Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 42: One More Round?

Coming of Age Sex Story: Chapter 42: One More Round? - '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  

January 16, 1982, Chicago, Illinois

“We should all shower,” Lucy said.

“Can I just cuddle for a few more minutes?” Bianca requested.

“If Jonathan is OK with it, I am,” Allyson said.

“Well, I don’t need a shower,” Paula complained.

The girls who lived in the dorm dressed and left the room, saying they were going to get fresh clothes, while Sally borrowed a robe from Allyson which barely hid her body as she was so much taller than Allyson. Allyson began dressing, as did Paula, and when they were both dressed, Allyson went to the door.

“Come talk to me, Paula,” Allyson said.

They left, leaving just Bianca and me in the room. She moved on top of me, crossed her arms, and rested her chin on them.

“Do you think you could do it again?” Bianca asked.

“Probably,” I replied.

“Would you? I don’t know if I’ll ever get another chance. I mean with you.”

“Paula might actually kill me!”

“I doubt it,” Bianca replied. “Allyson will keep her from doing that.”

Bianca kissed me and began gently grinding against me, but I knew it would take some ‘help’ to get hard. When she broke the kiss a minute later, I let her know.

“I think I need some assistance,” I said.

Bianca laughed softly, “My mouth?”

“That would help you achieve your goal!”

She gave me a quick kiss, then moved down and began licking and sucking. It took some serious effort, but she achieved her goal of getting me hard. She moved up, kissed me, then grasped me and held me upright so she could impale herself on me. She moaned softly as my glans passed through her labia, then worked me completely inside her. She put her hands on my chest and began moving up and down and back and forth.

The door opened and Allyson laughed, then closed it again. I heard voices in the hallway, and more laughter, though I was positive Paula was not laughing. Bianca leaned down to kiss me again, then offered me her breast to suckle which I gladly did. I heard the door open and in my peripheral vision, I saw the other girls come in, with four of them sitting on the couch, and Allyson and Sally sitting on the floor.

“Hope you don’t mind an audience,” Lucy exclaimed.

“You can watch for as long as I’m allowed to do this!” Bianca declared.

Bianca rode me for twenty minutes, having four good orgasms, before she lifted off, moved onto her back, and encouraged me to move on top of her. I did, and slipped into her, grinding against her clit. She wrapped her arms and legs around me, and began flexing her hips.

“Fuck my brains out,” Bianca gasped.

I did, and she had three more orgasms before I finally managed to have an orgasm, though I didn’t have much cum left to squirt into her spasming pussy.

“Cuddle for a bit,” she requested.

I moved off her, lay on my back, and pulled her to me.

“10.0 from the judge from Loyola!” Sally declared.

“Jonathan or Bianca?” Lucy asked.

“Both!” Sally exclaimed.

“He’s damned good,” Lucy declared.

“He is!” Sylvia agreed.

“Absolutely!” Sally added.

“Oh, shut up!” Paula ordered.

Bianca and I lay together for another five minutes, then got out of bed. I got my robe and she borrowed, Allyson’s. We left the room and I was surprised when Lucy followed us.

“What’s up?” Bianca asked.

“I thought you might like to shower with Jonathan. Use the girls’ showers; I’ll stand guard. I’ve done it and nobody will say anything, trust me! The RA is not on the floor.”

Bianca and I went into the girls’ showers, hung our robes on hooks, then went into a stall and pulled the curtain. Bianca turned on the spray, adjusted the temperature, then held out her arms. We stepped close, wrapped our arms around each other, and moved under the spray.

“Best day of my life!” she declared, putting her head on my chest.

“Craziest day of mine!” I chucked.

Bianca laughed softly, “I bet!”

“You were awesome,” I said.

“I was SO tempted to ask you that night at Allyson’s house, but this turned out WAY better.”

“Including the audience?”

“That made it even more exciting, believe it or not! There’s only one thing I didn’t do that I wanted to do.”

“What’s that?”

“Taste your cum,” she giggled. “Maybe at the party, if Allyson will allow it! You could lick me while I suck you.”

She wiggled and squirmed in my arms, her slick skin sliding over mine, and I realized how much I wanted her again. And after everything that had happened in the past five hours, there was no point in refusing. That said, as fun as the day had been, it seemed more than a bit over the top. I’d have to think about how I felt, but one thing I was certain of was that I wanted to be with Bianca again.

“If Allyson agrees,” I said. “But I’d say it has to be close to midnight so there’s actually something to taste.”

“Awesome!”

“If you want, we could start by fucking, then you can finish me with your mouth.”

“Now, if I could find a way to hide you in my dorm room...” she giggled.

“I need to work!” I declared. “You know, I don’t think I heard your major.”

“Computer Science.”

“I don’t know much about computers, but I’m going to have to learn.”

“Well, if you hide in my dorm room, I could teach you!”

I chuckled, “And work?”

“Oh, I know! I was just imagining what it would be like to have you fuck me four or five times every night before falling asleep from exhaustion!”

“Now there’s an image,” I replied.

That would be fun, I thought, and I very much enjoyed Bianca’s sexy body, but I knew it wasn’t really possible. Of course, had anyone asked me if I’d have a chance to have sex with six girls, one at a time, while all the others watched, I would have said that was impossible.

Bianca and I stood together for a couple of minutes, then I got the soap that Bianca had picked up before we came to the shower and began to wash her body, taking extra time to soap her breasts, butt, and mons. After she rinsed off, Bianca did the same for me. We dried off, put on our robes, and went back to the room to dress, finding only Allyson there.

“We’re going to meet downstairs in fifteen minutes to go for Chinese,” Allyson said.

“OK,” I agreed.

Bianca and I both dressed, and then Allyson asked Bianca to wait with Sally who was in the lobby.

“Can I talk to you in the hallway for a sec first, Allyson?” Bianca asked.

They stepped into the hallway and a minute later Allyson came back into the room and shut the door.

“Happy?” she asked with a smirk.

“Stunned is probably more like it!”

“Just so you know, I didn’t plan this.”

“I didn’t think you had,” I replied.

“It really was Paula’s idea, and just spur of the moment.”

“I do feel kind of bad for her,” I said.

“She’s not angry, just extremely disappointed. It’s OK for you to do what Bianca asked for later.”

“You’re sure?”

“Even if you and I just sleep naked together, I’ll be very happy. We can always do it in the morning before breakfast!”

“So long as you’re happy,” I replied.

“I was thinking next weekend we could stay at your place, just the two of us, if that’s OK.”

“It is,” I replied, thinking that was a good idea.

“If you want to make Paula happy tomorrow, I’m OK with it. Just don’t say anything to her tonight and let it be a surprise tomorrow.”

“I really do feel bad for her.”

“Then do it,” Allyson smirked, “with a full audience!”

I laughed and shook my head, wondering how things had become so crazy in such a short time, not that I was actually complaining. It dawned on me that I hadn’t even thought about the ‘audience’ as things had progressed during the afternoon, at least until I had asked Lucy about it, and Shelly had voiced her surprise.

“What happened today really doesn’t bother you?” I asked.

“No! It was awesome to watch,” Allyson exclaimed, “and WAY better than that show we went to in Amsterdam because here I got to participate! Is something bothering you?”

“I don’t know what to call it, because this was so far outside my experience that I’m not sure what I think. I mean, isn’t this just about the craziest things can get?”

Allyson laughed, “You have NO idea. You heard what Paula described, right?”

“You mean the porn movie?”

“Yes. She described stuff you haven’t done, and I know it gets even crazier than that!”

“Crazier than a girl, what was it she called it?”

“Pegging a guy?”

“That.”

“Triple penetration of a woman? Mouth, pussy, and butt by three guys at the same time?”

“OK, I am officially clueless!”

Allyson laughed, “About porn, or the extremes of sexuality? But I wouldn’t know nearly as much as I do if I hadn’t been in Amsterdam last year, or if I didn’t have Paula as a friend.”

“It just seems odd for a theology major to be an expert in porn!”

“She’s basically agnostic, but finds it interesting. She’s likely to go on to get her PhD and teach and do research. She’s a Junior, and probably knows more about what the Bible actually says than your average Baptist! Most of the girls are Catholic and I don’t think any of them ever picked up a Bible. And she’s studied Islam, Buddhism, Hinduism, and a bunch of other religions I’d never heard of before I met her. She says that if you want to see God, you just need to have great sex!”

I laughed, “That’s just too funny!”

“Shall we go meet the girls for dinner, then head to the party?”

“Where is the party?”

“At an off-campus townhouse that three guys are renting, rather than live in the dorms. There should be about forty people there, including all of us.”

“I suppose I should thank you for the craziest and most amazing day of my life!”

“You should!” Allyson declared mirthfully. “A kiss for now; real thanks later.”

We exchanged a soft kiss, then left the room, which I’d noticed had the distinct odor of sex, then headed down to the lobby. We walked to a Chinese restaurant, ordered their ‘Banquet for Eight’, which had ten different dishes, plus eggrolls, rice, and green tea and what I thought was a very reasonable price.

The food was awesome, and I learned more about the girls, including how they all met, and heard some stories about High School that made it clear that some of the rumors I’d heard about other kids might well be true. The fact that I had worked so much and never hung out very much, or went to dances or other events, meant I’d missed out on some of the shenanigans.

The most interesting thing, both to me and the other girls, was the ‘first-time’ stories. I obviously knew Bianca’s and Shelly’s, and had heard Allyson’s. Lucy and Paula were the surprises, as Sylvia and Sally had what I considered conventional first times — Senior Prom. The surprising things about Lucy and Paula were that they were nearly opposite — Lucy had lost her virginity on her fourteenth birthday, and Paula had been nineteen, something I wouldn’t have expected. I wasn’t the only one who was surprised.

“Believe it or not,” she said in response to Shelly’s question, “I was afraid. Part of the problem was that I was being hit on by guys who were way older than me. I’d go to the public swimming pool, and guys in their thirties would see my chest and not care that I was fourteen or fifteen.”

“Or, maybe because you were fourteen or fifteen,” Allyson observed.

“Yeah, I understand that better now, but it freaked me out at fourteen. Now, a guy who is thirty would be fine, though that’s kind of the limit — ten years older. But at fourteen, ten years is a huge difference, not to mention twenty-five years!”

“My mom was sixteen and my dad was around twenty-five,” I said. “I don’t know for sure because I never met him.”

“He left before you were born?” Paula asked.

“He died in a plane crash. Mom only found out when she tried to contact him after she discovered she was pregnant.”

“That’s rough,” Lucy said. “I did fail to mention that the next-door neighbor I was with on my fourteenth birthday was in his late thirties and married...”

“Seriously?!” Shelly gasped.

“Seriously. It was, and no disrespect to Jonathan, the most erotic, crazy, and amazing day of my life!”

“But a married guy? And that much older?” Sally protested.

“Well, first, how many guys who were my age would have been able to give me an awesome first time? He knew what he was doing, and I had more orgasms than I could count! As for being married, well, that’s between him and his wife, isn’t it?”

“Not really,” Shelly protested. “He made a vow.”

“I have to agree with Shelly on that one,” I said. “Your word defines who you are.”

Lucy shrugged, “But he didn’t lie to me nor did he make any promises. Well, beyond that he could make me cum until I couldn’t see straight, a promise he kept!”

All the girls except Shelly laughed. She just shook her head, because she was outraged. I realized other people had different opinions, but to me, cheating was wrong, and I wouldn’t do it, nor facilitate it.

“How did that happen?” Sally asked.

“He was a total hunk and he caught me watching him mow the lawn. He was wearing just shorts, and had a great tan, and I couldn’t take my eyes off him. He walked over to the fence and asked what I was doing. I stammered that I was just watching him, and he asked if I wanted to see everything. I totally did, so I just nodded. He invited me to come over, which I did.

“When I got inside the house, he asked me again if I wanted to see the rest and I nodded again. He pulled off his shorts and I couldn’t take my eyes off his dick. He asked if I wanted to touch it, and I said that I did. He said I could, if I took off all my clothes, which of course I did, and for the next six hours, we did everything you can imagine. I went home for my birthday party, already having received the best present imaginable.”

“So, why wait until last year, Paula?” Sally asked.

“I was still scared, believe it or not. The Summer between Freshman and Sophomore year, I was home and ran into a guy I knew from High School. We got to talking and he asked me out. We went to dinner, talked a lot, and when he took me home, he tried to kiss me, but I turned my head. He asked if something was wrong, and I basically spilled the whole thing about being nervous and scared. He said he understood and left without a kiss. I thought I’d totally messed up, but then he called me the next day. I invited him over and had my first real kiss. That kiss basically broke the dam, and we had our clothes off and were screwing in my bed less than ten minutes later.”

“You really hadn’t ever kissed before that day?”

“Nope. I didn’t go to parties like the one we had today because I knew all the guys cared about was my boobs. Charlie actually cared about me.”

“What happened?”

“He went back to college in Arizona and I decided I wanted the freedom to explore my sexuality, which I have! And despite being utterly frustrated today, watching others have sex in person is WAY better than watching porn!”

The girls all nodded in agreement or said “True!”.

“Shelly,” Lucy asked. “What was it like losing your virginity in front of the rest of us?”

“Weird,” Shelly declared with a silly smile. “But watching the rest of you made me really, really wet, and I just needed to get Jonathan inside me!”

“And Bianca?” Lucy asked. “Performance art?”

Bianca laughed, “I’d do it with Jonathan at halftime on the fifty-yard line at Soldier Field, if that was the only way to do it again!”

All the girls laughed.

“Seriously, though, it was unbelievably sexy to know that you guys were all watching. I was actually excited when you all came back during my second time and sat down like an audience!”

“Jonathan put on a pretty impressive performance today,” Lucy declared.

“Thanks,” I said.

We finished our meal, split the bill eight ways, then headed to the party. I had a great time, with beer from a keg, and lots of dancing. I made a point of mostly dancing with the girls I’d arrived with, making sure that Allyson had more slow dances than others. I did dance with three other girls, all of whom seemed as if they were available if I were interested.

“Are you staying tonight?” I asked Bianca when we danced just before midnight.

“Yes, and so is Sally. If you weren’t here, I’d be sleeping on Allyson’s couch, but I’ll sleep in Paula’s and Lucy’s room. Sally will stay in Shelly’s room, because her roommate is gone for the weekend.”

“Given what went on today, I can’t imagine Allyson would object to you sleeping on her couch.”

“I can ask her,” Bianca said.

“Where did you plan for us to go?”

“I have the key to Shelly’s room, but if Allyson is cool with it, we can just go there and not worry about logistics. Let me ask her after the song, OK?”

“Sure.”

We swayed together to the song by Air Supply, which was popular with the girls. When All Out Of Love finished, Bianca went to find Allyson and Shelly, and was back two minutes later.

“Allyson is cool with that. Do you want to stay longer at the party? The girls were planning to go back to the dorms around 1:00am.”

“It’s up to you,” I said. “If we go now, you have a full hour for whatever you like before Allyson comes back.”

“You’ve had about seven hours to recover; do you think you could go twice?”

“I’m pretty sure I can.”

“Awesome! Then let’s go!”

Bianca let Allyson know that we were leaving, then Bianca and I headed back to the dorm. Because we had the key, there was no problem getting into the building and up to Allyson’s room without her along. We quickly undressed, and because the sheets were already soiled and would have to be changed, we got into bed.

“I want you to cum in my mouth,” she said. “And then I want you to fuck me for as long as possible!”

Which would be a long time, I thought, as I knew there was no way I’d have an urgency to cum after Bianca sucked me, especially given the events of the day. I nodded and she moved to straddle my face, with her face by my groin. She lowered her labia to my lips, and began kissing along the length of my semi-flaccid shaft. I had the brief thought that I really wanted to watch the blowjob that I was about to receive, but I wasn’t going to interfere with what Bianca wanted.

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