Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 41: The First Hit Is Free

Coming of Age Sex Story: Chapter 41: The First Hit Is Free - 'Climbing the Ladder' is a story in the 'A Well-Lived Life' universe, and provides 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. Follow along as the adventures of Jonathan Kane continue!

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

January 1, 1983, Chicago, Illinois

We had a blast at the party, and at midnight, I'd been hugged and kissed by several girls, some of whom pressed tightly enough against me to imply they were available when it was time for bed. Violet obviously wasn't among those, though Lily was. Unfortunately, she had to leave at 1:00am with Violet because Mrs. Andros was being overprotective. That bugged me a bit given Lily was nineteen, but as she was still living at home, she had to placate her mom.

At 1:00am the car arrived, and I walked Lily and Violet out, made sure they were safely in the car, and after it pulled away, I went back inside. I spent the next hour dancing and chatting with quite a few girls, including Allyson and Sally, who had both brought dates and thus weren't available, along with Kristy, who absolutely wasn't available. On the other hand, Katy and Esme both suggested the three of us go to bed together, as had Ellie, Miranda, and Juliette.

"So many offers you don't know what to do?" Ellie asked with a smirk as we danced around 2:00am.

"I think the phrase is 'embarrassment of riches'!" I chuckled.

"Who besides me, Katy, and Miranda?"

"Esme, Juliette, and Julianne," I replied. "And even though they didn't suggest it directly, Ivy, Sophie, and Deanna are obviously available, though they've spent a lot of time with Tom and Stuart's firemen friends!"

"Well," Ellie said slyly, "you could do it five times, so we could all have a turn!"

"You're really pushing the whole 'harem' concept!"

"At some point, you'll decide to settle down, but why not have as much fun as possible before then? And it's not like any of the girls object! I do have one request, though."

"What's that?"

"That I can spend the night tomorrow, or tonight, or however you want to call New Year's Day night."

"Ask the other girls," I said. "If they can't agree, then I'll decide."

Ellie made a face, "Katy and Esme, unless I miss my guess."

"That would probably be the case," I agreed. "But you already promised for tomorrow night!"

"Me and my big mouth!"

"That's not a problem!" I grinned.

"The better to suck you with, Red?" Ellie teased.

I laughed, "Turning Little Red Riding Hood into some kind of sex romp?"

"Now there's an idea for a production for the drama department!"

"That might have caused parents back in Goshen to have strokes!"

"Seeing someone get stroked?" Ellie asked impishly. "Maybe they don't like to watch, but I do!"

"Go ask!"

She did, and I went to get a drink. I grabbed a Coke from the cooler, popped the tab, and took a big swig, as I was thirsty from nearly an hour of continuous dancing. About three minutes later, Ellie came over to where I was standing and stepped close.

"They all said 'yes'!" she declared.

"Let me make sure Bianca and Shelly are cool with me disappearing, as there are still guests here."

I checked with Bianca, who simply laughed and told me to have fun. I went back to Ellie, who said the girls would join me upstairs. I went upstairs, emptied my bladder, and when I walked out of the bathroom, all six girls were in my room with the door shut.

"Can I suggest something wild?" Juliette inquired.

"Sure!" Ellie replied. "Anybody can suggest anything, and we're all adults and can decide to do it or not."

"I want to go last," Juliette said, "but after he fucks each of you, I want to lick you to orgasm and taste him from inside you."

"Seriously?" Miranda asked, making a face that showed she was disgusted.

"Seriously," Juliette replied. "I'm not asking YOU to eat pussy! Just let me do it to you. I mean, seriously, my tongue and Jonathan's tongue are basically the same and he shaves, so it's not like you'll feel his whiskers on your thighs!"

"That just seems a bit, uhm, extreme," Miranda replied.

"You know what?" Julianne said, "I'm game. I mean, what the hell? So long as I don't have to put my tongue in HER cooch, I'll go for it!"

"Me, too," Katy replied. "On the same condition."

"Then I suppose I have to as well!" Esme said. "Not that I'm interested in doing a girl, but if Katy is game, I am."

"I still don't know," Miranda said. "I'm not lezzie."

"Me, either," Ellie said. "But I will if you will."

"Can I think about it?" Miranda asked.

"Of course," I interjected. "Nobody should feel pressured to do something they don't want to do."

"So long as I get to go last," Juliette said. "I want Jonathan to fuck me but cum in my mouth. That way I can taste him every time!"

"Along with your own pussy juice!" Ellie smirked.

"I bet you every single one of you has done that," Juliette said. "Jonathan kisses after oral sex, both ways!"

"That he does," Ellie agreed.

"She has a point," Katy said. "Who goes first?"

"Not Miranda or Ellie," Juliette said. "They should see it first so they can have more information!"

"I'll take one for the team!" Julianne declared mirthfully. "On condition I get to sleep with him afterwards."

"No objection here," I said.

"Then strip and fuck my brains out!" Julianne demanded.

Having exactly zero reasons not to do that, I did, using my mouth to ensure she was wet enough before we fucked hard for close to ten minutes before I came, which was after Julianne had two strong orgasms. I moved off Julianne, and Juliette quickly moved between Julianne's legs and buried her tongue in freshly fucked pussy. Julianne clearly enjoyed the experience, and after a few minutes, had an orgasm.

"Two great tastes that taste great together!" Juliette exclaimed as she got out of bed

We all laughed at the reference to the Reese's Peanut Butter Cups commercial.

"How do you feel, Julianne?" Miranda asked.

"It was weird at first," Julianne said, "but I just closed my eyes and enjoyed her tongue on my clit!"

"Would you do it again? Or do it?"

"I wouldn't actually do it myself," Julianne said, "but it felt really good. So, maybe?"

"I'm next!" Katy declared.

She quickly stripped off her clothes and got into bed, and I licked her until I was hard, then fucked her the way she preferred — slow and steady, rather than headboard-banging. When Katy and I finished, Juliette moved between Katy's legs and brought her off with her tongue.

"Now I know what my lesbian friends mean!" Katy declared. "Not that Jonathan is a slouch at eating pussy, but Juliette has a girl's knowledge of girl's anatomy! No offense, Jonathan!"

"None taken!"

"My turn!" Esme declared.

And a third repeat led to the same conclusion: three good orgasms for Esme from me and one from Juliette.

"What do you think, Miranda?" Ellie asked.

"I can't," she replied. "I'll give up my turn if I have to."

"Remember what I said?" I asked. "How about I lick you afterwards?"

"Yes!" Miranda exclaimed.

The fourth round was effectively the same as the first three, though I substituted for Juliette, bringing Miranda off an additional time with my tongue.

"I think I need a break," I said.

"How long?" Ellie asked.

"Twenty minutes before we start," I replied.

"If your jaw won't get too tired, I can think of a way to spend twenty minutes!"

I laughed, "Get undressed and get in bed!"

As I'd expected, based on past experience, it was just over twenty minutes before I felt the stirrings, and asked Ellie for an assist, which she was happy to provide. After a bit of sixty-nine, I was rock hard, and we had a semi-energetic screw, after which Juliette provided an additional orgasm with her tongue.

"Let's sixty-nine until you're hard, then fuck me, pull out, and cum in my mouth, OK?" Juliette requested.

"OK by me, but it's going to take some time to get hard for the sixth time!"

"I'm patient!" Juliette declared. "Especially with your tongue in me!"

It did take some time, but Juliette got her wish of me cumming in her mouth. In order to give her the same treatment, I moved between her legs to lick her, but felt a hand on my shoulder.

"Let me," Katy said. "I want to try it."

"You're sure?" Juliette asked.

Katy nodded, "One time is an experiment, and besides, I might have a threesome sometime at Princeton!"

"You and two other girls?" Esme teased.

"A guy and a girl, you nut!" Katy exclaimed. "Or maybe two guys!"

"Princeton is going to be fun!" Esme declared. "A LOT of fun!"

All the girls laughed and Katy got between Juliette's legs. She was tentative at first, but then got into it, bringing Juliette off after several minutes.

"So?" Esme asked.

"Totally weird," Katy replied. "But not disgusting."

"Showers, then sleep?" Ellie suggested.

We all went to the bathroom, and sadly, it wasn't possible for all of us to get into the shower together, but I took turns with two girls at a time, and when we finished, everyone except Julianne dressed, kissed me, and left the room. As promised, I got into bed with Julianne and we quickly fell asleep.

We woke up just after 11:00am, dressed, and went downstairs to have lunch, then helped Bianca and Shelly clean up. The rest of the day was relaxing, and as I'd agreed, Ellie spent the night.

January 2, 1983, Chicago, Illinois

Late on Sunday afternoon, after watching the Bears lose 23-20 to Tampa Bay, I dressed for Jeri's birthday party. A few minutes after I was ready, James arrived to pick me up to take me to Jeri's house. I had planned to drive, but decided that I'd accept the offered ride so that I could drink and not worry about having to stay long enough for all the alcohol to be out of my system. I was positive Jeri wouldn't play any games, as I'd been extremely clear with her about my response to any attempts to manipulate or control me.

I was somewhat surprised to find Jeri's parents were home, given what had happened the previous year, though I had no idea what Jeri might have told them about me. That meant being cautious about what I said to them and how I answered any questions they asked, especially about my relationship with Jeri and about her trust fund.

"Nice to meet you, Jonathan," Mr. Pemberton, Jeri's father, said.

"And you, Sir," I said, taking his extended hand.

His palm was cold and clammy, and his handshake weak, screaming 'wimp' in my mind.

"It's nice to have you here, Jonathan," Mrs. Lundgren, Jeri's mom, said. "Jeri has told us quite a bit about you."

"Thank you for your hospitality," I said. "And I hope what Jeri said was all good."

"It was!" Jeri said.

"Happy birthday!" I said, offering her the small wrapped gift I had in my left hand.

"Thanks!" she replied, stepping close and giving me a kiss on the cheek.

"We'll leave you two and see you at dinner," Mr. Pemberton said.

"Thanks, Dad!" Jeri exclaimed.

They left the great room and Jeri beckoned me to sit near the fire.

"They decided to stay home?" I asked.

"Mom had a thing here in Chicago on New Year's. Originally, it was going to be in New York, but something happened between her and Donald Trump, so she moved the soirée from the Grand Hyatt Hotel to The Palmer House."

"Who is Donald Trump?"

"A New York real estate developer. Think a sleazy version of your Uncle Alec."

"Miss Jeri?" Karolin, the maid, said, coming into the room.

"Yes, Karolin?"

"Is your young man staying the night?"

"We haven't decided."

"I'll make up the guest room just in case, then," she said.

"Thank you, Karolin," Jeri replied.

"I thought I was clear," I said quietly after Karolin had left.

"I promised not to pressure you, but left the invitation open. And Karolin was just doing her job, I didn't put her up to that. You have stayed in the past."

"What did you say to your parents?"

"That you're an up-and-coming analyst/broker who's on Murray Matheson's team. I may have jumped the gun a bit on the timing, but it is true in two weeks."

"And about us?"

"Just that I was interested in you, in addition to asking you to manage my money. They have no idea that you've spent the night here. And if you spend tonight, in the guest room or my room, they won't give me grief because you're no longer a commoner, but a potential donor."

"I'm not particularly interested in left-wing causes," I replied. "Or right-wing causes, for that matter. I could see giving to the Red Cross or some similar group, but not groups that push some ideology."

"That fits your attitude of letting everyone do their own thing so long as they don't hurt anyone else."

"The last thing I want is morals police checking up on me, which means I can't sanction them checking up on anyone else! And I think compromise in the center is the best possible path for the country. No extremes, right or left."

"You don't like Reagan?"

I shrugged, "He's OK, but I like having divided government, because then Reagan has to negotiate everything with Tip O'Neill, which means we don't get anything extreme. I figured out in American government that the perfect setup would be Democrats controlling the House by a comfortable margin, Republicans controlling the Senate by a comfortable margin, and then the President could be from either party."

"Why that way?"

"The House is for the people, right? And it should be looking out for them. The Senate would moderate things so that they didn't go to extremes. I remember reading about Jefferson comparing it to pouring tea into saucer to cool it down being the point of having a Senate — to moderate the populist House. It makes perfect sense."

"You can imagine I'm a Republican, along with almost everyone at Spurgeon."

"Oh, I know, and I stay out of politics, except to the extent I have to analyze things. I don't mind discussing politics, but people can become pretty animated about it, and I need to be cold and logical."

Jeri took a quick glance over her shoulder, then quietly said, "You were hot in bed!"

"Miss Lundgren, you're pushing the limits," I said firmly.

"Sorry," Jeri replied, seeming chagrined.

"If that were to ever happen, I'd have to be in complete control," I said. "And that is not you in any way, shape or form."

Jeri smirked, "I have some long scarves you could use to tie me to the bed!"

I laughed, "That is not what I meant, but good to know!"

"You meant the relationship, right?"

"Yes."

"Partners?"

"I'd prefer that, but you haven't shown me you could be an equal partner."

"I don't do submissive."

"No kidding! Though I think you play at being submissive to gain control. That said, I'm not asking you to be submissive, but equals. You do NOT do that. And I suspect you learned that from your mom, at least from what I've heard about her."

Jeri frowned but then nodded, "I suppose you're right."

"And if that works for you, fine; but it doesn't work for me, which means it doesn't work between you and me."

"And at this point, I can't play the shy, submissive girl with you."

"No, you can't, because I already know differently."

"You're pretty self-confident for someone who is just getting started."

"Do you think going to Mr. Matheson and meekly suggesting he think about an investment would be a good plan for success?"

"Well, no."

"The only way forward is confidence and strength. Will I make mistakes? Most assuredly. But if I'm confident, strong, and aggressive, I'll make up for those losses with bigger gains. Well, assuming I'm any good at analyzing the currency, stock, and commodities markets."

"So far, you've done pretty well."

"So far," I replied. "And that's the key thing to remember. I'm only as good as my last trade, as it were. Sure, overall gains are what matters, but every loss brings unwanted attention. Too many of them, even with an overall above-market gain, are a problem, because Spurgeon and Matheson rarely make errors, and they're just blips on their way to seriously out-performing the market."

"You don't seem as confident as you did a minute ago."

"Sure I am, but the key is not to be overconfident or cocky. If I believed I wasn't going to make mistakes, that would be a problem. Acknowledging that it's not only possible but likely ensures I temper my analysis and don't veer off into fantasy."

Jeri smirked, but didn't say what I was sure she was thinking.

"Not that kind of fantasy!" I declared. "And besides, I allegedly fulfilled yours. But set that thought aside, please. I did speak to Allyson, and she's agreed to come to dinner on the 21st."

"Good. A doctor, a lawyer, a political operative, a finance guy, and me is an excellent combination."

"I assume you're being properly groomed to take over your mom's foundation?"

"That's her pipe dream. I told you I want to go to college and get a degree in computer science. I really like computers, and that's what I think I want to do for my career. It's not like I have to worry about money."

"True."

"And I really don't like the political causes my mom supports, nor the bullshit galas she throws to raise money. And you know my opinion on certain individuals chasing young girls."

"I still don't believe he can get away with that forever."

"I know you don't, but he's rich enough that he can get away with it. And seriously, no girl who agrees to give him her cherry is going to complain once they start getting gifts from him. I bet you anything you care to wager, Lisa goes after him and gets something significant in exchange for her virginity."

"And to think you gave yours away for free!" I chuckled.

"Lisa doesn't have a trust fund, even if she's spoiled."

"That's close to the pot calling the kettle black," I observed.

"The difference is I've listened to you," Jeri replied. "And I didn't treat you like crap the way she does."

"Mostly because she can't gain anything from me and the fact that you were interested in me."

"You wouldn't be the first cousins to get it on."

"Please don't make me ill," I replied. "She's thirteen. And a bitch."

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