Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 43: All You Have to Do is Play the Game
Fiction Sex Story: Chapter 43: All You Have to Do is Play the Game - 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
"Hi!" Allyson exclaimed when I arrived at her house at 1:30pm on Saturday.
"Hi!"
"Come in!"
She invited me into the house, where I slipped off my shoes, then followed her into the great room.
"Nobody else is here?"
"They're arriving at 2:00pm. I wanted to make sure you were cool with the games. If not, we can agree on any changes."
"What about the girls agreeing?"
"I gave broad outlines and made it clear what was likely to happen if they played."
I chuckled, "Likely?"
"Well, Paula was completely frustrated by the randomness of the bottle!"
"True, though she did finally get what she wanted after Lucy felt she had teased her sufficiently!"
"That was hilarious. It's just so sad what happened to Paula."
"It is. So, what's the plan?"
"I invited four girls, and verified they're all on the Pill. All of them are recently graduated from High School, so they're all eighteen."
They met my minimum age, and I trusted Alysson that they were all sufficiently mature to participate.
"They're about three years younger than you are," I observed. "How do you know them?"
"They're all little sisters of friends who are friends with each other. One of them — Desirée, is Lucy's little sister."
"I think I know how THAT came about!"
Allyson smiled and nodded, "Lucy, of course. Do you get the connection?"
"Connection?" I asked.
"Names?"
"No," I replied.
"Desi Arnaz was Lucile Ball's husband and played Ricky Ricardo on I Love Lucy. Desirée because of Desi Arnaz and the production company he ran with Lucile Ball — Desilu Productions."
"Their parents are weird."
"I know, right? The second girl is Claudia, the little sister of a guy I date off and on. The third is Isabella, Claudia's best friend. The fourth is Dewi, who is Desirée's best friend. I confirmed all four are on the Pill, as I said."
"So, what's the plan?"
"We'll start the same way we did with strip Spin the Bottle, with the same basic rules we used before. Whoever the bottle points to gets to make out with you for a minute, then removes one piece of clothing. If the bottle points to you, the girl gets to make out with you, and you remove a piece of clothing. If the bottle points to the spinner, they have to take off two pieces of clothing and don't get to make out.
"Each girl will receive three poker chips — white, red, and blue. Once she's naked, she's eligible to turn in a chip when the bottle points to her. The white chip is for giving a blowjob; the red chip is for having her pussy eaten until she comes; the blue chip is for fucking.
"She can only use the white or blue chips if you're already naked, and she has to turn in either the white or red first, before the blue chip. After using either the red or white chip, she can use the ones she has left, however she sees fit, again, with the caveat that you have to be naked for white or blue. Nobody has to turn in any of their chips; they can just make out if they prefer."
"Five girls turning in all their chips would be ten times!" I chuckled. "I'm not Superman!"
"Once you've cum five times, we'll take a dinner break and use the hot tub. I figure two hours will be enough, if experience is any guide. And ten would be the most, assuming all of us cash in our white and blue chips, which is no guarantee. If you run out of gas, so to speak, whoever has a chip left can collect in the morning."
"I have to leave here no later than 10:00am, but that would work."
"Good. My plan is that we start with an icebreaker, rather than just going right into the game. We'll sit together, and everyone will introduce themselves and tell their major. For you, obviously, you tell about your job. I have some questions to ask after that, too. I figure twenty to thirty minutes, then we can start the game."
"One more question — what happens when I'm naked and the bottle points to me, rather than a girl? I don't have chips to turn in."
"Hmm. I think having her spin again makes the most sense."
"Sounds good to me. Where are we playing?"
"My bedroom; there's enough space, and there's a bed and a loveseat, if you remember."
"I was more focused on the occupant than the interior design!"
Allyson laughed, "I would hope so! Unless it was MY interior design!"
"I did very much enjoy that! And I'll enjoy it again!"
"Yes, you will! While we have time, I want to ask about Ellie. She really messed with you, didn't she?"
"It was more the intent of what she was doing, as well as the constant escalation. Those actually dovetailed because it appears her goal was to find a way to upset Keiko enough that she wouldn't accept my proposal. That made me a bit wary when you made your request, and I honestly considered saying 'no'. I decided I could do this because you never did anything wrong, and quite a bit of good came out of those parties, especially Bianca, which led directly to Sofía.
"Then there are Deanna and CeCi, not to mention Shelly and Sally, though Shelly is married and Sally has a steady boyfriend. If we follow the thread, Phoebe, despite the problems, led to Deanna, who led to the girls at the School of the Art Institute, who led me to meet people at Lehman Brothers and Bank of New York, and to gain capital for my fund."
Allyson smirked, "So, in the end, it's all about money!"
I chuckled, "I see how you could make that connection, but it really is about people, as I said, especially Bianca, Deanna, and CeCi."
"Deanna and CeCi are because of the waitress at Ed Debevic's when you were there with Phoebe, right?"
"Yes. That was Sophie, who ultimately introduced me to Deanna."
"Phoebe married in May, and she's due next month."
"Given none of my grandfather's grandkids or great-grandkids was conceived when their parents were married, that's par for the course in my extended family!"
Allyson laughed softly, "Given his religious views, that must drive him to distraction."
"I'd say, though my grandmother seems willing to overlook the indiscretion, as it were. She actually came to see Sofía, though I don't believe my grandfather knows about it."
"I've run into people like that. I was tempted to invite a girl like that to that first party, but I think that would have turned out very badly."
"I'd pretty much bet on it, unless she was ready to throw off the shackles."
The doorbell rang, and Allyson excused herself to answer it. She returned almost right away with two pretty girls, one with long red hair who had to be Lucy's sister Desirée, and one with long black hair and features I felt were Southeast Asian, but couldn't place.
"Jonathan, meet Desirée and Dewi," Allyson said. "Desirée, Dewi, my friend Jonathan."
We all greeted each other just as the doorbell rang. Allyson went to answer it and returned with the other two girls — a blonde and a brunette.
"Jonathan, meet Isabella and Clauda; Claudia and Isabella, my friend Jonathan."
With her head, Allyson had indicated Isabella was the blonde and Claudia the brunette.
"Let me get everyone drinks," Allyson said. "What do you all want?"
We answered, and she and Desirée went to the kitchen and returned a minute later with six bottles of pop. Allyson suggested we all sit, which we did. I took an easy chair, and the girls sat on a sofa and a loveseat.
"We'll go around the room," Allyson said. "Say your name, your college, and your major. I'll go first. Allyson, I'm at Loyola, and I'm pre-med."
Everyone gave their names and majors. Desirée would attend UofI in Champaign and would major in computers, while Dewi was heading to Purdue to study chemistry. I, of course, was working full-time and enrolled part-time at Circle. Isabella would be at UofC to study economics, and Claudia would major in physics at Stanford.
"Next, say your favorite sport, your hobby or favorite activity, and the coolest place you've visited. For me, it's baseball, traveling, and Mallorca."
We went around the room again, with Desirée saying she liked both watching and playing tennis, and that the coolest place she had visited was Paris. For Dewi, her favorite sport was cricket; she enjoyed playing the keyboard, and her coolest trip had been to Sydney, Australia.
"Mind if I ask where your family is from?" I inquired when it was my turn.
"Jakarta, Indonesia," Dewi replied. "My parents moved here right before I was born."
I nodded and stated that I was a baseball fan, that I enjoyed modeling at the School of the Art Institute, and that I hadn't really been anywhere I would call 'cool' except perhaps Boca Raton, Florida. For Isabella, her favorite sport was football; she was an avid reader, and her coolest trip had been to Rome. Finally, Claudia said she was a soccer fan, practiced Taekwondo, and her coolest destination had been Buenos Aires.
"Next, your dream date," Allyson said. "Mine is Richard Gere."
For Desirée, it was John Travolta, and for Dewi, it was Tom Cruise. I could choose from several, and I considered Phoebe Cates, Jaclyn Smith, and Lea Thompson before I gave my answer.
"Jan Smithers," I said. "If you don't know, she was Bailey on WKRP in Cincinnati."
For Isabella, it was Richard Gere, and finally, for Claudia, it was David Bowie.
"Before we begin, I want to go over the rules one more time, so everyone understands."
She explained the rules, as well as the planned break for dinner and the hot tub, and the contingency if physiology prevented completing the game.
"Just so we're clear," Allyson said, "you do not have to turn in a chip; you can just make out if you don't want to do more. No pressure, OK?"
All the girls agreed.
"Remember, once you turn in all your chips, you sit out, so the other girls have a chance, and we go until the break. After the break, we go until nobody has a chip, or nobody wants to turn one in. Cool?"
Again, all the girls agreed.
"Then let's go upstairs!" Allyson exclaimed. "I have the bottle, a ceramic plate, and the chips. There's a very convenient, very comfortable bed in my room!"
All the girls laughed, and we made our way up to Allyson's spacious room, where the plate and bottle were on the floor. It was more comfortable than her dorm room by far, and the bed was bigger. I was very curious to see which of the girls would turn in all their chips, if any, because I understood it was possible none of them would, except for Allyson. Of course, if the party went the way the others had gone, all of them would!
"What happens if the randomness of the spin means Jonathan still has clothes after all the girls are naked?" Desirée asked.
Allyson considered, "I'll set a timer for twenty minutes. When it goes off, everyone takes off one piece of clothing. At that point, if he still has on any clothes, I'll set it for ten minutes, then five minutes. I doubt it will come to that, but you never know. Also, once the timer rings the first time, we'll switch to two minutes for making out, and obviously as much time as necessary for any chips you want to turn in."
All of the girls were dressed in polo shirts and jeans and were wearing socks. If I assumed they had bras and panties, that meant they'd have five 'hits' before they were naked. I was wearing my chinos, a polo shirt, socks, a belt, and briefs, so I had on an equal number of items.
A rough calculation said we'd spin the bottle about fifteen times in twenty minutes, allowing for a minute to make out after each spin. With a total of thirty items, the odds were that one or two of us would be naked before the timer went off, especially given the double whammy of spinning yourself. Once the timer rang, at least two-thirds of our clothes would be off, assuming girls who were naked didn't spin themselves and simply lose a turn, though that would mean no make-out minute.
"Who spins first?" Isabella asked.
"I say it should be Jonathan!" Claudia exclaimed.
All five girls agreed, so I spun, with the bottle landing on Allyson. Per the rules, she moved to my lap and put her arms around my neck. We shared a soft, sensual French kiss, and I gently cupped her breast through her shirt and bra. About a minute later, Desirée called 'time', and Allyson moved from my lap back to her spot.
Allyson promptly removed her polo, revealing a lacy blue bra.
"My toes might get cold," she smirked, causing all the girls to laugh.
That made me realize that all the girls shared similar builds — between 5'6" and 5'8", with slender or medium bodies, small to medium-sized breasts, and long hair. Isabella, who was to my left and was not quite tall enough to be called a 'willowy blonde', spun with the bottle pointing to me.
She moved to my lap, and I cupped her small breast while we shared a soft, sexy French kiss that tasted of cherry lip gloss. When Allyson called time, Isabella broke the kiss and moved her lips near my ear.
"I hope you really like cherries!" she whispered, squeezing her arms around me.
She got up quickly and moved back to her spot, and if I took her meaning correctly, she was a virgin and intended to turn in her blue chip. I smiled at her and nodded, then took off my belt.
"Well, THAT reveal was boring!" Claudia declared.
"All in good time," I replied with a smile.
It was Claudia's turn, and she spun herself, which caused the other girls to laugh.
"Serves you right!" Isabella teased.
Claudia stuck her tongue out at Isabella and removed her socks and polo, revealing a sexy black bra covering the largest breasts in the room, though they weren't big by any stretch of the imagination. Dewi spun next, and it landed on Isabella, who happily climbed into my lap for another sexy French kiss. As we kissed, I fondled her small breast through her polo and bra until time was called.
Once again, when she broke the kiss, she moved her lips close to my ear.
"I'm going to swallow every drop," she whispered.
One thing was clear, and that was Isabella had absolutely no qualms or reservations, and I was positive that, despite being a virgin, she was going to be a fantastic partner. That said, most of the virgins I'd been with had been great partners, with really the only exception being Nikki. Isabella moved back to her spot and removed her socks.
Next up was Desirée, who spun herself, which meant no kissing, but she had to remove two pieces of clothing. She chose her socks and polo, revealing a white lace bra.
Allyson had the final spin of the round, and it landed on Claudia, who happily climbed into my lap so we could share a searing French kiss while I gently cupped and squeezed her breasts. When Allyson called time, Claudia stood up, removed her jeans, and stood for a few seconds with her panties close to my face before sitting down.
It was my turn again, and when the bottle stopped, it was pointing to Dewi. She got up and came over to me, but instead of sitting, she took my hand and urged me to stand. I did, and she pressed her body against mine. We wrapped our arms around each other, and she squirmed in my arms as our tongues tangled. I moved both hands to her jean-covered butt cheeks, squeezed, and pulled her against me.
Dewi moaned softly, but our embrace had to end when Allyson called time. Dewi squeezed tightly, then moved back to her spot. We both sat down, and she removed her socks. Isabella spun, and the bottle once again pointed to Dewi, who immediately stood up.
I stood as well, and we embraced, then shared a very sexy kiss while she squirmed in my arms, giving me the strong impression she intended to turn in her blue chip as well. When Allyson called time, Dewi squeezed her arms, then returned to her spot. We both sat down, and she removed her polo, revealing a plain, light-purple bra.
Claudia spun, and when the bottle pointed back at her, she groaned.
"Seriously?!" she groused.
"I love it!" Isabella tittered.
Claudia rolled her eyes, stood up, and removed her bra. She let it drop to the floor, then quickly stripped off her panties. She tossed them aside and did a quick pirouette, showing off her sexy body with a neatly trimmed V of pubic hair. She sat back down, as she wasn't allowed to make out or turn in a chip when she spun herself.
Dewi spun Allyson, who moved to my lap for a sexy kiss, after which she removed her jeans, causing the other girls to laugh.
"Saving your socks for last, Ally?" Claudia asked.
"Hey, I was serious about my toes being cold!" Allyson smirked.
The girls all laughed, and it was clear that none of them believed her, though I could see it with the air conditioning on.
Desirée spun, and the bottle pointed to Dewi, and, as before, we stood and kissed, holding each other tight. When our time was up, Dewi returned to her spot and removed her jeans. I noticed a small wet spot on her panties, which didn't surprise me given the close contact we'd had while kissing.
Allyson took her turn. The bottle pointed to me, so after we kissed for a minute, I removed my socks.
"Boo!" Claudia groused good-naturedly.
"You do realize he has to take off three more pieces before we get to see the good stuff, right?" Isabella teased.