Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 7: That’s All Anyone Can Do

Coming of Age Sex Story: Chapter 7: That’s All Anyone Can Do - '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  

July 17, 1982, Greater Chicagoland, Illinois

I had not been at all surprised when Jack let me know after we’d had our pizza dinner that he wouldn’t need a ride back into the city, and that Kristy would take him home. I found Bianca to let her know that neither Jack nor I would be going back with her and Shelly.

“Did you have plans for tomorrow afternoon?” Bianca asked after I told her.

“No.”

“Shelly and I were discussing going to see the Cubs play the Braves at Wrigley.”

“What time?”

“We plan to get to the ballpark at 11:30am.”

“Let me check with Katy and see if she’ll drop me at Wrigley at 11:30am.”

I went to Katy and asked the question.

“Sure! So long as we leave my house by about 10:00am, we’ll easily get there by 11:30am.”

“Thanks.”

I went back to Bianca to let her know, then went to find Allyson, and saw Clara, who had been at Kristy’s house with Kristy’s little sister, Marie.

“Hi!” Clara exclaimed. “Wanna spend the night?”

“You’re still sixteen,” I said, which was the best defense because she couldn’t counter it.

“Mark January 7th on your calendar! I’ll be seventeen and I’ll show you I’m WAY better than Allyson! And I’ll do anything you want!”

“You’re free to ask me then, but I’m not making any promises, because I might have a girlfriend.”

“Don’t! It’ll be worth it, I promise!”

I almost laughed because there was no way for her to know that, and I’d had awesome sex with quite a few girls. In fact, I was going to have sex with two girls, and I expected that to be awesome. January was a long way away, and I was fairly certain I’d be together with Huifen in some fashion that would preclude what Clara wanted.

“Get in touch in January,” I said, though I fully expected to turn her down then, too. I walked away and headed to the kitchen, where I found Allyson.

“I’m going to leave with Esmeralda and Katy,” I said.

Allyson smirked, “Of course you are! That was obvious from the way Katy has been looking at you all afternoon — a lioness ready to pounce!”

“Jack let me know he’s going to hang out with Kristy,” I said.

Allyson smirked, “I might ‘accidentally’ stumble into the guest room.”

I laughed, “Have fun!”

We hugged, exchanged a friendly peck on the lips, then I walked out to the backyard where Katy and Esmeralda were waiting. The three of us said ‘goodbye’ to the others, then walked to Katy’s Ford Escort, which was parked in the driveway. Ten minutes later, we were at her house, which wasn’t nearly as large as Kristy’s or Allyson’s, but was larger than Bev’s.

When we went inside, Katy took my hand and led me upstairs to her room, which had a large canopy bed. The walls were adorned with rock posters, including REO, Styx, Pink Floyd, the Beatles, and the Rolling Stones. Esmeralda followed us into the room and sat down in a large, comfortable chair.

Katy closed the door, turned down the bed, then turned on her stereo and put an album on the turntable. I suppressed a groan when Lost in Love by Air Supply wafted from the speakers. I didn’t mind an occasional song by them, but a whole album was almost more than I could stand. That said, I was in no position to complain, given what Katy was offering!

“I want to put on something different,” Katy said. “I’ll be right back!”

She went to a dresser, took something from a drawer, then disappeared into the bathroom, closing the door behind her. That gave me a chance to ask Esmeralda the question that had formed in my mind.

“What’s going on?” I asked.

“I get to watch!” she smirked. “That was my condition.”

“You shouldn’t have made that a condition,” I said. “YOU didn’t want an audience.”

“I told you I would if that was the only way! Katy giggled and agreed in a split second! Ask her.”

“Agreeing when it’s the only way to get something you want is very different from having a choice and agreeing freely.”

“She’s going to watch us, too,” Esmeralda said defensively. “Turnabout and all that.”

“I get that, and that’s OK, though there’s a difference with your first time. I’m going to give Katy the same option I gave to other girls in the same situation.”

“I’m confident,” Esmeralda declared.

As Lost in Love gave way to Every Woman in the World, Katy came out of the bathroom wearing a filmy red garment I recognized as a teddy, because prior to getting pregnant, it was what Bev had worn to sleep during the Summer, wearing a long flannel nightgown over it during the Winter. It perfectly accentuated Katy’s curvy body, and showed just enough skin to be enticing.

“You like?” she asked.

“I do! I mentioned this to Esmeralda — you don’t have to have an audience for your first time, no matter what you two agreed.”

Katy smirked, “Bianca said it was the most exhilarating, most liberating thing she’s ever done! Besides, I get to watch you and Esme!”

“If you’re sure,” I said.

“Positive!” Katy declared. “Esme, ‘Show and Tell’?”

“Yes!” Esmeralda exclaimed. “Jonathan, let’s show her how it’s done!”

“What’s your pleasure?” I asked.

“Orgasms, obviously!” Esmeralda exclaimed. “But how about what we did at your house? Well, I guess I need to ask how many times you can go.”

“Six, at least,” I replied.

“Cool! Then exactly what we did. Katy, we can alternate, or we can show you everything first.”

“Katy,” I interrupted, “how much have you done?”

“The same as Esme — a lot of making out, some ‘Spin the Bottle’ and getting felt up outside my clothes. I want to watch you guys do everything, then I’ll do the same stuff, plus more, if Jonathan is up for it!”

I would most certainly be ‘up’ for anything she wanted! Esmeralda quickly undressed, so I followed suit. She came over to me, grabbed my hand, and pulled me into the canopy bed. With Katy paying rapt attention, we followed the same pattern as we had at my house — Esmeralda gave me an awesome blowjob, we screwed, we engaged in sixty-nine until I was hard, then Esmeralda rode me until I came. Katy had flipped the album partway through, then replaced with ‘Paradise Theater’ by Styx.

“Got the idea, Katy?” Esmeralda asked with a smirk.

“I’ve known how it works for years!” Katy replied, laughing softly. “But it was really cool to watch!”

“Let me get him cleaned up, and he’s all yours!”

Esmeralda led me to the bathroom, where we got into the shower. We quickly washed, then went back to the bedroom where Katy had obviously changed the sheets on the bed and was lying on it. She beckoned me, and I went over to the bed and got in while Esmeralda sat down to watch her best friend give me her cherry.

Katy and I shared a soft French kiss that tasted of cherry lip gloss, then Katy moved down to take me into her mouth. Having watched Esmeralda, and with a bit of experimentation, Katy gave me a very nice blowjob, bobbing, stroking, licking, and sucking until I came in her mouth.

“I love how that tastes!” Katy exclaimed, licking her lips.

She moved up, we exchanged another French kiss, then she lay on her back. I slipped the straps of her teddy from her shoulders to reveal her large, firm breasts and suckled each one in turn, before removing her teddy completely and burying my tongue in her cherry pussy, which, to my delight, tasted of cherry lip gloss.

After bringing Katy off twice, I moved up, positioned my glans against her labia, then lowered my lips to kiss her while pushing my hips forward. As my tongue entered her mouth, my dick entered her virgin pussy. Our tongues tangled, and I made several short thrusts to bury myself completely in her tight, wet tunnel.

“Holy shit!” she gasped, breaking our kiss. “SO full!”

“You OK?” I asked.

“God, yes!” she exclaimed, breathing hard. “Just fuck me!”

I lowered my head next to hers and did exactly as she asked. After half-a-dozen thrusts, Katy began moving with me, moving her hips with wild abandon.

“Fuck me!” she gasped over and over as I did my best to drive her through the mattress.

After five minutes of hard pounding, she groaned, tightened her arms and legs around me, then let out a primal scream as her pussy spasmed hard around my dick and her body shuddered.

“Keep ... going...” she demanded, gasping for breath.

I did, and having no urgency because I’d already cum four times, I fucked her hard for a long time, giving her three more huge orgasms before I came into her tight, spasming pussy.

“Jesus!” she gasped, when I pulled out and moved to lie next to her.

“I TOLD you he was good!” Esmeralda said.

“He’s HUGE!” Katy replied, trying to catch her breath. “And I came SO hard!”

We lay quietly for about ten minutes, and after Katy’s breathing returned to a semblance of normal, we began our next round with sixty-nine. Katy unhesitatingly took my dick, which was covered with our combined fluids, into her mouth, and I sucked her clit.

It took a bit of work for her to get me hard, but when she did, she turned, lifted up, then impaled herself on me. She leaned down for a kiss, then began riding me hard, her hair flying every which way. I put my hands on her hips and simply enjoyed the pleasure her tight, slick tunnel gave me as she moved up and down and back and forth, and ground against me, bringing herself off four times before I had my release.

“Wow!” she gasped, stretching out on top of me with her legs on either side of mine, and my dick still embedded in her pussy.

I cupped her firm butt with my hands and she put her head on my shoulder.

“You kind of went crazy!” Esmeralda said.

“I can’t believe how good it feels!” Katy said through labored breaths. “Rubbing myself was NOTHING like this!”

“No kidding!” Esmeralda said with a soft laugh. “Though it was exciting to watch you and rub myself!”

“Hussy!” Katy teased.

“Like you didn’t rub yourself while you were watching us?”

“Maybe,” Katy giggled. “Let’s get a drink and something to eat. Then I want Jonathan to fuck me again and again!”

“I’ll do my best,” I promised, having already cum six times. “But maybe we should shower first.”

“Yes!” Katy exclaimed giddily.

She moved off me, we got out of bed, and went to the shower, which I thoroughly enjoyed, soaping her curvy body, sexy breasts, and tight butt. We finished our shower, dried off, and went back to the bedroom.

“Let’s go downstairs naked!” Katy suggested. “Nobody else is home, and all the curtains are drawn.”

I certainly didn’t have a problem with it, and Esmeralda didn’t object, so we went downstairs to the kitchen to have Cokes and chips.

“Any chance of you staying until Friday and fucking me all day and all night for the whole week?” Katy asked.

“As much fun as that would be, I have to work, and I have plans tomorrow, Monday evening, and Tuesday evening.”

“Bummer!” Katy exclaimed. “But you can call me anytime you want to fuck! I mean it!”

She was fun, curvy, and enthusiastic, and would make a fun occasional partner, just as Esmeralda would, but I was quickly running out of Summer — Bev would be visiting in two weeks and then Huifen would return.

“We’ll have to see,” I said. “I have a friend visiting soon for a week, then a girl I was dating in the Spring is coming back to college.”

“Bummer!” she exclaimed again. “I leave for Princeton in about a month. I guess we’ll just have to do it all night tonight!”

“As I said, I’ll do my best, given I’ve already cum six times! But I’m happy to use my mouth and fingers, too!”

“I won’t object to that!” she declared.

“I’m going to walk home,” Esmeralda said. “Katy, you’ll take Jonathan to Wrigley Field tomorrow, right?”

“Yes, of course!” Katy exclaimed.

Esmeralda came to me for a hug and kiss, pressing her naked body against mine.

“Thanks for a second time! Call me if you have time!”

I kissed her again, and she went upstairs to dress. She came back down a few minutes later, hugged and kissed me again, then left. Katy and I went back up to her room, got into bed, and began fooling around.

July 18, 1982, Chicago, Illinois

“Have fun?” Bianca asked when I met her and Shelly outside Wrigley field.

“I did!” I replied.

Katy and I had fooled around most of the night, catching a couple of naps. I’d spent most of the time using my mouth and fingers, but I had managed three more times between when we’d gone up to bed and when we’d left the house for her to bring to me the ballpark. I was glad we were going to the game, as I needed time to recover before Shelly and Bianca took advantage of our living arrangement for more wild sex.

“Bleachers OK?” Shelly asked. “There are plenty of regular seats, but if we sit in the bleachers, it’s way more fun and we can get in for about a quarter of the cost of regular seats. We can have Cokes and hotdogs and still spend less than for box seats.”

“Bleachers work for me,” I said.

Bianca agreed, so we bought our tickets and headed into the stadium. It was much better than Comiskey Park, in my mind, and seemed far friendlier and cozier. We made our way to the benches in the outfield bleachers, bought Cokes and hotdogs from a vendor, and settled in to wait for the game to start.

The Braves got out to a great start with a single, a sacrifice bunt to advance the runner, another single, a fly out, then three straight singles driving in three runs. The only thing that kept it from being worse was that a Brave runner was thrown out at second to end the inning.

The Cubs never recovered from the 3-0 first-inning deficit, though they did score runs in the bottom of the first and the bottom of the fifth to make it 3-2. The Braves scored an insurance run in the top of the sixth, and that’s how the game ended — a 4-2 Cubs loss.

We left the ballpark, took the L home, and I went up to my room to take a nap. Bianca woke me for dinner at 5:45pm, and after we ate and did the dishes, we watched The Postman Always Rings Twice on the VCR.

“Kitchen table, hmm...” Bianca teased after a truly hot sex scene between Jack Nicholson and Jessica Lange.

“That looked almost real,” Shelly said. “I mean, as in, they really did it!”

“Nah,” Bianca replied. “She kept her underwear on and he never took off his pants. It was just amazing editing!”

“That part where he rubbed her had to be real, at least,” Shelly said.

“True,” Bianca agreed. “But it could have been a body double as they used for Brooke Shields in The Blue Lagoon.”

“But not in Pretty Baby!” Shelly exclaimed. “She was totally full-frontal, despite only being twelve!”

“You’re joking!” I exclaimed, surprised.

“Nope. She played the daughter of a prostitute, and you saw her several times completely naked, and she’s basically auctioned off to a guy to have sex, but it’s off screen.”

“At twelve?!” I asked incredulously, shaking my head.

“Yes.”

We watched the rest of the movie, then went for a walk in the warm Summer air, with the temperature around 80°F, despite it being 10:00pm. When we returned to the house, Shelly, Bianca, and I went to bed together, and as usual, after a couple of rounds, they went back to their bed and, after a quick shower, I changed the sheets, got back into bed, and fell asleep.

July 19, 1982, Chicago, Illinois

“Did you enjoy yourself at the party?” I asked Jack when he came into the mailroom on Monday morning.

“Are you kidding?” he said, shaking his head. “Let’s just say nothing I did in High School even comes close!”

“Allyson?” I asked with a knowing grin.

He nodded, “Kristy and I were fooling around and Allyson just waltzed in and got into bed with us. I didn’t get home until late last night! I bet that voluptuous blonde was a lot of fun!”

“Saturday night was not boring,” I replied.

Jack laughed, “I bet!”

“Are you seeing Kristy again?”

“We have a date for Friday.”

“I’m glad you guys hit it off!”

“Any chance I could bring her on Saturday?”

“I don’t see why not. The guys are couples, so bringing someone shouldn’t be a problem. I’ll ask someone, too.”

“That blonde? Or her Mexican friend?”

I was actually thinking of Lily, but either of those girls would be fun, too. I’d need to check with Costas if he was OK with Lily joining us. I was sure he would be, but it was safer to check first.

“I’m not sure,” I replied. “I need to see who’s available.”

“Morning!” Bob O’Day called out, coming into the mailroom.

“Hi, Bob!” Jack and I both said simultaneously.

“I think the fictional Bob Hartley made a lot more money as a psychologist than I do here!” Bob declared.

“The building they used for the exterior shots of his office is just down the street,” Jack said. “430 North Michigan.”

“Right next door to our old offices,” I said. “We were at 444 North, but couldn’t get more contiguous floors in that building.”

“The building they used for exterior shots of his apartment is in Edgewater on North Sheridan,” Jack added. “And there were plenty of other shots of Chicago used for flavor. But his commute home was nuts! In reality, he should have just taken the Howard line north from Grand to Thorndale, about three blocks from the apartment building. But no! He walks south into the Loop, gets on the wrong train, takes it to freaking Evanston, and then walks something like fifty-five blocks home!”

“Touchy, touchy!” Bob retorted. “It’s fiction!”

“It’s stupid!” Jack exclaimed. “I mean, seriously!”

“TV trivia time is over,” I chuckled, deciding to end the debate. “Let’s get to work!”

“One last comment,” Jack said. “Good Times, Kolchak: The Night Stalker, and The Untouchables were all filmed here. And for movies, of course, The Blues Brothers takes the cake!”

“No sunglasses, no cigarettes, but lots of work to do,” I said. “Hit it!”

Both Bob and Jack laughed, and we got to work. I was actually happy neither of them smoked, and with Mr. Nelson being forced to quit by the tag-team of his wife and doctor, the air in our area was markedly better. The maintenance guys smoked, but they mostly kept that in their small office and kept the door closed, and I had no reasons to visit them on a normal day.

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