Climbing the Ladder - Chutes and Ladders
Copyright© 2024 by Michael Loucks
Chapter 65: Certified Mail, Return Receipt Requested
Coming of Age Sex Story: Chapter 65: Certified Mail, Return Receipt Requested - The world of finance is, in its simplest form, just like a game of Chutes and Ladders. There are only two things that matter to the bottom line: profits and losses. The goal is to climb to the finish and thrive, not fall back down the chute. Having been named the manager of the newly created Research Department at Spurgeon, Jonathan's career is soaring. However, as tends to happen, profit is balanced by loss. The next rung of the ladder will be much harder to reach, but he continues to climb.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Tear Jerker Workplace
May 19, 1984, Chicago, Illinois
When I arrived home on Saturday evening, Deanna was watching TV alone.
"Hey," I said, walking over and sitting down in a comfortable chair next to hers.
"Hey. How was your date?" she asked.
"We went to the Shedd Aquarium and the Natural History Museum, had dinner at Lou Malnati's, then saw a stand-up comedian. We had a good time, but I'm not sure I'll see her again."
"You or her?"
"Me, but her decision. She's looking for Mr. Right, and she's pretty sure I'm him, but I can't offer what she needs."
"Typical Midwestern girl from a smallish town who didn't go to college and wants to marry and have a family?"
"Exactly. I like her, but even if I hadn't concluded that I most likely won't marry, I'm not ready to get involved with someone in a serious way and can't say when I will be."
"Mind if I ask how that came up on the second date?"
"It started when I challenged her comment about keeping a scorecard. I asked to see it, and she said she'd be drummed out of the club. I pointed out that it was a trap for a guy in that he had to guess what the girl wanted, and it was far better to just tell him what she wanted. That conversation led to her understanding I wasn't ready for a girlfriend. That led to me explaining my thinking. Based on everything I said, she asked if I expected her to stay the night."
"Did you?"
"No. I actually hadn't given that much consideration, and I said that. She challenged me, saying in her experience, guys always expect that. I countered with the logic that if you accept a second date, you're expressing an intent to eventually consider having sex, though the timing could well be after vows. She was offended, but after a bit more discussion, she admitted the logic was sound."
Deanna laughed, "So you used rhetoric to force her to admit she wanted to sleep with you?"
"To admit that was the logical conclusion of the sequence of events that begins when you go on your first date."
"How did you leave it?"
"She said she had a lot to think about. I promised to call her in a week or so. I honestly don't think she'll accept another date because I'm not able to commit to her."
"Which is why you're concerned about Violet."
"If I hurt her, even inadvertently, it would be devastating for me and possibly disastrous for her."
"I believe she's stronger than you think," Deanna said. "Consider what she's overcome — only a truly strong person could do that. You two have had deep conversations about your relationship and the future, right?"
"We have."
"Then you have to trust her to make the decision that's best for her. Don't decide for her."
"She told me she was infected by the Sofía virus and wants to be a couple and have a baby together."
"What did you say?"
"That I'd love to have a baby with her when we're both ready. I'm not sure she's able to accept what I can offer."
"That's up to her," Deanna said firmly. "Just be honest and let her decide what to do. Maybe you two become an exclusive couple; maybe she agrees I can be your mistress; maybe she doesn't put any demands on you and decides just to have great sex and eventually have a baby together.
"You have a huge advantage in that you're in a situation where you are truly free to arrange your life in any way you wish. You're a millionaire on paper at age twenty-one, and that gives you options that most people do not have. You're also in an industry where infidelity is part of the culture, so nobody is going to question you having sex with more girls than your friend Stuart could dream of!"
I laughed, "To hear Dustin tell it, Stuart slept with more girls in High School than I have in my entire life! According to Dustin, that included some girls AND their moms, and I have no reason to doubt Dustin. That said, it's not a competition, and I know you didn't mean it that way."
"Rich, average-looking guys have more options than even the best-looking firemen. And you have better-than-average looks to go along with the bigger-than-average ... wallet!"
I chuckled, "Beth made that point, as have others — wearing one of my tailored suits to a bar and paying with my Amex card would have girls throwing themselves at me. It appears meeting an art student at Ed Debevic's is equally effective!"
Deanna laughed, "I have no complaints! I bet you don't, either!"
"You'd win that bet!"
"Are you going to see any of the Art School Girls again?"
"They all went home over the Summer — Tara to New York, Stefi to Oklahoma, and Krissy to Oregon. I will see Krissy when she comes back, but I'm not sure about the other two."
"Well, this art student is here! Care to take me to bed?"
I shut off the TV, took Deanna's hand, and led her up to my room.
"What time did Bianca go to bed?" I asked, as Deanna and I began undressing.
"Around 9:30pm. Sofía was cranky this afternoon, so Bianca didn't get her nap."
We got into bed and came together with a kiss.
May 20, 1984, Chicago, Illinois
"Can I ask about your preferred way for me to finish?" I asked as Deanna and I got into the shower on Sunday morning.
"I know you know this, but we do things to give our partner pleasure, sometimes even if we don't derive pleasure from them. I do, of course, but think about things you've done, including letting CeCi and me use the strap-on or kissing us before we swallow your cum."
"So, do you derive pleasure from it?"
"Yes. I think it's sexy, I like how it tastes, and guys absolutely get off on it. In fact, I bet you've suggested it with at least one other girl!"
I chuckled, "Maybe..."
"You like eating pussy, right?"
"I do."
"And you'll stick your tongue in a freshly fucked pussy because you know it gives the girl pleasure, even if you don't particularly want to taste your own cum."
"It's a non-issue at this point, but it did take some getting used to. The idea bothered me."
"When did that first happen?"
"The third girl I was with surprised me with a French kiss after a blowjob. I objected, and she made the point that if I wanted to have sex with her, I'd accept the kiss. I discovered just how foolish voicing my objection had been when, after a blowjob in the shower, she kissed me without swallowing, and I nearly lost my lunch. I didn't say anything, but it was the deciding factor in not wanting to see her again."
"You clearly got past that," Deanna observed.
"I had the same general reaction to anal sex."
"And that one, too! Both giving and receiving!"
"What I concluded was that my best strategy was to keep the girls happy."
"Thus, assuring repeat customers and word-of-mouth advertising!"
"That did seem to work to my advantage, at least until Ellie took things too far."
"That was actually more about Ellie than about nine girls, though I know that factored in as well. Ellie was doing her best to find a way to prevent you from committing to Keiko, or setting things up so Keiko would reject your proposal."
"Ellie misjudged Keiko," I said.
"I think all the girls misjudged Keiko in the sense that nobody expected you to fall so hard for her. And that is the main source of your muddled thinking — Keiko dying really hurt you, and you're afraid of being hurt that way again. Sadly, it's going to happen because life is like that. And it won't matter if you have a marriage certificate or not."
"Those are actually two different issues," I said as we got out of the shower. "My aversion to commitment is probably what you say, but my decision about marriage is about Keiko always being my wife with no qualifications."
We dried off, and Deanna put on her robe to go to her room to get clean clothes. I dressed, then went downstairs to find Bianca and Sofía in the conversation pit.
"Deanna said you were tired last night. Did you get enough sleep?"
"Yes. Sofía just had a bad afternoon. Nothing to worry about, just a case of baby-itis. She was fine so long as I walked with her, but the second I sat down or put her down, she cried and fussed and wouldn't sleep."
"I'm going to make breakfast. Any requests?"
"Waffles would be good."
"Then waffles it is!"
Deanna came downstairs and came to the kitchen to help make breakfast, and twenty minutes later, we served waffles, bacon, eggs, and juice. CeCi joined us just as we sat down.
"How was work last night?" I asked.
"We're busier now that it's warm out, so tips are better. Otherwise, waiting tables doesn't change much."
"It's good practice for when you go to Hollywood to make movies!" Deanna teased.
CeCi laughed, "That is the stereotype! But I'm hoping to find a way to catch on with someone when I graduate, so I don't have to go through that part of it."
"Jonathan, you should try to make some contacts in Hollywood," Bianca suggested. "Maybe speak to agents similar to how you did with athletes. That way, you have someone to call when CeCi graduates."
"That's not a bad idea," I said. "And we have about three years. I'll look into it."
"Cool!" CeCi declared. "I did check out the video store they don't have the three movies."
"Which movies?" Deanna asked.
"In the Realm of the Senses and the two Swedish I Am Curious films. Jonathan, Bianca, and I were discussing filmmaking. Bianca teased about pornography, and I suggested those as examples of erotic movies — explicit sex but also a legitimate plot. I haven't actually seen them; I only know about them from a textbook. I'm going to ask a professor if she knows any way to obtain those movies."
Bianca smirked, "I suggested Jonathan find a virgin, fuck her on the new pool table while CeCi records, and not use the corny lines!"
"I'd pay to watch that!" Deanna declared.
"What do you say, Jonathan?" CeCi asked with a smirk.
"That what I think doesn't matter given the chance that you'll find a virgin willing to lose her virginity on camera is vanishingly small if not nonexistent."
"Assuming I could?" CeCi asked.
I chuckled, "I'll give you an actual answer if you find an actual willing virgin. Let's stick with the photo shoot for now."
We finished breakfast, and CeCi and Deanna cleaned up while I sat with Bianca and held Sofía.
"She seems content today."
"She is. Don't worry about her being occasionally fussy; «Abuela» says it's normal. She says babies get in moods the same as adults, and the only way they have to express themselves is to cry."
When Sofía fell asleep, I put her in her crib, then CeCi and I began the photo shoot. I dressed in one of the outfits Beth had helped me pick out, and after CeCi shot a complete roll of film in various poses, I changed to the other outfit.
"It's cloudy today, and I want the outdoor shots in sunlight, so we'll have to wait on those," she said. "Hopefully, next weekend will be sunny."
"Next weekend, I'm modeling for Britney on Saturday morning, and Violet and I have Cubs tickets for Sunday, but we should be able to find some time."
"Great!"
May 21, 1984, Chicago, Illinois
On Monday morning, when I got out of bed after the alarm rang, CeCi went to her room to go back to sleep. I put on my robe and went downstairs to have breakfast. I started a pot of coffee in the Mr. Coffee, then filled a bowl with Rice Krispies. I sliced a banana into the bowl, then added milk and began eating.
"Good morning," Chelsea said, coming into the condo.
"Good morning," I replied. "There's coffee."
"Thanks. I'm going to check on Sofía, and I'll be right back."
She went upstairs and returned with my daughter.
"She was awake; Bianca is finishing her shower."
I walked over and kissed Sofía on the forehead, then finished my cereal. Bianca came downstairs as I went upstairs to dress, and fifteen minutes later, I was at my desk.
It was a fairly quiet day, with the only major news, if you could call it that, was the Edmonton Oilers winning the Stanley Cup over the weekend. That did remind me that I'd need to choose my tickets for the Bears, as well as the Hawks, so after lunch, I checked the schedules and then spoke to Julie to confirm my game choices.
At the end of the workday, Violet and I left together and decided against a cab in favor of a leisurely thirty-minute walk to Smith & Wollensky, as our reservations were for 5:45pm.
"I reserved tickets for a Bears pre-season game against the Bengals, plus a regular season game against the Raiders. If the Bears have a home playoff game, I'll have a chance at tickets, though I'm fairly low on the list. And speaking of playoffs, I'll be able to get Sox playoff tickets if they make it."
"Not Cubs?"
"I could get them if such a thing actually existed! That said, they are 23–15, so who knows? Anyway, for the Hawks, Red Wings, and Blues before the end of the year; Penguins, Capitals, and Leafs next year. And two rounds of playoff tickets."
"That's a good mix of teams," Violet observed. "What's the plan for Sunday?"
"How about we meet at the North Avenue and Clybourn L station at 11:00am? That seems easiest."
"That sounds good. We should do something after the game. Maybe dinner?"
"Asking for a second date when we've only just started the first?" I teased.
"Nancy suggested that we've been dating since the 'gum incident', but I objected because there was no way that was true once you and Keiko were engaged."
"I actually don't completely disagree with Nancy's observation. We absolutely were spending time together, really getting to know each other, and developing our relationship. The divergence would be that it wasn't romantic, nor was it physical except for hugs and kisses on the cheek. And I don't feel I was doing anything inappropriate, nor was I hiding it from Keiko."
"I think you're right because I wasn't even able to kiss you properly. And you know I spent time with Keiko, and I would never have done anything to violate her trust any more than you would have. But we did, and do, have a special relationship."
"That's true."
"And that's why you're being so cautious, right? Because you don't want to mess things up?"
"Yes, though it's more complicated."
"Because of my past, right?" Violet asked.
"Yes. But for me, it's about ensuring you feel safe and comfortable. I can't decide what's right for you; only you can do that. What both of us need to do is understand what we want and what the other person can offer."
"We already agreed to have a baby together!"
I chuckled, "True."
"And that means we have to ... make love."
"Yes, and the fact that you can say it out loud is a big step."
"I could say what Lily said!" Violet teased.
"You are you; Lily is Lily."
"When I saw her at the housewarming, she asked if we had. I said 'not yet'. Can I ask you something?"
"Yes."
"If we make love, are you still going to have sex with other girls?"
I found it interesting that she considered that we would 'make love' while I would 'have sex' with other girls. To me, that was a bit of insight into her thinking.
"Remember what I said about communicating what we want? You have to tell me what you want and what you can accept. If I can't meet your conditions, so to speak, then we can't."
"You're obviously OK with having a baby without being married, or else Sofía wouldn't be here!"
"Obviously, though not all babies are planned! She was, but Heather wasn't. Nor was I, for that matter."
"I know I shouldn't ask this because it's very personal, and you can refuse to answer, but you're sleeping with the girls who live with you, right?"
I knew Bianca, Deanna, and CeCi wouldn't be bothered by me admitting to my relationship with them, and if Violet was going to be part of my life in the way we discussed, I felt she had a right to know.
"Yes," I said. "Bianca prefers girls, but she likes being with me, too. CeCi intends to sleep with me until she moves to Los Angeles after she graduates. Deanna, if she had her way, would be my lover for life."
"Are they the only girls?"
"No."
"Seriously?" Violet said, though I could see in her face that she wasn't angry. "Three isn't enough?"
"Apparently not," I replied. "But I was perfectly faithful to Keiko. And it was a few months before I was with Deanna again, then later, CeCi, and after them, other girls. Bianca is still recovering from having Sofía, but you know she prefers girls. She and I sleep together several nights a week, but it's just sleeping."
"Do you have another secretary I don't know about who keeps track of them for you? Or one of those 'Take A Number, Please' machines like at the deli counter?"
"It's not that many. Well, from my perspective, at least."
"And you don't want to stop, do you?"
"As I said the other day, I'm not sure what I want. You know I miss Keiko, and I can't give my heart to anyone that way at this point. Down the road? Maybe, but I can't promise right now. As for sex, you know my view."
"That it's OK to do it just for fun, so long as both people agree."
"That's the gist of it," I said. "You made a distinction between making love and having sex earlier. Was that intentional?"
Violet thought or a moment before she answered.
"Yes, because I love you, but I think Deanna loves you, and I know Bianca loves you."
"They do."
"Then I guess you make love with them, too."
"I'd say that's accurate."
"If we have a baby, how would that work?"
"The usual way," I replied with a grin. "Sending the appropriate signal to the stork!"
Violet laughed, "I'm not totally clueless, you goofball! I mean, where would we live?"
"Unless you're planning for nine months from now, once CeCi moves out, we'll have plenty of room. I'd prefer raising my kids together."
"But I wouldn't sleep in your room?"
"That's a question for the day we decide we're going to make a baby. Right now, I can't look that far into the future with any certainty. All I know is I want you to be part of my life, and I hope you want the same thing."
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