Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 60: Well, This is Awkward
Fiction Sex Story: Chapter 60: Well, This is Awkward - 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
October 11, 1984, Cincinnati, Ohio
Both girls laughed.
"In that testosterone-fueled fantasy, I think it's Rose who would be more reluctant!" Cathy exclaimed.
"Wait!" Rose gasped. "You mean..."
Cathy and I both laughed.
"That was Jonathan's implication, at least from what I saw in his eyes and tone of voice!" Cathy declared.
"You'd actually do it with Jonathan?" Rose asked in disbelief.
"I might be convinced to take a walk on the wild side if YOU were!" Cathy declared.
"Seriously?" Rose gasped. "You'd let him fuck you?"
I chuckled, "You missed the clues, Rose! I wouldn't be the center of this threesome, YOU would! Her comments about you and me were because she's jealous of ME, not of you!"
"What?!" she gasped, her eyes widening in surprise.
"Perfect analysis, Jonathan!" Cathy declared. "I have a soft spot for redheads with green eyes and freckles!"
"Me, too!" I agreed.
"It's not too useful if it's soft, from what I hear!" Cathy exclaimed.
"Well, this is awkward," Rose observed.
"It shouldn't be," I replied. "Once, when I was modeling, a guy hit on me. I politely explained I was straight, then invited him to have a beer. He's a good friend now."
"It didn't gross you out?" Rose asked.
"Why should it?" I asked. "I wouldn't be grossed out by a girl in whom I wasn't interested asking me out. It would only be a problem if she persisted, knowing I wasn't interested. It really isn't any different from you saying 'no' to a guy trying to pick you up in a bar and not being upset if he leaves you alone, is it?"
"But ... never mind. I'm going to lose this argument."
"It's not about winning or losing an argument," I countered. "It's about being chill and not getting your panties in a twist when the person doesn't mean to offend you. It's a different story if someone is being a jerk. It's also about not doing anything you're not comfortable doing."
"Man, if everyone had that attitude, the world would be a MUCH better place!" Cathy observed.
"I'm an atheist, but I agree with Jesus about treating others the way you want them to treat you and loving your neighbor. Too many people who call themselves Christians don't follow either of those, especially the ones who are the loudest about their beliefs."
"I'd say that's about right," Cathy agreed. "As I see it, this can go two ways. First, I bow out and leave the field clear for Rose if she wants to play; second, if she agrees to take a walk on the wild side, I will, too, though as Jonathan said, Rose would be the center of the threesome."
"Er ... I don't think I can do that," Rose said quietly.
"Then I'll leave you two to whatever it is you want to get up to," Cathy said. "I'm not upset or anything, Rose. We're still cool, right?"
"Yes, it's just ... I can't."
"I get it," Cathy replied. "I'll say good night."
She stood up and moved over next to my chair, and I took the hint. I stood up, and we exchanged a hug, which was much tighter than I would have expected. She kissed me on the cheek, then stepped back.
"Next time you're in town, give me a call," she said, handing me a piece of paper with her name and phone number. "We'll get drinks again. You're a lot of fun!"
"You, too! Good night."
"Night!"
She left, and I sat back down.
"Sorry," Rose said. "I messed up your fantasy."
"I'll point out that it was Cathy who suggested it, and I played along with no belief it might actually happen."
"You're not disappointed?"
"Not the way I think you mean. Did the fantasy play out in my head? Absolutely. Am I upset about not being able to fulfil it? No. And it's not as if you're a consolation prize or anything, assuming you're actually interested."
"You think I'm not?" Rose asked.
"I think people behave differently in front of their friends, especially in groups, and especially when there is serious teasing. Add to that the usual fronts people often put up, especially in pubs, and it can be difficult to discern what someone is thinking. If you don't know someone very well, you can totally misinterpret their behavior. I'm sure you've seen girls flirt hard with guys, and even imply they want to get together, but ultimately not go through with it."
"Sure," Rose confirmed. "That happens a lot at bars. Does it frustrate you?"
"I don't hang out in bars or pubs very often," I replied. "Most of the girls I meet are from the School of the Art Institute, through friends, or through work."
"Can I ask you a personal question?"
"You can always ask," I replied. "I won't be offended, no matter what you ask."
"Did you join us because you were hoping to get together with Debbie, and we kind of blocked you?"
"Actually, when Debbie and I first spoke, she suggested I call her the next time I was in town. My client suggested his wife would be happy if he were home early, and that I would probably enjoy having drinks and dinner with five cute girls instead of him. He wasn't wrong! In other words, I wasn't expecting anything beyond drinks and dinner. It was fun, and I enjoyed the joking around. My worst-case scenario was going back to my room alone, which was my plan before I even set foot in Arnold's."
"I'm not used to guys in bars not being totally aggressive."
"What I said earlier is true — I believe being cool and friendly and having a good sense of humor is far more effective than being aggressive or crude."
"I can totally see that, because while all the other guys are blatant about what they want, you're subtle, which makes girls feel more comfortable."
"I could say there's a method to my madness, but it's neither a front nor an act; what you see is what you get."
"This is where Cathy would say I haven't seen it!"
I chuckled, "Neither have I, so we're even in that regard!"
"What are you doing tomorrow? I mean, if it's OK to ask."
I was actually going to visit Heather, but I didn't want to have to explain that disaster to Rose, so a bit of obfuscation was necessary.
"I'm visiting some friends late in the morning, then having lunch with my mom. After that, I'll head to the airport to fly back to Chicago. What time is your shift tomorrow?"
"I actually have Fridays off. I work Sunday through Thursday, 5:00am to 5:00pm."
"How long is each clinical rotation?"
"Twelve weeks for the Emergency Department, because it's one of the core rotations; others can be shorter. What classes are you taking?"
"Just one — English Lit. Once I finish, I'll have two years of independent study to earn a BS in Business with a minor in Finance."
"Independent study?"
"It's a pilot program for people with significant work experience to complete a degree without having to spend much time in class once the core courses are out of the way."
The waitress came by to see if we wanted another round, but Rose said she didn't. I closed out the tab and tipped the waitress generously.
"If you want to get ice cream or see a movie or something, I'm cool with that," I offered, because I sensed some trepidation.
"I thought you wanted something else," Rose said.
"I'm interested, but I get the sense you aren't sure."
"Let's go for ice cream," she suggested.
I nodded, and we got up from our seats. We both put on our light jackets, then left Arnold's.
"Where to?" I asked.
"Graeter's," Rose replied. "This way."
I followed her to the Graeter's shop, where I bought each of us a turtle sundae. The weather was nice enough, so we went to sit on a bench outside at Rose's request. We ate, and she didn't say anything, which reinforced my belief she might have felt obligated by Cathy's teasing.
"I won't be upset if you decide to go home," I said after about three minutes.
"It's ... I, er, want to, but ... uhm ... I haven't, you know, actually done it."
"Don't let your friends pressure you into doing something you aren't ready to do."
"I do want to, it's just ... it's a long story."
"Is this something you want to talk about, or should I walk you to your car?"
"I said I want to," Rose replied.
"Yes, but your body language, tone of voice, and what you said give off a very different vibe. Obviously, you don't have to tell me anything you don't want to."
"I get the feeling that if I don't, you won't."
"I'm concerned because you went from bubbly, fun, and teasing to quiet and trepidatious once your friends left."
"Trepidatious?" Rose asked.
"Expressing trepidation, which means being fearful or uneasy," I replied. "I keep a thesaurus on my desk so I don't sound as if I'm constantly repeating myself in my analyst reports, and I found quite a few interesting words that way. The change in your demeanor was almost night and day as soon as Cathy left, and I had the sense that my concern about her teasing you into it might have been valid."
"But I said I wanted to," Rose protested.
"The only way to get there is to talk about it," I replied.
"Forget I said anything. I'll just go home."
"I didn't mean to upset you; sorry. Let me walk you to your car."
"It's OK. Just go."
I realized I wasn't going to make any headway, but I was concerned about her. I didn't know her very well, so I wasn't quite sure what to do.
"If you're sure."
"I am."
I got up and began walking back to the Netherland Plaza, and when I reached my room, I decided my best course of action was to call Cathy and express my concern. I wasn't sure if she'd be home, but it had been about forty minutes since she'd left, which meant she might be. I pulled out the piece of paper she'd given me, checked how to make an outside call, then dialed.
"Cathy Schmidt," she said.
"Hi, Cathy, it's Jonathan Kane."
"Hi! What's up?"
"After you left, Rose started acting strangely, and I'm a bit concerned."
"What do you mean, strangely?"
I had to walk a fine line not to give away a confidence.
"She became skittish, I guess, and when I asked about it, she decided she was going to go home."
"I think I know what the problem is," Cathy said. "If you don't mind some company, I'll come there, and we can talk and have a drink, if that's cool."
Given Cathy's orientation, and despite her teasing, I was positive it was simply a friendly invitation, which was fine with me, as it was still early. I had nothing to do for the evening, and didn't have to be up too early in the morning.
"Sure," I said, then provided my room number.
"See you in about twenty-five minutes!" Cathy declared.
After we ended the call, I pulled out Hamlet and began reading, not putting the book down until I heard a knock on the door. I got up, opened the door, and let Cathy into my room.
"Want something to drink?" I asked.
"What do you have?"
"Whatever is in the minibar," I replied. "Or I can call room service if you want a mixed drink."
"Rum and Coke will work for me."
She found a small bottle of rum and a can of Coke, and I got a small bottle of Jack Daniel's. She mixed her drink, then we sat down on the small sofa.
"What do you think is wrong?" I asked.
"Completely confidential, right?"
"Of course."
"Unless I miss my guess, she's repressing her attraction to girls. I could be way off base, but I don't think so."
I nodded because that might make sense of Rose's behavior. If she were fighting with her sexuality, the act in front of her friends made sense, as did the sudden trepidation when it was time for us to come back to the hotel. The one thing that didn't quite fit was her claim that it was a 'long story', but she could have meant 'complicated. Her unwillingness to tell me also fit, because if she was trying to prove to herself she was straight, telling me she was struggling was not something she'd want to do.
"The facts do seem to support that theory," I observed.
Cathy laughed, "OK, Mr. Spock!"
I chuckled, "I suppose that appellation fits!"
"You're too funny!"
"Thanks. I am a bit concerned about your teasing Rose, given what you believe about her."
"You mean saying she wanted to fuck you?"
"Yes, and the threesome offer. Obviously, I don't know her well enough, but it just seems a bit much."
"Yes and no. I can't really treat her differently based on a suspicion, especially given we've teased and joked about sex as a group since we met about sixteen months ago. I only came to that conclusion about a month ago, and, honestly, I was giving her a way to experiment, if she wanted."
"OK," I said, nodding. "I can see that because she could test the waters, so to speak, both ways, though she might have felt pressured into screwing when she wasn't really interested."
"I think you'd have made it clear she could stop any time, and if you hadn't, I would have."
"You're right about that."
"In that case, I'd have taken one for the team, as it were."
I chuckled, "That almost sounds like the 'Oh, if I have to' response kids sometimes use on their parents."
Cathy laughed softly, "I guess it does! But seriously, I'm not grossed out or weirded out about it, and I do want to have a kid eventually. I mean, I could try to go the artificial route, but it's expensive and doesn't always work."
"You do realize it's not 'one and done' to make a baby, right?" I asked.
Cathy laughed, "I'm a nursing student, you nut! Of course I know that! I'm curious, and you obviously can tell me to mind my own business, but how did it work with the mom of your kid?"
"It took a few months with numerous attempts at her statistically most fertile time."
"Is she bisexual or exclusively lesbian except for that?"
"I'd say she's bisexual, but strongly prefers soft and cuddly to muscular."
"Don't you mean hard and muscular?" Cathy asked with a smirk.
"As I said earlier, I love your sense of humor! You said earlier you weren't really interested, which makes me curious about how you'll handle sex with the father."
"You mean, will I enjoy it? Will I do more than just screw?"
"However you want to answer that," I said.
"I actually hadn't thought about it in any detail. Are you fishing for my interest?"
"You made your feelings clear earlier, and when I called, I took what you said as merely a friendly offer to hang out, nothing more."
"I did say I would take a walk on the wild side!" Cathy declared.
"You made it conditional on Rose doing the same. When the premise of a conditional is false, you cannot draw any inferences about the conclusion! That said, it would be a logical fallacy to reject the conclusion because the premise is false; that's called denying the antecedent. So, in this case, because Rose didn't take you up on your offer, I can't draw an inference about whether you would do it without that condition."
"Wow!" Cathy exclaimed.
"Logic," I replied. "It's an important part of my analysis – if my analysis is inaccurate, that does not mean the result won't happen. That's why we tend to propose a range of possible outcomes and assign probabilities to them. Sometimes it's a coin flip, and if so, we say that. Sometimes, deciding heads or tails is the difference between making a shedload of money and going bankrupt."
"You'd bet everything on a 50/50 chance?!"
"Oh, hell no!" I chuckled. "If I had to act, I'd hedge by using futures, options, or other ways of protecting my position. That can be complicated, and I'd probably need to explain too much to make it make sense. To put it in simple terms, I can, in effect, buy insurance to protect myself. The same kinds of tools can be used to make money when the stock market is dropping."
"You can make money when prices go down?"
"Absolutely. Anyway, all of that was to say I can't make any inferences about what you might do!"
Cathy laughed, "I wish you still lived in the area! You're a lot of fun to be around."
"You're always welcome to find a job in Chicago when you graduate from nursing school in a year and a half."
"I just might do that! You absolutely should call when you're in town again, though I suspect you're more interested in calling Debbie. Her boobs are to die for!"
I chuckled, "Competition, as you said!"
"She's totally straight, as are Laura and Shelly."
"And it's not all about that! You sitting here having a drink with me is proof!"
"I'm positive I know the answer, but did the idea cross your mind?"
"Only in the sense that I was sure your offer wasn't that."
"That has to be because you have gay and lesbian friends; most guys would think otherwise."
"Probably," I replied. "I generally don't make assumptions in that regard, and you, in effect, laid your cards on the table at Arnold's."
"True. Were you frustrated when Rose decided to go home?"
"Is this where I say I am and ask you to help relieve my frustration?"
Cathy laughed, "You are really smooth! You just asked me to go to bed with you without asking me to go to bed with you!"
"Did I?" I asked with a raised eyebrow.
"How about I say you made a joke about it to leave open the slim possibility?"
"I actually was just teasing with no expectation that it would have any effect on what happens when we finish our drinks."
"But isn't that part of the dance? I mean, at least for guys who aren't complete jerks."
"So I'm only a partial jerk?" I asked with a sly smile.
"That is not what I meant!" Cathy declared.
"But it is an inference one could draw from your use of 'complete', implying that there were guys who were only partial jerks! Had you not used 'complete', then it would be jerk or no jerk, not levels of jerkiness."
Cathy rolled her eyes, "Seriously?"
"This is what living with me is like," I chuckled. "You can ask my daughter's mom, her girlfriend, and my other roommates if you come to Chicago. Or any of my friends, actually. They call it 'Jonathanland', which is either a reference to being overly logical or overly pedantic, often both at the same time!"
"It sounds like fun!"
"We do try to have a good time, though life often intrudes."
"I think that's true for everyone, unfortunately."
We finished our drinks, and as I expected, Cathy said she was going to head home because she had class in the morning. I walked her to the door, and she hugged me tightly as she had earlier. This time, I returned the hug, pulling her firm body against mine.
"OK to kiss you?" she asked.
"If you dare," I chuckled.
"Oh, please! You think a single kiss will cause me to demand you take me to bed?"
"Maybe I'm just that good," I said smugly.
Cathy laughed and gave me a soft, closed-mouth kiss on the lips.
"Oh," she squealed when she broke the kiss. "Take me to bed, Jonathan!"
I decided to have some fun with her, so I quickly picked her up and turned to carry her to the bed, with no intention of actually following through. She laughed hard, and I put her down after taking only two steps.
"I should have expected that!" she declared.
"You did give me the perfect opening!"
"Oh, the opening is perfect, for sure!" she smirked.
"And this is where I demand proof, right?" I chuckled.
"Good luck with that idea!" she declared mirthfully. "Seriously, call me when you come back to Cincinnati. You are WAY more fun than just about everyone I know."
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