Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 17: Holy God!
Fiction Sex Story: Chapter 17: Holy God! - 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 4, 1984, Chicago, Illinois
On Wednesday morning, Deanna and I slept in, getting up around 8:00am so we could shower before Violet arrived for breakfast. Strangely, Misty had come into the bathroom and watched us in the shower.
"What's with her?" I asked.
"Pussy just can't stay away from you!" Deanna teased.
"Yeah, yeah," I chuckled. "But seriously?"
"I have no idea why she's imprinted on you. She was annoyed when you didn't let her in your room when you and Violet came upstairs."
"Violet wouldn't tolerate having the door open a crack," I observed.
"Are you sure about that?" Deanna teased.
"Actually, yes, given she said watching and being watched were completely off the table. That was in response to teasing her about Bianca and Nicole, by the way. Changing topics — I meant to ask last night how Stacey is doing."
"OK, I guess," Deanna replied. "She agreed to see the counselor you recommended. Violet provided her name and phone number."
"That's good, but she really should report the guy."
"Kendra and I both talked to her, but she doesn't want to."
"Well, at least she's going to counseling."
When we finished our shower, we dried off, dressed, and headed downstairs, with Misty following us. Violet arrived at 8:30am as usual, and after breakfast, Violet, Deanna, CeCi, and I got into my Saab, while Bianca and Sofía got into her Ford, and we drove to the house in Rogers Park to help Jack and Kristy set up for the Fourth of July party.
Our guests began arriving at noon, and over the course of the afternoon, everyone except Tom and Stuart showed up. Both of them were on shift, though I was fairly certain Tom would have declined the invitation no matter what. A few college students were missing, but that was mostly because they'd gone home for the Summer.
Fortunately, Perry didn't have a shift at the hospital, so he and Shelly could attend, which was a rare occurrence, given his insane schedule. I spent some time talking to him and heard several 'war stories' from the Cook County ER, which reportedly saw more gunshot wounds than any other ER in the country.
As I was circulating and mingling, Esme reminded me of the desire she and Katy had to be with me before they went back to Princeton. We agreed on the 21st, with them arriving at the condo at about 4:00pm, so I had some time to do homework after class.
I also had a chance to meet Willa and Anji, the two girls Deanna had suggested should join us in Saint Martin. Both were what I would call 'nerdy' looking, with glasses and straight hair, and both dressed similarly to how Deanna had when I first met her — loose, baggy clothing. They seemed nice enough, but both were extremely introverted, and other than the small amount of time they spent with me, they mostly hung around Deanna, CeCi, and Natasha.
I spent most of my time with Dustin, Archie, Trevor, Costas, and Rick, as I hadn't really seen them as much as I would have liked so far during the Summer. I checked with Violet and Bianca and invited the guys for dinner on July 15th.
As we usually did for the Fourth, we ate burgers and brats, then headed as a group to Grant Park, with most everyone taking the L, though Bianca and I drove to the Hancock Center because we could park in our spots, with Bianca bringing Jack and Kristy with her. After the fireworks, I escorted Violet home via the L, then returned to the condo, where Natasha was waiting for our usual Wednesday night together. Once again, our kitten followed me upstairs, and once again, I left the door open a crack so she could leave.
July 7, 1984, Chicago, Illinois
On Saturday morning, after waking up with Taya and showering together, I headed to Violet's house for breakfast. After breakfast, I headed to class. The Saturday morning Sociology class wasn't as boring as the English class I had on Mondays and Wednesdays, but it wasn't much better. I was really looking forward to the end of July when classes ended, and I would only have one class. Even more encouraging was that in January, I could begin my independent study and set my own hours.
Class dragged, and when the professor finally dismissed us, I headed back to the condo to change clothes, then headed for Oak Park to pick up Jennifer for our date. As I drove, I thought about the conversations I'd had with Bianca, Deanna, and Violet, and wondered if I was handling everything correctly. The girls all agreed I was, but I wasn't so sure, at least with regard to how I was handling girls outside my inner circle.
Fundamentally, so long as Violet, Deanna, Bianca, and CeCi were happy, and Sofía was properly cared for, I was more or less free to do whatever I felt was in my best interest. Ultimately, the true master trump was held by Sofía, as she wouldn't be able to care for herself for at least ten or eleven years. The other consideration was work, which was going very well, though I had to make sure I kept my focus.
I was curious what Jennifer would decide to do, but the one thing I had to do was ensure that whatever happened, it didn't create problems with Jessica, as she was an excellent nanny and Sofía really liked her. That meant ensuring I didn't make any missteps with Jennifer. I'd been clear with her on our first date, and I'd have to be equally clear on this one.
I arrived in Oak Park and had to park three blocks from Jennifer's house. I locked the car and walked the three blocks, then rang the bell. She opened it, called 'goodbye' to her mom, and then stepped out of the house, closing the door behind her.
"What are we doing today?" I asked as we began walking towards my Saab.
"Would you kiss me?" Jennifer asked.
I had a reasonably good idea why she'd asked, and it concerned me.
"I'd love to kiss you, but if what I infer from your question is correct, that's probably not the best way to make that decision."
"You're supposed to be a hotshot analyst, and your analysis is off! Try again!"
I thought back to our first date, and it immediately hit me — her comment about me putting my arm around her had led her to want to have sex, she'd imagined how it might be, and the kiss was validation.
"I'm going to assume you want a direct answer, not embroidery," I replied.
"That's a good assumption!" Jennifer declared.
"Based on what was discussed on our first date, going to bed together would be casual — just fucking for fun. You thought your first time would be with someone with whom you'd be in a relationship that had the possibility of ending in marriage. Over the past two weeks, you reconsidered your thinking about that and decided you wanted to fuck, and you didn't need the possibility of marriage in the future.
"Given that, if the kiss turns you on the way you think it will, you'll ask me to take you to the condo to deflower you. If not, we'll have dinner, see a movie, then I'll bring you home. If it's the former, and it's as good as you believe it will be, you'll want to see me again; if it's the latter, or it's not as good as you expect it to be, then we won't see each other again. How'd I do?"
"Nailed it! Now, kiss me, and we'll see if you get to nail me!"
I chuckled, "A foregone conclusion!"
"How do you know that?"
"I should say that I'm just that good, but if putting my arm around you made you tingle..."
Jennifer laughed, "Busted!"
I stopped, took her in my arms, and we shared a soft, sexy French kiss, which lasted about thirty seconds.
"Cherry lip gloss," I observed. "I like it!"
"My cherry is yours, if you want it," she said with a twinkle in her eye.
I took her hand and led her to the car. I unlocked the doors, helped her in, then got into the driver's seat. Once we were buckled in, I started the car and headed for the Hancock Center.
"Birth control?" I asked. "I do have rubbers if we need them."
"I'm on the Pill. I started taking it last December because I thought I might do it at Prom, but my date's kiss left me cold."
"What time does Cinderella's coach turn back into a pumpkin? Or is she planning to stay out all night?"
"It would be more peaceful at home if I were home by 1:00am. I plan to live at home while I'm in nursing school, so I need to keep things cool with the parental units, especially my dad. Doubly so, given he's paying for school."
"Wise. May I ask a question that you don't have to answer?"
"Sure," Jennifer agreed.
"When did you decide you wanted to go to bed with me?" I asked.
"In the car on the way to Miller Meadow. That's why I wanted to hold hands when we walked! But then you threw me a real curveball at the restaurant."
"Because you were expecting to date exclusively?"
"Yes, or at least work towards that. I told you I felt marriage had to be a possibility, but I also knew it would never be a sure thing unless I waited until I was engaged."
"And your Prom date?"
"He asked me to Prom, and we went on two dates before Prom, and I liked him well enough to consider he might be serious boyfriend material. He got a goodnight kiss on the cheek after the first date, and a peck on the lips after the second one. We made out a bit at Prom, but as I said, it left me cold, so I just had him take me home. When he called the next week, I told him I didn't want to see him again because we didn't click, which I realized was true at Prom. With you, we clicked right off the bat."
"Had you made out with someone before Prom?"
"At a couple of Spin the Bottle parties when I was in eighth grade and with my boyfriend when I was a Sophomore. I got felt up outside my clothes at the parties and by my boyfriend."
"What happened? If it's OK to ask."
"What do you like to say? It's always OK to ask, and it's up to me to decide whether or not to answer."
"I do say that quite often!"
"He wanted to go all the way, but I was only fifteen and wasn't ready. I didn't mind him trying that first time, but after I told him I wasn't ready, he kept pushing, so I dumped him. I dated several different guys during my Junior and Senior years, but none of them got more than a 'good night' kiss, except the guy who took me to Prom. Mind if I ask about your first time?"
"I lost my virginity on my girlfriend's sixteenth birthday. She kissed me — each of our first kisses with anyone — and five minutes later, both of us were no longer virgins."
"First kiss to sex in five minutes?" Jennifer asked. "Wow!"
"I know, right?" I chuckled. "But you and I had our first kiss about five minutes ago, so it won't be more than an hour for you!"
"Yeah, but I've kissed before! You hadn't!"
"True!" I agreed.
"When did you decide you wanted to sleep with me?" Jennifer asked.
"When you asked me to kiss you."
"You seriously didn't think 'I want to hit that' when you saw me at your condo?"
"I noticed you were a drop-dead gorgeous strawberry blonde with a sexy body. Believe it or not, my first thought when I see a girl is not, 'I want to sleep with her'."
Mainly because I didn't have to, because, as Deanna had pointed out, they all seemed to want to sleep with me.
"And your second thought?"
"Someone at home might have put the thought in my mind with simply a look."
"I thought guys always thought about sex and wanted to sleep with every girl they met."
"If that were true, no work would ever get done!" I chuckled.
"OK, Mr. Literal!"
"Actually, I'm going to be completely straight with you. With few exceptions, girls come to me the way you did today. Lots of girls. And with few exceptions, I take them up on their offers. So, really, I don't have to think about it."
"Not exactly a good marketing plan, telling me you sleep with lots of girls."
I shrugged as much as I could while keeping my hands on the steering wheel and wearing a seatbelt.
"From one perspective, I don't need to market myself because we've already closed the deal. From another, it's a show of honesty, and to let you know what you're getting into when you let ME get into you!"
"I'm going to ask a question I probably shouldn't ask, and one you don't have to answer — how many girls?"
"I don't keep a list or a black book or anything like that, but if I had to estimate, I'd say around fifty."
"You're serious?" Jennifer asked in surprise.
"As a heart attack."
"How was your VD test?"
"Clean as a whistle."
"Have you ever had VD?"
"No. And I'm going to be direct again — most of the girls were before I married, and, believe it or not, since then, most of the girls have been virgins."
"And they asked you?"
"The same as you did!"
Jennifer laughed, "Point taken."
"As I said, that's the usual thing that happens, both before and after Keiko."
"I know I'm changing subjects, but it actually follows — you said you messed it up by not inviting Bev to move to Chicago, right?"
"Yes."
"Did she ask you if she could move with you?"
"No, but Bev and I shared literally everything except our clothes, and I didn't tell her I was going to call my uncle and ask for help finding an entry-level job in Chicago. I didn't tell her until I'd agreed to the mailroom job at Spurgeon, and then I didn't invite her. Yes, I could point my finger at her and say she could have asked, but it was on me for not sharing.
"I didn't realize how badly I hurt her, and she didn't let on. As soon as I left, maybe even before, she started seeing another guy. She was sleeping with him, and we all thought he was the father of her baby. He wouldn't have anything to do with her after she said she wanted to keep the baby, and Bev and I reconciled. I was with her when she gave birth to Heather, and when she went for child support, the blood tests surprised all of us by proving that the guy she had been seeing wasn't the father.
"At that point, she obviously knew Glen Rodgers was the baby's father. She refused to say who it was for some time, but eventually, she swore me to secrecy and told me who it was. Unfortunately, her mental state was not good, and that's when things began spiraling out of control. I tried to help her, but eventually, I realized the only one I could help was Heather. I did the right thing, and that led directly to Bev taking her own life when she lost custody of Heather."
"I'm not even sure what to say about that," Jennifer said. "But I don't see how you can take the blame for what happened."
"It's not blame so much as acknowledging that I screwed up at first, and things might have been different. It's also acknowledging that doing the right thing sometimes has terrible consequences. I don't believe in the concept of sin, but I don't believe that rejecting the idea of sin gives me license to ignore the consequences of my actions."
"And the consequences of sleeping with fifty girls?"
I shrugged, "I don't hold Abrahamic views about sex, so virginity isn't important one way or the other. It would make no difference to me if you'd slept with fifty guys, five guys, one guy, or no guys."
"Fifty guys? Seriously?"
"I used that number to make a point; it wasn't an accusation. My point is, even if that were true, I wouldn't care."
"You wouldn't consider a girl who did that a slut?"
"That's a value judgment that I would never make against a girl," I replied. "It's nobody's business how many girls I've slept with, or for that matter, how many guys you've slept with. I honestly don't care, and it never enters my thinking about whether or not I want to sleep with a girl. There's simply no way I would reject a girl for a long-term relationship because she had multiple sex partners.
"I thought guys liked virgins."
"I know some guys get off on that, but it's not something that makes much difference from my standpoint. Yes, there's the chance you have an intact hymen, and if you do, it's literally a split-second thing that has no real bearing on having sex."
"Blood?"
"A tiny amount, if any. Again, there are rare cases where there is more blood, but from my understanding, that's mostly with younger girls. But again, it's a very minor thing. The bottom line is your virginity only matters if it matters to you."
"An interesting point I hadn't considered."
"Let me put a very fine point on it — is it any of your dad's business if you're a virgin or not?"
"He sure thinks so!"
"Yes, but do you think so?"
"Obviously not. I mean, I'm not going to advertise or anything, but it's totally none of his business!"
"And you won't discuss it with him, right?"
"I'd tell him to butt out."
"Which is my point. In the end, if a guy is that concerned about your virginity, and he's not a virgin, he's a hypocrite."
"True. So, girls really ask you?"
"Yes, and they give referrals, too!"
"Seriously? Referrals?"
"Seriously. Referrals. I've had girls who have never met me before come up to me and say they want to sleep with me."
"Weird. But I actually have to confess something. I decided I wanted to sleep with you when I saw the painting, but obviously, I had to be circumspect with my mom there. Of course, I was thinking 'boyfriend' at that point, not casual sex. I did give you a clue; you just missed it."
"Holding my hand at Miller Meadow?" I asked.
"Yes."
"Subtle, and it did convey a message, and I thought it was out of the ordinary, but I didn't draw the conclusion you'd hoped."
"Obviously," Jennifer replied, "given your response when I said we both knew where this was headed."
"At this point, I think I need to ask what you want to do."
"Spend the next eight hours in bed with you."
A few minutes later, I turned into the parking garage for the Hancock Center. I parked, and we made our way through the series of elevators to the condo. When we entered, we took off our shoes, and I hung my car keys on the hook by the door. Bianca was the only one home and smirked when she saw Jennifer, deducing the situation.
I took Jennifer's hand and led her upstairs to my room, closing and locking the door behind us. That appeared to seriously annoy Misty, who scratched at the door, but I ignored her.
"Any last requests?" I asked with a goofy smile.
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