Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 31: Come See Me
Fiction Sex Story: Chapter 31: Come See Me - 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
August 5, 1984, Chicago, Illinois
The first thought that came to mind was what Kayleigh — a beautiful girl with black hair and green eyes, long legs, and modest breasts — would look like naked. I pushed that aside for the moment, in favor of my second thought, which was my statement to her the last time we had been sitting in the loft — that when she knew what she wanted and could tell me, then we could discuss it and decide what to do.
As I quickly analyzed the situation, I concluded there were two possible scenarios. Both started by going to bed with me, but what happened after that was an open question. If, for whatever reason, it didn't fulfill her expectations or her needs, she'd go to confession and then continue down the path she'd envisioned.
On the other hand, going to bed with me was a way to break the hold of the Church by breaking one of the cardinal rules. Having done that, she could, in effect, walk away from the pre-programmed life of a Catholic homemaker with a large family, and instead begin a legal career, which would, in all likelihood, lead her to a partnership at Hart-Lincoln at some point in the future.
"If you recall," I said, "the last time you made that suggestion, I proposed that we'd discuss what to do when you explained what you wanted. Do you remember?"
"Yes, of course."
"You presented an obvious dilemma, and a proposed way to determine which way you should go, though I'm not sure that's the best way to decide."
Kayleigh laughed softly, "Wow!"
"What?"
"You're usually extremely accurate, but in this case you missed it completely."
I thought for a second, then laughed.
"You didn't say that you hadn't decided, only that you were dealing with two diverging views of the future. I apologize, though I think the rest of my analysis is likely correct."
"I'd like to hear it," Kayleigh prompted.
"You've decided to go to Stanford with the ultimate goal of admission to the Illinois Bar so you can work for your grandfather. I suspect he offered that solution around the time you graduated from High School, if not before, but your view of the future at that time only included being a wife, a mom, and a faithful Catholic.
"The compromise, if you will, was that you'd become a paralegal and keep open the option of going to your grandfather's alma mater. You completed the paralegal program and went to work for Hart-Lincoln as your grandfather's paralegal about two years ago. Since then, you've tried to find Mr. Right, but haven't, for whatever reason. At the same time, your grandfather has been gently pushing you towards Stanford and encouraging you to consider an alternative future.
"You met me and were attracted to me, but I was married to Keiko, which precluded even getting to know me. After Keiko died, you and I saw each other again, and you encouraged me to get in touch, most likely because your grandfather spoke highly of me. We met, and even though the conversations didn't go the way you wanted, that was only because of completely incompatible views of the future.
"You've been struggling with your attraction to me, your goals for the future, your faith, and your general approach to life. When you were here the last time, you offered to go to bed with me, but neither of us was ready for that step because you were still confused about the future.
"Now, you've made your decision, and to do what your grandfather is encouraging you to do, you need to make a clean break with your past. Your proposed way of doing that is to violate one of the most important rules of the Catholic Church. Doing so will, in your mind, break the bond, so to speak, and free you to go to Stanford and complete a law degree. How did I do?"
"I'd say you got it completely right. Will you take me to bed?"
"Will you tell me what you expect to happen?"
"Is this where I say something silly about how sex works?"
I chuckled, "You could, but I'm fairly certain you know what I meant by that question."
"If I pursue a law degree, I'm going to be at Stanford for at least five years — some of my undergrad classes will transfer credit. Once I come back, I'm going to want to marry and have a family, but the pool of potential candidates will be larger, and who knows, I may meet him at Stanford, assuming he'd move to Chicago for me.
"You're not going to marry, and that is important to me, so that means we couldn't have a family together the way I want. That said, my grandfather believes you'll be an excellent mentor, and I'm sure we can find a way to work together in the future. Of course, if you changed your mind about marriage, I'd want to know."
"The answer to this question will have no bearing on what happens next — do you plan to continue going to church?"
"I don't think I can go as far as my grandfather has gone, so I probably will go, at least occasionally. I don't not believe, I'm just not as sure as I was a year ago."
"Another question that won't have more than a minor bearing on what we do next — birth control?"
"I started taking the Pill in May, so I was safe when I was here in June."
"I'm going to guess that was when you decided on your most likely way forward; In May, I mean."
"Yes."
"Last question — did you have a specific plan or some specific way you want this to go?"
"Taking into account what you said last time, I don't want to ... uhm ... screw; I want it to be tender, loving, and gentle."
"I can do that," I replied.
"Then take me to bed, please."
I stood up, took her hand, and we walked to my bedroom with Misty padding softly a pace behind us.
"Our cat is going to insist on coming into my bedroom," I said. "If I don't let her in, she'll scratch at the door."
"We have cats, so I understand. She won't bother me."
We entered the room, and once Misty walked in, I shut the door.
"Any last requests?" I asked with a silly smile.
Kayleigh laughed softly, "I don't think a cigarette is what you want to see in my mouth!"
"You're not wrong! That said, if it's not something you want to do because it's a taboo, that won't cause me to send you away."
"Before today, I'd have said it was gross, but I want to do it precisely because it's taboo. I'll wager you'll use your mouth on me?"
"Yes, and ... well, I don't plan to wash my face before I kiss you after doing that, just as I won't ask you to rinse your mouth before I kiss you after you use your mouth. Is that a problem?"
"You don't think it's gross?"
"No. The only limits are the ones you set. All you need to do is say 'no' or 'stop'. OK?"
"Yes."
I was positive, from her request, that taking things slowly was not just the right approach, it was the only reasonable approach. And, in my mind, that meant taking the bases one at a time. I remembered CeCi's Air Supply compact discs were in the changer, and felt that was a good choice for Kayleigh, as opposed to the usual deep-cut cool jazz radio station most of the girls preferred.
I stepped over to the stereo, turned it on, and then started the CD player in random mode, which would play random tracks from all five discs until it finished. I adjusted the volume, then walked back to Kayleigh. I took her hand and led her to the loveseat, where I sat down and had her sit in my lap.
"Why not the bed?" Kayleigh asked.
"You asked for it to be tender, loving, and gentle," I said. "This is where we start."
Kayleigh smiled and moved her head so she could touch her lips to mine, and I tasted cherry lip gloss. I gently pressed my tongue forward, parting Kayleigh's lips, and Kayleigh moaned softly as our tongues touched and began a slow dance.
We kissed for a few minutes before I moved my hand to cup her firm breast, though it was encased in a bra and covered by her polo shirt. When I rubbed my thumb over Kayleigh's nipple, she again moaned softly into my mouth. I very much wanted to get her hard nipple into my mouth, but I reminded myself to be patient and take things slowly.
After we kissed for a bit, I slid my hand down Kayleigh's side and along her leg to her knee. I let it rest there for a moment, then moved it towards her waist, my thumb tracing along the seam of her jeans until I came to the place where her legs joined. I gently rubbed my thumb over the seam that was covering her panties and clitoral hood, which caused Kayleigh to suck in her breath and break the kiss. Rather than kiss again, she sighed deeply and put her head on my shoulder.
"That feels good," she whispered a minute later.
"I'm glad," I said gently.
I continued moving my thumb in small circles, and about a minute later, there was a hitch in her breathing, she shivered, then moaned softly.
"No wonder they told us not to touch ourselves there," she said quietly.
I had heard from some of the other Catholic girls that the nuns called it 'self-abuse', which made zero sense to me, as it wasn't abusive to give yourself pleasure. The fact that Kayleigh had just had her first orgasm — a small one — at age twenty-two boggled the mind.
I moved my hand to Kayleigh's chin and gently lifted so we could continue kissing while I cupped her breast and rubbed her nipple with my thumb. After about five minutes, I broke the kiss.
"I want to take off your shirt," I said.
Kayleigh nodded and sat up. Only one of the three buttons of her polo shirt was buttoned, so I unbuttoned it, then gently pulled her shirt from her jeans. I lifted it up, and Kayleigh raised her arms so I could fully remove it, exposing a plain pink cotton bra that encased her breasts, as well as exposing her soft, but trim, torso.
We kissed for a few minutes before I moved my hand to the clasp of her bra and deftly unhooked it, then slid one strap down Kayleigh's arm. She moved her arm from around my neck, and I pushed the other strap down, allowing the bra to fall away from her gorgeous breasts, which were capped by hard pink nipples.
I carefully laid the bra on the arm of the loveseat with her polo shirt, then moved my hand to her exposed breast and cupped it in my palm. We kissed again, and I ran my thumb over Kayleigh's engorged nipple, once again causing her to moan softly into my mouth. After a minute or so, I broke our kiss and planted several kisses on Kayleigh's shoulder, then gently leaned her back and lowered my mouth to her breast.
When I took Kayleigh's nipple into my mouth, she gasped and moved her hand to the back of my head, gently stroking my hair. I moved my hand between her legs and began gently rubbing along the seam over her clit. It didn't take long before Kayleigh shuddered and moaned softly as she had another small orgasm.
"You make me feel so good," Kayleigh whispered.
I released her nipple and gave her a quick kiss.
"That's the entire point!" I declared.
I helped Kayleigh from my lap, stood up, and moved my hands to her waist. I unbuttoned her jeans, then drew down the zipper. I knelt down and pulled down her jeans, then helped her step out of them, exposing her pink cotton panties with a wet spot between her legs. I stood up and looked at Kayleigh, waiting to see what she would do. When she didn't move after about twenty seconds, I decided I needed to guide her.
"This is where you take off my shirt and shorts," I prompted.
Kayleigh was only about five inches shorter than me, so she had no problem pulling my T-shirt over my head, though I had to hold my arms at an angle. She put the T-shirt on top of her clothes, then carefully pulled down my shorts, exposing my briefs, showing a bulge the loose-fitting shorts had hidden. She put the shorts with the other clothes, and I pulled her tightly to me, crushing her breasts between us, her nipples pushing into my chest.
We began kissing, and I ran my hands over Kayleigh's back and butt, and after a minute or so, she copied my actions. When I pushed my hands past the elastic of her pink cotton panties and cupped her butt cheeks, Kayleigh did the same, and I pulled her groin firmly against mine.
A minute later, I broke the kiss and carefully pushed Kayleigh's panties down, over her butt, then moved my hands to her hips and slowly slid her panties down her legs, revealing a thatch of black pubic hair and plump labia, glistening with her juices. Kayleigh stepped out of her panties, and when I stood, she bit her lower lip, then carefully pulled my briefs forward, then down, releasing my raging erection. She knelt and helped me step out of my briefs, then stood before me.
"Third base?" I asked.
"You mean oral?"
I nodded, "Yes. It's up to you, but physiology means you should go first."
"Physiology?"
"About ten minutes between erections," I replied. "I'll use my mouth on you during that time, then we hit a home run."
"I, uhm, have no idea what to do."
I sat down on the loveseat and encouraged Kayleigh to kneel in front of me. When she did so, I took her hand and guided her to my rock-hard shaft.
"Just close your hand lightly and start stroking up and down," I said.
Kayleigh started to stroke me, tentatively at first, then a bit more forcefully.
"Next," I instructed, "kiss it, mostly the glans — the fleshy part at the top — but also along the shaft.
Kayleigh nodded, bit her lip once again, then kissed the tip of my dick with her full lips. After about a dozen kisses on my glans and shaft, I gave her the next guidance.
"Now, pretend it's soft-serve ice cream in a cone," I directed.
Kayleigh nodded and carefully touched her tongue to my glans, then carefully traced a circle around it. After that first tentative lick, she gave my glans and shaft a wonderful tongue bath.
"Now, like a popsicle, and continue stroking," I said.
"Uhm, how much comes out?"
"Maybe a tablespoon."
"And, er, you want me to ... swallow?" she asked quietly.
"Yes," I confirmed.
Kayleigh took a deep breath, parted her lips, touched them to my glans, and took me about an inch into her soft mouth. The pleasure was intense, enhanced by the sight of a woman giving her first blowjob. I watched intently as Kayleigh began to bob slowly, taking about half my length into her mouth while continuing to stroke me.
As pleasurable as it was, and as much as I wanted it to last a long time, I wasn't going to make Kayleigh work for it, and I didn't resist as my pleasure built. Even with that, it was about six minutes before I felt that irresistible pressure.
"I'm close," I said. "Just keep the glans in your mouth, swirl your tongue, and stroke."
She did as I requested, and a few seconds later, I groaned as the first spurt of cum jetted into Kayleigh's mouth. She coughed but didn't stop stroking, licking, and sucking, as several strong spurts were followed by a few weaker ones. I felt Kayleigh swallow after the last pulse, and when she released me, I helped her into my lap and French kissed her. Our tongues swirled, sharing the coating of cum that was on hers.
"I think you liked that," Kayleigh said when we broke the kiss.
"I liked it very much! Let's get into bed."
Kayleigh got up from my lap, and I stood, then led her over to my bed. I turned down the duvet, helped her in, then climbed in after her. We shared a soft kiss, then I shifted so I could kiss, lick, and suck her nipples, though I didn't spend too much time doing so, as I had a much more interesting place to use my tongue and lips.
I slowly kissed my way down Kayleigh's body to the thatch of soft, black pubic hair. She didn't trim it, which didn't surprise me, but it also wasn't 'overgrown' in the sense that it basically stopped where her labia joined. I rested my nose in her pubic hair for a moment, then planted a soft kiss on the inside of each thigh. Kayleigh shivered, and when I kissed her plump labia, she sucked in her breath. I pressed my tongue between them and flicked her clit.
"Oh!" she gasped.
I gently probed her opening, slowly pressing my tongue into her and coating it with her musky juices. I swirled my tongue a few times, then closed my mouth around the top of her labia, sucking gently on her clit as I teased it with my tongue. Kayleigh moaned almost continually, then, after about two minutes, groaned and shuddered as she had her third orgasm from either my fingers or mouth.
Over the next ten minutes, she had two more, at which point I was rock hard again, aching to be inside her. I moved up, my shaft resting on her mons, and we exchanged a French kiss, this time sharing her juices, just as we had shared mine. I broke the kiss and looked directly into Kayleigh's eyes.
"Ready?" I asked.
She bit her lip and nodded, so I shifted a bit, grasped my shaft, and rubbed my glans along her labia. When it was coated with her natural lubrication, I positioned it at her opening, then gently pushed my hips forward. My glans split Kayleigh's labia and slipped into her. Her eyes went wide, and she gasped at the first penetration, which was only about two inches. I pulled back and pressed forward slowly, this time going an inch further. Five more gentle thrusts, an inch at a time, resulted in me being buried in her snug tunnel.
"Wrap your legs around me and move with me," I said.
Kayleigh was breathing hard and answered with a nod as she moved her legs so they were around my thighs. I pulled back and then gently thrust forward. I did that twice more, and on the fourth thrust, Kayleigh raised her hips as I pushed into her, beginning our slow-motion lovemaking.
We French kissed, but Kayleigh was breathing too hard to hold each kiss for long. We continued moving, and about every dozen strokes I ground my pubic bone against her mons. As we continued to move, Kayleigh's breathing grew ragged, and suddenly her arms and legs tightened around me. She groaned loudly as her pussy spasmed around my shaft. I continued thrusting through the orgasm, and Kayleigh moved her legs to just below my butt and squirmed and wriggled as waves of pleasure crashed over her.
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