Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 55: Upstairs Before the Night's Too Old...
Fiction Sex Story: Chapter 55: Upstairs Before the Night's Too Old... - 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
September 27, 1984, Chicago, Illinois
"Chelsea is joining us for dinner," I said to Bianca.
"You mean she's coming to dinner and cumming after dinner!"
I chuckled, "Something like that."
"Let me call «Abuela». Nicole, Sofía, and I can have dinner at her house. That way, you'll have the condo to yourself because CeCi and Deanna are out."
"I'd appreciate that, thanks."
"So will «Abuela»! She's already planning Sofía's «quince»!"
I laughed, "Why am I not surprised? She should get together with Beth's mom and grandmother! They're driving Beth nuts with wedding planning."
"I think it's all ethnic grandmothers and mothers. Anglos don't seem to be as intense about it. I mean, sure, some are, but it's not universal, like with ethnic ones. Changing subjects, did you tell Ellie?"
"Yes. She didn't even let me finish the sentence before she said 'yes'."
"I bet!"
"She did playfully suggest a condition for acceptance."
"Of course she did! And?"
"I told her I'd think about it. I didn't want to get into a discussion of why in the office."
"Probably wise. Would you?"
"It's an interesting question, but I'm leaning against," I replied. "I mean, there's no way I'm going to have any kind of relationship with her beyond work, mentoring, and friendship, and it's not as if I'm lacking in female companionship!"
"You did note that girls are dropping out."
I chuckled, "Oh, woe is me, I only have Violet, Deanna, CeCi, Nicole, and you to fuck! I may as well kill myself now!"
Bianca laughed, "You forgot Erin, Jennifer, and Kayleigh, as well as your once-a-month with Allyson!"
And Marlena, though Bianca didn't know about that, though I was certain she suspected it, despite my avoiding directly answering the question she'd asked about that.
"True," I agreed. "Though after January, it all depends on Violet."
"Are you really going to let her decide who you can sleep with?"
"I absolutely let Keiko decide, and I don't see this as categorically different; we just won't have the government paperwork, which Violet doesn't care about. She put off even discussing it until after Saint Martin and Hawai´i because she doesn't feel I should go back on my word to the girls. Honestly, beyond wanting to move in and have a baby, she hasn't expressly said anything one way or the other."
"What's your ideal situation?" Bianca asked as we got off the elevator at the Sky Lobby to change to the elevator that would take us to the 92nd floor.
"Ideal? I honestly can't say right at the moment. I want to be happy. I want Violet to be happy. I want Deanna, CeCi, and you to be happy. I want Sofía to be happy. Finding the right balance will be tricky. Maybe it's in stages? I have time to think about it before Violet and I discuss the future. We also have the challenge of not wanting to reveal our relationship to anyone at Spurgeon beyond you and Jack."
"That's a serious challenge unless you can leave Spurgeon soon."
"I know. It's one of the things Violet and I will discuss in January."
We reached the condo and greeted Jessica. She left a few minutes later, and Bianca made the call to «Abuela», then let Nicole know the plans. Once they left, I changed into comfortable clothes, then started making dinner. I opted for grilled chicken, corn on the cob, coleslaw, and dinner rolls, and timed everything so it would be ready at 6:05pm.
Chelsea arrived just before 6:00pm, letting herself in with her key. She was carrying a bag, which surprised me, but I didn't say anything.
"Hi," she said demurely.
"Hi," I replied. "Dinner will be ready in about six minutes."
"You cooked?"
"Yes," I replied. "I have many talents, and one of them is being a halfway decent cook."
"The only thing my dad does is grill. I'm not sure he knows how to turn on the stove."
"I hope you're joking about that last bit, but I know quite a few guys who only grill and don't cook. I think it's pretty common for people our parents' ages, but most of the younger guys I know cook."
"It's considered women's work."
"Right, because the greatest chefs in the world are all women, not men!"
"That's, uhm, different."
"I disagree. What else is women's work in your mind?"
"Cleaning, washing dishes, laundry, taking care of the kids, grocery shopping, you know, all the stuff a wife does."
"I do all of those things, including changing Sofía's diapers, though we have a cleaning service for the condo. Honestly, what you're describing is a servant, not a partner."
"That's ... er ... never mind."
"God's plan?" I asked.
"Yes," she admitted.
"Men run your church, and men wrote the Bible, right?"
"Inspired by God, but yes to both."
"Shockingly, a bunch of guys wrote a book that gives them permission to treat women like servants, or worse, like property, and a church run by guys is happy to follow the instructions in the book."
"Property?"
"In your marriage service, does it say, 'Who gives this woman to be married?'. And it's your dad, or perhaps your uncle or grandfather, or brother, if your dad is deceased?"
"Uhm, yeah."
"If your dad can give you to your husband, then you must be his property. Sofía is not my property, and when she marries, I won't 'give her away' because it'll be her decision and her agreement with the guy. I'm pretty sure your Bible tells you to obey your husband, right?"
"Yes."
"So you have to do whatever he says?"
"I guess."
The timer rang, indicating dinner was ready, so I quickly moved everything to the table, and we sat down.
"You don't say grace, do you?" she asked.
"No, because I don't make it a habit of talking to imaginary sky beings, nor am I interested in thanking some mythical being for the food I purchased with money I earned and which I prepared and served."
"Why are you being this way?"
"What way? Honest about what I believe? If you can express your beliefs, I can express mine. For now, let's eat, and we can talk while we're resting."
"Resting?"
"Resting. You'll see. Let's eat."
I was fairly certain she said grace silently, but I wasn't going to make a further point of it, and we both began eating.
"This is very good," Chelsea said.
"Thanks. As I said, one of my many talents."
"What do you actually do at work?" she asked.
"Mostly I read the news, company reports, economic reports, and those kinds of things, and perform analysis to figure out the best investments. I also spend time trying to find new investors and talking to the current ones to ensure they feel well taken care of."
"Where is everyone else?"
"They all had things to do this evening, which is another reason I felt it was better if you came back now. Can I ask you a personal question?"
"I guess. What?"
"From everything I hear, girls in churches like yours are almost always married by the time they're twenty-two, if not sooner. You're twenty-three, right?"
"Twenty-four last week."
"Happy belated birthday. I'd at least expect you to be engaged. Why not?"
"I don't know."
"Have you been on a date?"
"Not like you mean; I only went out with the Youth Group in High School, and now I go out with the Young Adult group, which is people under twenty-five, married or single."
"There were no guys you liked?"
"Not really, no."
"Let's try a different approach — why do you like me?"
"I'm, uhm, not sure."
"Actually, I think you know, you're just afraid to say it."
"I ... I ... uh ... uhm ... want to be with you," she said, blushing. "I ... uhm ... never felt that way about any other guy."
"Even though I can't marry you or even be your boyfriend."
"Yes," Chelsea admitted, blushing even deeper red.
"That's what you want to do with me; the question is 'Why?'. What's different about me?"
She didn't answer right away, so I simply continued eating, waiting to see what she might say. I was certain the silence was uncomfortable for her, and I could tell she was struggling to find the right answer. I had some suspicions, but I really wanted her to answer unprompted.
"You're ... strong and confident," she finally said. "The guys at church mostly aren't. Or if they are, they're ... controlling."
"That should tell you something," I said. "It also confirms what I said about your church. Guys who feel a need to control others are actually weak. Do you think any of them could successfully defend their beliefs with me?"
"No," she admitted. "I'm not even sure my pastor could."
"Think about that," I said firmly.
"But I'm sure God exists!" she protested.
"I will, for the sake of the immediate discussion, concede the point. If that is the case, then perhaps the problem is not your god so much as the men telling you what to do and what to think."
"But we follow the Bible."
"Then I'm going to repeat what I said — 'If you end up with a boring, miserable life because you listened to your mom, your dad, your teacher, your priest, or some guy on television telling you how to do your shit, then you deserve it'."
We finished our meal, and after I put the dishes in the dishwasher, I washed the skillets and utensils. I had considered not doing that, but I wanted to give Chelsea time to reconsider. As I put the last utensil away, I felt I had to ask her one more time if she really wanted to go through with it.
"You have to be sure about this," I said. "There's no going back, and you can't undo it. Are you sure?"
"Yes," Chelsea said, her voice shaking, which I attributed to nerves.
I nodded, took her hand, and led her up to my room, with Misty padding behind us. The three of us went into my room, and I closed and locked the door.
"Your cat?" Chelsea asked.
"She'll scratch at the door if I don't allow her in. Don't mind her. Let's get undressed."
"With all the lights on?" she asked, a hitch in her voice.
"And no covers! I want to see you naked and watch in the mirror, and I want you to do that, too. Would you take off your clothes for me?"
Chelsea bit her lower lip but then began unbuttoning her polo shirt. Her hands trembled, but she managed the three buttons, then slowly pulled the shirt over her head, revealing a plain white bra and a flat stomach. She folded her shirt and put it on the loveseat, and I wondered what she would do next.
I was surprised when she reached around and unhooked her bra, then pushed the straps from her shoulders. She allowed her bra to fall free, catching on her elbows, and I smiled appreciatively at her gorgeous breasts, which were about the size of a half grapefruit, firm, and capped by hard, pink nipples. I very much looked forward to getting them into my mouth.
Chelsea's hands were still trembling when she unbuckled the thin brown belt that held up her jeans. She unbuttoned her jeans and pulled down the zipper, revealing plain white cotton panties, matching her bra. When she pushed her jeans down, I saw a small wet spot just above where they disappeared between her thighs. She stepped out of her jeans, folded them, and put them on the loveseat with her other clothes.
She sat down on the edge of the bed, removed her white ankle socks, then stood up. She put the ankle socks on the loveseat, then hooked her fingers in her panties. She took a deep breath, let it out, then slowly drew down her panties, first revealing wispy blonde pubic hair, then plump labia, glistening with her juices, which I longed to taste.
I made a point of looking her up and down, her long, blonde hair draped over her shoulders and her gorgeous body on full display, then moved my hands to the buttons of my polo shirt.
"My turn," I said.
I didn't rush, but I also didn't dawdle, and Chelsea watched intently while I quickly stripped down to my briefs. I put my clothes on top of Chelsea's, as Misty was stretched out on half the loveseat. When I slipped off my briefs, Chelsea's eyes went wide, and she gasped as my erection sprang free.
"Th ... th ... that will go inside me?" she asked nervously.
"It will fit perfectly," I said. "But first, we're going to do what I said."
"In my mouth?" she asked, her eyes still wide.
"Yes, before that, your first kiss."
I held out my arms, and Chelsea stepped close, but not close enough for our bodies to touch. I took a step to close the gap and wrapped my arms around her, pulling her naked body tightly against mine. She mimicked me and turned her face up for her first kiss. I touched my lips to hers, then carefully pushed my tongue forward, pressing the tip against her lips. Chelsea parted her lips, and when my tongue touched hers, she moaned deeply.
Chelsea quickly got the hang of French kissing, and we kissed for a few minutes before I broke the kiss and released her from my arms. I pulled down the light Summer comforter and top sheet, propped pillows against the wall, then climbed into the bed. I propped myself against the pillows, then patted the mattress next to me. Chelsea climbed in and moved close enough for our shoulders and hips to touch.
"Start with a few kisses, then treat it like soft-serve ice cream — licking and using your lips. Do that for a minute or two, then treat it like a popsicle, just don't take it too far into your mouth. When you do that, wrap one hand around the shaft and gently stroke up and down while swirling your tongue, sucking, and moving your head up and down, but be careful with your teeth. When I cum — shoot my seed — keep going and swallow it."
"Swallow it?" she asked skeptically.
"Yes. Then we'll share a kiss like the one we just had."
"You're sure?" she asked tentatively.
"Positive."
Chelsea moved to kneel next to me, took a deep breath, then lowered her head and planted a single soft kiss on my glans. A second and third followed, then she kissed along my shaft to the base and back to the tip. I felt her lips part, and then the soft, wet warmth of her tongue on my glans. The first licks were tentative, then she gently grasped me and held me upright and began doing as I'd asked, running her tongue over my glans and the upper part of my shaft.
I watched Chelsea as she pleasured me with her tongue alone for several minutes before she parted her lips and took the tip of my glans into her mouth. She sucked gently and wiggled her tongue, then took my entire glans into her mouth. She continued sucking and sliding her tongue around, then began gently stroking me.
For a girl who had never so much as kissed before, she was doing a great job, though having my glans in any girl's mouth was erotic, no matter how experienced she was. Watching her do it enhanced the eroticism and the pleasure. Chelsea began bobbing slowly, taking about a quarter of my shaft into her mouth, swirling her tongue, and sucking gently.
Over the next few minutes, Chelsea bobbed, sucked, stroked, and swirled her tongue, taking me about halfway into her mouth. The pleasure slowly built, turning into pressure, until it led to the inevitable conclusion. I twitched, then groaned as the first spurt of cum blasted into Chelsea's mouth. She choked and coughed and released me. The second spurt hit her lips, and the third her nose, but then she took me back into her mouth and sucked and swirled her tongue as she pumped the remaining spurts of cum from my balls into her mouth.
"Come kiss me," I said after the last spurt.
"But..." she protested.
I took her hand and tugged gently, and she moved up so we could kiss. She touched her cum-covered lips to mine. They parted, and our tongues met, and we exchanged a soft, sexy French kiss. I moved my hand to Chelsea's breast and cupped it gently in my palm, then strummed my thumb over her nipple. She moaned, and the intensity of the kiss deepened.
After a minute, I broke the kiss and gently maneuvered Chelsea onto her back with her head on the pillows. I turned and kissed Chelsea's nose, which still had a bit of my cum on it, then her lips, and then her neck. I scooted down and lowered my mouth to take one of her bright pink nipples into my mouth. Chelsea moaned as I gently sucked and teased her nipple with my tongue, and teased the nipple of her other breast with my thumb.
I spent about two minutes before switching my mouth to her other nipple, and after a short time, I released it and began kissing my way down her breastbone. I trailed kisses across her stomach and mons, then moved between Chelsea's legs and slipped my arms under them. I planted a single kiss on her clitoral hood, then raised my head and saw Chelsea had her eyes closed.
"Open your eyes and watch in the mirrors," I said with a smile.
When I saw Chelsea open her eyes and look into the mirror, I lowered my head and planted several soft kisses on the inside of each of her thighs. My next kiss was on her labia, and I touched them with my tongue to get my first taste of her juices. They had a tangy, coppery flavor, and I wanted more, so I gently pressed my tongue between Chelsea's labia. She gasped and tensed, then squeaked when I touched her clit with the tip of my tongue.
I lapped up her juices, then closed my mouth around the upper part of her labia and began sucking gently while I teased her clit with my tongue. Chelsea began moaning continuously and pushed her hips upward, increasing the pressure of my mouth on her pussy. Her breathing quickened, and she tensed, then shuddered and groaned.
"Wha ... wha ... what was that?" she gasped.
I lifted my face from between her legs and smiled.
"An orgasm," I said with a smile. "The first of many."
There were two more before I was hard, and when the third had passed, I moved up next to her. I reached over to the nightstand and grabbed a condom packet and tore it open.
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