna declared. "I could have made ten times as much if I'd been a madam!"
I laughed, "The girls were hit on?"
"So was Pete, though he's gay, and it was two older women hitting on him."
"Well," I chuckled, "as Noel Spurgeon and Murray Matheson opine, what's worth doing is worth doing for money!"
"We wanted to hire YOU out, and you objected!" Bianca exclaimed.
I chuckled, "I did, and Deanna knows I'm pulling her leg. No problems, Dee?"
"None at all. The girls made some nice tips, in addition to their base pay."
"Mind if I ask how much?" Bianca inquired.
"Base pay? Minimum wage. Kassie made the most in tips, around $30; the other girls and Pete made a bit less."
"Not bad," I interjected. "So about $50 for the evening for Kassie, then."
"Now I just need more gigs," Deanna declared. "But I'm hoping word of mouth helps."
"It should," I observed.
CeCi came down just then and joined us.
"Do you two want breakfast?" I asked. "I'll make it for you."
"That would be great!" CeCi exclaimed.
"Bacon, eggs, and waffles?" I asked.
"You had me at bacon!" she declared.
I laughed and handed Sofía to Bianca, then went to the kitchen area to begin making breakfast. Deanna came to sit at the breakfast bar while I cooked.
"Barney faxed me the itinerary for San Francisco," she said. "Depart on August 30th at 6:00pm and return on September 3rd, leaving San Francisco at 3:30pm. Three nights in a suite at the Mark Hopkins InterContinental, which is about fifteen minutes by cable car from the gallery. Golden Gate Livery will handle rides to and from San Francisco Airport, and Chicago Livery from here to O'Hare and back."
"Sounds good! Have you decided on your schtick?"
"It's a high-end gallery, so elegant chic for me; professional for you."
"So just my usual business suits, then?"
"Yes."
"How much do you need for clothes?"
"I'm not sure. I need to do some shopping."
"I'll get you some cash on Monday to start. I have no idea what women's clothing costs, so I'll get $500."
"That's a VERY expensive fuck," CeCi declared mirthfully.
"And if I were paying her for sex, she'd be worth every penny and then some!" I declared.
"Thank you!" Deanna said smugly and stuck her tongue out at CeCi.
We all laughed, and thirty minutes later, having eaten, Deanna left for Ateljé D.
"CeCi, want to break in the pool table with me?" I asked.
"Let me get my video camera!" CeCi smirked. "Bianca can film!"
"I meant playing pool!" I chuckled.
"SURE you did!" Bianca exclaimed.
"Besides," I said piously, "that would require a virgin, and there are no virgins here!"
"Misty!" CeCi exclaimed mirthfully.
"Steve Martin's skit aside, NO!"
"She does like to sleep with you, just like all the other pussy!" Bianca smirked.
"Are we going to play pool or not?" I asked, pretending to be cross.
CeCi laughed, "Sure."
I put the balls in the rack and handed CeCi the cue ball.
"You know, I'm positive I could find a virgin who'd make the movie," CeCi said as she lined up to break.
"Of that I have no doubt! Play!"
"You're just no fun, Jonathan!" Bianca declared.
I laughed, and as CeCi hadn't sunk a ball on the break, I took my turn, sinking a stripe. The game was close, as we were both equally mediocre pool players, but CeCi won.
"Good game!" she declared. "Unfortunately, I have to get ready for work. Rematch later?"
"Sure," I replied.
She gave me a quick kiss and headed upstairs, so I went to sit with Bianca. As soon as I sat down, Misty jumped onto the couch and then into my lap.
"What is with this cat?" I asked.
"Stroke the pussy, Jonathan," Bianca smirked.
"Oh, shut up!" I chuckled.
"All kidding aside, just rub her belly, under her chin, or between her ears. You'll know you're doing it right when she purrs. If you do it wrong, she'll let you know by clawing you."
"So, like ALL of the women I know?" I chuckled.
"Oh, give me a break!" Bianca exclaimed, rolling her eyes.
I stroked Misty under her chin, and she purred.
"OK, you're right," I said with a grin. "Not all the women I know — Sofía is cuddly!"
Bianca laughed, "Let's see how that goes in about thirteen years when she's a teenager!"
"I got along great with my mom as a teenager."
"You were an infant when your mom was a teenager!" Bianca tittered.
I rolled my eyes and said, "I meant when I was a teenager!"
"I know that! I also know we all agree you are NOT normal!"
"You won't get any debate from me," I chuckled. "In all seriousness, I hope we're able to have a good relationship with Sofía when she's a teenager."
"I think we will. What's your plan for today?"
We were briefly interrupted when CeCi came down and said 'goodbye'. She came over for a kiss, then left the condo.
"Nikki's coming here," I said, picking up the conversation where we'd left off, "and should be here in about an hour. How about you?"
"Nicole should be here any time now. She's bringing a couple of girls from Loyola. Are you and Nikki going out?"
"If I had to guess, I'd say we weren't, and we'll order food."
"The girls and I are going to order from Harold's Chicken Shack, if you're interested."
"I am, but I'll have to check with Nikki. Which girls?"
"I don't believe you met either of them — Shandra and Denise. I had classes with them before I stopped taking classes to work at Spurgeon."
"Cool. Before I forget, I'm going to go see my mom at Christmas, and Violet is coming with me. It'll be a really short trip — drive down on Christmas Eve afternoon and drive back on Christmas Day. If you wanted to come along, there are two guest rooms, and I'm sure my mom would love to see Sofía."
"I would, but what about CeCi and Deanna?"
"I honestly hadn't thought about it. Last year was..."
I felt tears well up in my eyes, something that hadn't happened in several months. Bianca scooted closer and put her arm around me.
" ... a blur," I finally said. "The year before, I went home. Let me think about it, please."
"Yes. Are you OK?"
"It snuck up on me," I said. "And it just dawned on me, I leave for Hawai´i on the 26th, and Keiko's memorial is the 27th."
"Is there any way to change that ticket?"
"No. The entire thing is a package deal, and I'm not sure I can go because I don't want to offend Keiko's family."
"May I make a suggestion?"
"Sure."
"Talk to her grandfather and ask his opinion."
"I'll do that."
We were interrupted by the doorman buzzing the condo. Because Misty was curled in my lap, Bianca got up to answer and had him send the girls up. When they arrived, I got up, despite Misty's protests, and Nicole gave me a quick hug. She introduced Shandra and Denise. I greeted them, then went up to the computer loft so as to not interfere with their time together.
I had things to do — balance my checkbooks, both personal and household, as well as revise the household budget. With three months of data, I now had a better idea of what our monthly costs were, and a cursory review showed I had, as I'd hoped, overestimated our costs. That meant I could increase the amount I saved — a combination of a passbook savings account and CDs — for emergencies.
The return on those instruments was low, but the point of having them was liquidity. The savings account was immediately liquid, and I used staggered, rolling six-month CDs, with one maturing each month to provide backup liquidity, albeit with a potential thirty-day wait. For most things, that would be sufficient, but it was possible to cash in the CDs with a penalty if it became necessary.
Another hedge, but more against a complete collapse or some kind of extreme emergency, was gold and silver coins. With gold trading around $1025 an ounce and silver trading around $21.50 an ounce, I'd decided to purchase a single one-ounce Canadian Maple Leaf gold coin and twenty Morgan Silver Dollar coins per month. I'd eventually change the ratio, but I wanted a sufficient supply of silver, as that was likely to be the main unit of exchange, as it had been for most of the history of Western Civilization.
Of course, I didn't expect anything like that to happen, and felt survivalists were borderline crazy, but if 1929, along with other massive economic upheavals in the past two centuries, proved anything, it was that it could happen, despite the best efforts of governments and central banks, or because of them. Fortunately, my coins were not restricted to monitored accounts, as they were not 'marketable securities', but monetary units with a fixed face value.
Most silver coins sold by dealers were fixed at a single unit of currency, USD1, US50¢, CAD1, and so on, while gold coins varied in face value. One exception was the South African Krugerrand, which had no face value struck into the coin, but was still legal tender. I wouldn't buy those because I had committed to my new Hollywood investors to adhere to the Sullivan Principles, so instead, I'd buy Canadian Gold Maple Leafs with a face value of CAD50, but a gold value twenty times the face value.
Those coins would be kept in the fireproof safe that was being delivered and installed on Monday afternoon, along with $2500 in cash and my important documents, including my birth certificate, passport, marriage certificate, Keiko's death certificate, and a copy of my will. Violet and Bianca would have the combination, though the safe also required a key. I'd keep one key, and the other would go into a safe deposit box to which Violet and Bianca would have access.
I finished with the computer, then sat down on the loveseat to read The Economist until Nikki arrived, which she did about fifteen minutes later. The doorman sent her up, and when she walked into the condo, she had the usual reaction most people had when they visited for the first time.
"Holy cow!" she exclaimed.
"The views are pretty impressive," I said. "I'd appreciate it if you took off your shoes — we don't wear shoes in the condo to protect the hardwood floors and area rugs."
She slipped off her brown loafers and followed me into the open living space, where I introduced Bianca, Nicole, and their friends from Loyola. I offered Nikki a drink; she asked for a Sprite, so I got a bottle of Sprite and a bottle of Dr Pepper, and invited her to the computer loft, where we sat on the loveseat.
"I can't believe this condo," she said, shaking her head. "I mean, it would be crazy for someone who was in their thirties, let alone twenty-one! I understood you were successful, but just wow!"
"Hard work, determination, and analytical skills have led to success," I replied. "If I can sustain it, the story will be similar to that of Carnegie and Rockefeller, or, in more modern times, Bernie Madoff. All of them started with basically nothing and became fabulously wealthy through hard work, determination, and analytical skills."
"But a millionaire by age twenty-one?"
"The key is not just making that million, but having continued success. While a million bucks seems like a lot, once you account for taxes, what you have left is the equivalent of twenty years of $30,000 in take-home pay. Granted, you could invest it and, because of high nominal interest rates, live longer off it, but in the end, inflation would erode the purchasing power, and it would, in twenty years, be akin to making around $19,000 a year now.
"Understanding that, someone with a million dollars of income subject to taxation is not 'rich'. Are they well off? Absolutely. Are they better off than most? Yes. But even with that million, they'd still need to work to be able to save for retirement, pay for their kids to go to college, and so on. They certainly couldn't retire and live an opulent lifestyle — they'd be upper-middle-class at best.
"It's also the case that while I have what appears to be significant wealth, it's all leveraged. I have mortgages on the condo and my investment properties, and a car loan. Taking everything into account, if I had to liquidate and pay taxes, I'd walk away with maybe $750,000 in cash. A good amount of money, and it could be invested to make more, but nowhere near what my total assets appear to be on paper because they have to be offset by my liabilities."
"You don't think you're rich?" Nikki asked.
"I think I'm comfortable; I plan to become rich. I don't deny I'm better off than most people, but I still have a lot of work to do, and success is not guaranteed. The vast majority of people who do what I do burn out after three to five years. Those who don't become incredibly wealthy."
"I suppose that makes sense. The girls who are downstairs – only Bianca is your housemate, right?"
"For the moment. Nicole is Bianca's girlfriend and will move in on the 15th. The other two are their friends. My other two housemates are Deanna, who is at her gallery, and CeCi, who is at work. My daughter, Sofía, is sleeping, and at some point, you'll see our cat Misty. I'd like to ask a question, and I want to preface it by saying it's not an attempt to derail your plans — what changed?"
"You're joking, right?!" Nikki exclaimed. "When I was in Chicago for our most recent date, I offered to spend the night without any conditions and you derailed it! Not to mention tying me up in mental knots! You were the one who told me what phrase to use to express myself, and I used it when I called you. Nothing changed other than using a vulgar word. If, at this point, you ask me what I want for the future, I'm literally going to dump the rest of the Sprite over your head! Do you want to fuck or not?"
There really was only one question to ask; well, two, really.
"Yes, I want to fuck. How long are you staying?"
"I took tomorrow off so I could spend the night."
"Birth control?"
"I started taking the Pill after our first date in Milwaukee."
I stood, took Nikki's hand, and led her to my bedroom, nearly tripping over Misty as she scampered into the room. There was something strange about that cat, but I wasn't going to ponder what it was, given I had a pretty, willing blonde girl in my room. Misty jumped onto the loveseat and stretched out as she so often did.
I turned my attention back to Nikki, whom I was certain, from our interactions, was inexperienced and likely a virgin. That said, given her request, I felt the best plan was simply to press ahead unless she objected. I closed and locked the door, then stepped close to Nikki.
"What's with the cat?" she asked.
"Don't ask me! She's Deanna's cat but seems to have adopted me. She usually sleeps in here. If it's a problem, I can shoo her away, though she'll be annoyed and scratch at the door."
"It's OK. I like cats; I was just curious because you had said you didn't have pets."
"Deanna got her about a month ago, and, as I said, she became attached to me almost immediately. Are we going to talk? Or..."
Nikki laughed, stepped close, and put her arms around my neck.
"Or!" she smirked.
I wrapped my arms around her, and we exchanged a soft French kiss. Nikki tightened her arms around me, and I did the same, as the kiss became more intense. I pulled Nikki's polo shirt out of her jeans, and that led to a mad scramble to remove each other's clothes. Less than two minutes later, we embraced again, this time skin to skin, with her large, firm breasts mashed against my chest and my erection trapped between us.
I broke the kiss and led Nikki to the bed, which I'd turned down after changing the sheets. I helped her in, then climbed in after her. I immediately moved on top of her, kissed her lips, then slid down to take one of her engorged nipples into my mouth, using my thumb to rub her other nipple. Nikki moaned softly and wriggled under me, rubbing her mons on my abs. I'd get there, but I wanted to play with her breasts a bit before I moved down.
I enjoyed kissing, licking, and sucking her left nipple for a few minutes, then switched my mouth to her right nipple, and used my left thumb to rub the one I'd just released from my mouth. Nikki wriggled more urgently, and I took the hint. I released her nipple and slowly kissed my way down her stomach, then planted a few kisses on the sparse, wispy blonde hair on her mons.
Following one further kiss on the place Nikki's thin labia joined, I pressed my tongue as far into her tunnel as I could. Nikki gasped, and I began swirling my tongue, tasting her musky juices. She moaned, and when I touched the tip of my tongue to her clit, she gasped. I sucked gently on it, then alternated between swirling my tongue and teasing her clit.
Nikki began undulating her hips and moaning softly, and moved her hand to the back of my head, encouraging me, not that I needed encouragement to eat pussy. Despite my experience and the gusto with which I pleasured her for ten minutes, Nikki hadn't had an orgasm.
I was reluctant to stop before she came, but I didn't feel I was making progress, so I moved on top of Nikki, grasped my shaft, rubbed my glans along her labia, then pushed slowly into her sopping wet tunnel, pushing all the way in with one long, smooth stroke. Nikki groaned deeply and wrapped her arms and legs around me. I lowered my head and kissed her, then began fucking her.
Nikki moved with me, and we developed a rhythm, slowly at first, but then faster with harder strokes. Nikki was obviously into it, but despite my best efforts, she hadn't had an orgasm after ten minutes of screwing, even with me grinding against her. I decided to try a new position, so I pulled out, turned onto my back, and helped Nikki mount me.
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