Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 44: Let Yourself Go!
Fiction Sex Story: Chapter 44: Let Yourself Go! - 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 25, 1984, Sugar Grove, Illinois
Food and slightly more than two hours of relaxation meant I was recharged and fully ready to go when we returned to Allyson's bedroom to restart the game. Allyson had been eliminated, and three girls still had their blue chips — Isabella, Claudia, and Dewi. In addition, Desirée had her white chip and Isabella, her red chip.
We all removed our clothes, including Allyson, which drew an eye roll and a smirk from me. I was positive Allyson was hoping for another chance, and I certainly wouldn't mind that, though, if I had to choose from all the girls, Isabella would be first and Dewi second, mainly because it was unlikely I'd ever see them again, though perhaps I might see Isabella, as she was going to be at UofC. I knew for sure I'd see Allyson, as Jeri's gathering was about two weeks away.
Because Allyson was out, it was my turn to spin, and the bottle landed on Isabella.
"If I use the blue chip, we can do anything, right?" Isabella asked.
"Yes," Allyson replied.
"Then I want Jonathan to lick me while I suck him, then take my virginity. After screwing until I have an orgasm, he'll lick me while I suck him, then screw me and cum in me. I can give up my red chip, too."
"If that's what you want, go for it!" Allyson declared.
Isabella spread her towel on the bed and climbed in. I got into bed next to her, and she turned to lean against me so she could put her lips to my ear.
"Make me cum once with your tongue, then I want to watch when you take my virginity," she whispered.
"OK," I agreed.
She kissed me, then turned and straddled my face. I began kissing Isabella's labia, and she took my glans into her mouth and began sucking gently. I carefully pressed my tongue between Isabella's plump labia, getting my first taste of her tangy juices, but also discovering a ring of flesh I would have to push through when I entered her. I used the tip of my tongue to tease Isabella's clit, and she moaned, though it was muffled by my glans in her mouth.
I closed my mouth around the top of her labia and began sucking gently as I used my tongue to pleasure her. I was quickly rock hard, but it took a few minutes for me to get Isabella there with my mouth. When she came, she released me from her mouth and groaned loudly. After her orgasm passed, she moved off me and lay on the towel with her legs spread. I moved between them and considered the best way for her to watch while lying on the bed.
"If you prop yourself with pillows, and I lift your butt, you should be able to watch."
"Yeah," Isabella breathed.
She moved and propped herself so she was bent slightly at the waist. I lifted her up and scooted forward so that her butt was on my thighs. I rubbed my glans, already slick with her saliva, along her labia to coat it with her juices. I considered lube, but she was very wet, so I didn't think there would be a problem.
I saw movement, and the other four girls moved to either side of the bed so they could watch. When Isabella didn't object, I positioned myself at her entrance, rose up a bit, and pushed forward. My glans split her labia and came into contact with the ring of flesh. A bit of pressure allowed me to push through it, causing Isabella to grunt.
"So cool," she gasped. "Keep going!"
I continued pushing, gaining about three inches, then pulled back, so just my glans was in her. I looked down and saw red streaks along my shaft, making it obvious to the watching girls that Isabella had been a virgin. I pushed forward, pulled back, and pushed forward again until I was completely buried in Isabella's tight, silky pussy, enjoying the ripples along my shaft.
Isabella moved the pillows and lay back, and I repositioned myself on top of her. We kissed, she wrapped her arms and legs around me, and I began screwing her with slow, gentle strokes. After five strokes, Isabella began moving with me, and we kissed as we screwed, our tongues dancing together. After perhaps five minutes, Isabella began squeezing her internal muscles, providing delicious friction, and every dozen or so strokes, I ground against her mons for about thirty seconds, which led to Isabella's first orgasm.
Isabella tightened her arms and legs around me, wriggled and squirmed, then broke our kiss. She gasped, then groaned as her pussy spasmed around my shaft. I continued grinding against her until her orgasm passed, then slowly pulled back. After Isabella released her arms and legs, I pulled out and helped her move so we could sixty-nine. She took me into her mouth, and I pressed my tongue into her, tasting her virginal blood mixed with her juices.
It was easier to bring her off this time, and once she'd had her orgasm, I helped her move to straddle my waist and impale herself on me. She put her hands on my chest and rode me gently, grinding against me and bringing herself off twice, before she lifted off and lay on her back. I moved between her legs, entered her, and after she wrapped her arms and legs around me, we began screwing vigorously.
Isabella had another orgasm, and the ripples of her pussy walls and her squeezing her muscles were enough to take me over the edge. I groaned and ground against her as jets of cum spurted from my dick into her spasming pussy. After the last spurt, I began screwing her again, bringing her off once more. I stayed inside her, and we kissed softly for a minute.
"That," she gasped when we broke the kiss, "was perfect!"
We kissed again, then I gently pulled out, and the girls all applauded.
"Seriously?" I chuckled.
"That was a great show!" Desirée exclaimed. "It was so cool to watch!"
"I'm going to wash," I said.
I went to the en suite bathroom and used a wet washcloth to clean Isabella's blood and juices from my glans, shaft, and groin, then washed my face. I had just finished when Isabella came into the bathroom.
"If Allyson says it's OK, could I spend the night with you and do that again?"
"If it's OK with her, yes, though sex might have to wait for morning."
"That's OK with me!" she agreed.
"I do have to leave by 10:00am," I added.
"OK."
She gave me a kiss and got a clean washcloth while I went back to the bedroom. There were only three girls left now — Claudia, Dewi, and Desirée. Claudia spun, and the bottle pointed to Dewi, who handed Allyson a white chip. I moved to the loveseat, and Dewi sat in my lap. We kissed for a bit, then she moved to kneel before me and gave me a very sexy blowjob. When she released me, she sat in my lap once again, and we shared a soft French kiss.
Dewi spun, and the bottle pointed to her, so she lost her turn, though at this point it didn't much matter. Desirée spun herself, causing the girls to laugh. I spun, and it pointed to Desirée, who tossed her white chip to Allyson, then proceeded to give me a very, very sexy blowjob, though it took several minutes before I was hard. After I came, she moved to my lap, and we exchanged a searing French kiss. Unsurprisingly, she hadn't swallowed, but by this point in my life, I was totally used to it.
"You can go next, if you want, Claudia," Dewi said. "I'm OK with being last."
"OK by me," Claudia agreed.
"I'll need ten minutes or so," I said.
"We can sixty-nine until you're ready to go," Claudia suggested.
"We certainly could," I agreed.
She spread her towel on the bed, and we orally pleasured each other until I was hard, at which point Claudia moved off and lay on her back. I moved between her legs, rubbed my glans along her labia, then positioned myself at her entrance. As I began entering her, she pushed her hips up hard, taking me about halfway in. Not missing the cue, I pulled back and pushed forward forcefully as she thrust her hips upward. That began a very energetic fuck that resulted in four orgasms for Claudia before I came.
"Exhilarating!" she exclaimed when I pulled out and moved next to her.
Given I needed recovery time, we stayed in bed for about ten minutes, then I went to wash up. When I came back to the bedroom, Dewi was in the bed, lying on her towel. I climbed in and lay next to her, and she turned towards me so we could exchange a kiss. Given she hadn't suggested what we should do, I elected to follow my usual practice and gently pushed her to her back.
After a soft French kiss, I moved to suck and lick her nipples, then kissed my way down her body. I used my mouth to bring her off twice, then moved between her legs, lodging my glans against her labia. I rubbed it up and down a few times, then looked into Dewi's eyes for permission.
"Be very gentle," she requested. "And go slow."
I was positive that meant she was a virgin, and I decided it would probably be best to use lube, given she seemed a bit nervous. I reached over to the nightstand for the tube and liberally applied lube to my glans and shaft. I returned the tube to the nightstand, then positioned my glans against Dewi's labia. I lowered my head so we could exchange a French kiss and gently pushed my hips forward, causing my glans to split her labia and enter her tight tunnel.
Dewi broke the kiss and gasped, "Oh!"
Dewi panted and moaned as I gently pushed forward until I was fully inside her.
"Unreal," she gasped.
I waited for a minute to allow her to become accustomed to me, then pulled back until just my glans was in her extremely tight tunnel, then once again slowly pushed forward. Dewi moaned and panted, and I felt her hands on my butt, pulling me against her. I took the hint and ground against her for a bit, then pulled back, pushed forward, and ground again. Dewi spread her knees wide and put her heels on my thighs and began wriggling as I moved in and out of her.
After just nine of those strokes, Dewi had her first orgasm, followed by five more over the next fifteen minutes, before I had my own release. When the pulses ceased, I gently pulled out, moved down, and licked her to a final orgasm, before moving up to French kiss her. I lay next to her on my back, and she turned to snuggle close.
"Just ... wow..." she said, breathing hard.
We lay together for about ten minutes before I got up and went to the en suite bath to shower. I smiled when Isabella came in and asked if I needed help. I nodded, and she got into the shower with me. We soaped each other and rinsed off, then exchanged a soft kiss. We got out, dried off, dressed, and everyone went downstairs to have ice cream.
"I have to ask," Claudia said, "because my curiosity is killing me — was anyone a virgin besides Isabella?"
"Me," Dewi acknowledged.
"Me, too," Desirée admitted. "You obviously weren't, Claudia!"
"True, but my first and only time was at Prom in May. This was WAY better!"
I was actually slightly surprised by Desirée's admission, given her sister, but then I remembered Sophie and Alexa. We finished our ice cream, and Allyson suggested we use the hot tub before everyone went to bed. I hadn't realized they were all spending the night, but it made sense. After the hot tub, Allyson pulled me aside.
"I'm OK with Isabella's request, on one condition," she said with a smile.
"Yes, you may spend the night after Jeri's gathering. Deanna won't be upset."
"That obvious?" Allyson asked.
"We discussed our relationship at length, so, obvious enough, anyway."
"Use the guest room. I'm sleeping in my parents' bed, and the other girls are using my room and Clara's room."
"OK."
I went upstairs to the guest room, and a minute later, Isabella joined me. We quickly undressed and got into bed.
"Are you completely used up?" she asked.
"I think it would be better to wait until morning. If you want to set the alarm clock for 6:00am, we'll have a few hours to fool around, and I'll be completely recharged."
"OK," she agreed.
She set the alarm, turned out the light, and snuggled close.
"Can I ask something?"
"Sure."
"Could an economist be a research analyst where you work?"
"Yes. The most important skill is critical thinking. Besides that, the ability to read and digest large amounts of material and produce an analysis that guides traders. Having specific knowledge is helpful, but not required. You have four years before you graduate, six if you're going for your Master's, so there's plenty of time."
"I would like to see you again," she said.
"How much do you know about me?"
"Not much, really," Isabella said. "Just about your job, that you're single, and that you're originally from Ohio. Why?"
"My life is extremely complicated," I replied. "Let's sleep, and I'll explain in the morning after we fool around. OK?"
"Is there a problem?"
"No, but some of it is depressing, and I don't want to take away from you having great sex!"
Isabella laughed softly, "Nor do I!"
She kissed me, snuggled close, and we quickly fell asleep.
August 26, 1984, Greater Chicagoland, Illinois
When the alarm went off, Isabella and I fooled around for two hours, including a very sexy blowjob and a trio of very nice fucks; then, after a shower, I explained my complicated situation.
"That does kind of put a different spin on things," Isabella said. "It sounds as if a relationship is out of the question."
"I think it depends on what you mean by that," I said. "We can be friends, and if you truly are interested in working in the industry, I can mentor and guide you, and potentially hire you, though, as we discussed, that's six years down the road. Sex is, well, optional, I guess is the best way to put it."
"But you aren't looking for a girlfriend, are you?"
"Not in the sense I think you mean that word. Last night and this morning were, well, a casual fling because you agreed to play the game. Anything that happens now would still be casual, but we'd also be friends. If you're looking for a steady boyfriend, or a husband, I'm probably not the right guy."
"I'm nowhere near ready to marry!" Isabella declared. "I mean, sure, I really like you, and I really enjoyed what we did together, but marriage is WAY in the future. A steady boyfriend is fine, but that's it."
"As I've pointed out, that's a stage on the road to marriage," I replied. "Logically speaking, if you're exclusive, the obvious destination is marriage, unless you plan to break up."
"I suppose that's true, but it's different, right? I mean, you can break up."
"Sure, and you can break an engagement or get a divorce, too. But you don't plan those things."
"I hadn't considered that," Isabella replied. "I'm not quite sure what to say."
"Then don't say anything until you've had more time to think about it. What I can offer is friendship, mentoring, and, at least for the short-term, sex. It's up to you if you want to develop a friendship or a mentoring situation, or both, and if you want to have sex. Take some time, then call me, OK?"
"Yes."
We left the bedroom and went downstairs to join the others for breakfast. After we ate, I helped Allyson clean up, then bade everyone 'goodbye'. All five of the girls hugged me and kissed me, and Dewi pressed a folded note into my hand. I didn't look at it until I got into my car, where I unfolded it. She'd written, 'I really want to see you again, soon!' and given her phone number, as well as the main number of the dorm she'd be living in at Purdue.
She, of course, likely didn't know any more than Isabella had, and I wondered how she'd respond. I considered whether or not I should call her and was unsure about the wisdom of doing so. I could simply let it go, as the party had been a one-off casual thing, and none of the girls should have had any expectations beyond what Allyson had discussed with regard to what could happen at the party.
As I pulled out of the driveway, I considered the other dilemma I had — Chelsea. Both Erin and Bianca had made a good point about ignoring her, which, all things being equal, wasn't bad advice except for one thing — it was happening in my condo. As much as I agreed that I could ignore her, I didn't feel it was on me to accommodate her. The question was, what to do about it.
I was certain that Bianca, Deanna, CeCi, and Erin had all analyzed the situation correctly and that Chelsea did want to go to bed with me. As I saw it, the tension was going to continue to build until one of two things happened — she left for a new assignment, either voluntarily or involuntarily; or I set aside my concerns and took her to bed. I wasn't sure, and all I could do was wait and see if Chelsea kept her opinions to herself.
A more pressing matter was Nikki. I was absolutely certain I should end things with her, because she was very much focused on the idea of marriage and family, and living a sedate suburban life. The more I thought about it, the more I was convinced that her call saying she wanted to 'fuck' was a way to advance things.
Nikki was very different from Kayleigh in that regard. For Kayleigh, it was about a transition to a new and different stage of life; for Nikki, it was a way to try to bring me around to her thinking. That wasn't going to happen, even if the sex had been out of this world, which it hadn't. In that regard, she was more like Marcia and Leslie. The three of them had been barely adequate sex partners, for whom sex was more like what I'd heard from older married guys about their wives.
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