Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 54: How late can you stay?
Fiction Sex Story: Chapter 54: How late can you stay? - 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
September 25, 1984, Chicago, Illinois
I hadn't shown emotion in Noel Spurgeon's office, nor as I walked through 32, but as soon as I was in the stairwell going down to 29, I pumped my fist and said 'yes!' in a low voice. In one sense, the numbers were mind-boggling. Just over three years ago, I had left Ohio, where I'd worked jobs at or just above minimum wage, and come to Chicago with $800 in my pocket — my life savings. This year, I'd make over $300,000, not including the significant bonus I expected and my carried interest.
In 1985, I'd make $2.5 million base, plus a significant bonus. If everything went as I expected, my carried interest could top $25 million by the end of the year, possibly significantly more. I had, in just three years and three months, earned enough so that I could live a comfortable life without ever working another day. If I kept working, I was on a trajectory to match Noel Spurgeon's net worth by the time I was thirty.
What I couldn't do was let it go to my head, nor allow it to convince me that that future income was guaranteed. Unlike almost everyone at Spurgeon, except Noel and Murray, I was not going to spend it before I earned it. I had intended to make an exception for my investment in Golden Gate Livery, but now I wouldn't have to because of the special bonus Noel had granted.
As I began processing what I would do with the increased income, the first and most important thing was to refinance the notes I had on the three buildings and pay down the principal. I could invest the money, but in my mind, making the buildings profitable would increase my free cash flow, which was crucial to ensuring that if things somehow went wrong, I'd have income from those assets.
When I reached the Research Department, I wanted to share with Violet and Bianca, but didn't want to do it in the office, so it would have to wait. I could tell Bianca when I went upstairs to change before heading to Marlena's condo for dinner, but I felt if I didn't tell Violet first, she'd get on my case. That meant waiting until the following evening, when Violet and I would have dinner.
The fax from Lyle Danforth had arrived, so I took it up to Jack and asked him to walk it through, ensuring nobody in Legal, Compliance, or New Accounts dawdled.
"Same allocation?" he asked.
"Yes, but I've decided to double the accumulation — 200,000 shares of each. Make sure to do it carefully. I'd rather have fewer shares than cause a big move in the market."
"If you're right, you could double your AUM."
"Re-run those numbers in your head and tell me why that's not true."
"The Treasury holdings, and you cannot really get away from them."
"Exactly. As long as they're earning at least 10%, I don't want to decrease the holdings because they provide me with a lot of security in exchange for some of my upside. I don't need to double the market, I just need to beat Noel Spurgeon!"
Jack laughed, "Haven't you heard the maxim about never beating your boss at golf?"
"Yeah, but we aren't playing golf! If Noel Spurgeon thought I was tanking to let him win, he'd fire me faster than you can say Jack Nicklaus or Arnold Palmer!"
"Are you sticking with Research for another year?"
"Yes."
"With the AUM you have, you should have a proper desk," Jack observed.
"I know. I discussed it with Noel, but I can't say anything at the moment."
"Got it."
"Get that application from Sierra Nevada Re moving; see you at lunch."
We both left my trading office on 31, with Jack going to 30 to see New Accounts and me to 29 to the Research Office. The rest of the day was routine, though I did read several analysis pieces on the Hong Kong Agreement, which would return Hong Kong to China in 1999.
I had the feeling that would not work out well for the people of Hong Kong, but in the overall scheme of things, it wouldn't affect the markets in the short term. In the longer term, I expected all the major banks and financial services companies to relocate some, if not all, of their people to Tokyo, Singapore, or Kuala Lumpur before the final handover.
At 5:00pm, I went up to the condo to change for dinner with Marlena. Sofía was wide awake, so I took ten minutes with her, then headed upstairs with Misty accompanying me as she nearly always did. I called Traci, and after comparing our schedules, we agreed I'd pose for her on Saturday afternoon.
Once I was dressed, I said 'goodbye' to Bianca and Sofía, then headed down to the lobby. The Lake Shore Drive Condominiums, where Marlena lived, were so close that it was silly to take my car, and just as silly to call Chicago Livery for a three-minute drive. I decided to take the 151-Sheridan Bus to her place and a cab home. The bus arrived about three minutes after I reached the stop at Michigan Avenue and Chestnut Street.
The bus was crowded because it was rush hour, but there was still room for me to get on and ride north eight stops to Lake Shore Drive and Banks Street. From there, it was but a few hundred feet to the entrance, and after I identified myself, the doorman buzzed Marlena, who instructed him to allow me to come up to her condo on the twentieth floor.
"Hi!" she exclaimed when I stepped off the elevator.
"Hi!" I replied, walking a few steps down the hallway to her door.
She greeted me with a 'society kiss' and let me into her very fashionable condo. It absolutely had a woman's touch, whereas mine, despite having been designed by Natasha, had a guy's feel.
"Want some wine while I finish dinner?"
"Whatever you're having."
She smirked, "Later, too?"
I laughed, "If that's your marketing plan, you might want to rethink it!"
"You didn't strike me as a prude," Marlena observed.
"Because I'm not! I'm not afraid to kiss after a blowjob, but that is not what your question implied!"
"You're right, and the question remains."
"Whether I'd do it or not has no material bearing on my comment that you might want to rethink your marketing plan, nor should it have indicated I was a prude. It was, in fact, neutral except for implying that guys might not respond well to that kind of marketing!"
"Are you freaking serious?" Marlena asked.
"It's what I do," I chuckled. "And to a point, who I am. On the plus side, you can count on me using every bit of analytical skill to ensure maximum, multi-orgasmic pleasure."
"That's so sexy," Marlena said flatly.
"If you don't know by now that I'm going to yank your chain at every opportunity when we're not discussing business, you haven't been paying close attention."
She poured me a glass of red wine.
"Marketing and chain-yanking aside..." Marlena said.
"Is that something that gets you off?" I asked.
"I've actually never done it! It was just a goofy thing to say."
"But then you suddenly made it serious."
"I'm not nearly as good at banter as you are, and that didn't come out the way I intended it to. Could I get a serious answer? Without a smart ass one first?"
I chuckled, "You could..."
She rolled her eyes in exasperation.
"Sorry. The answer is I won't be upset if you do."
"Mama!" Vesper called out.
I turned and saw her in a play area with gates around it.
"Caged?" I asked with a grin.
"When I'm cooking," Marlena said, walking over to Vesper and picking her up. "She can get into more trouble in five seconds than you would ever believe. You'll find out when Sofía begins walking. You have to watch them like a hawk!"
"I suspect I'm about to learn! When does she usually go to bed?"
"About 8:00pm. We go to bed about five minutes after that!"
"Birth control?"
"I'm on the Pill. I'm curious: did you bring rubbers?"
"Yes, because that specific topic hadn't come up in our conversation. Had I agreed to come here the other day, I'd have asked so I could stop at a drug store if you weren't on the Pill or didn't keep condoms here."
"Logical. I should have asked — how did your trip to San Francisco turn out?"
"Successful. I'll significantly increase my AUM thanks to that trip."
"Congrats!"
"Thanks. You know, I never asked, is Volkmer your maiden name?
"Yes. My ex-husband's last name is Hunter. I changed mine back and changed Vesper's in the divorce decree."
"Changing topics, what's for dinner?"
"Cajun chicken, baked potatoes, and a small tossed salad. Vesper, Mama needs to put you down so she can cook."
"NO!" Vesper insisted.
"Oops," I chuckled.
"Let me try to put her down. She might fuss, but she usually doesn't throw a tantrum."
Marlena put Vesper down, and Vesper scowled, then cried.
"Where were we?" Marlena asked.
"You had just told me what we were having for dinner, and I was about to say, 'sounds good enough to eat!'"
"Me or dinner?"
"Yes!" I declared.
"Do you do that because you like to or because you feel you have to?" Marlena asked
"I like how girls taste," I replied. "What about you?"
"I've never tasted a girl!" Marlena teased.
"Good one!" I chuckled. "That said, I suspect you've tasted yourself on a guy's lips and tongue."
"True, but different."
"Obviously! And the same goes for what you're requesting. So?"
"I'd say 'obligated', like most girls I know. But, weirdly, I want to do it for you, not out of obligation. Don't ask me why, because I couldn't tell you; I just want to."
"But not for your husband or your other lover?"
"No, but both of those relationships developed differently and kind of moved through the usual sequence. This will be more like your first time — first real kiss to sex in fairly short order."
"Tell me to mind my own business if necessary, but I'm going to guess there was pressure after make-out sessions, or whatever you want to call it, to give 'relief'?"
"I think the generic term is 'heavy petting' — I don't hear the bases used as often as when I was in High School. And yes, that's exactly what happened. I guess that wasn't the case with you, given the way your first time happened."
"True, and oral sex wasn't a major part of our fooling around, and when it was, it was way more giving for me than receiving, and no, that didn't bother me in the least."
"I'm going to surmise from everything you've said that you're fairly conventional," Marlena observed.
"I'd say that's true, though a few adventurous girls have pushed the limits. You strike me as conventional as well."
"Maybe I'm a total freak in the bedroom?" Marlena suggested.
"It's possible, but I don't get that vibe at all."
"I suppose we'll find out after dinner! Changing topics, besides word of mouth, how does Spurgeon market itself?"
"A mix of word-of-mouth and direct contact. We don't advertise or anything like that because it doesn't make sense. Our clientele is drawn from a fairly small pool, as you can imagine. There are significant restrictions on who can invest, mainly meeting a minimum government threshold for investable assets, except for 'friends and family' investors."
"How many clients do you have in your fund?"
"There's actually no easy answer to that because some of the investors use trusts or corporations expressly formed to invest. One way to answer is that we generate twenty monthly client reports, but those reports represent between fifty and sixty individuals, not to mention the union members for the pension funds. I have eight named 'friends and family’ investors, but one of those is a partnership of five guys. To give examples, I have athletes through MTB Sports Management in Cincinnati and Hollywood people through RKO Pictures and the William Morris Agency."
"And they don't want it known, right?"
"We're allowed to name some people, but most individuals do not want the information released. The union pension funds don't have a choice, really, because they have to inform their members and make public statements about their investments. The same is true for the client we just signed — Sierra Nevada Reinsurance — who'll have to disclose it on regulatory filings and corporate reports, including to the insurance companies for whom they provide reinsurance."
"What's 'reinsurance'?"
"Insurance companies take out their own insurance policies to protect themselves against catastrophic losses, or just to spread their losses to protect their reserves. It can be done several ways, and mainly it's a hedge against a massive hurricane, flood, or earthquake."
"That's not something I'd ever thought about, but it makes perfect sense — State Farm and Allstate have to ensure they don't run out of money to pay claims."
"Exactly right."
"Dinner's almost ready. Let me get Vesper situated in her booster seat, then I'll serve."
"Is there anything I can do?"
"Have dessert, once Vesper goes to bed!"
I chuckled and watched as she put Vesper into a booster seat, then fixed two plates with Cajun chicken and baked potatoes, put them on the table, then retrieved small bowls of salad from the fridge. The last thing she did was cut up some plain chicken for Vesper and put it on a plate along with boiled potatoes.
We sat down to eat, and I observed how Vesper handled her meal and the amount of help she required from Marlena. It would be about twenty months before Sofía would be this age, but all the tips and ideas I could gather would ultimately pay off. While we ate and I watched, Marlena and I chatted about High School, her time in college, and our outside interests, including a joint appreciation of baseball and football.
After we finished eating, I helped Marlena clean up. When the last dish was put away, we had just over an hour before Vesper went to bed. That wasn't something I was used to, as Sofía only stayed awake for a few hours at a time at most, though that was changing as she was sleeping longer at night. Bianca was happy about that because she was down to getting up once during the night to feed Sofía.
I could feel the anticipation growing as Marlena and I talked while Vesper played on the floor in front of us, but we were on Vesper's schedule, not ours. Fortunately, she did keep to her schedule, and just after 8:00pm, Marlena beckoned me to her bedroom. I followed her, and she closed the door, then turned on her baby monitor. She walked back to me and stood close, her nipples just barely poking my chest through our polo shirts.
"I want to suck you," she said invitingly.
"Mutual?" I inquired.
"Sure!" she exclaimed.
"Given what you said you want to do, we could save our first kiss for after," I suggested.
"Kinky!" she said mirthfully.
"I'm not sure I'd go that far, but I will add that you should impale yourself on me before you kiss me."
"A blowjob and screw before kissing? Seriously?"
"It's up to you."
"I'm game if you are! Let's get undressed!"
My response was to pull my polo shirt over my head, and Marlena followed suit. We both quickly scrambled out of the rest of our clothes, and I very much enjoyed the view of her lithe, sexy body with modest breasts and a clean-shaven mons.
"I was right!" Marlena smirked. "VERY filling! You could warn a girl!"
I laughed, "Excuse me, Miss, but other girls have said I'm hung like a horse. Care to check?"
"Maybe not, though, at a fraternity or sorority party, that might actually work!"
She took my hand and led me to the bed, where I lay on my back, and she climbed in and moved on top of me, planting her labia on my lips and taking my glans into her mouth. I put my hands on her butt cheeks and pulled her firmly against my mouth, then flicked her clit with my tongue. Marlena moaned softly and began bobbing, licking, and sucking as I used my mouth to pleasure her.
Despite Marlena's comments about feeling obligated in the past, the blowjob was slow and sexy, and she really knew how to use her tongue and the right amount of sucking, bobbing, and stroking to slowly build me to my release. It took me a few minutes to figure out exactly what worked for Marlena, but once I did, she had three good orgasms before I groaned as cum spurted into her mouth, and she lashed me with her tongue.
When my orgasm had passed, Marlena did as I'd suggested and impaled herself on my erection before leaning down to share a deep French kiss. As she'd implied would be the case, she hadn't swallowed, and cum ran from her mouth into mine as our tongues tangled and she ground against me, bringing herself off for a fourth time.
"Wild!" she breathed when she broke the kiss. "You really know how to use your tongue!"
"For someone who doesn't like giving blowjobs, that was a VERY good one!" I declared.
"Probably because it was the first one I actually wanted to give. How long can you stay hard?"
She flexed her hips to grind against me.
"In tight confines, several minutes if you keep doing that!"
"I can't imagine any girl not being snug given the size of your dick unless she had zero muscle tone!"
She continued flexing her hips and grinding until she brought herself off once more, and a short time later, I softened and slipped from her, but she stayed on top of me.
"How late can you stay?"
"I don't have a curfew," I replied. "The only question is if you want to keep this on the QT, in which case I can't stay the night, given my housemates know we're having dinner."
"As much as I'd like you to stay, that's probably best for both of us at this point, given it's just casual. Will you get enough sleep if you stay until midnight?"
"Yes."
"I think I want to start with sixty-nine, but this time, ride you until you cum in me."
"I think that sounds great!"
"Repeat until you have to leave?"
"That works for me."
September 26, 1984, Chicago, Illinois
"You got in late last night," Bianca observed as I made breakfast for us on Wednesday morning.
"I'm over eighteen, Mom!" I said with a grin.
Bianca laughed, "Not the fantasy I'd expect from you."
"I suppose I deserved that!"
"Waiving your rule about clients?"
"I did come home last night," I replied. "It was never a strict rule, as in 'never', just extreme caution. Marlena and I click really well as friends, and I enjoy her company, and she enjoys mine. I think she'll be a good long-term friend, and hopefully Vesper and Sofía can be friends, even though Vesper is close to two years older."
"Can you imagine the trouble those two might get into in about fourteen years?!"
I chuckled, "As a Dad, I don't want to; as Jonathan, I can imagine some teenage boys being very happy about that kind of trouble!"
Bianca laughed, "I wasn't specifically thinking that."
"Yes, you were!" I countered.
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