Climbing the Ladder - The Second Rung - Cover

Climbing the Ladder - The Second Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 26: A Baseball Game, Part II

Coming of Age Sex Story: Chapter 26: A Baseball Game, Part II - 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  

November 13, 1982, Chicago, Illinois

“Showoff!” Meg declared when Ellie got me completely into her mouth just before her minute expired.

“I’m just that good!” Ellie exclaimed. “Josie, your turn!”

Ellie moved out of the way and Josie knelt in front of me. She grasped my shaft gently and then tentatively licked my glans, reinforcing my belief she was the rookie, though it was possible she’d never given a blowjob even if she had screwed. I pushed those thoughts out of my mind and watched as Josie treated my dick like an ice cream cone. She hadn’t taken me into her mouth before her minute was up, and planted a soft kiss on my glans just before she stood up.

Kasey was next and began with a few licks before taking me into her mouth and bobbing a few times before her time ran out. Miranda took her place, winked and pressed her breasts around my shaft before licking and sucking for her minute. I was pretty sure that was an invitation and I’d absolutely take advantage of it. Meg was last in the first round, and mimicked Miranda, and I realized I might get to do that twice!

Round two was similar to the first, though Josie took me about an inch into her mouth. Because of the breaks in between, I wasn’t close and suggested a change to Ellie.

“Make it two minutes for round three,” I suggested. “Then three minutes for round four.”

“You can last that long?” Meg asked.

“Stopping for thirty seconds in between really takes the edge off,” I replied. “I think I’ll be fine for one more round, then someone will get me close.”

“We need to redraw the order each round,” Meg suggested.

They all agreed and round three began with the same order, and with two minutes, I lasted round three, but was sure that with three minutes in round four, one of the girls would bring me off. I could probably control it a bit, and thought about which of the girls I’d like to have in my bed, but couldn’t decide. I was sure that I’d enjoy a second screw with whichever girl won.

The girls redrew their cards, and the new order was Kasey, Ellie, Josie, Miranda, and Meg.

“Hold out!” Meg begged. “Please!”

“Luck of the draw!” Ellie exclaimed.

“Easy for you to say, because you’ve slept with him!” Meg protested.

Kasey tried her best, but going first after a break meant I wasn’t even close, and when her three minutes expired, I pulled her up for a French kiss. Ellie was next, and she made a supreme effort, deep throating me three times, along with stroking and sucking. She got me close, but ran out of time before she could get me all the way there.

Josie was next, and I was fairly certain she could win if she wanted to. Her four minutes over three rounds had been tentative and slow, and if she did that now, then one of the two girls with the large breasts would win. I’d win no matter what, even if it somehow went to round five, which I didn’t expect.

Josie started with a few licks, then took me into her mouth. She sucked gently at first, running her tongue around my glans. After about thirty seconds, she grasped my shaft and began stroking as she bobbed her head. I felt the urge building slowly and was sure that Josie would run out of time.

She apparently had other ideas, as her other hand moved to my sack and gently squeezed, causing me to twitch. She began stroking faster and sucking harder, racing the stopwatch. I was so close that I was afraid Ellie would call time just before I came, and I’d miss cumming in one of the girl’s mouths.

Physiology beat the clock, I twitched hard, groaned, and fired the first blast of cum into Josie’s mouth. She swallowed and didn’t stop stroking, bobbing, sucking, and licking as I continued to spurt into her mouth. She continued until after the last dribble, then when she was sure I was done, released me, looked up, and smiled. I took her hand, pulled her up, and we exchanged a fierce French kiss.

“Well, that sucked!” Meg groused.

“Yes,” I grinned. “It did!”

“Ha ha ha.”

“I suggest Miranda and Meg go first now,” I said. “And then cycle back with Josie last.”

“Fine with me,” Ellie agreed. “Miranda, assume the position!”

I stood up, and Miranda sat on the edge of the bed. She leaned back on her elbows, and spread her legs, her plump labia almost completely hidden by her thick, black bush. I moved between her legs, planted a kiss on her stomach, then lowered my mouth to her pussy. Her pubic hair tickled my nose, and her scent was intoxicating, and when I ran my tongue along her labia, it tasted fantastic. Getting a bit of hair in my mouth wasn’t a big deal, and didn’t interfere with me pleasuring her, using my tongue on her clit and sucking on it until she came.

“God, he’s good!” Miranda declared.

“And that’s not even his best skill!” Ellie exclaimed. “Wait until you get that baseball bat inside you! Meg, assume the position!”

Miranda got up and Meg took her place, spreading her legs for me. Meg was as different as possible from Miranda, with only thin, wispy pubic hair, which barely covered her mons and completely exposed her thin labia. She smelled heavenly as well and tasted almost as good as Miranda. It took longer to make her cum, but that didn’t bother me, as I very much enjoyed performing oral sex. After she had her orgasm, she gave me a fierce French kiss, tasting herself on my lips and tongue.

Kasey was next, and she, like Ellie, was shaved bare, and had a pronounced clit which was very sensitive. She moaned and groaned right from the start, and had an orgasm in less than two minutes. She was replaced by Ellie, who I had been with several times, and I knew what worked for her, and had no problem bringing her off fairly quickly.

That left Josie, the smallest of the girls, but with the plumpest labia, not at all hidden by her neatly trimmed blonde pubic hair. She assumed the position at Ellie’s command and completely exposed herself to me by spreading her legs wide. I planted several kisses on her labia, then probed between them with my tongue. I closed my mouth around her, tasting her musky juices, sucked gently, and flicked her clit with my tongue.

Josie moaned softly and tensed her muscles, squeezing my tongue with her labia, giving the strong impression that she’d be really tight. I had to work the hardest to bring her off, and it took nearly ten minutes before she shuddered and groaned. I stood up, and she simply lay there, trying to catch her breath. After two minutes, she sat up.

“Wow!” Josie breathed. “Just wow!”

“Time to turn over our final cards,” Ellie commanded.

They did, and the order was Ellie, Meg, Kasey, Josie, and Miranda.

“He’ll need about fifteen minutes between times, right Jonathan?”

“A bit less at first,” I replied. “But after a few times, yes. That said, proper encouragement helps!”

The girls laughed.

“Jonathan,” Ellie said with a smirk, “assume the position!”

“Which one?” I asked with a grin.

“I figure a demonstration is in order! Get on your back, and we’ll start with sixty-nine, then me on top, then sitting up, then from behind, and then finish with you on top! Gather around girls! It’s show and tell time!”

It was obvious that Ellie not only got off on watching, but she also got off on being watched. I pulled down the duvet and top sheet, got into my bed on my back. Ellie climbed into bed with me and we did exactly as she’d suggested, in effect, putting on a show for the other girls, all of whom seemed transfixed by what they were seeing. We finished energetically, with Ellie having her second orgasm just before I had mine.

“You should wash,” Ellie suggested as I moved off her.

She had a good point, given the next girl most likely would not be interested in tasting Ellie on me. I went into the bathroom, used a washcloth to clean my groin of Ellie’s juices, then returned to the bedroom.

“How long? Meg asked.

“About ten minutes,” I replied.

“Could we make out while we wait?” she asked.

“Sure,” I agreed.

I looked at the bed and decided to get a soft towel from the bathroom, so neither Meg nor I had to lie in the wet spot. I did that, then Meg and I climbed into bed and lay side-by-side. We kissed for a bit before I lowered my head to kiss Meg’s breasts and tease her nipples with my tongue. After a minute or so, I slid down, moved between her legs, and pressed my tongue between her labia.

I pleasured Meg until I felt the first stirrings in my groin, and then turned so we could move to sixty-nine with Meg straddling my face, allowing me to pleasure her while she took me into her mouth. It didn’t take long before I was hard, and Meg moved off me, lay on her back, and spread her legs for me. I moved between them, grasped my shaft, rubbed my glans along her sopping wet labia, then slowly pushed into her silky tunnel.

“Jesus!” Meg gasped when I was fully inside her.

I leaned down to kiss her, then she wrapped her legs around my thighs and we began moving together.

“Jonathan?” she breathed, breaking the kiss.

“Yes?”

“Fuck me hard!” she demanded.

I obliged and pounded Meg hard as she energetically raised her hips each time I thrust into her. We had an energetic fuck, with Meg cumming twice before I pushed deeply into her and fired jets of cum into her spasming pussy. I withdrew, and we lay together to get our breath before I got up to wash myself again. When I returned, I brought a fresh towel with me which I put on the bed, removing the sodden one and tossing it into the hamper.

It was Kasey’s turn next, and she came over to me, put her arms around my neck, and pressed her firm body against mine.

“I want it slow and gentle,” she said. “And make it last.”

We got into bed and began the same way as I had with Meg, though Kasey being very sensitive meant she had three strong orgasms before we switched to sixty-nine. Once I was hard, I moved between her legs, rubbed my glans along her dripping labia, and very slowly entered her, using several soft, gentle thrusts to bury myself completely inside her.

Kasey wrapped her long legs around me and I began fucking her with long, slow strokes as we exchanged a soft French kiss. Whereas Meg had been energetic, with Kasey it felt more like making love, but given her sensitive clit, moving slow allowed me to grind against her with each thrust, and that gave her a series of gentle orgasms which built into a tremendous one that had her groaning loudly as her pussy spasmed around my shaft.

I’d already cum three times, so there was literally no urgency, allowing me to continue our slow-motion screw, giving Kasey several more small orgasms before she had another big one, this time, at a point where I was close enough that I joined her, pumping cum into her as her pussy milked my shaft. We kissed softly several times before I moved off her and got out of bed.

I washed myself and changed the towel, then held out my arms to Josie, thinking that because she was so small, she should probably be on top.

“Could I go last?” she asked. “Then we can just stay in bed?”

“Miranda?” I inquired.

Miranda quickly agreed, and we got into bed. Given I’d cum four times, I knew it would take longer for me to get hard, which would allow me plenty of time to play with Miranda’s huge chest. I took full advantage, kissing, caressing, licking, and sucking, and Miranda clearly enjoyed the attention, as she moaned softly when I teased her nipples with my tongue while sucking on them.

When I felt enough time had elapsed, I gently maneuvered Miranda into sixty nine, her thick bush tickling my chin as I pressed my tongue into her. She tasted the best of all the girls, so I ignored the hair, and lapped up her juices as she sucked and licked my glans. She had to work a bit, but eventually I was fully erect, and she moved off me, allowing me to position myself between her legs.

“I’m a rookie,” she whispered. “Be gentle.”

I nodded, kissed her softly, then rubbed my glans against her plump labia, coating it with her juices. I kissed her again, then slowly pushed into her, filling her virgin tunnel with my long, thick shaft.

“Oh, God,” Miranda groaned when I was fully embedded.

“You OK?” I asked.

“Yes,” she whispered. “Go slow, OK?”

I nodded, kissed her, then began slowly thrusting in and out. After about a dozen strokes, Miranda wrapped her legs around me and began matching my movements. We continued our slow-motion screw for several minutes, then Miranda asked if she could be on top. I wasn’t going to object, given it meant I could play with her breasts, so I pulled out, turned on my back, and Miranda straddled my groin.

I held my shaft while she positioned herself and then slowly slid down, groaning as I filled her once again. Miranda began moving tentatively, searching for the best motion to provide her with pleasure, and I cupped her large breasts, strumming her nipples with my thumbs. Miranda quickly found what worked for her, sliding back and forth, grinding against me, and occasionally lifting up and sinking down.

“Lean forward,” I suggested.

Miranda did as I asked and I took her nipple into my mouth, causing Miranda to moan. I sucked and teased her nipple with my tongue, and less than thirty seconds later she groaned deeply and had her first orgasm, her pussy spasming around my shaft. We continued that way, and she had two more orgasms, before lifting off and turning to her back so we could finish with me on top. We fucked at a moderate pace until I finally had my release. Not that I objected to how long I was in her tight, slick tunnel.

When I moved off her, Miranda snuggled close and we lay together for a bit before getting out of bed.

“Let’s take a short break,” I suggested. “I need more time to recover. I have soda and snacks in the kitchen.”

“Everyone stay naked!” Ellie commanded.

I went to the bathroom to wash and get a clean towel for the bed, then the six of us trooped down to the kitchen where everyone got a Coke and either pretzels or chips. Once we all had our snacks and drinks, Miranda came to stand close to me.

“I really liked what we did, and it made me feel really good,” she said. “I’d like to spend the night with you sometime soon, if that’s OK.”

I didn’t see any harm in fulfilling her request, and I certainly wasn’t about to pass up an opportunity to play with her large breasts!

“I’m sure we could arrange that,” I replied. “I’m free Monday, though I have to be out of the house by 7:15am for work on Tuesday, sooner if I’m giving you a lift back to Loyola.”

“Monday night?” she asked. “I don’t have class until 10:00am on Tuesday.”

“Sure. Do you need me to pick you up?”

“That would be great! What time?”

“About 5:30pm,” I replied.

“Cool!” she exclaimed, her breasts pushing into my chest as she gave me a quick peck on the lips.

The snacks gave me a twenty-minute respite, which I was sure would help, as I’d already cum five times. As we left the kitchen, Josie put her hand on my arm and nodded to the front room. I followed her there.

“I’ve never done it before,” she said quietly.

“You don’t have to, if you don’t want to,” I replied.

“No!” she said quickly. “I want to! Really! But you’re so big and I’m so small.”

“It’s just a matter of ensuring you’re wet enough,” I replied. “Remember what Ellie said when you asked earlier?”

“That a baby fits, so you’ll fit!”

“I do think you should be on top, given how much taller and heavier I am than you.”

“I think sitting in your lap the way you did with Ellie,” Josie suggested.

I had some baby oil that Huifen had left in my bathroom and thought that might help if Josie was as tight as I thought she was.

“And I think a bit of baby oil will help, too,” I replied.

“OK,” Josie agreed.

I took her hand and led her back up to my room. I went to the bathroom and got the bottle of baby oil, then returned to the bedroom and set it on the nightstand. The other girls gathered around the bed to watch Josie and me.

“Let’s make out for a bit first,” I suggested to Josie.

She nodded, so I got into bed and sat cross-legged. She climbed into my lap, facing me, and knelt with her legs on either side of mine, making it easier to kiss. I wrapped my arms around her, our lips touched, and we exchanged a series of soft kisses, before Josie parted her lips and our tongues began to dance. We kissed for about ten minutes before Josie broke the kiss and leaned back.

“Can we try?” she asked breathlessly.

I nodded, then leaned back and Josie turned so that she could suck me while I licked her. It had been about forty minutes, and that made Josie’s task easier, though it still took about five minutes of her running her tongue around my glans while sucking gently. When I was fully erect, she released me and we returned to our previous position. I reached over and grabbed the bottle of baby oil.

“Hold out your hand,” I said.

She did, and I squirted some baby oil into her palm, then returned the bottle to the nightstand.

“Just spread it on me,” I said.

Josie grasped me gently and slid her hand up and down my dick, coating my shaft and glans with the baby oil. When she finished, she rose up on her knees, I grasped my shaft and helped her position herself correctly so that my glans was touching her labia.

“Just lower yourself slowly onto me,” I instructed.

She nodded, kissed me, then put her hands on my shoulders and then pushed down, my glans spreading her labia and popping into her extremely tight tunnel, encountering the briefest of resistance.

“Oomph!” Josie gasped, blowing out a long breath.

I realized that she’d still had her cherry, something I knew wasn’t common for a girl who was eighteen or nineteen.

“Are you OK?” I asked.

“Yes,” Josie said breathlessly.

She kissed me and slowly lowered herself further onto me, pausing after I was another two inches into her.

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