Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 72: They All Want It
Fiction Sex Story: Chapter 72: They All Want It - 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
December 18, 1984, Saint Martin, Leeward Islands, Lesser Antilles
I had a bit of trepidation that evening after watching a pair of movies on videotape, when Stacey walked up the stairs with me. When we entered the master bedroom, I closed the door and contemplated the best approach. I had to be careful, but not overly cautious, as I didn't want her to think I was rejecting her or had a negative view of her.
On the other hand, I felt being too aggressive was equally problematic, so it was a matter of finding the right balance. She and I had never kissed, so I decided to hold out my arms and see how Stacey responded. She stepped forward, pressed against me, and put her head on my chest, then wrapped her arms around me. I wrapped my arms around her and simply held her for a couple of minutes before she turned her head up for a kiss.
We exchanged a series of soft kisses, then what I could only describe as a gentle, loving French kiss. When Stacey broke the kiss after a minute, she put her head on my chest and sighed deeply. I held her for a bit while I considered my next step, and decided to finesse it.
"Do you want to talk, cuddle, or make love?" I asked.
"Make love," she whispered.
And so we did — gentle, slow, and loving, with Stacey having two orgasms before I had mine. When I moved off of her, I pulled her to me, and she snuggled close.
"Thank you," she said softly.
"Are you OK?"
"Yes. It was perfect. Is it OK if we just sleep now?"
"Of course," I replied.
I reached over, flipped off the lights, and we both fell asleep a short time later.
December 19, 1984, Saint Martin, Leeward Islands, Lesser Antilles
On Wednesday morning, Stacey and I showered together, though we didn't dress, given the 'nude' dress code for the duration of our time in Saint Martin.
"Are you disappointed?" Stacey asked as I was about to open the door.
"No," I replied. "I wouldn't have been disappointed if all you had wanted to do was cuddle."
"Thank you."
"You're welcome. If I can help in any way, let me know."
Stacey sighed, "He's too powerful. He laughed at the attorney I retained and basically dared him to make the allegation public, implying he'd smear me."
"I'm not sure how to ask this delicately, but do you know if there were other girls?"
"No. Why?"
"There is power in numbers," I replied. "If there were other girls, you'd have some leverage, because smear tactics wouldn't work, especially if the group could point to specific facts that lent credibility to the claims. I know a couple of fearless attorneys if you're interested, and I'll cover the cost."
"How would I find other girls?"
"That's the rub," I replied. "The offer is there if you decide to act."
"I think at this point, it's better to just get on with my life. Last night was a big step forward."
"I'm glad I could help."
Stacey smiled and gave me a quick peck on the lips, then we left the room. We headed downstairs, and I went to the kitchen, donned an apron, and prepared breakfast.
"What's the plan for today?" Kassie asked when she came into the kitchen.
"I didn't have one," I replied. "I'm enjoying relaxing, using the pool, and going to the beach."
"And screwing!" Kendra declared, coming into the kitchen.
"That, too!" I chuckled.
"Kassie, shall we have another repeat after breakfast?"
"I'm game if Jonathan is!" Kassie declared. "Then again, after lunch?"
"Oh, I suppose..." I said with a theatrical sigh, causing all the girls to laugh.
We had a nice breakfast, and then Kassie and Kendra double-teamed me, which they did again after lunch. We spent an hour at the beach, then returned to the house and dressed so we could have dinner on the Dutch side of the island, and afterwards, go dancing. As had happened the first night we'd gone dancing, I had a couple of opportunities to pick up other girls, but I let them pass as I already had bed partners for each night.
My partner for the night was Liz, who had acted in CeCi's movie, and she and I enjoyed several hours of great sex before falling asleep spooned together.
December 20, 1984, Saint Martin, Leeward Islands, Lesser Antilles
"Do you know when CeCi will have the movie edited?" Liz asked as we showered.
"She planned to have at least a rough cut when she comes home. If she does, and she's willing, we could call the other girls and screen it."
"That would be cool! My film debut!"
"You surprised me in more ways than one!" I said.
"I'd actually have done it X-rated!"
"Your first time?" I asked.
"The idea of being filmed made me hot! Don't ask me why, it just did. Can I ask why you were concerned about keeping it softcore?"
"Reputational risk," I replied.
"Risk?! It would be advertising!"
I chuckled, "Not that reputation. I have some fairly conservative clients, and Nuclear Family is pushing the edge of the envelope in that regard."
"But with your co-workers, being hung like a horse and having tremendous stamina would enhance it, right?"
"Probably, but I prefer to allow my portfolio results to make them all cry!"
"CeCi said you were the top guy at your firm."
"There's a good chance I'll have the best returns for this year," I replied. "I'll know when I get back from Hawai´i."
We finished our shower, dried off, and headed downstairs for a late breakfast. The day was much like the others, including Kassie and Kendra double-teaming me both before and after our late lunch. Because I hadn't had much sleep despite rising late, I went upstairs to take a nap, and wasn't surprised when Deanna followed me so we could nap together.
"I fleshed out a larger plan for «Joie de vivre et la petite mort», beyond The Source of Life," she said. ("Joy of life and the little death")
"This ought to be interesting," I observed.
Deanna laughed, "If by interesting you mean pushing the edge of the envelope."
"That would be one way to take that. What's your plan?"
"A multi-pane work that starts with the images I mentioned before — a penis and a vulva — and also includes a pane with breasts, one of an erection, one of penetration, and one of ejaculation. No faces would be shown. The idea would be to sell it as a complete set of works, sometime towards the end of next year, at a San Francisco gallery that highlights erotic works."
"What medium?" I asked.
"Graphite. I think Chelsea will do it, given she's already agreed to pose for the Venus painting."
"You're really branching out from your abstract work."
"I think it's a phase," Deanna said. "The other work, I mean. I have no intention of giving up on abstract work, but I want to explore other things. Are you willing to pose?"
"I'm open to the idea," I said.
"What would make you say 'no'?"
"Nothing I can think of, but ask me again when we get back from Hawai´i. I expect I'll agree, but I want some time to let it percolate."
"OK. I drew some sketches of you with Kassie and Kendra, though your face is obscured."
"Your version of Octopus and Ama?" I asked with a grin.
"I hadn't thought of that, but that does work."
"Do the girls know?"
"That was one of the reasons they went for multiple repeats!" Deanna declared. "I have two sketches — one each way. They actually agreed I could sell them, if I chose to."
"Of course you do! And of course they did!"
"Actually, I'm also going to use them as inspiration for some abstract pieces, the same as I will with the Venus painting, and if I can complete them before New York, I'll offer them for sale."
"Along the same lines as «La petite mort»," I observed.
"Yes."
"I mentioned to Chelsea that I want to buy the Venus painting," I said.
"She let me know. Obviously, as my patron, that's your prerogative, but I'd really rather sell it to a collector. What if I did a second one, slightly different, for you?"
"I don't want to block your progress, which would be self-defeating, so do what you think is best, please."
"Thank you. I'll offer the first one for sale at the New York show, then work on the second one after the show."
"Shall we go downstairs?"
"Yes."
We spent time by the pool, had dinner, and watched a pair of movies before Anji, the short, voluptuous redhead, and I went up to the master bedroom.
"You probably won't believe me," Anji said after I closed the door, "but I've never done this before."
Given my experience since moving to Chicago, the only actual surprise was that she hadn't decided to lose her virginity in front of the other girls.
"Then I have one question — any last requests as a virgin?"
Anji laughed, "Having seen you with Kassie and Kendra, I'm positive it's going to be awesome, so the only request I have is for you to spend the night fucking my brains out!"
"Your wish is my command!" I declared.
Ten minutes later, I was fully embedded in her tight, no-longer-virgin pussy.
"Jesus," she breathed. "SO full!"
"And so tight!" I declared.
"You may proceed with fucking my brains out!" Anji declared.
That initiated about four hours of fooling around, where I had five releases, and Anji had dozens of orgasms, after which we collapsed together to fall asleep.
December 21, 1984, Saint Martin, Leeward Islands, Lesser Antilles
"I suppose I should give my first blowjob," Anji said when we woke up on Friday morning.
"That's up to you," I replied.
Anji winked, slid down, and took my glans into her mouth, and began giving her first-ever blowjob. About twelve minutes later, I groaned as cum jetted into Anji's soft mouth. After she released me, we exchanged a deep French kiss, then went to the shower.
"Satisfied?" I asked.
"Very!" Anji declared. "If you want another night like last night, just call!"
"I'd absolutely enjoy that, though I can't commit to anything."
"No commitment, no strings!"
We finished our shower and joined the others for breakfast.
"What are we doing for our last full day?" Liz asked.
"Did you have something in mind?" Deanna asked.
"We could all have sex with Jonathan on the patio!" Kassie interjected.
"You have him tonight, and you want to wear him out?" Willa asked.
"I'm not sure that's a good idea," I said, thinking about Stacey.
"I agree with Jonathan," Deanna said. "Obviously, anyone who wants to fool around can ask, but not everyone wants to have sex in front of other people like you and Kendra, Kassie."
"Sorry," Kassie said, sounding chagrined. "I didn't mean to upset anyone."
"I don't think anyone is upset," I said. "It's just not everyone is an exhibitionist or a voyeur. Some people are neither, and some people are both."
"Guilty as charged"! Liz declared. "Both, I mean."
All the girls laughed.
"Then go for it!" Kassie declared.
"Maybe I will!" Liz replied.
"I dare you to go around the world!" Kassie smirked.
"You might want to ask Jonathan about that first," Willa interjected. "Not everyone is into that."
"What guy would say 'no' to anal?" Kassie asked. "They all want it!"
"I'm not sure that's accurate," I said. "I've done it, but it's not something I've ever sought."
"I lean towards Willa's view," Kassie said. "But obviously, for every generalization there's a rule."
"Same," Kendra said.
"Have you done it, Kassie?" Liz asked.
"Yes. Anyone else?"
"Me," Deanna said.
None of the other girls answered, and I inferred that none of them had.
"Jonathan, can I ask what you think about it?" Kassie asked.
It was an interesting question, given I'd actually enjoyed anal with Kaitlin and Isabella, and on a few other occasions, including with Deanna, CeCi, and Jennifer. I realized my aversion was a combination of originally thinking it was gross and Jeri surprising me, doing it without asking. Of course, I would very likely have refused, and that would likely have meant not doing it with any of the other girls.
"As I said, I've done it, but the idea doesn't turn me on, and, honestly, it doesn't do anything special for me. All things being equal, I strongly prefer oral and vaginal sex to anal. As for wanting it, the first time was the girl's insistence, and most other times have been either because the girl asked for it, or a result of a conversation about how crazy things could get."
"OK, now you have me curious!" Kassie declared.
"Pretty much anything you can think of that a guy and a girl, or multiple girls, can do together.
"Bondage?"
"Tried it, but it didn't do anything for me."
"Another thing I would expect most guys to want," Kassi said.
I shrugged, "Stereotypes and generalizations are almost always rooted in some fact, but they don't apply to everyone. May I give an example?"
"Of course."
"The stereotype is that girls hate giving blowjobs, but in my experience, nearly all girls are enthusiastic about it and want to do it. That said, I've run into some who aren't. If I were to draw from my experience, it would be that most girls love giving blowjobs, but that doesn't match the stereotype. I'm curious what you think is actually true."
"I know my friends in High School hated giving them, and most refused; my friends at the School of the Art Institute are more willing. Your experience actually doesn't match what the girls say."
"I'd say that's right," Willa said. "Most of my High School friends thought it was disgusting, too. Now, I'd say it's closer to fifty-fifty, but I wouldn't draw an overall conclusion from girls at the Art Institute."
"I wonder if any of the sex researchers like the Kinseys looked into that," Kendra said.
"Self-reported data is extremely unreliable," I replied. "Imagine asking a guy how big he was!"
All the girls laughed.
"I'd say that would be totally unreliable data!" Deanna declared. "Kind of like government statistics!"
I chuckled, "The difference is, it's impossible to independently verify a government statistical claim!"
All the girls laughed.
"So, Liz, if Jonathan is willing, will you go for it?" Kassie asked.
Liz considered, then slowly shook her head.
"He's so big, I don't think I could do it. I'm not even sure I'd try it with a guy who was a lot smaller."
"I'll do it if you will, Kassie," Anji offered. "Assuming Jonathan will do it."
"Actually, we'd need lube, and I didn't bring any," Kassie said. "Does anyone have baby oil?"
None of the girls did, so there was no way to fulfill their request.
"Anji," Liz said, "we could double-team him."
"I'm in!" Anji exclaimed. "And Jonathan will be, too!"
All the girls laughed once more, and we all went to the deck where we used a chaise, and Liz rode me while Anji straddled my face. Unlike with Kassie and Kendra, the girls didn't wait until after lunch; as soon as my refractory period passed, they switched places. We spent the rest of the day lounging around the pool and the house, and after dinner, we watched a pair of movies.
Kassie joined me in the master bedroom, and we spent several hours fooling around before spooning to fall asleep.
December 22, 1984, Aboard the Gulfstream En Route to Chicago
Both Anji and Liz wanted to join the Mile-High Club on the flight back to Chicago on Saturday, and I certainly wasn't going to refuse them. We repeated the threesome we'd had by the pool, both ways, and the girls wanted to cuddle, but I needed to relieve myself, so I quickly put on my briefs and T-shirt and went to use the lavatory.
"Is this what I need?" Anji asked when I returned, holding up a tube.
"Where did you find that?"
"In the drawer, along with rubbers and a vibrator. Will you?"
"If you really want to, yes."
"I do. Liz, you can watch!"
"Cool!" Liz exclaimed.
"How do we do it?" Anji asked.
"You need to get me hard, then lie on your stomach, and completely relax.
Anji did exactly that, and after spreading a generous amount of lube on my glans and shaft, I straddled her and placed my glans against her rear entrance.
"Take a deep breath and let it out slowly," I suggested.
Anji took a deep breath, and as she began blowing it out, I pushed forward, my glans popping past her sphincter.
"Fuuuuuuuccccccckkkkkkkk," Anji groaned.
"Are you OK?" I asked.
"Yeah," she panted. "It feels weird, but keep going."
I slowly worked myself completely into her tight butt, then began gently thrusting. I slipped my hand under Anji and rubbed her clit with my finger as she grunted, groaned, and moaned. I was careful not to thrust too hard, and once Anji had an orgasm, I let myself go, pumping cum into her butt about a minute after her orgasm.
"How was it?" Liz asked when I pulled out.
"Weird, but cool," Anji replied.
"Would you do it again?"
"Maybe. I'm totally glad I did it, but it would only be with a really special guy. You should try it!"
"I don't know," Liz said. "He's so big,"
"Don't do anything you don't feel comfortable doing," I counseled.
"It fit in me, and I'm smaller than you," Anji said.
"I don't think so."
There was a pitcher of water and a bowl, so I used that and a washcloth to clean up, though I'd need to do a better job before I had sex with anyone. Once I'd done that, the three of us got back into bed and snuggled until we had to get dressed for landing.
December 22, 1984, Chicago, Illinois
"That was a fun week," Deanna said once she and I were in the Town Car, which would take us from Meigs to the Hancock Center.
"I agree," I replied. "A last, wild, crazy week before things calm down."
"So I guess the Bacchanalia is going to be completely tame, then?" Deanna asked.
I chuckled, "It was never going to be what Bianca suggested, mainly because an orgy is out of the question for all of us. Bianca acknowledged that when we first discussed the party."
"You'll be propositioned by more than one girl," Deanna observed.
"And I'll gently rebuff them," I replied. "The last four years have been a lot of fun, and I've been with a lot of girls, but I'm ready to settle down again."
"The past year was about missing Keiko, wasn't it?"
"I'd say that's a large part of it, and you know my preferred solution."
"Violet being your long-term partner without marrying, having a baby with her, and having me as your lover."
"That is pretty much the sweet spot," I agreed. "CeCi is a bonus I didn't expect."
"And Chelsea is a short-term playmate?"
"Something like that. Honestly, she needs to find a guy, get married, and have a bunch of kids like she wants to. I certainly can't be that guy."
"Marriage? No. A bunch of kids? Why not?"
"My own concerns aside, for her, having kids requires marriage."
"Are you sure about that?"
"Absolutely. It came up in the context of our conversation after she offered to marry me. I reminded her of my thinking on that, and what she said made it clear that wasn't something she'd consider, even if I were willing, which I don't think I am. As I see it, two kids would be perfect."
"Why? It's certainly not about being able to afford them!"
"I can't tell you why, but two is right for me, just as zero is right for you."
"A reasonable point. Since we're talking about her, I'll speak to her about The Source of Life and the other images before we go to Hawai´i, and she can answer after we come back. Can you talk to Jack before New Year's?"
"The tenth consecutive trading day is December 31st, so I won't speak to him until we come back from Hawai´i. I can speak to Violet and Bianca, but they know not to discuss anything about work."
"So you won't know if you beat Spurgeon until after we come back?"
"Correct."
When we arrived at the Hancock Center, I signed the form for the driver, adding a generous tip, and Deanna and I made our way up to the condo. CeCi, Bianca, Nicole, and Chelsea all greeted me with hugs, and Misty scampered over to rub against my legs.
"She missed you," Bianca said. "She paced and looked for you and moped!"
"She'll have to get over it," I chuckled. "How is Sofía?"
"Sleeping. I think she missed you, too. Your Christmas bonus check is on your nightstand. Mine was very, very good."
"Thanks."
"What do you want to do about dinner?"
"Let's order Chinese," I suggested.
"I'll make the call."
"Thanks. "I'm going to shower and unpack, then I'll start a load of laundry.
I went upstairs with Misty padding behind me, not showing any signs of being angry or even annoyed with me. I picked up the envelope with the Christmas bonus check and was pleased with the $25,000, which more than covered all the gifts I'd bought and the money I'd spent in Saint Martin, with plenty left over. I unpacked my bag, put my shaving kit in the bathroom, and CeCi came into the bedroom.
"Hey," she said.
"Hi. How was California?"
"Great!"
"What can you tell me?"
"You? Anything, but you know it's all confidential."
"Of course."
"Principal photography ended on the 21st," CeCi replied. "Now we move to editing, mixing, and visual effects. Once all of that is done, then the final edit is completed, and the film is submitted for an MPAA rating."
"Do you know the expected release date?" I asked as I began undressing.
"As of now, they're expecting late July or early August."
"Where?"
"I won't know until the distribution deal is completed, which will be in late June."
"What's the most exciting thing you did?" I asked as I got into the shower.
CeCi came into the bathroom so we could continue talking.
"All of it! It's my first movie, so pretty much everything is new and exciting, even getting coffee for the director!"