Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 18: That's a Whole Other Story
Fiction Sex Story: Chapter 18: That's a Whole Other Story - 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 7, 1984, Chicago, Illinois
"Are you OK?" I asked.
"I have no idea!" Jennifer replied. "That was ... weird!"
"I agree. That's why it's only upon request and only in special circumstances."
"None of my friends had a first time even close to this, and we still have three hours!"
"I am your humble servant, M'lady!" I chuckled.
"Show me how to use the harness thing."
I helped her step into it and explained the basic principle, warning her to take it slowly.
"I take it, this doesn't do anything for you," she said.
"Not really, but some girls get off on it, so, as I said, in special circumstances."
"Assume the position!" Jennifer smirked.
I did as she asked, lying on my stomach with my hips on the pillow. I did my best to relax and silently thanked Deanna for choosing a small dildo. Jennifer moved between my legs, and I guided her on what to do. Soon, there was pressure, so I relaxed, and a few seconds later, I felt the dildo enter my butt. As I had done, Jennifer used a few strokes to enter me, then waited.
"Go ahead," I grunted.
Jennifer began pegging me with slow, measured strokes.
"This is SO weird but SO cool!" she exclaimed. "How do you cum?"
"We'll screw," I said, panting.
I let her go for about five minutes, then asked her to stop. She pulled out, I helped her out of the harness, and took it to the bathroom. I put it in the sink, then returned to the bed. I gently rolled Jennifer on her back and licked her until I was hard, then we screwed hard for fifteen minutes. Jennifer had three good orgasms before I came, and I licked her to a fourth before we snuggled.
When our breathing returned to normal, I got up and set the taps on the whirlpool tub, then washed the dildo in the sink. When the tub was full, I called Jennifer, who joined me, sitting between my legs and leaning back. I pressed the button to turn on the jets, and we sat for about ten minutes before I had her turn around and straddle me. We kissed and touched, and when I was hard, I helped Jennifer impale herself on me.
She quickly got the hang of how to move to give herself pleasure, and because I'd already cum so many times, I lasted close to twenty minutes before we had a joint orgasm, her fourth one in the whirlpool. Given we still had some time, she lifted off, turned around, and lay back. We spent another ten minutes in the water, with me fingering her to two more orgasms. After the second one, we got out and went to the shower.
"I really like shower blowjobs!" I grinned.
Jennifer laughed, winked, and dropped to her knees. She had to work a bit to get me hard, but she was determined, and I very much enjoyed watching her fellate me. After I came, she rose and kissed me. Unsurprisingly, she hadn't swallowed, but there wasn't much cum because I'd already cum six times.
"Sorry," she smirked.
"No, you aren't!" I exclaimed.
"True! One of my friends told her boyfriend the only way she'd let him cum in her mouth was if he kissed her before she swallowed. He refused."
"I probably would have in High School," I replied. "The first time a girl did that to me was after I moved to Chicago, and I was weirded out."
We began washing each other, something I very much enjoyed doing, and when we were clean, we dried each other. We returned to the bedroom and dressed, and then I asked Jennifer to help me change the sheets, which she happily did. I looked at the clock, and it was five minutes past midnight, giving us more than enough time to get Jennifer home before 1:00am.
"We need to be quiet," I said. "People are probably sleeping."
"OK," she replied.
We left my room, and, as I'd suspected, all the bedroom doors were closed. I saw Misty curled up in the loft, and she opened one eye, but then closed it. Jennifer and I went downstairs and saw nobody was there, either. We put on shoes, I grabbed my keys and hat, and we left the condo. Ten minutes later, we were on Michigan Avenue, heading south towards Congress Parkway.
"I only have one regret," Jennifer said.
"What's that?" I asked.
"Not being able to spend the night. I'd have loved to sleep in the same bed, but it's not worth the hassle at home. That'll probably be true most of the time we see each other. When?"
"My schedule is packed, as I said. How about August 4th?"
"Cool! Same time?"
"Yes."
"That's close to my period, so that might mean we just have dinner and see a movie, or whatever."
"I'm game if you are," I replied. "I've earned my red wings."
"I don't know that expression."
"From oral sex on a girl having her period. Blood gets on your chin and cheeks, and on her thighs, thus 'red wings'."
"Before tonight, I'd have said, 'no way', but after tonight, I don't doubt for a second you'd do that!"
"What did you like best?"
"All of it!" Jennifer declared mirthfully. "You made me cum so hard, especially that first time! And your tongue feels positively heavenly! Do you really like doing that?"
"Absolutely. I love how a girl tastes, and it actually gets me hard."
"I was a bit concerned about how you would taste, but it's fine; just a little bitter and salty. Have you done anything we didn't do?"
"Multiple girls at once," I replied.
"Of course you have!" Jennifer said, laughing. "I should have known! And they've done stuff with each other?"
"Some have, yes."
"Not my thing."
"And that's just fine. You agree with your partner what's OK and what's off-limits, and you do that stuff that's OK. If you want to try something new or different, you talk about it and come to an agreement, if you can. If you can't, you don't do it."
"Practical and logical."
"I try!"
We arrived in Oak Park about fifteen minutes before 1:00am, and there were no parking spots in sight. I double-parked, turned on the flashers, and walked Jennifer to the door.
"Thank you for the most exciting first time imaginable!" Jennifer exclaimed.
"It was very enjoyable!"
We exchanged a quick kiss, and after she went inside, I returned to the car. I drove back to the Hancock Center, and when I walked into the condo, it was dark, so I went up to my room. Misty padded down the hallway after me, and I shook my head. I closed the door most of the way, then got into bed. Misty hopped onto the bed and curled up near my feet. I totally didn't understand her, but I didn't let it bother me, and I quickly fell asleep.
July 8, 1984, Chicago, Illinois
On Sunday morning, after breakfast, Bianca, Sofía, and I went with Deanna to Ateljé D so we could pose for the third painting in the Nuclear Family series. She unlocked the door and disabled the alarm, then we followed her in. She locked the door behind us, and we went to her studio.
"Same pose?" I asked.
"Yes," Deanna replied. "The series is about the changes in how you look. For now, it's mostly about Sofía changing, but ten years from now, you and Bianca will have changed."
"I'm still not sure we should continue past Sofía's second birthday."
"I know," Deanna replied, "but that's still twenty-one months away, and you did agree to consider it. Go ahead and undress, and we'll get started. I already did the pencil sketch of you because not much has changed, really, unlike Bianca, who is losing her baby weight, and Sofía, who is growing like a weed!"
The three of us undressed and posed in the same way we had for the first two paintings.
"How was Jennifer?" Bianca asked with a silly smile.
"We both enjoyed ourselves. The situation with her reinforced what I was feeling about Tara and Taya, so I made it absolutely clear two weeks ago that if we got together, it would be casual, and that if she was looking for a husband, now or in the future, that most likely wasn't in the cards. That also got me to thinking about Violet and our relationship, but the major impediment there is not wanting to reveal anything to anyone at Spurgeon."
"One more reason for you to figure out a plan to walk away," Bianca observed.
"Easier said than done," I replied. "I'd have to do it with Noel Spurgeon's blessing, or at least his tacit approval, because otherwise, he could basically take all my clients and blackball me in the industry. He's done it before, and I'm positive he'd do it again."
"Is there any way you could negotiate that?" Deanna inquired from behind the canvas on the easel where she was working.
"Why would Noel Spurgeon negotiate?" I asked. "He holds all the cards and has all the power. What could I possibly offer him that would compensate for taking millions of dollars in fees and commissions with me? I couldn't even offer to cut him in, as that would mean I was paying both my own costs and part of his, with nothing in return."
"The golden handcuffs are nice and tight," Bianca declared.
"Unless you had something to hold over his head," Deanna said. "I advised Stacey to speak to an attorney and seek a settlement from the attorney with no admission of liability in exchange for keeping it quiet."
"Is she going to?"
"She's thinking about it, but the attorney who raped her is powerful and has powerful friends."
"So do we," I said. "Are you able to give me his name? I remember more or less what he looked like, so, in the long run, I could figure it out."
"Mark Stroud," Deanna replied.
"Son of a bitch!" I exclaimed, breaking the pose for a moment. "I was at a party at his house with Missy Monroe. It was hosted by his son, who's also named Mark."
"The one where they were doing lines of coke?" Bianca asked.
"One and the same," I replied.
"A neat solution presents itself," Bianca said. "Report the coke usage to the cops and have the kid busted."
"OK, sure, that hurts Stroud, but how does it help Stacey?"
"Piling on," Bianca replied as we got back into the pose. "There is no way Stroud would want to have a public accusation of rape made while he's trying to negotiate to keep his kid out of prison. Stacey simply says she'll go to the cops if he doesn't pay her off."
"That seems risky," I replied. "I mean, it could work, but even so, Stacey refused to go to the cops."
"She refused because Stroud is so powerful," Deanna said. "So maybe if Stroud were in jeopardy, she'd reconsider."
"That could have significant blowback," I countered. "If it got back to Matheson that I had anything to do with it, it could be a serious problem."
"Not if you protected Missy from the bust," Bianca said. "Find out when the next party is, and make sure Missy doesn't attend. That's your ace in the hole in case it does get back to Matheson or Monroe."
"But Missy's friends could get caught up in it as well," I objected. "I see far too many downsides to doing what you suggest. I think the best approach is to have Stacey speak to an attorney."
"Dee," Bianca said, "what if we set some kind of trap for Stroud? You know, set him up with an opportunity to do it again."
"Don't do that," I quickly interjected. "It could go wrong in so many ways and would put someone we care about at serious risk. And how would we prove it? You'd need a chemical test of whatever he provided to drink, and I'm not sure how you'd do that."
"So we just ignore it?" Bianca asked.
"No, we encourage her to report it to the police and contact a lawyer," I said. "If she isn't interested in doing those two things, I'm not sure how we can help her except by being supportive."
"I hate to say it," Deanna said, "but I think Jonathan is correct."
"Maybe that Italian guy could help," Bianca suggested.
"And then the Outfit would own us for the rest of our lives!" I replied. "I mean, sure, there's some satisfaction in having the guy's legs broken, but it's not worth the price we'd have to pay."
"I was TEASING!" Bianca protested.
"Well, I can't see your face," I countered, "and you said it as if it was a legit suggestion!"
"And if it were Sofía?"
"I might have to rethink my pacifism," I replied. "But more likely, I'd need a squeegee and a snow shovel to clean up after you!"
"You have that right!" Bianca declared fiercely.
We spent the entire morning at Ateljé D, taking a break so Sofía could nurse, then headed home to have lunch. After lunch, we relaxed until Alexa arrived for our photo shoot with CeCi.
"I think we'll go outside for the first set of shots," CeCi said. "We'll take four rolls, then come back here and shoot three more rolls."
"That's fine with me," I replied.
"Me, too," Alexa agreed.
We left the condo and took the elevator down to the 47th floor.
"Could we shoot at the pool?" CeCi asked.
"We'll need to ask the floor concierge," I replied.
We walked over to the concierge office, and I asked about using the pool for a photo shoot, and was told it wasn't a problem. Of course, a problem surfaced immediately — Alexa didn't have a bathing suit.
"We could shoot with Alexa in her shorts and T-shirt, sitting on the edge of the pool with her back towards the skyline and you in the water in front of her," CeCi suggested.
"It's your photo shoot, so I'm cool with whatever," Alexa said.
"Let's shoot outside," CeCi said. "We'll figure out the pool after."
We took the elevator down to the ground floor and walked to a small park, where CeCi took 'candid' shots of Alexa and me lying on the grass, sitting on a bench, and walking hand in hand. We moved from the park to North Michigan Avenue, and CeCi took shots of Alexa and me looking in store windows, sitting in a café, and walking along the sidewalk.
When CeCi finished all four rolls of film, the three of us went back to the condo, and CeCi shot a roll of individual model shots — portraits and full-lengths, using the city skyscape as background for some and a white wall for others. When we finished those, she had us pose together, sitting on the couch, sitting at the breakfast bar, and cuddling in the Japanese room.
When the second roll was completed, we went upstairs, and she took a series of pictures that were either PG-13 — a new rating — or R, ending with us in bed with arms around each other and our chests exposed.
"I could get my Polaroid and take some action shots," CeCi offered with a smirk. "Or my 8mm camera!"
"I'm game!" Alexa said quickly.
"You know my objection," I added. "Reputational risk."
"Won't your reputation be enhanced if pictures of 'Big Jon' are leaked?" Alexa tittered.
I chuckled, "Possibly, but it could cause serious problems with some of my conservative clients, which include police and fire pension funds and white-shoe lawyers. It's not that I don't trust CeCi, because I do; it's that some things happen that are completely beyond our control."
"You mean like if someone broke in?" Alexa asked.
"I wasn't thinking anything specific, but that is one possibility. Or cleaning staff. Or maintenance staff. Sure, the building is secure, and everyone who works for the building is vetted, but even vetted people can do bad things. Everything else is insured; the photos would be a very different thing."
"It was just an idea," CeCi said. "It's not something I could turn in for this class, anyway."
"What if you got a safe, Jonathan?" Alexa asked.
"I actually probably should," I replied. "I'll look into it."
"Does that mean you would?" CeCi asked, hopefully.
"I'll think about it," I replied.
"CeCi," Alexa said, "if you don't mind, I'd like to spend some quality time with Jonathan."
"I don't mind at all!" CeCi declared.
She left the room, nearly tripping over Misty, who darted in. CeCi closed the door, and I just laughed.
"What's with the cat?" Alexa asked.
"No clue," I said. "She seems to have imprinted on me. If she bothers you, I can put her out."
"She can stay."
"What did you have in mind?"
"Blowjob, fuck, sixty-nine to get you hard, fuck?" Alexa suggested.
"I'm game!"
July 9, 1984, Chicago, Illinois
"I'm glad Alexa didn't wear you out yesterday afternoon!" CeCi said when my alarm went off on Monday morning.
"I did have six hours to recover," I chuckled. "Are you getting up?"
"Just to go to my room so I can sleep two more hours."
"OK."
We exchanged a quick kiss and got out of bed. I went to the shower, and CeCi left to go to her own bed, with Misty leaving the room as well. Just under an hour later, I was at my desk, reviewing overnight headlines on Bloomberg. Nothing market-moving had happened over the weekend, and per Rich, the Asian markets had been calm, so I didn't need to make any portfolio adjustments.
Just before 8:00am, as I was working on my portion of the daily analyst report, Violet let me know I had a phone call from Beth Schoenburg.
"Kane," I said when I picked up the call.
"It's Beth! I know you're getting ready for the markets to open, so I'll keep this brief. Are you free for lunch tomorrow or Thursday?"
"Tomorrow is good," I replied after consulting my calendar. "The deli by your grandfather's tailor shop? 11:45am?"
"Perfect! See you there!"
We said 'goodbye', and I replaced the receiver. I made a note on my calendar, then resumed working on the analyst report. I finished that, then scanned the other portions of the report and called in Tony.
"How sure are you of this?" I asked, pointing to a name on the screen.
"I spoke to a friend who has a source inside the Mondale campaign. He trusts his source, and his source is confident that Mondale will select Congresswoman Geraldine Ferraro from New York as his running mate."
"I've seen significant talk about San Francisco Mayor Dianne Feinstein and Senator Lloyd Bentsen of Texas," I countered. "Though I discount Los Angeles Mayor Tom Bradley and Jesse Jackson, despite their names being thrown around. Are you sure enough to say it unequivocally in an analyst report? It's not something we want to get wrong."
"As I said, I trust my contact, who trusts his source. That source has fed us other accurate information."