Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 49: Play the Game

Coming of Age Sex Story: Chapter 49: Play the Game - 'Climbing the Ladder' is the story of Jonathan Kane, a young man from rural Ohio, who begins a new life in Chicago in the mailroom of Spurgeon Capital. This is a story in the 'A Well-Lived Life' universe, and provides history and backstory for Spurgeon Capital, the Spurgeon family, the Glass family, the Lundgren family, Anala Subramani, Tom Quinn, and others from the 'A Well-Lived Life' series. The story stands on its own, and does not require reading any other stories in the universe.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Rags To Riches   Workplace  

February 19, 1982, Chicago, Illinois

Allyson took the L downtown and met me when I came out of the Hancock Building.

“We’re meeting the girls at 8:00pm at Loyola,” Allyson said after greeting me with a kiss.

“OK,” I said, taking her hand and leading her towards Bennigan’s, where we had agreed to have dinner.

“I want to clear what I have planned with you, and we can change it if anything is a problem.

“OK,” I said, electing to keep Bianca’s confidence.

“First, Sylvia has a date, so she won’t join us. Paula has two friends she wants to invite instead.”

“I take it you know these girls?”

“Yes. I’ve hung out with them a few times and been to parties with them. They’re basically the same as the other girls in that they don’t do drugs, don’t drink heavily, and are both on the Pill.”

“And they’re cool with what you’re proposing?”

“Yes. Paula and I both talked to them and they’re OK with the games.”

“Before you tell me about the games, can I ask you something?”

“Of course. What?”

“Why?”

“You mean why am I arranging this?”

“Yes.”

“Because it’s fun! Paula and Lucy practically begged me to arrange it, and I was sure you wouldn’t object. Also, I’m pretty sure at this point we both know that we’re just fuck buddies. If we were going to be a couple, one of us would have taken the next step, and neither of us has. So why not have as much fun as we can?”

“Sure,” I agreed, realizing almost immediately that I didn’t sound enthused.

“Nothing needs to change,” Allyson replied, “if that’s what you’re thinking. I still want you to spend the weekend at my house, come to my birthday party, and the Memorial Day party. And I want to fuck! Neither of us is looking for an exclusive relationship, so why not keep having fun?”

“Sorry,” I said. “I didn’t mean to sound like I was unhappy. I was just surprised at how direct you were.”

“Says the man who told me to just be direct and say what I’m thinking!”

“I’ll go throw myself in Lake Michigan for being an idiot!” I chuckled.

“It’s OK. And just so we’re completely open, I went on a date last night.”

Allyson’s comment about neither of us taking the next step rang true. And I was positive she was right in her assessment that we were just casual sex partners. Even if I wasn’t thinking that consciously, my behavior with other girls made it pretty obvious. I actually appreciated Allyson being direct, as I had with Bianca and Mary, and, I realized, Violet, though that was a different thing altogether.

“And you know Bianca has been staying over,” I said.

“But she took the next step, right? Something we never did.”

“Did she tell you?”

“She asked me first. She wanted to make sure we weren’t more serious than it seemed. All us girls are careful that way. May I give you my opinion?”

“Can I stop you?” I asked.

Allyson laughed, “Probably not! I think you and Bianca make a great couple, and I know she’s really into you in a way I’m not. Wait, that didn’t sound right. I’m into you, but she really likes you.”

“I got your drift,” I replied. “Bianca and I are kind of feeling our way forward, sort of like you and I were, though you and I kind of stopped.”

“Which is why I said what I said before! Shall I tell you about the games?”

She went on to describe what Bianca had told me, finishing right before we got to the restaurant.

“You OK with all of that?”

“Are you kidding?” I chuckled.

“You can stay tomorrow night, if you want. Or I can come to your place.”

“Let’s see if I’m still alive after your games! I might not be of much use!”

Allyson laughed, “I have faith!”

We had a nice dinner together, then took the L to Loyola. I dropped my bag in Allyson’s room, then we went to Paula’s room to let her know we had arrived. She introduced the new girls — Huifen Huang, who Paula said also went by Hannah, and Julianne Hodges. Huifen was a cute, small Chinese girl with long black hair, almost down to her waist. Julianne was what I’d call a typical Midwestern girl who had shoulder-length dirty blonde hair.

“He’s a giant!” Huifen said with a soft laugh.

“Only because you’re five-foot-nothing!” Julianne teased.

“Good things come in small packages!” Huifen exclaimed.

She appeared to have a bubbly personality, and I was sure she was going to be a lot of fun.

“Let’s go to my room and wait for the other girls,” Allyson suggested.

“Jonathan, help me carry the cooler, please,” Paula requested.

She and I picked up the cooler and we followed Allyson, Julianne, and Huifen to Allyson’s room.

“What are your majors?” I asked.

“Math,” Huifen declared.

“Environmental Science,” Julianne added.

“Where are you from?”

“Des Moines,” Julianne replied.

“San Francisco,” Huifen said. “Are you from Chicago?”

“No. I was born and raised in Ohio.”

“We’re here!” Shelly exclaimed as she and Bianca came into the room.

Two minutes later, Sally and Lucy joined us, and Allyson closed and locked the door.

“I have beer and pop in the cooler, and snacks,” Allyson said. “Does everyone remember the games and the rules?”

All of us nodded and said, “Yes.”

“Then everyone get naked!” Allyson declared.

Clothes were quickly shed, landing in a jumbled pile. When we were all naked, I took stock of the two new girls. Huifen was a foot shorter than me, thin, with small breasts, and a tuft of black pubic hair. Julianne was about five inches shorter than I was, and had nice breasts, though they weren’t as large as Paula’s. She also looked as if she’d gained the ‘freshman fifteen’, though she wasn’t fat.

“Jonathan, on the bed, please!”

“Wait,” Paula said. “I want a minor modification.”

“What?” Allyson asked.

“Each girl gets a nice kiss before we start! Everyone agreed to play the game, but our new players should at least get a kiss before they have Jonathan’s gorgeous cock in their mouths!”

“She has a point,” Lucy interjected.

“OK,” Allyson agreed. “Everyone draws a card. We go high to low, with same ranks decided by Bridge suit order — spades, hearts, diamonds, clubs. It’ll be the order for the first round, too.”

She produced a deck of cards, and all the girls drew one.

“Hah!” Paula exclaimed. “Ace of spades! My luck is changing!”

“We’ll see,” Lucy smirked. “Remember what happened last time!”

“Don’t be a bitch!” Paula exclaimed.

She and I exchanged a nice French kiss, and she made a point of rubbing her large breasts against my chest.

“I plan to win game two,” Paula said after she broke the kiss.

I kissed the rest of the girls, surprising Huifen by picking her up to kiss her. She was very light, and giggled and squirmed as we kissed, confirming in my mind that she was going to be a lot of fun. Shelly ended up with the lowest card, so she received the last kiss before I sat on the bed and leaned against the pillows Allyson had arranged.

“Cards, please,” Allyson said. “You’re first, Paula!”

The girls returned the cards, Allyson shuffled the deck, and set it aside while Paula moved to kneel in front of me.

“Going first is NOT to your advantage!” Lucy teased Paula.

“We’ll see!” Paula retorted.

I was positive Lucy was correct, because I wasn’t even hard. Paula would have to survive by drawing a high enough card. In fact, I was reasonably sure that none of the girls would get the ‘free pass’ for making me cum during the first round. That said, I felt I had enough control that I could ‘protect’ one of the last two or three girls if I wanted to. I was very happy that the trio of Bianca, Huifen, and Shelly was last in this round, though choosing between them would be difficult.

Allyson had some kind of clock that had two faces and two buttons. She pressed one of them and said “Go!”

Paula quickly got me hard, but there was no chance I was going to cum quickly enough for her to get an automatic advancement to the next round, no matter how enthusiastic she was in using her mouth. She was followed by Allyson, who took a slower, gentler approach; then by Lucy who tried, but I simply felt no urgency to cum at that point. The new girl, Julianne, was next, and adopted a different strategy, kissing me along my shaft, and running her tongue around my glans, never once taking me into her mouth.

“Hey!” Paula protested when Julianne’s time ran out.

“What?” Julianne asked.

“You didn’t try to make him cum!”

“Why would I help the girls who have turns after me? Hmm?”

All the girls laughed, Julianne moved away, and Sally took her place.

“You’re not close, are you?” Sally asked.

“No.”

She winked, then followed Julianne’s strategy of just kissing and licking. Paula protested again, but the other girls just laughed. When Sally finished, Bianca knelt before me, looked up, and mouthed ‘Shelly’, and I gave a very slight nod to acknowledge her request. Bianca grasped my shaft, then took me in her mouth and began stroking and bobbing, trying to bring me close enough so Shelly could get the ‘free pass’. I savored the sensations of her hand, lips, and tongue, and the gentle suction, and felt my pleasure rising.

The flaw in Bianca’s plan was that Huifen would have her turn before Shelly. Huifen’s approach was different as she grasped me with both of her small hands. She squeezed and rotated them while licking my glans, then taking just the tip of my dick into her mouth, sucking softly, and flicking me with her tongue. It was almost enough to get me to cum, but I managed to hold back, wanting to please Bianca.

Shelly took her place before me, and as I remembered back to the previous game, it dawned on me that she’d never had me in her mouth. She took hold of my shaft, opened her mouth, and slowly took me in, sliding her tongue around me as she took me deeper. She got me about halfway into her mouth, but gagged and backed off. I felt her thumb and finger encircle my shaft just above where her lips and been, then she wrapped her other hand around my shaft. She began bobbing, using her encircled fingers as a gauge.

Shelly licked, sucked, and stroked, and I relaxed completely, not trying to hold back at all. It was going to be a close thing, but my pleasure was building from her ministrations, and just as Allyson called ‘Time!’, I groaned and came. Shelly didn’t stop bobbing, sucking, licking, and stroking until I finished, then released me, licked her lips, and winked.

“Shelly wins the round!” Allyson declared.

“You called time before he came!” Paula protested.

“Don’t be a bitch, Paula!” Lucy ordered. “It was basically a tie, and tie goes to the sucker!”

All of us laughed at the baseball reference, and Allyson picked up the deck of cards.

“Jonathan, how long do you think we should wait?”

“Ten minutes should be enough,” I said.

“How about a minute of kissing each before we draw cards,” Paula suggested.

The girls quickly agreed, and Paula sat in my lap so we could exchange a French kiss. She grasped my wrist and directed my hand to one of her large breasts. I fondled it as we kissed, and when her minute was up, Allyson took her place, then Lucy and I fondled their breasts as well. I did the same for Julianne, Sally, Bianca, Huifen, and Shelly, then all the girls drew cards which would determine both who was eliminated and the order for the next round.

Bianca’s request turned out to be wise, as Shelly drew the 3 of clubs. That led to Lucy and Allyson being eliminated, with the new order being Sally, Huifen, Bianca, Julianne, Paula, and Shelly. That gave Shelly a distinct advantage, though I was sure that Paula was going to do everything in her power to win the round.

Sally was first, and it took about a minute for her to get me hard, and she bobbed and stroked slowly, knowing she had no chance to make me cum given I’d cum once already. She gave way to Huifen, who repeated what she’d done before, which was basically a French kiss of my glans, and was very erotic. Bianca went next, but this time, she didn’t make an effort to bring me close. Julianne, VERY wisely, in my opinion, did the same as she had done the first time — just kissing and licking me, never once taking me in her mouth.

Paula, on the other hand, was determined to make me cum, and I almost laughed when I realized that if I held back, Shelly would get the free pass again. Twelve minutes of pleasure by the first four girls made Paula’s task easy, and my last coherent thought as she deep throated me and gently squeezed my sack was about the previous game when she’d ‘lost’. I twitched, pulsed, and the first spurt of cum went straight down Paula’s throat. She backed off and sucked hard while swirling her tongue around my glans.

“Hah!” she said triumphantly when she released me after swallowing my last spurt.

“Yes, yes, you’re very good!” Lucy teased.

Paula gave me a searing French kiss, then Shelly took her turn, which felt good, but had little real effect as I’d just cum hard.

“Ten minutes again, Jonathan?”

“Yes, please.”

We all got drinks from the cooler, with everyone opting for pop except for Paula and Lucy, who each chose an Old Style.

“Kissing again?” Paula asked.

The girls agreed and I received nice French kisses from each of the girls, including the ones who had gone out, fondling their breasts as we kissed. When we finished kissing, Allyson shuffled the deck and held it out for the girls to draw cards.

“Oh, sure,” Paula groused, “Ace of spades!”

Lucy laughed, “Poor baby. You’re still in!”

“And I plan to win!” Paula declared.

Sally and Bianca had the lowest cards, and the new order was Paula, Shelly, Julianne, and Huifen. With each girl only getting three minutes, and having cum twice, I was positive that none of them would succeed in getting me to cum. My predictions proved true, as only Shelly made a strong effort, with Julianne once again simply kissing and licking, and Huifen doing as she had the three previous times.

“No break,” Allyson said. “Draw!”

She held out the shuffled deck and Shelly and Huifen had the lowest cards, with Paula going first. She smirked, then winked and did her best to get me to cum in her four minutes, but I didn’t feel the urge because of my two earlier releases. Julianne started the same way she had before, but after a minute, took my glans into her mouth and sucked gently as she stroked me.

“That’s cheating!” Paula protested.

“It is NOT!” Lucy smirked. “She’s just playing the cards she was dealt! He’s already cum twice, and she judged rightly he’s not ready!”

Julianne’s four minutes ran out just as I was beginning to feel the first twinges signifying an impending release. Paula made a supreme effort, but couldn’t quite get me there, despite me not resisting or trying to hold back. I twitched, but Allyson called ‘Time’, and Paula had to stop. That made it simple for Julianne, she grasped me, stroked me, and sucked as she bobbed and finally brought me off by swirling her tongue. I groaned and fired jets of cum into her mouth.

“Shit!” Paula swore.

After the last spurt, Julianne released me, swallowed, and then stood up.

“You win, Julianne!” Allyson said. “You can collect your prize!”

“Here?” she asked.

“Those are the rules,” Paula said firmly. “Or you can decline and the runner-up will claim the prize!”

“You wish, Paula!” Lucy said, laughing and shaking her head.

I decided I had to speak up, because it was one thing to play the game, but a very different thing to screw in front of all the other girls. I didn’t think it was particularly fair to force that, even if Julianne had agreed in advance. I knew Paula would have a fit, but that was her problem, not mine.

“I think that has to be up to Julianne to decide,” I said. “And I’m in control of what I do, so I say she can request privacy.”

“But she agreed when she decided to play the game!” Paula protested. “Either she follows the rules or she drops out and leaves!”

“You forget that I can leave at any point, and that I can refuse to do anything with anyone.”

“Jonathan has a point,” Sally said. “Let’s take a vote.”

“Follow the rules!” Paula declared.

“That’s your vote,” Sally retorted. “I agree with Jonathan.”

“Me, too,” Bianca said quickly. “Jonathan is right.”

“It’s a fine line,” Lucy said, “but I think Paula is right because Julianne agreed to the rules. It’s not about forcing her to do anything, but about following the rules. She has a choice, but the choice is to drop out.”

“I kind of agree with Jonathan,” Shelly said, “but you all watched me lose my virginity! I could have refused and dropped out, but I chose not to. I’m with Paula and Lucy. Julianne can drop out if she doesn’t want to do it.”

“I don’t think we should be that strict on the rules,” Huifen said. “I vote with Sally and Bianca.”

“Well, that makes me the tie-breaker,” Allyson sighed, “because only the girls should vote, and Julianne is the person we’re discussing. We should have made it a secret vote. But I’m going to put a different spin on it, and that is that it’s up to Julianne. She has to choose between here or not at all, BUT if she chooses not to, then nobody gets the prize.”

“I know that’s what the rules say,” I said. “But I don’t think that’s really fair. Whoever wins the second game gets the rest of the night with me, in private. At least that’s how I understood it. And I’m going to point out that you didn’t tell me that the winner of the first game had to do it in front of the group.”

“I thought that was obvious to you from last time,” Allyson said. “But we did tell Julianne, and she did agree. Nobody says she has to fuck in front of us, just that if she wants to claim the prize, she has to.”

“And the second game?” I asked.

“Sex is a ‘spectator sport’, at least as part of this game,” Allyson said firmly. “I think anyone who wants to watch, could. All of us except Julianne and Huifen already had sex in front of the rest of the group, and both Bianca and Shelly had their first times in front of us and Sylvia!”

“Huifen, what would you do?” Paula asked.

“I’d follow the rules, but I don’t think we should force Julianne to do anything she doesn’t want to do.”

“We’re not,” Lucy said. “She has a valid choice.”

“One other point I need to make,” Allyson interjected, “is that in the second game, you’re out if you refuse to do what the die says. The same is true for tomorrow. So, really, the choice is between doing it here or dropping out completely.”

I didn’t like the peer pressure, and I felt I needed to talk to Julianne privately. The thing was, I had limited control, except to refuse to participate, something I would do, albeit reluctantly.

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