Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 9: Home Runs

Coming of Age Sex Story: Chapter 9: Home Runs - How do you maintain your personal integrity and loyalties to those you care for in the face of unbelievable temptations? Is it even possible, or will Jonathan's principals be compromised as much as the ones of those whose fortunes he seeks to match? The only way to truly find the answer is to keep climbing up.

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

July 30, 1982, Chicago, Illinois

I pulled Julianne aside and asked her about Ellie, and Julianne assured me Ellie knew about the game she’d played and had said she was willing to participate if something like that happened. I nodded, and we rejoined the others.

“Who goes first?” Sally asked.

“Let’s use a deck of cards,” Shelly suggested. “I’ll take out one suit, we draw, and go in card order, highest to lowest.”

“Redraw each round?” Lucy suggested.

“Sure,” Shelly agreed.

She went to her room and came back with a deck of playing cards. She separated out the hearts, then had all the girls draw a card. She drew last and laughed when she showed the Ace. The order after her was Julianne, Sally, Katy, Ellie, Esmeralda, Sylvia, Bianca, and finally Lucy.

I French kissed each of the girls in turn, enjoying the different tastes, as several of them were wearing flavored lip gloss. Esmeralda and Katy tasted of cherry, Ellie of Strawberry, and Julianne of green apple. When Lucy and I finished our kiss, Shelly collected the cards and shuffled them.

“Inside or outside clothing?” Esmeralda asked.

“How about we make it three minutes and Jonathan undresses each of us?” Lucy suggested.

“Who undresses him?” Sally asked.

“How about whoever goes first?” Lucy replied.

“How about we go in card order, one piece of clothing per girl, before the round actually starts?” Shelly offered. “I believe he has seven pieces of clothing, if each sock counts and his belt counts.”

“There are nine of us!” Bianca protested.

“Luck of the draw!” Sylvia exclaimed.

“Then the order of clothing removed is sock, sock, belt, shirt, t-shirt, pants, briefs,” Bianca smirked. “Being first isn’t a double advantage!”

The girls drew cards, and Esmeralda and Shelly each removed one of my socks, Sylvia my belt, Katy my shirt, Sally my t-shirt, Shelly my pants, and Ellie my briefs.

“Whoa!” Ellie gasped. “He’s huge!”

“It gets even bigger!” Julianne declared, causing all the girls to laugh.

“Hung like a horse!” Lucy declared. “And I plan to ride him like Ron Turcotte rode Secretariat!”

“The last thing you want is him crossing the finish line in record time!” Sylvia declared.

All the girls laughed again.

“Hands only this round, right?” Sally asked.

“Yes,” Shelly said. “Next round, which is longer, is mouths and hands. Though this round you can kiss if you want, but only above the shoulders.

I thought about how to approach undressing the girls and settled on a strategy. I’d remove their blouses or t-shirts and bras, then stand behind them and fondle their breasts, then unbutton their jeans and slip my hand inside to massage their mounds while I kissed their necks.

Esmeralda was first, and I followed my plan, ending up with my left hand cupping her left breast from behind, and my right hand inside her panties, using my finger to rub her clit while I kissed her neck and shoulders, while she moved one of her hands behind her so she could run her fingers over my shaft. When time was almost up, I pushed her jeans and panties down, helped her step out of them, then engaged in a nude full-body hug while we French kissed. I did the same with each girl in turn, with Lucy being last. The only surprise was that Ellie was shaved smooth, something I hadn’t encountered before.

As Shelly shuffled the cards after the undressing round, I realized it was in my best interest to cum at least once during the oral round, as that would allow me to give two girls a full ten minutes without any real risk of ‘crossing the finish line’ too early. When the girls had drawn their cards, they showed them, and Sylvia was first. That made me happy, as I was positive she’d repeat what she’d done at Paula’s party.

“Suck my nipples for a minute, then sixty-nine?” Sylvia offered.

I was more than happy to oblige. I sat down on the couch, had her sit in my lap facing me, and suckled each nipple for about twenty seconds before lying down on the rug in front of the couch. Sylvia straddled my head with her thighs, lowered her labia to my mouth, then quickly and easily took my entire length into her mouth.

“Whoa!” Katy gasped.

“She’s a showoff!” Lucy declared.

I pressed my tongue into Sylvia and sucked on her clit, hoping I could get her off before the five minutes were up. When she closed her hands around my sack and squeezed gently, and began bobbing, licking, and sucking, I wondered if I’d make the entire five minutes. She gave the best blowjobs I’d ever had, bar none, and I didn’t think it would be embarrassing to cum fairly quickly from a girl deep-throating me. I focused on bringing her off, rather than trying to prolong my orgasm, and achieved my goal just before Sylvia achieved hers. She moaned, shuddered, and squeezed her thighs against my cheeks as I spurted into her mouth, with two of my spurts going straight down her throat.

She continued sucking me until Shelly called time, then turned and gave me a deep French kiss. Kisses after blowjobs certainly didn’t thrill me, but there was no way I was going to refuse Sylvia anything she wanted to do.

“How do you do that?” Katy asked, incredulous, when Sylvia and I got up.

“Breathe through your nose and overcome your gag reflex,” Sylvia said. “Learn to do it, and a guy will do anything you want!”

She wasn’t kidding! That included kissing after cumming in her mouth, and I’d even give serious consideration to doing the thing Jeri had first tricked me into doing, then demanded I repeat. The blowjobs were that good.

“We can take a short break to allow Jonathan to recover,” Shelly suggested.

“No way!” Sally, who was next, exclaimed. “The clock starts when he gets hard!”

“Only in the ‘home run’ round!” Shelly countered.

“You can’t blame a girl for trying!” Sally exclaimed.

She sat down on the couch, scooted forward, leaned back, then spread her long legs, revealing her plump labia. It was obvious what she wanted, so I knelt in front of her, licked each nipple once, then lowered my head to her pussy and began pleasuring her. Sally always had good orgasms when we screwed, but five minutes of oral wasn’t enough to get her off.

After Sally, I engaged in sixty-nine with Esmeralda, Bianca, and then Katy, who made a valiant effort to try to take my entire length into her mouth but couldn’t get me completely in because of her gag reflex. The blowjob was excellent, despite the fact she felt she’d failed, and I told her so.

“I’ll just have to practice!” she exclaimed after I reassured her how much I enjoyed her mouth.

Lucy was next, and she reclined on the couch so I could pleasure her, and I managed to give her an orgasm before our time was up. Ellie was next, and she came up to me and put her arms around my neck.

“I’ll blow you tonight,” she said, “just lick me, OK?”

I nodded, and we exchanged a French kiss, then she sat on the couch, leaned back, and I explored her clean-shaven pussy with my lips and tongue, savoring her coppery flavor. As I explored her silky insides, Ellie tensed her muscles and squeezed my tongue. She was going to be a great fuck, I was sure, as if she did that when I had my dick inside her, she’d be almost as tight as Allyson.

Julianne, Lucy, and Shelly all chose to sixty-nine, but only Lucy had an orgasm before time ran out. That wasn’t going to be a problem during the ‘home run’ round, as I was positive each of the girls could cum given ten minutes of screwing, especially if they were on top. The fact that Sylvia had made me cum meant I easily lasted for the rest of the time.

“Let’s move to our room,” Shelly suggested as she gathered the cards. “That way, we can use the bed.”

We went up to their room, Shelly shuffled the cards, then everyone drew cards. Sally squealed with delight when she drew the King and nobody drew the Ace. She and I got into bed, we French kissed, I sucked each of her nipples, then moved down to lick her until she was wet. Once she was, I moved up, slowly entered her, she wrapped her long, athletic legs around me and we fucked HARD. Sally and I were very good at fucking, and I knew exactly how to make her cum, which I did just before time ran out. I wanted to continue, but the rules didn’t allow it, so I reluctantly withdrew.

Lucy was next, and requested I lie on my back, which I did. She straddled me, then ground against my shaft, which was wet with Sally’s juices. Once Lucy was wet enough, she took hold of me, held me upright, and lowered herself onto me. She put her hands on my chest and began riding me, gently at first, but then wildly, as she’d promised earlier. She had two orgasms before her time was up, and had brought me very close. Fortunately, the urgency dissipated when she lifted off.

Bianca was next, and she rode me, though more gently, which I was sure was a strategy, as she didn’t cum for nine minutes, thus extending her time, and I had no urgency at all, so I simply enjoyed the feeling of her pussy around my shaft. Bianca was followed by Shelly, who used the same strategy, and then by Julianne, who wanted me to screw as we usually did — me on top, starting slow, and building into an energetic fuck. She came after about six minutes, and I was right there with her, so I kept going for another few seconds, then pushed deep into her spasming pussy and came hard.

Shelly was next, and I was totally not surprised when she suggested we sixty-nine until I got hard. I offered to clean up, but she winked and happily licked Julianne’s juices from my flaccid shaft. Shelly’s strategy worked perfectly, as she had two good orgasms from my tongue before I was hard. Once I was, she turned, mounted me, and gave herself two more orgasms by grinding her clit against my pubic bone, as she’d done many times in the past.

Katy was next, and she rode me for seven minutes before she came, and was followed by Sylvia, who asked me to do her ‘doggy style’, something I’d never done before. I pounded her for a good seven minutes and my urgency got the best of me. I came hard, which was enough to take Sylvia over the edge as I pumped cum deep in her pussy.

We took a break, and because Esmeralda was next, I went to the bathroom to clean myself, then joined the girls downstairs for a Coke. A fifteen-minute break was just what I needed, and then we all went back to the girls’ room, where it was Esmeralda’s turn. She used the same basic strategy as Shelly had — sixty-nine, but she was in no hurry to get me hard while I licked her to a pair of orgasms. When she finally got me hard, she invited me on top of her and we spent nearly ten minutes slowly screwing, which I was positive was her way of prolonging things, giving her a total of close to twenty minutes, and a third orgasm.

That left Ellie for last, and I anticipated the feel of her tight pussy around my shaft. It was in my interest to prolong things, but then I hit on a better idea.

“The bonus for going last is Ellie gets as long as it takes for me to cum,” I announced.

“Oh, sure!” Sally groused good-naturedly.

“You’re welcome to spend the night one night after the seventh,” I offered.

“Deal!” Sally exclaimed.

“Can anyone do that?” Katy asked hopefully.

“My social calendar is fairly open between the 8th and the 21st,” I replied. “Just call.”

“Awesome!”

“Ellie,” I said, taking her hand, “we haven’t been together. What would you like?”

“Take it slow and make it last as long as possible!”

“I can do that!”

“And make me cum!” she added.

“That, too!”

We got into bed, French kissed, then I suckled her small nipples for a bit before kissing my way down her chest and stomach, stopping to swirl my tongue in her belly button. I planted several soft kisses on her bare mons, then gently pressed my tongue between her thin labia, once again savoring her juices before teasing her clit with my tongue, and closing my mouth around it. I sucked, licked, and nipped Ellie until she groaned and bucked her hips.

When Ellie’s orgasm passed, I moved on top of her, grasped my shaft, and rubbed my glans against her slick labia. Once it was coated with her juices, I gently pushed my hips forward and my glans slowly spread her labia. Ellie spread her legs as wide as she could, and I used several gentle thrusts to bury myself inside her tight tunnel.

“So huge!” she groaned. “So deep!”

I leaned down to French kiss Ellie, then pulled back and began slowly fucking her as she’d requested. After a few strokes, Ellie moved her legs and rested her heels on my thighs. She lay still as I moved in and out of her, then after a dozen strokes, she began moving her hips up to meet my thrusts and we began what amounted to a slow-motion fuck. She felt really good, and her walls massaged my shaft and glans as I moved in her.

I’d already cum several times, so I knew I could last a long time, and I intended to do exactly that. Every few dozen strokes, I pushed in as deeply as possible and ground against Ellie’s clit, and she squeezed her muscles, making a tight fit even tighter. Because we weren’t exerting ourselves, we could continue kissing while we screwed. I fucked her tight tunnel for more than twenty-five minutes, giving her four good orgasms before I could no longer hold back, and began firing jets of cum into her spasming pussy.

When our mutual orgasms passed, I gently pulled out and went to my shower to clean up before bed. When I came out of the bathroom, I found Julianne and Ellie sitting on the end of the bed.

“Got anything left?” Julianne asked.

“So long as I get a few hours of sleep, yes, I do,” I replied. “What did you girls have in mind?”

“Ellie wants to keep her promise to blow you, then we want you to fuck us, but one at a time. Then we can go to sleep.”

“I think I can manage!”

I got into bed, propped two pillows behind me, and leaned against them. Ellie moved so that her head was level with my groin and I watched as she gently took hold of me and planted soft kisses all along my shaft and on my glans. Ellie ran her tongue over my glans, licking it like an ice cream cone while she stroked my shaft with her hand. When she had me hard, she opened her mouth and took my glans in. She continued stroking my shaft while she sucked gently and ran the tip of her tongue around my glans.

After a few minutes, Ellie took me further into her mouth, testing how much she could take without gagging. She managed about half, but I wasn’t going to complain about being in her soft mouth. Because I’d cum numerous times, it took Ellie some time to bring me to release, but she got me there, and I groaned loudly as I pulsed into her mouth. When I stopped pulsing, Ellie licked me clean, then sat up.

“Your turn, Julianne!” Ellie declared with a smile.

“I need a bit of a recovery period,” I said.

“Mind using your tongue?” Julianne asked.

“I don’t mind at all!”

I licked Julianne to two orgasms before I felt I could get hard, and we switched to sixty-nine until I rose to attention. We had one of our usual screws, starting slowly and ending energetically. I washed before I began with Ellie, and licked her to a pair of orgasms before she sucked me to get me hard, and we had another long, slow screw. When we finished, we changed the sheets, then I got into the center of the bed, with Julianne on my right and Ellie on my left. They put their heads on my chest and I put my arms around them.

“A single, a double, a triple, and a pair of home runs in my rookie appearance in the majors!” Ellie declared.

I didn’t doubt her, but I certainly wouldn’t have guessed she’d been a virgin.

“I certainly enjoyed playing baseball with you!” I declared.

I was tired, and thankfully, the girls simply snuggled close and were quiet. I quickly fell asleep, enjoying the warmth of two wonderful female bodies.

July 31, 1982, Chicago, Illinois

“Do we have time for you to hit two home runs before we have to get out of bed?” Ellie asked on Saturday morning.

I checked the clock radio and saw that it was just past 9:00am, which meant I could spend another hour in bed before the time Bianca and I had planned to leave to do the shopping.

“Yes,” I replied.

The girls decided that Julianne should go first, and an hour later, having enjoyed hitting two more home runs, the three of us showered, though individually, not together. I gathered the two sets of sheets and took them downstairs to put in the washer, then walked the girls out to Julianne’s car. I kissed both of them, then went back inside and heated some Pop-Tarts so I didn’t have a completely empty stomach. I poured some coffee from the pot Bianca had made into a travel mug, then she and I left in her car for Jewel.

“Have fun last night?” Bianca asked.

“Obviously!”

“OK to ask a pointed question?”

“Sure. By now, you should know you don’t need to ask if it’s OK to ask.”

“Do you plan to get engaged to Hannah?”

“Would you do me a favor?”

“What’s that?”

“Call her by her proper name, please?”

“Does she object?”

“I have no idea, but there’s no reason to not call her by her given name.”

“Sorry. I didn’t realize that bothered you.”

I shrugged, “I guess to me it’s about respect. That said, if she’s OK with the nickname, then I’m OK with it. To answer your question, that’s about three steps ahead of where we are, at least. Why?”

“Because you’re only nineteen and appear to be having the time of your life! If you aren’t planning to marry her, why tie yourself down?”

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